pachycereus pecten-aboriginumthe-eye.eu/public/concen.org/alexander shulgin books/the... ·...

Definitions:

Consider botany. What is a taxon? It is the name which identifiesa plant. A taxon is made of two parts. First, there is the genus,which is a general name given to a group of closely related plants.Second, there is the species, which is the distinguishing namegiven to a specific plant in that group. A taxon is always writtenin italics. Thus, for example, Pachycereus pecten-aboriginum is thename of a cactus.

Consider chemistry. What are isoquinolines? These are chemicalstructures built around a two-ring compound. This compound,Isoquinoline, consists of a benzene ring and pyridine ring fusedtogether at a specific bond. There is a pattern of substitution thatgives an isoquinoline its absolute definition. Thus, for example,Salsoline is an isoquinoline, which is a major component of thePachycereus pecten-aboriginum plant.

One can identify a plant by what it looks like, or by what is in it.One can identify a natural compound by its structure, or by whatplant it is in. Know one, find the other. This reference book hasbeen designed to make this cross-identification easier to achieve.

TABLE OF CONTENTS

Foreword I vi

Foreword II xi

Introduction xiii

TrivialName Index 1

Structural IndexUnsubstitutedMonosubstitutedDisubstituted

5,6- 5,7- and 5,8-substituted6,7 -HO,HO-substituted6,7-HO,MeO-substituted6,7-MeO,HO-substituted6,7-MeO,MeO-substituted6,7-MDO-substituted6,8-substituted7,8-substituted

Trisubstituted5,6,7-substituted5,6,8-substituted6,7,8-substituted

Tetrasubstituted

3941

46475288

161245347349

372425426455

Taxon Index 458

Plant Families Appendix 602

Isobenzofuranone Appendix 610

Journal Names Appendix 616

v

vi

FOREWORDI

The passion of my life over the last forty years has been a compellinginterest in psychedelic drugs. They have given me not only an excitingarea of research and discovery, but also a personal understanding of justwho I am and why I am. Certainly these guides and sacraments willeventually play an accepted role in our community and in our culture.Almost all of these drugs have either been isolated from psychoactiveplants, or are the results of subtle variations of the molecular structures ofthese isolates.

I have always looked at these plants and the compounds they containin the same way that the Romans dreamt of their ultimate empire. It wasCaesar who acknowledged that all of Gaul was divided into three partsand to understand it, to conquer it, each part had to be respected as aseparate entity. It is exactly the same way with understanding the worldof psychedelic drugs. There are three domains of inquiry that must bestudied independently before one can begin to appreciate just how theymight integrate into a single concept. These three are now, I believe,coming together.

One part is the large collection of psychoactive compounds known asthe phenethylamines. The first known plant psychedelic was mescaline,or 3,4,5-trimethoxyphenethylamine. This simple one-ring alkaloid wasdiscovered in the North American dumpling cactus Peyote (Anhaloniumtoilliamsii) in the late nineteenth century, and is now known to be a com-ponent of over fifty other cacti. Over a dozen other cactus phenethyl-amines have been isolated and identified, and there are perhaps a hun-dred synthetic analogues that are now also known to be psychedelic inaction. This body of information has been published by my wife Ann andme as a book entitled "PIHKAL: A Chemical Love Story." PIHKAL standsfor Phenethylamines I Have Known and Loved.

An almost-as-large chemical group contains the tryptamines. N,N-Dimethyltryptamine (DMT), its 5-hydroxy analogue (bufotenine) andthe O-methyl ether homologue 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) are widely distributed in the world of natural plants. Thereare also the well-established mushroom alkaloids 4-phosphoryloxy-N,N-

vii

dimethyltryptamine (psilocybin, and the dephosphorylated indolol psilo-cin)and the mono- and didemethylated homologues baeocysteine andnorbaeocysteine. These seven natural alkaloids have provided the tem-platefor perhaps two dozen analogue structures that are now well-estab-lishedpsychedelic agents. Ann and I have written a companion volumeto PIHKAL called "TIHKAL: The Continuation" (TIHKAL stands forTryptaminesI have Known and Loved), which has brought together mostofthese natural and synthetic tryptamines into a single reference site.

The remaining third of the above Gallic synthesis deals with what Ihad originally called the "Q" compounds, as distinguished from the "P"compounds and the "T" compounds (the phenethylamines and thetryptamines). The actual parent structural element is the isoquinoline ringsystem,and my initial plan was to give this third book a name similar tothe first two. IIHKAL wouldn't do it, but QIHKAL shows a good bit ofclass, at least in my opinion. Or maybe THIQIHKAL because most ofthem are really tetrahydroisoquinolines. Well, all these names are nowon hold, as Ann is uncomfortable with them. No name has yet beendecided upon, but ideas such as The Third Book, or Book Three, areunder consideration. Names like these resound with a rather strikingarrogance, if nothing else.

Tounderstand the relationship of the isoquinolines to the phenethyl-amines and the tryptamines, the concept of ring closure must be used.Thisisa sort ofsynthetic scorpion sting at the molecular level. A tryptaminehas an indole ring as its centerpiece and from it there extends a floppytwo-carbon chain terminated by an amino nitrogen atom. A small butvery important family of plant alkaloids is the product of this amine ex-ploitinga carbon atom from somewhere, and making a new six-memberedringby that "sting" reaction back onto the parent indole ring. This familyhasthe name,~-carbolines, and the formed compound is 1,2,3,4-tetrahydro-[3-carboline.

QCNHNIH

tryptamine 1,2,3,4-tetrahydro-~-carboline

Aphenethylamine has a benzene ring as its centerpiece and it, too, hasa floppy two-carbon chain extending out from it and also terminating inan amino group. In a reaction that is exactly analogous to that of thetryptamines, this amine can pick up a carbon atom and bend back to react

viii

with the parent benzene ring forming a six-member ring. This is the ori-gin of the isoquinoline family of natural products, and the formed com-pound is l,2,3,4-tetrahydroisoquinoline.

phenethylamine 1,2,3,4-tetrahydroisoquinoline

As mentioned above, this third part of the plant psychedelic alkaloidworld involves tetrahydroisoquinolines and is the substance of our thirdbook. A very reasonable appendix to be written for this book would be asearch of the chemical literature for the known isoquinolines that mightbe of interest as pharmacological agents. There are certainly many plantproducts, as well as a monster inventory of synthetics, some of which aremade based on plant examples, but many others are simply laboratorycreations of the imaginative chemist.

It was soon apparent that this compilation would become unmanage-ably large. The first major trimming was the elimination of the compoundsthat were synthetic, and the limitation of the listing to those compoundsthat have been reported as plant products. These isoquinolines could playthe dual role of serving not only as potential contributors to the action ofpsychoactive plants but also as prototypes for the synthesis of newmaterials that might themselves be biologically active.

But even this restriction to only plant compounds was not sufficientlysevere. There seemed to be no end to existing isoquinoline treasures. AsI wandered deeper into the literature, I kept finding an ever-increasinginventory of research papers that described fantastic stuff. As a totallymake-believe example, pretend that there was a compound namedDogabinine that has only been found in the Dogabic tree in the Twathturainforest, which the natives say cures leprosy, and which has a complexchemical structure that just happens to carry an isoquinoline ring in itslower southwest corner. To include all such monsters would make theappendix many thousands or even tens of thousands of pages long. Andif you were to add into this compilation all the known derivatives, exten-sions and chemical modifications of Dogabinine, then you would have areview entity that would be several volumes in length. If such a collectionwere to exist, I would have it in my library right now. But it does not existand it may never exist.

IX

Some middle ground, some rational compromise, had to be found. Iwanted this collection to present all isoquinolines that are known to beplantalkaloids, but respecting carefully defined restrictions that excludehorrormonsters such as Dogabinine. The final compromise was to estab-lishseparate entries for all the known two-ring isoquinolines that are fromnatural sources, including those that carry a third ring as a substituent(suchas a benzyl group) at the I-position. And within each of these en-tries,there are included all natural alkaloids that can be seen as productsofa hypothetical attack of an ortho hydrogen of this substituent on someotherposition of the isoquinoline nucleus. This "ortho-X attack" is ex-actlydefined and illustra ted in the Foreword tha t follows. All plant sourcesare recorded (or representative sources if there are too many) and litera-turecitations are also included in each entry.

But even with these restrictions, this "appendix" to a third book wasbecominglarger and larger, and it soon became apparent that it was to-tallyinappropriate. There would be far too many pages for a minor ap-pendixin a book that is to be dedicated to cactus and isoquinolines. Andby the time my stream-of-consciousness commentary was added in thetextwhere I felt it should be added, the mass increased to the extent that ithad to be a reference book in its own right.

Voila. Let's try to get all that information together into a single modestpackageand make it available to the chemists and botanists who mightwant it. Should it be a review article in Chemical Reviews or the Journalof Natural Products? Several factors said "No." Most botanical reviewsurveysare not searchable except by taxon name (that would assume thatyouwould know the plant from which it came) or by some complex andmaddening Chemical Abstracts entry that dealt with some alphabetiza-tionthat demanded the knowledge of the structure and the way the struc-turewould be listed. And most review articles also insist on a tidy forma tthat is without editorial comment and does not contain volunteered ideasand extrapolations.

An obvious solution became apparent. Create a single reference bookto contain all this information. Use the chemical substituents as analphabet. Visually travel around the structural image of the molecule in alogicaldirection, address the substituent groups in some logical way whichwillbe called alphabetical, and progress until you find the target you aresearchingfor, or until you find an empty hole where it would have beenhad it been known. So this book has come into existence simply to meetthis need, and to relieve the potential "Third Book" readership of a killerofan appendix.

Thenature of the substituents and, especially, the connection betweensimplebenzylated isoquinolines and the nature of the cyclized productsofortho attacks, are the heart and substance of this review book.

x

One additional comment is essential in this introduction. The exten-sive literature searching, and commingling of the accumulated plant andchemical data, taxed my capability and exceeded my patience. This wasindeed a compilation that was essential to my current cactus research forthe third book, but the task of its organization created a disruptive inter-ference to my exploration of new psychedelics in unanalyzed cacti. Theearly help given me by Ann's daughter Wendy quickly evolved into herplaying an indispensable role as my co-author. The final organizationand structuring of this book has been largely the result of her dedicatedlabor. It is an honor to share the authorship with her as, without her help,this book would not exist today.

Alexander T.Shulgin

Xl

FOREWORD II

When Sasha and I began this project it was meant to be an appendixforthe next book in the series of PIHKAL and TIHKAL. It became so bigthatwe knew after some time it could not be an appendix; it was its ownbook. Sohere it is, a collection of all the information we've compiled overthelast two years. It's been a daunting project at times. If we had includedall the variations of isoquinolines that we had originally planned to, thisbook would have been a series of volumes. Along the way we had tomakedecisions about what was important to keep in, what we could leaveout,what our focus was, what our intentions were. We pared down con-stantly,finally settling on the criteria that Sasha has laid down in the in-troduction.

It is my belief that what we have put together here will be of great useto anyone interested in this particular field of botany and chemistry. Wehavetried to make the information as easy to find and review as possible,taking into consideration what it was like for us to search through theliterature. Hopefully this compilation will make others' work much easier.Wefound so many mistakes in the literature, and even in the ChemicalAbstracts, that we had to make educated guesses as to the correct waysomethingwas spelled, or what a certain substituent was on a given ring;sometimeswe simply made comments in the text about a particular dis-crepancy.We welcome corrections and comments that come to us, as wesurelyhave made errors ourselves.

What I observed while going through the literature was enlightening.What stood out for me was how much of the plant research done onisoquinolineshas been in countries other than the United States. As manypeopleknow, the state of objective, independent scientific research in thiscountryis a sad one. Research is at the mercy of special interests, govern-ment funding, and of harsh regulations and restrictions. It's rare to havea situation where a scientist is free to explore and discover, much less en-couragedto do so. We are left to rely on research done in countries wherethe scientists' findings are not bought and paid for in advance, as hap-pens in this country too often. Sasha is a rare chemist indeed, workingindependently for so long, free of those controls, and following his pas-sionto discover tools to understand the mind and the brain in the face of

xii

much misunderstanding and misguided assumptions about psychoactivematerials. As it is now, the pharmaceutical industry is bridging the gapbetween what is socially and legally acceptable to do to one's brain chem-istry in order to feel well, and what is currently considered unacceptable,which is using chemical or plant medicines to look at why one is not feel-ing well to begin with.

There is great hypocrisy, fear, and thoughtlessness afoot in the UnitedStates regarding psychoactive drugs. Their benefits and potential uses arelost in the rhetoric of the "drug war," and in the fear that it generates.There are many examples of healthy and informed use of psychoactivemedicines throughout the world, and throughout the ages. They havebeen used in the past, and are being used today, as healing tools. We needthat kind of thinking in this country, we need that kind of healing.

Hypocrisy exists in the laws regarding alcohol and tobacco, which arelegal, and are the most damaging and widely abused drugs in our culture.Many pharmaceutical drugs are not without their dangers and abuses aswell (it's a fact that far more Americans die from pharmaceutical drugsthan illegal drugs). What are the fears of psychoactive drugs really basedon? I encourage those who start with the arguments of brain damagecaused by this or that drug to obtain the actual scientific papers that makethose claims (not just the titles of the papers) and read them carefully.They will find much misinformation due to political pressure, economics,and fear.

It's been a blessing to work with Sasha, who is not only a brilliantchemist but a fantastic teacher. I had no background in chemistry when Ibegan working with him; he has taught me so much. His passion andenthusiasm for chemistry is infectious; he has made it a delight to learn,and has shown me how magical it all is. It is magical, and mysterious, thisworld we live in and the stuff that it and we are made up of. It should becherished, protected, and explored, with honesty and courage.

Wendy E. Perry

Introduction xiii

INTRODUCTION

Forthis book to serve as a completely satisfactory reference, it mustbestructured so that a reader who comes to it with one specific wordin mind that is related to the simple, natural isoquinolines, can imme-diatelylocate all other related entries. Total cross-referencing is needed.Asa way to simplify this type of search, the main part of this book isactuallya collection of three indices. Each index is arranged alphabeti-cally,very much like a dictionary. The first index lists the commontrivialnames, the second lists the structures of the compounds them-selvesand the plants that contain them, and the third lists the taxo-nomicnames of these plants and the compounds that have been foundin them.

Part 1: Trivial names of the plant alkaloids:

Allof the known simple plant isoquinolines have been entered intothisindex under their common, or trivial names. Originally, there wasalinearstructure code attached to the trivial name entry which allowedthereader to immediately deduce the chemical structure and to accessthecompound directly in the structural index. It became apparent thata singlepage reference would do as well. Each trivial name thus leadsto the chemical structure, the plants that contain that compound, andappropriate literature references.

Many compounds have a number of trivial names. These may bepuresynonyms for a single compound, or they may distinguish differ-ent structural or optical isomers. The quaternary amine alkaloid saltspresentan unusual problem. There are three naming procedures thatare frequently encountered. The quaternary salt may have a distinctone-wordname. Here there is no problem. However, the other twoexamplesare two- or three-word names, with the anion involved be-ing incorporated into the second word. As the fourth alkyl group onthenitrogen is usually a methyl group, the anion name would take oneof two forms. If the parent tertiary amine is, say, the alkaloid Cana-dine, then the methyl quaternary salt could be called either N-Methylcanadinium iodide or Canadine methiodide. Both are faultedin that the presence of the iodide anion in the product is the work of

xiv The Simple Plant Isoquinolines

the analyst, and it is not what was originally present in the plant. Andif five people were to independently isolate this plant product and char-acterize it as a salt using the anions chloride, iodide, picrate, perchlor-ate and oxalate (all commonly found in botanical papers) it would de-mand five different index entries for a single plant alkaloid. In thispresent compilation, N-Methylcanadine quat will be the name used.But some quaternary amines are internally tetra-substituted. With com-pounds such as the berberines where the c-ring is aromatic, there is noexternal "methyl" group to call upon. Here, using Caseadinium io-dide as an example, the anion will also be dropped and it will be listedas Caseadinium quat.

Part 2: Structural formulae of the plant alkaloids:

The second, and major, index is the collection of structures and theirplant sources. This section is also organized in an alphabetical way,but clearly the use of the classical A to Z order does not apply to thevarious arrangements of atoms. Let's say you have the structure of asimple isoquinoline in mind, and you would like to know if it is a knownplant alkaloid. The classic academic process is to head over to the Uni-versity library and start going through the many collected indices ofthe Chemical Abstracts, and search it out by what you hope is the rightchemical name. But sadly the rules of naming are continuously chang-ing. Sometimes 5,6,7,8-tetramethoxy precedes l,2,3,4-tetrahydro, andsometimes it follows it. Sometimes 6,7-methylenedioxy-l,2,3,4-tetrahydroisoquinoline is filed in just that way, but sometimes it is filedunder benzodioxolol4,5-gJ5,6,7,8-tetrahydroisoquinoline. And justwhat are the Chemical Abstracts' structural naming rules and number-ing systems for four-ring systems such as aporphines, isopavines orberberines?

The "alphabet" used in this structural index is totally indifferent tothe capricious and arbitrary rules laid down by the Chemical Abstracts.Quite simply, it is based on the location of the substituents and theiridentity in the nuclear isoquinoline skeleton before it is distorted by ahypothetical "ortho attack." The definition of this "atomic" alphabetis the substance of this introduction. The nature and variety of this"ortho attack" is addressed here as well.

Part 3: Botanical names for the plants that contain these alkaloids:

All plants have been entered into the third index alphabetically,according to genus and species. Under each of these taxa are listed thetrivial (or chemical) names of the alkaloids reported to be in that plant.

Introduction xv

Part 4: Appendices:

There are three appendices located at the end of this volume. Thefirstis a listing of the botanical families that are mentioned in this book,and the Genera that each contains. Second is an analysis of the non-intuitive process used by Chemical Abstracts to create the name of anisofuranone-substituted isoquinoline. The third is the list of actual jour-nal names that are given only as initials in the references in the struc-tural index.

THEATOMIC ALPHABETIZATION OF COMPOUNDS

There are two "alphabets" used in the organization of this book.Boththe index of trivial names and the listing of the botanical binomi-als use the English A to Z, 26-letter convention, like a dictionary, andthewords can be of any length. The listing of compounds in the struc-tural index is also "alphabetical," but it employs a hierarchy of posi-tionallocations and structural substituents as its alphabet. Each struc-ture is a five-lettered "word" and the priority follows the rules of thedictionary. With the structure being sought in mind, one must gothrough the list of compounds with the first "letter" (substituent) inmind, and then the second "letter" is located, and on, and on. Below isa list of the priorities each substituent ("letter") follows.

(l) POSITION ON THE AROMATIC RING

Here is the primary assignment of numbered positions, and theassignment of letters to the individual bonds, of the isoquinoline ring:

5 4a 4600~37 ~ I ~N2

8 8a 1OJ

fed C-:/'" I ~9 b

~ ~Nh i j a

The first "letter" of the chemical name of the structure being soughtis created from the position of the substituents on the aromatic ben-zene ring. There are four positions available (5,6,7,8), and they are al-phabetically arranged from small to large and from few to many.

xvi The Simple Plant Isoquinolines

This is the order:

none 5 5,6 5,6,7 5,6,7,86 5,7 5,6,87 5,8 5,7,88 6,7 6,7,8

6,87,8

Thus a compound with a 5,6-disubstitution pattern is to be foundin this dictionary immediately following the 8-monosubstituted entriesand immediately before the 5,7-disubstituted entries. All numberinghas been taken exclusively from the assignments given to theisoquinoline ring. There are situations such as the methylenedioxy-isoquinolines where the nature of the substituent constitutes a new ring.In this case, as in many others, Chemical Abstracts would assign to-tally different numbers to these four positions on the aromatic ring.Currently correct numbering systems are ignored here, and the primi-tive 5,6,7 and 8 positional identifiers are used exclusively. This firstletter of the structural alphabet is used as a heading for the appropri-ate subsection of the second index, the structural formula group.

(2) THE SUBSTITUENTS ON THE AROMATIC RING

The second "letter" of the chemical name is the actual substituentor substituents found at the positions designated by the numbers above.There are only three substituents to be considered in this chemical al-phabetical sequence; they are, in order:

code atomic commonused: connections: name:

HO HO- (hydroxy)MeO CH30- (methoxy)MOO -OCH20- (methylenedioxy)

The HO- group is exactly what it appears to be. It is a hydrogenatom bonded to an oxygen atom which is, in turn, bonded (at least inthe case of the second letter of this chemical alphabet) to one or moreof the available positions on the aromatic ring of the isoquinoline, i.e.,the 5,6,7 and/or the 8 positions. The MeO- group, as drawn, is an ab-

Introduction XVll

breviationfor a slightly more complex structure, a methyl group (H3C-or-CH3)bonded to an oxygen atom which is, as above, attached to one(or more) of the four positions of this aromatic ring. The MOO, ormethylenedioxy group, is yet a bit more complex. It is unique in that itis a double-ended substituent. It is a short chain that involves an oxy-genatom (0) connected to a methylene group (CH2) connected in turnto another oxygen atom. Drawn out as a collection of atoms it is-OCH20-and thus requires two adjacent substituent positions and mustbe associated with two numbers.

Let's use the 5,6 substitution position as an illustration template,and we'll introduce some substitution second "letter" examples, in al-phabeticalorder:

5,6 HO HO5,6 HOMeO5,6 MeOHO5,6 MeOMeO5,6 MOO

precedesprecedesprecedesprecedes

A few things are obvious. Where a thing is located (shown by thenumberor numbers) has priority over what a thing is (the substituentor substituents). This same locating and identifying code will be usedfor the benzyl group on the I-position, but with some extensionswhich will be explained below.

There is, of course, a fourth allowable substituent. This is H (ahydrogen atom), but it is automatically assumed to be on every num-beredposition not carrying one of the three given oxygenated examples.It is generally accepted, in the creation of a name to represent a chemi-cal structure, that if there is no substituent specified on the aromaticring the substituent is hydrogen, and is not entered. The presentationof the entry

5,6 MeO HO - without this exclusion, would have been5,6,7,8 MeO HO H H

What about substituents that are groups other than HO, MeO orMDO(and of course the unsubstituted H)? Homologues of Mea suchasethoxyand benzyloxy (Eta, BzO), alkyl groups such as methyl, phe-nyl,halides, carboxy or substituted carboxy groups, esters of phenols,

xviii The Simple Plant Isoquinolines

nitrogen-containing groups such as nitro or amino derivatives, thiocompounds, all are regularly encountered as substituents ofisoquinolines in the chemical literature. And since almost all of themare products of synthesis rather than plant products, they are ignoredin this compilation. There is an occasional exception, like an O-acetylderivative that appears to have been isolated from some natural source.

There are plant alkaloids known that can, within the plants' envi-ronment, undergo extensive oxidation. In the aporphine group, a com-pound such as Norcorydine can go to the quinone, all four rings com-pletely aromatic and a carbonyl at the 7-position where the hydroxygroup once was. This is the base Pancoridine. So a quinonic carbonylcan appear in the aromatic ring. But its origin was a hydroxy group.So, for all practical purposes, we are staying with the three substitu-ents mentioned above (other than hydrogen). The substituents that areon the benzene ring are listed on the first line in the box at the upperleft corner of each compound's entry, in the sequence that correspondsto the number or numbers at the top of the page.

6-MeO 7-HO3,4-MeO,MeO-benzylH IQ

(3) THE I-POSITION

The third "letter" of this alphabet is the substituent that is found atthe I-position of the isoquinoline ring. This is the first involvement ofthe pyridine ring position of the isoquinoline system, so a number ofnew factors must be considered. There are always two substituents atthis position but, depending on the degree of aromaticity of this ring,one of them might be meaningless. And, as there are two substituents,there must be a rule that ranks them. If they are different, the heavierwill precede the lighter. This lighter one will be a hydrogen or a me-thyl group (abbreviated Me). And occasionally there will be a sub-stituent that embraces both substituents as a single thing. And again,as above, there will be occasions where the unnamed substituent issimply hydrogen, and is not mentioned.

Here is the sequence that will be used, listed by what the substitu-ents really are, and by how they will be entered.

Introduction xix

Heavier substituentat the I-position:

Lighter substituentat the [-position:

Appearance of thisthird chemical letter:

HMeMeOHOHRRR

HHMeHMeHMeHO

HMeMe,MeOH or (=0)OH,MeRR,MeR,HO

In those cases where there are two different substituents, this car-bon atom becomes chiral. Most natural products have optical activity,but in many plant analyses, the optical rotation is not reported andprobably not measured. In the literature there is no way to distinguishbetween an unknown rotation and a racemate. In these cases, all plantsources for a given isoquinoline have been commingled without re-gard to the reported optical activity, unless it is known.

The "R" that is mentioned above is one of five aromatic systems,and these are usually substituted themselves. These aromatic systemsand their numbering are ranked as shown below:

.c.' ~6cr5 ~ 3 4 ~ 2 6 2

4 35 3

R= phenyl R= benzyl

R= ~-phenethyl

5¢¢ 5~I 0 I 06 ~ 6 ~

7 OH 7 0

R= isobenzofuranol, 3'-yl R= isobenzofuranone, 3'-yl

The priorities for both the numbering and the substituents followthe same patterns established for the first and second chemical letters.

xx The Simple Plant Isoquinolines

Numbering priority:

none 2 2,3 2,3,4 2,3,4,5 2,3,4,5,63 2,4 2,3,5 2,3,4,64 2,5 2,3,6 2,3,5,6

2,6 2,4,53,4 2,4,63,5 3,4,5

And once the numbers have been decided upon, then the substitu-ent is chosen from the following sequence:

HOMeOMOO

Again, there are many known compounds that have phenyl, ben-zyl or phenethyl rings at the 'l-position with substitutions other thanthese three (and the understood and unstated hydrogen atom of course).And, as with the 5,6,7,8 substitution story, most of these are syntheticproducts and are not part of this book. The few unusual substitutionsthat are known to be in compounds from natural sources, such as theformyl (CHO) and the carboxyl group (C02H), will be included. Therule of organization is: a group bonded with a carbon atom has prior-ity over a group bonded with an oxygen atom.

Occasionally there is a carbon or an oxygen substituent found onthe alpha-carbon atom of the benzyl group. This is taken into accountin the alphabetization. These substituents have the following priority:

Mono-substituted Oi-substituted

Me (methyl)HO (hydroxy)AcO (acetoxy)MeO (methoxy)NH2 (amino)

Me,Me (dimethyl)Me,HO (methyl, hydroxy)= CH2 (rnethenyl)= 0 (oxo) or (keto)

The presence of a carbonyl at the 'l-position introduces an ambigu-ity. In most cases, the structure of the I-keto product can be redrawnas a I-hydroxy tautomer with the inclusion of a double bond in thepiperidine ring to balance the equation. When this situation occurs,the compound will be entered as the keto tautomer.

Introduction XXI

OQOH

O)Ha

This third letter of the atomic alphabet, the 'l-position, is entered onthe second line in the box found at the upper left corner of each entry.

-~.-6-MeO 7-HO3,4-MeO,MeO-benzylH IQ

(4) THE 2-POSITION

The fourth "letter" in this chemical alphabet is the substituent atthe 2-position, the nitrogen atom, of the isoquinoline ring. The pri-mary substituents found here are the hydrogen and methyl groups,and they are arranged by increasing number:

HMeMe (+)Me,Me(+)CHOC02HAc (COCH3)CONH2C02MeC02Et

(formyl)(carboxy)(acetyl)(carbamoyl, or urea)(carbomethoxy)(carboethoxy)

An "H" as the fourth letter does not necessarily mean that there is ahydrogenat this position. It is an indicator of the absence of any substitu-tionon the nitrogen. This, as with the absence or presence of a (+) chargeat that position in the methylated examples, reflects the aromaticity of thepyridine ring. This is discussed below in section (5). There are also found,occasionally,amide functions on this nitrogen atom.

Oxidation at this position is frequently found. Hydroxylaminesand N-oxides are entered either as footnotes to their non-oxygenated

XXll The Simple Plant Isoquinolines

counterparts or as entries in their own right. There are about a dozenplant isoquinolines that have benzyl substituents on the nitrogen atom.They are included in this collection.

This fourth letter of the atomic alphabet is found at the left side ofthe third line in the box at the upper left corner of each entry.


t(5) HYDROGENATION

The fifth letter of the chemical alphabet is the simple statement ofthe degree of hydrogenation of the pyridine ring, and the three codesare ranked in the order of increased aromaticity,

THIQDHIQIQ

tetrah ydroisoq uinolinedihydroisoquinolineisoquinoline

THIQ is l,2,3,4-tetrahydroisoquinoline. Both double bonds in thepyridine ring are hydrogenated. If the fourth letter is an "H," there isindeed a hydrogen on the nitrogen. If there are methyl groups there, asingle methyl will be without a charge, but two methyls will require a(+) charge.

DHIQ is specifically 3,4-dihydroisoquinoline. If the fourth letter isan "H," there is no substitution on the nitrogen, even though there willbe an H written on the third line on the left side. If there is a methylgroup indicated, there must be a (+) associated with it. There is anoccasional natural dihydroisoquinoline in which the hydrogenation isat the l,2-positions and the unsaturation is at the 3,4-positions. Thesehave been entered as a footnote under the THIQ compound as 3,4-ene.

Introduction XX111

IQis the completely aromatic compound. Again, in this case, if the4thletter is indicated as an H, there is no substituent on that nitrogenpositionand if there is a methyl there, it must have a (+) on it.

This last letter is noted as a THIQ, DHIQ or IQ on the right-handside of the third line in the box at the upper-left corner of thecompound's entry.


tTHEoRTHo ATTACK

Oneof the little appreciated but totally fascinating properties sharedby perhaps a dozen of the classes of four-ring isoquinolines is that mostofthemcan be visualized as resulting from an 11 ortho attack," from the2- or 6-hydrogen atom of the I-substituent (usually a benzyl group) tosomespecifically identified position of the isoquinoline ring. Theseconversionsmay certainly have biosynthetic reality. But they have agreatdeal more importance for this book in that they allow a simpleandfoolproof way of organizing the compounds in text. To locate thetargetcompound under which the four-ring material will be found,simplymentally note the I-benzylisoquinoline that constitutes itschemicalskeleton. The bond forming the fourth ring can be identifiedasgoingfrom an ortho-position of the benzyl to some numbered atomonthe isoquinoline. Below they are illustrated and identified as to thealkaloidalclass name. One must keep in mind that the benzyl ring hastwoortho hydrogens. If it is not symmetrically substituted, the nor-malnumbering priority sequence is used, and that will dictate whethertheorthohydrogen employed in the attack is a 2- or a 6-hydrogen. Theexamplesbelow show ortho (2,X)attacks. It should be understood thatthesubstitution pattern on the benzyl ring could require that they becalledortho (6,X) attacks. The ortho attacks will be indicated in eachsectionin a separate box from the first. Thus, the first box in eachsectionis the parent compound, and any additional boxes will be modi-fications,such as an ortho attack, an N-oxide, or other changes.

xxiv The Simple Plant Isoquinolines

Spirobenzylisoquinolines

The ortho (2, 1-Me) attack

This family is classified in this collection as an ortho-attack on al,l-disubstituted tetrahydroisoquinoline where there is a methyl, orsome other group (an ortho (2,1-XX)attack).

Dibenzopyrrocolines

The ortho (2,N) attack

Here the hypothetical2,N (or 2,2) attack produces a five-memberedring. The tetracyclic product is treated here as an isoquinoline, but itcan also be seen as a disubstituted dihydroindole. The usual chemicalclassification is that of a substituted pyrrocoline, the name for the het-erocycle that is the middle two rings of this system.

Introduction xxv

Protoberberines (Berberines) and Protopines

The ortho (2,N-Me) attack

with ring C aromatic

The N-methyl oxo and oxy forms

Thisis one of the more common ortho attacks, and gives rise to theprotoberberines and, with a minor substitution change, the protopines.I have always assumed that the protoberberines were the saturatedprecursoralkaloids (proto- meaning early or source) which upon aro-matizationgave the berberines with an aromatic ring "c." It now looksasifthe entire group is often simply called the protoberberines. In thefour-ringprotoberberine with the ring "C" aromatized, the hydroxyla-tionof the carbon atom that was the original N-methyl group leads to

XXVI The Simple Plant Isoquinolines

a group of compounds called 8-oxy (or 8-oxo) berberines. This tauto-meric interconversion is shown above.

If there is a hydroxy group as well as a benzyl group on the I-posi-tion and there are two N-methyls in the THIQ ring (the quaternarysalt), another family can be explored through this 2,N-Me attack. Thesealkaloids are of the protopine class, but to understand their structureslittle tautomeric manipulation is needed.

an ortho (2,N-Me) attack Tautomeric equilibrium

A tautorner is a bit of structural sophistication. One can move theelectrons around, without moving any of the atoms, and some end upwith quite a different looking thing. Which is it? It's a bit like theproblem with the duality of the photon. It is a particle and it is a wave,both. It pretty much depends on how you look at it. The middle struc-ture, with an 0- and an N+, should be rather soluble in water. It is anionic doubly charged molecule, after all. But the structure on the rightis a ketone and an amine, and would probably be lipophilic, andwouldn't dissolve in water. Is it water soluble? Hard to use that as away of telling the structure because just the act of putting it in watermight shift the electrons towards the ionic configuration. As they sayin quantum mechanics, you can't observe anything without changingit in some way. These compounds will be portrayed in the 4-ring struc-ture with the 0- shown as a hydroxy group in the structural index.

Introduction xxvii

Pavines

The ortho (2,3) attack

The pavine family, created by the ortho-3 attack, has an unusualproperty not shared by any other isoquinoline group. The pavine canbe viewed in either of two ways, left to right, or right to left. This isbest seen in the above structural diagram on the right. View the left-handbenzene ring as the aromatic ring of the THIQ, and then go to thefirst carbon atom at the 4 0'clock position. The nitrogen bond in thecenterdemarks the second ring of the isoquinoline, with the I-positionbeing the point between these two locations, at the bottom. The car-bonbond out to the right of this point shows the benzyl group.

Now view the right-hand benzene ring as the aromatic ring of theisoquinoline,and then go to the carbon atom at the 10 0'clock position.The nitrogen bond in the center demarks the second ring of theisoquinoline; the point above is the I-position, and the carbon bondout to the left is the benzyl group.

Thus any pavine with different substituents on the two benzenerings could result from an ortho (2,3) attack of either of two differentisoquinolines. These items are entered both ways in this book. And inthe caseof pavines here, and the isopavines below, if there is a methylgroup on the nitrogen, it will be represented by the abbreviation Meinstead of CH3.

XXV111 The Simple Plant Isoquinolines

Isopavines4

1 4

~ 2I~

~

The ortho (2,4) attack

Unlike the pavines, the unusual internal N-bridged heterocycle ofthe isopavines admits to an isoquinoline classification in just one di-rection.

Morphanans

The ortho (2,4a) attack

This ortho-4a attack, forming the carbon skeleton of the morphinemolecule, is one that is not easily visualized by non-chemists. It re-quires an out-of-plane manipulation to bring the benzyl group into con-junction with the ring-juncture 4a carbon atom. The I-benz yl-isoquinoline is shown in its conventional form on the left. To picturethe attack, mentally take hold of the benzyl group and bring it back,

Introduction XXIX

out of the plane of the paper, to where the 2-position is pointing di-rectlyat the 4a-position. This is the only one of the ortho attacks that issuperficially not an oxidation. The consequence is that the aromaticresonancestatus of the benzenoid ring of the THIQ is permanently lost.Thelocation of the residual double bonds and other electrons dependstotally on the substitution pattern of the isoquinoline aromatic ring.Once the attack has been achieved, the plant world makes many fur-ther chemical steps, leading to a host of alkaloids related to thebaineand morphine, both of which contain an additional heterocyclic furanring. They lie beyond the scope of this compila tion. An unna tural, butfascinating compound is the (+) isomer of the product of this attackwith a 4-methoxybenzyl on the I-position, a methyl on the nitrogen,and hydrogenation of the resid ual benzene ring of the pa ren tisoquinoline. This product is the broadly abused antitussive,dextromethorphan, or DXM.

Another family of alkaloids, the Hasubanans, are often lumped to-getherwith the Morphinans beca use of a superficially similar morphol-ogy. As an illustration:

HO

CHsO

CHsOo OCHs

Sinoacutine (a Morphinan) Cepharamine (a Hasubanan)

They are actually indoles, not isoquinolines, and so they are notincluded in this listing.

xxx The Simple Plant Isoquinolines

Aza£luoranthenes

The ortho (2,8) attack (with a 1-phenyl)

Although most ring-substituents on the 'l-position of the naturaltetrahydroisoquinolines are substituted benzyl groups or isobenzo-furanones, occasionally a phenyl grou p is observed, bound directly tothe isoquinoline ring. An ortho (2,8) attack leads directly to theindino[l,2,3-ij]isoquinolines, known commonly as the azafluoranthenes.

Aporphines

The ortho (2,8) attack (with a 1-benzyl)

This family is viewed as an ortho-attack on the S-position of theisoquinoline ring. This produces a four-ring system known as anaporphine.

Well over a hundred years ago it was discovered that morphine,when treated with a strong acid, gave rise to the compound apomor-phine, an aporphine. It is now known that the lower of the two aro-matic rings of apomorphine is the result of the rearomatization of thebenzyl group, which was compromised by the ortho-4a attack men-

Introduction XXXI

tionedabove. But at the time it was thought to be a simple conversion,and for a long while the structure of apomorphine was thought to rep-resentthe skeleton of morphine itself.

Cularines

The ortho (2,8-0H) attack

Hereis the generation of a 7-membered oxygen-containing heterocycle.

Proaporphines

The (1,8) attack

This is a Ll-spirobenzyl intermediate to what is quite likely theentire family of the aporphines. The "pro" part of the name suggeststhat this is a biosynthetic precursor to these alkaloids. Very often thereis a keto function at the 4-position of the benzyl group (equivalent to ahydroxyl group on the original benzyl), to facilitate the spiro loss ofaromaticityneeded to achieve this type of coupling. This is directlyanalogousto the (2,4a)attacks needed to get into the morphinans, where

XXXll The Simple Plant Isoquinolines

a ketonic presentation of an aromatic hydroxyl group permits the bond-ing to occur.

5-p hen y lfurano [2,3,4- ijIisoq uino 1ines

/OH/8-HO a-H

The a,B-HO attack

There are several reports of tetrahydroisoquinolines with a fusedfuran ring that could be argued (for the sake of the classification usedin this collection) as an oxidative attack by the a-hydrogen of the 1-benzyl onto the 8-HO substituent, in a manner similar to the formationof a seven-membered ether ring seen in the cularines. It can also beseen as a similar oxidative attack from an a-hydroxy group (a com-monly encountered benzyl substituent) on the 8-hydrogen position. Thefirst of these two mechanisms (illustrated above) is used in this collec-tion.

THE SECOISOQUINOLINES

The prefix "seco" is an unusual term occasionally encountered inthe literature of natural products. Just as the term "or tho-attack" indi-cates the generation of a new ring, the term "seco" indicates the de-struction of a ring. A secoisoquinoline is formed from a 1-substitutedtetrahydroisoquinoline by the loss of the 1,2-bond. Transferring a hy-drogen atom from the a-carbon to the nitrogen, and reshuffling theelectrons, results in the formation of a new double bond.

Introduction

Phenethylamines

a a

1,2 seeo bond loss

Inan appendix to the book "TIHKAL: The Continuation" there werelisteda number of the phenethylamines known to be in the cactus fam-ily. These were all of classical simplicity with the phenyl ring substi-tuted with one or more hydroxys and methoxys, and an occasionalmethylenedioxy group. There was also an occasional hydroxy groupon the beta position of the chain, and on the nitrogen atom there werezero, one, or two methyl groups. There was no mention made of asubclassof phenethylamines which are intimately associated with theisoquinolines. The chemical term "seco" is a clever device for main-taining a structural relationship between two chemicals after having,magically,removed a structural bond. Illustrated here is an aporphinewith the electrons from that l,2-bond having been rearranged into themiddle ring. It would probably be chemically classified as anaminoethyl-substituted phenanthrene, rather than a phenethylaminewhich had been fused (2,3a) with a naphthalene, but in this book itwill be listed in the section describing the parent I-benzyl-tetrahydroisoquinoline, modified with an ortho attack if appropriate,followedby a l,2-seco bond removal.

XXX111

XXXIV The Simple Plant Isoquinolines

With the simpler l-benzyl derivatives (those which have not un-dergone any ortho-attack), the removal of the 1,2-bond usually pro-duces a 2-styryl substituted phenethylamine. Again, this would be lo-cated in the entry that described the parent isoquinoline.

The second illustration above is a phthalide THIQ, and thesephenethylamines are sometimes referred to as secophthalide-isoquinolines. Here, the oxygen atom of the original isofuranone ringis substituted on the newly formed double bond. This structure caneasily open up to the corresponding ketonic carboxylic acid. These seco-modifications of the attacked isoquinoline (first example, illustratedwith an aporphine) and the simpler I-substituted isoquinolines (sec-ond example, as illustrated by the isobenzofuranone) are the only onesincluded in this book. The standard phenethylamines that are com-monly found in cacti, compounds which are not from these seco-mecha-nisms, have been tabulated in TIHKAL and will not be repeated here.

There have been many compounds excluded from this compila-tion, but to give examples would increase the mass of this collectionwithout any useful information. They are, in a general hand-wavingsense, those compounds not explicitly allowed in the above inclusioncriteria.

To all rules, there are always exceptions. These have been made toallow unexpected natural isoquinolines that just happen to presentunexpected substituents that nature for some reason chose to contrib-ute to this collection. Mention has been made of an occasional carbo-nyl group disrupting the aromaticity of the benzene ring (this is thebasis of the quinonic isoquinolines). The nitrogen atom (position 2)occasionally displays an amide group (these have been entered at thefourth letter of the structural alphabet). Several natural compoundsdemand a hydroxyl or methoxyl function at the isoquinoline 3- or 4-positions. When this occurs, the compound is listed as a footnote un-der the parent structure.

More difficult to generalize, are the isoquinolines with new ringsresulting from biosynthetic attacks from here to there that are excludedfrom this study. In a broad, inclusive statement the line has again beendrawn to exclude everything that has not been included above.

Originally it was intended to list every plant in which these natu-ral isoquinolines are found, documented with a literature reference.The project became unmanageable in that some of the more commonalkaloids have been found in literally hundreds of plants. So, in somecases, if there are many species from one Genus, the plant listing willbe condensed to mention the particular Genus, the family, plus a lit-erature reference; e.g., Corydalis spp. (Papaveraceae) jnp 51, 262 '88.This way the broadness of distribution is established. Also, there are

Introduction xxxv

sectionsin the structural index where there is a compound that hasoneor more synonyms. In some instances, synonyms of what are sup-posed to be the "same" compound have been given different lists ofplants. So, it could be that different names are given to represent dif-ferentoptical isomers, we don't know. But in most cases the differen-tiation was respected, the lists of plants to a given name were keptseparatewithin a given section.

For much of the plant information we are most grateful for beingallowedaccess to the NAPRALERT (sm) database at the University ofIllinoisat Chicago, and would highly recommend the use of their ser-vicesif more detailed information is wanted. In particular, we appre-ciate the help of Douglas Trainor there. Also, we'd like to give greatthanksto Jim Bauml, the Senior Biologist at the Arboretum of Los An-gelesCounty, for helping to resolve many plant name and family is-sues,Amy Rasmussen for her supurb proofreading skills, and FraniHalperin for her artwork on the cover of this book.

Trivial Name Index

TRIVIAL NAME INDEX

Acetonyl-reframidineN-AcetylanolobineN-AcetylanonaineN-AcetylanhalamineN-AcetylanhalonineN-AcetylasimilobineD-AcetylfumaricineN-AcetyllaurelliptineN-AcetyllaurolitsineN-Acetyl-3-methoxynornantenineN-Acetyl-3-methoxynornuciferineN-AcetylnomantenineN-AcetylnomuciferineN-Acetyl-seco-N -methylla urotetanineN-AcetylstepharineD-AcetylsukhodianineN-AcetylxylopineActinodaphnineAcutifolidineAdlumiceineAdlumiceine enol lactoneAdlumidiceineAdlumidiceine enol lactoneAdlumidineAdlumineAducaineAequalineAlborineAlkaloidFk-5AlkaloidPO-3Allocryptopinea-AllocryptopineAlpinone

I

312263252431445

5716513368

407396229172196181282269284

8524324334434434024113970

45010896

327327223

2 The Simple Plant Isoquinolines

AmurensineAmurensinineAmurineAmurinol IAnalobineAnaxagoreineAnhalamineAnhalidineAnhalinineAnhalonidineAnhalonineAnhalotineAnibacanineAnicanineAnisocyclineAnnocherine AAnnocherine BAnnolatineAnnonelliptineAnolobineAnomolineAnomuricineAnomurineAnonaineAobamineAobamidineApocavidineApocrotonosineApocrotsparineApoglaziovineAporeineAporheineAporpheineArgemonineArgemonine me tho hydroxideArgemonine N-oxideArgentinineArgentinine N-oxideArizonineArmepavineArosineArosinine

29230115415526259

42943143943244343293

17540310410510738826238837639924632434415760

1001032482482482132182145656

354178152133

Trivial Name Index

Artabonatine AArtabonatine BArtavenustineAryapavineAsimilobineAsimilobine- 2-0-~-D-glucosideAtherolineAtherospermidineAtherosperminineAtherosperminine N-oxideAurotensineAyuthianineBackebergineBaicalineBelemine2-Benzazinel-BenzylisoquinolineBerberastineBerbericineBerbericinineBerberilycineBerberineBerberrubineBerbervirineBerbineBerbin-8-oneBerbithineBerbitineBerlambineBernumicineBemumidineBemumineBerolineBharatamineBicucullineBicucullinidineBicucullinineBiflorineBisnorargemonineBoldineBoldine methiodideBracteoline

255410

63449

5455

199411172172114261161424264

3939

299297210300297285324

4028532132129953

16553

28591

342243345329

71, 1226768

138

3


BreoganineBromcholitinBulbocapnineBulbocapnine methiodideBulbocapnine N-oxideBulbodoineBuxifolineCaaverineCalifomineCalifomidineCalycinineCalycotomineCanadalineCanadinea-Canadine~-CanadineCanadinic acidCanelillineCapaurimineCapaurineCapaurine N-oxideCapnoidineCapnosineCapnosinineN-CarbamoylanonaineN-CarbamoylasimilobineN-CarboxamidostepharineCarlumineCamegineCarpoxidineCaryachineCaryachine methiodideCaseadineCaseadine N-oxideCaseadinium quatCaseamineCase amine N-oxideCaseanadineCaseanidineCaseanineCassamedineCassameridine

34921428628828632641291

311314318166296296296296324

9343643743734090

16225157

182242164305

82,28783,288

365365365362362364364207419317

CassyfilineCassyformineCassythicin eCassythidineCassythineCatalineCatalpifolineCavidineCeltineCeltisineCephakicin eCephamonineCephamulineCephasugineCerasodineCerasonineChakranineCheilanthifolineCherianoineCinnamolaurineCissaglaberrimin eCissamineOarkeanidineClaviculineCoclanoline BCoclaurineCocsarmineCodamineCodamine N-oxideColchiethanamineColchiethineColletineColumbamineConstrictosin eCoptisineCorarnineCoreximineCorftalineCorgoineCorledineCorlumidineCorlumine

Trivial Name Index 5

41541528741841521720523036334942642842842613714719781

42727538212835934919197

2041411418585

10614342

309121121335

898686

242


CorphthalineCorunnineCorybrachylobineCorybulbineCorycavidineCorycavamineCorycavineCorycularicineCorydaldineCorydalidzineCorydalineCorydalisolCorydalispironeCorydalmineCorydalmine methochlorideCorydalmine N-oxideCorydecumbineCorydineCorydine methineCorydine N-oxideCorydinineCorygovanineCoryrnotineCorynoxidineCorypallineCorypalmineCoryphenanthrineCoryrutineCorysamineCorysolidineCorystewartineCorytenchineCorytenchirineCorytensineCorytuberineCoryximineCotarnineCotarnolineCoulteroberbinoneCoulteropineCrabbineCrassifoline

335152221

79328331331353239

72220321332202221203335143152145329154221209

8874

217338315157326196196340120325447445448448194359


Crassifoline methineCrebanineCrebanine N-oxideCristadineCrotoflorineCrotonosineCrotsparineCrotsparinineCrychineCrykonisineCryprochineCryptaustolineCryptocavineCryptodorineCryptopineCryptopleurospermineCryptostyline ICryptostyline IICryptostyline IIICryptowolidineCryptowolineCryptowolinolCucolineCulacorineCularicineCularidineCularidine N-oxideCularirnine

• Cularine• Cularine N-oxide

Cyclanolinel a-Cyclanolinet p.cyclanolineIDanguyelline

l~DasymachalineDauricoside

· Decumbenine· Decumbenine-CC Decumbensine· epi~-Decurnbensine

~lucopterocereine· Deglucopterocerelne N-oxide

36128128113499609999

311178179146233307233334167167168

8215415865

349353350351363366366128128128377305

63335334340340372372


Dehassiline1,2-Dehydroanhalarnine1,2-Dehydroanhalidinium quat1,2-DehydroanhalonidineDehvdroanonaineDehydroboldineDehydrocapaurimineDehydrocavidineDehydrocheilanthifolineDehydrocorybulbineDehydrocorydalineDehydrocorydalmineDehydrocorydineDehydrocorypallineDehydrocorytenchineDehydrocrebanineDehydrodicentrineDehydrodiscretamineDehydrodiscretineDehydroformouregineDehydroglaucentrineDehydroglaucineDehydroguattescine1,2-Dehydroheliarnine1,2,3,4-DehydroheliamineDehydroisoboldine3,4-DehydroisocorydioneDehydroisocorypalmineDehydroisolaurelineDehydroisothebaine1,2-DehydrolemaireocereineDehydrolirinidineDehydronantenineDehydroneolitsine6,6a-Dehydronorglaucine6,6a-DehydronorlaurelineDehydronomuciferine1,2-Dehydronortehuanine1,2-DehydronorweberineDehydronuciferineDehydroocopodineDehydroocoteine

10843043243324767

4372308179

22120314688

1962813027076

396146216271161161127238143268

9537092

227312206277169391455171323417


1,2-Dehydropach ycereine1,2,3,4-Dehy dropach ycereine1,2-Dehydropellotinium quatDehydrophanostenineDehydrophoebineDehydropredicentrineDehydropseud och eilanthifo lineDehydroremerinea-DehydroreticulineDehydroroemerine1,2-Dehydrosalso lidineDehydrostephalagineDehydrostephanineDehydrostesakineDehydrothalicmineDehydrothalicsimidineDehydroxylopineDehydroxyushinsunineDelporphine6-O-Demethyladlumi dine6-O-DemethyladlumineN-Demethy lamurine8-DemethylargemonineDemethylcoclaurineN-Demethylcolletine1Q-O-Demethylcoryd ine3'-0-Demeth ylcularine1Q-O-Demethyldiscretinen-0-Demeth yldiscretineDemethyleneberberineN-Demethy lfumaritine0-7' -Demethy 1-l3-hydrastine9-O-DemethylimeluteineN-Demethy lisocorytuberineN-Demethyllinoferine04-Demethy lmurarnine3'-Demethylpa paverine7-DemethylpapaverineN-Demethylstephalagine3-0-Demethy lthalicthuberine2-Demethylthalimonine9-Demethylthalimonine

456457435293406

7815425011425016440926028041740226724837816086

153147,203

47105137360

716650

157335393134201200190140409

84237,423

84,423


10-Demethylxylopinine 203Densiberine 217Deoxythalidastine 2677-0-Desmethylisosalsolidine 90Desmethylnarcotine 446O-Desmethylweberine 455N,O-Diacetyl-3-hydroxynornuciferine 375N,O-Diacetylisopiline 386N,O-Diacetylnoroliveroline 257Dicentrine 301Dicentrinone 306Didehydroaporheine 250Didehydroocoteine 417Didehydroglaucine 216Didehydroroemerine 2505,6-Dihydroconstrictosine 42Dihydrocoptisine 3095,6-Dihydro-3,5-di-O-methylconstrictosine 43Dihydroguattescine 271Dihydroimenine 3978,9-Dihydroisoroemerialinone 202Dihydro1inaresine 322Dihydromelosmine 3871,2-Dihydro-6,7-methylenedioxy-l-oxoisoquinoline 3333,4-Dihydro-l-methyl-5,6,7-trimethoxyisoquinoline 3923,4-Dihydronigellimine 1648,14-Dihydronorsa1utaridine 110Dihydronudaurine 155Dihydroorientalinone 13511,12-Dihydroorientalinone 135~-Dihydropallidine 124Dihydropalmatine 209Dihydroparfumi dine 165Dihydrorugosinone 3228,14-Dihydrosa1utaridine 119Dihydrosecoquettamine 3574,6-Dihydroxy-3-methoxymorphinandien-7-one 494,6-Dihydroxy-2-methyltetrahydroisoquinoline 413,9-Dihydroxynornuciferine 3765,6-Dimethoxy-2,2-dimethyl-l-(4-hydroxybenzy1)-I,2,3,4-THIQ quat 466,8-Dimethoxy-l,3-dimethylisoquinoline 3486,7-Dimethoxy-N,N-dimethyl-l-(2-methoxy-4-hydroxybenzy1)-THIQ 188

Trivial Name Index

1,2-Dirnethoxy-ll-hydroxyaporphine1,2-Dirnethoxy-3-hydroxynora porp hine1,2-Dirnethoxy-3-hydroxy-5-oxonora porphine2,9-Dimethoxy-3- hydroxypa vinane6,7-Dirnethoxy-l-(6',7 -methy 1enedioxyisobenzofurano1, 3'-y 1)-

2,2-dimethy1-1,2,3,4- THIQ6,7-Dimethoxy-l-(3,4-meth y1enedioxypheny 1)-2-methy 1-DHIQ6,7-Dimethoxy-l-(3,4-methy 1enedioxypheny 1)-2-methy 1-IQ6,7-Dirnethoxy-l-( 4-methoxybenzy l)-IQ6,8-Dirnethoxy-l-methyl-3- hydroxymethy lisoquinoline6,7-Dimethoxy- 2-met hylisocarbostyril6,7-Dirnethoxy- N -meth y lisoquinoline6,7-Dirnethoxy-2-methylisoquinolium quatN,o- Dimethy1actinoda p hnineN,o-Dimethy1armepavine0,o-Dimethy1bo1dineN,o-Dimethylcassyfiline0,0- Dimethylcissamine3,5-Di-O-methylconstrictosineO,o-Dimeth ylcorytuberineN,o-Dimethy lcrotonosineN,o-Dimethy lcrotsparineO,o-Dimeth ylcyclanolineN,o-Dimethy1hemovine0,0- Dimethy1isobo1dineN,o-Dimethy 1isocorydineN,N-Dimethy llindcarpineO,N-Dimethy lliriodendronine0,0- Dimethyllongifo1onine0,0' -Dimethy1magnoflorine0,o-Dimethy1munitagineN,o-Dimethy1nandigerineN,o-Dimethy1oreolineN,o-Dimethy1oridineN,N-Dimethy1pavinium quatN,o-Dimethy 1thaicanineDinorargemonineDisco1orineDiscretamineDiscretineDiscoguattineDomesticine

175373373

44,106

244168168184348240240162301185214323218

43212179179218

762142186893

186218

212,371300180180218403

71,122487076

320155

11


DomestineDoryafranineDoryanineDoryfornineDoryphornineDoryphornine methyl etherDuguespixineDuguetineDuguevanineDuguexineDuguexine N-oxideDysoxylineEgenineElmerrillicineEnneaphyllineEpiberberineEpiglaufidine10-Epilitsericine6-Epioreobeiline14-EpisinomenineEpisteporphineEscholamidineEscholamineEscholidineEscholineEscholinine (also see under Romneine)EschscholtzidineEschscholtzidine methiodideEschscholtzineEschscholtzine N-oxideEschscholtzinoneEximineEvoeuropinea-FagarineFiliformineFissiceineFissicesineFissicesine N-oxideFissilandioneFissisaineFissistigine AFissistigine B

22627933416016024058

30541926426423934041136022514527412466

249293312293129303

225,301228,304

311311317301178327416289183183326378318348

Trivial Name Index

Fissistigine CFissoldineFK-3000FlavinantineFlavinineFloripavidineFloripavineFormouregineN-FormylanhalamineN-FormylanhalinineN-FormylanhalonidineN-FormylanhalonineN-FormylanonaineN-Formylbuxifoline7-Formyldeh ydro hernanergineN-Formyldehydronorn uciferine7-Formyldeh ydrothalicsimidineN-FormylduguevanineN-FormylhernangerineN-Formyl-0-meth ylan halonid ineN-FormylnomantenineN-FormylnornuciferineN-FormylovigerineN-FormylpurpureineN-FormylputerineN-FormylstepharineN-FormylxylopineFugapavineFumaflorineFumaflorine methyl esterFumaramidineFumaramineFumaricineFumaridineFumarilineFumarine

~ Fumaritine~ Fumaritine N-oxide[ Fumariz'" meJ FumarophycinolIFumschleicherineiFuzitine

13

14731842513813456

118395430440436445251413290173405420294442229173314404269181269275236236243346165339283329108108324108346189


GandhararnineGentryamine AGentryamine BGigantineGindarineGlaucentrineGlaucineGlaucine methineGlaucine methiodideGlaucinoneGlaufidineGlaufineGlaufinineGlaunidineGlaunineGlauventGlauvineGlaziovineGnoscapineGorchacoineGortschakoineGoudotianineGouregineGovadineGovanineGroenlandicineGuacolidineGuacolineGuadiscidineGuadiscineGuadiscolineGuatterineGuatterine N-oxideGuattescidineGuattescineGuattouregidineGuattouregineGusanlungAGusanlungBGusanlungCGusanlungDn-Hainanine

18234834737320714321421921922214563

20115219921415210245235835837645513714681

31832026527332041041026527138738828529744

24879

Trivial Name Index

HeliamineHemiargyrineHenderineHernagineHernandia baseHernandia base IIHernandia base IVHernandia base VIIIHernandonineHernangerineHernovine (also see under Ovigerine)HexahydrofugapavineHexahydromecambrineHexahydrothalicminineHigenamine~-HomochelidonineHomolaudanosineHomolinearisineHomomoschatolineHumosine-AHunnemanineHydrastidineHydrastinea-HydrastineI}-HydrastineHydrastinimideHydrastinineHydrocotarnineHydrohydrastinine4-Hydroxyanonaine4-Hydroxybulbocapnine4-Hydroxycrebanine7-Hydroxydehydroglaucine3-Hydroxy-6a,7 -deh y dronuciferine8-Hydroxydehydroroemerine4-Hydro xy dicentrine4-Hydroxyeschschol tzi dine3-HydroxyglaucineN-Hydroxyhernangerine41}- Hydroxyisocory dine2'-HydroxylaudanosinelO-Hydroxyliriodenine

161122446201290290306292316290

69276276415

4732723961

396340289335336337336339333447245247287281222374259302

235,382380294194234277

15


1o-Hydroxymagnocurarine13~-Hydroxy-N-rnethylstylopine quatHydroxynantenine3-Hydroxynantenine4-Hydroxynantenine3-Hydroxynornantenine4-Hydroxynornantenine3-HydroxynornuciferineN-Hydroxynorthalicthuberine3-HydroxynuciferineN-Hydroxyovigerine8-Hydroxypseudocoptisine4-Hydroxysarcocapnidine4-Hydroxysarcocapnine8-Hydroxystephenanthrine8-Hydroxystephenanthrine N-oxide13~-Hydroxystylopine3-Hydroxy-2,9,10-trirnethoxytetrahydroprotoberberine4-HydroxywilsonirineHyndarinHypecournineIrneluteineIrnenineIntebrirnineIntebrineIsoanhalarnineIsoanhalidineIsoanhalonidineIsoapocavidineIsoauturnnalineIsobackebergineIsoboldineIsocalycinineIsocanadineIsococlaurineIsocoptisineIsocorexirnineIsocorybulbineIsocorydineIsocorydine N-oxideIsocorydioneIsocoryne

105318230381224380224373227374314311360365259259316

741402073343933971633344274274278486

37012431830059

31166

150192194238336

IsocorypallineIsocorypalmineIsocorypalmine N-oxideIsocorytuberineIsocularineIsodomesticineIsofugapavineIsoguattouregidineIsohydrastidineIsolaurelineIsolaureline N-oxideIsomoschatolineIsonorargemonineIsonorteh uanineIsonorweberineIsooconovineIsoorien talinoneIsopachycereineIsopacodineIsopellotineIsopilineIsopycnarrhineIsoquinolineIsoremerineIsoroemerialinoneIsosalsolidineIsosalsolidine N-oxideIsosalsolineIsosalutaridineIsoscoulerineIsosendaverineIsosevanineIsosinoacutineIsotembetarineIsothebaidineIsothebaineIsouvariopsineIsovelucryptineIzmirinelaculadine[acularineJatrorrhizine

Trivial Name Index

52141142137364

83276384335268268375

77, 19439145638913545773

428385

5239

248201164164

90123

6552

284137361

9495

2796287609975

17


[uziphine[uziphine N-oxideJuzirineKarnalineKikernanineKuafurnineKukolineLaetanineLaetineLarnbertineLanuginosineLastourvillineLatericineLaudaneLaudanidineLaudanineLaudanosineLaudanosolineLauforrnineLaunobineLaurelineLaurelliptineLaurepukineLaurifolineLauroli tsineLauroscholtzineLaurotetanineLauterineLedeborineLedecorineLernaireocereineLeonticineLeucolineLeucoxineLeucoxylonineLeucoxylonine N-oxideLirnousarnineLinaresineLincangenineLindcarpineLinearisineLiridinine

35535610057

202414

656980

303273

5010219119119120749

27428427911126313264

195190279157323370357

393214214213513223796461

383

LiridineLirinidineLirinineLirinine N-oxideLiriodendronineLiriodenineLirioferineLiriotulipiferineLitsedineLitseferineLitsericineLitsoeineLongifolidineLongifolonineLongimammamineLongimammatineLongimammidineLongimammosineLophocereineLophocerineLophophorineLophotine saltLotusineLuteanineLuteidineLuxandrineLysicamineMachiglineMachilineMadeyineMacrantaldehydeMacrantalineMacrantoridineMagnococlineMagnocurarineMagnoflorineMagnoporphineMajarineManibacanineMarshalineMecambridineMecambrine


39692

374374

47257204

72295290274190370100

454245419191

444444

6219215949

170289

97329451449449358104129218297175324450275


MecambrolineMelosmidineMelosmineMenisperineMescalotama-N -MethopapaverberbineMethoxyatherosperminineMethoxyatherosperminine N-oxideI-Methoxyberberine10-Methoxycaaverine3-Methoxyglaucine3-MethoxyguattescidineMethoxyhydrastine10-MethoxyliriodenineIl-Methoxyliriodenine3-Methoxynordomesticine3-Methoxynuciferine3-Methoxyoxoputerine13-Methoxy-8-oxyberberine4-MethoxypalmatineMethoxypolysignine3-Methoxyputerine8-MethoxyuvariopsineN-MethylactinodaphnineN-Methyladlumine3-MethylallocryptopineO-MethylanhalidineN-Methylanhalidine quatO-MethylanhalonidineN-Methylanhalonidinea-8-MethylanibacanineN-MethylanolobineO-MethylanolobineN-MethylanonaineN-MethylapocrotsparineN-Methylarmepavineo-MethylarmepavineO-Methylarmepavine N-oxideN-MethylasimilobineN-Methylasimilobine-2-0-~-D-glucopyranosideN-Methylasimilobine-2-o-a-L-rhamnopyranosideO-Methylatheroline

276399387197442448395395447105402412452279273390395414305403217412282287242328440432441434

942632662481031811851855555

561220

Trivial Narne Index

N-MethylboldineQ-MethylbracteolineN-MethylbulbocapnineQ-Methylbulbocapninea-Q-Methylbulbocapnine N-oxide~O-Methylbulbocapnine N-oxideN-MethylbuxifolineN-MethylcalifomineN-MethylcalycinineQ-Methy1calycinineN-MethylcanadineQ-Methy1capaurineQ-MethylcaryachineN-Methylcaryachinium quatN-MethylcassyfilineQ-MethylcassyfilineN-MethylcassythineQ-MethylcassythineN-Methylcheilanthifoline quatQ-MethylcinnamolaurineN-MethylcoclaurineQ-7-Methy1coclaurine13-Methylcolumbarnine3-Q-Methy1constrictosineN-MethylcoreximineQ-Methy1corledineN-MethylcorydaldineN-Methy1corydaline quatN-Methylcorydalrnine quatN-MethylcorydineQ-Methy1corydineQ-Methy1corydine NsoxideN-MethylcorypallineQ-Methylcorypallinel-Methylcorypalline2-MethylcorypalliniumN-Methylcorypalrninell-MethylcorytuberineN-MethylcrotonosineN-MethylcrotsparineN-MethylcrotsparinineN-Methylcrychine

68149288300300300413314319320303442

225,30183,288

415416415416

8327910017615143

13224123922120415121221289

162908979

14361

102103314

21


O-MethylcularicineN-MethylcularineN-MethyldanguyellineO-MethyldehydroisopilineN-Methyldihydroberberine quat0-Methyl-8,9-dihydroisoorientalinoneO-MethyldihydrosecoquettamineO-MethyldomesticineN-MethyldomesticiniumN-MethylduguevanineN-MethylelmerrillicineO-Methylelmerrillicine6,7-Methylendioxy-1-<4-methoxybenzyD-IQ6,7-Methylendioxy-1-<4-methoxybenzyD- THIQ6,7-Methylendioxy-l-t 4-methoxy-a-hydroxybenzyD-3,4-DHIQ2,3-Methylenedioxy-4,8,9-trimethoxy-N-methylpavinaneN-Methyl-10-epilitsericineN-Methylescholtzine0- MethylflavinantineN-Methylfissoldine7-Methyl-N-formyldehydroanonaineO-MethylfumarophycineO-MethylfumarophycinolN-MethylglaucineN-MethylheliamineN-MethylhernangerineN-Methylhernangerine /3-N-oxideN-Methylhernovine10-0-MethylhernovineN-MethylhigenamineN-Methylhigenamine, 7-O-~-D-glucopyranosideN-Methylhigenamine N-oxideN-MethylhydrasteineN-Methylhydrasteine imideN-MethylhydrastineN-Methyl-~-hydrastine quatO-MethylisoboldineN-MethylisococlaurineN-MethylisocorydineN-Methylisocorypalmine quatO-MethylisomoschatolineO-Methylisoorientalinone

368361377394304202358155156420411412278277278

235,4162763141473192521651652191622922927173484848

33833933833714960

197151396201

Trivial Name Index

0-MethylisopilineN-MethylisopilineN-Methylisosalsoline1-0-MethylisothebaidineN-MethylisothebaineN-Methylisothebainium cation0-MethylisovelucryptineN-Methyllaudanidinium iodideN-MethyllauformineN-MethyllaunobineN-Methyllaurelliptine9-0-Methylla urolitsineN-MethyllaurotetanineN-Methyllaurotetanine N-oxideO-MethylledecorineN-Methyllindcarpine0-MethyllirinineN-MethyllitsericineN-Methyllophophorine quatN-Methylmecambridine2-Methyl-1-(4-methoxybenzyD-

6,7-methylenedioxyisoquinolinium quatN-Methyl-10-G-methylhernovineO-MethylmoschatolineN-MethylnandigerineN-Methylnandigerine ~-N-oxideN-MethylnantenineN-Methyl-a-narcotineO-MethylnarcotolineN-Methylneocaryachine quatD-Methylnorarmepa vine9-0-Methylnorboldine8-O-MethyloblongineN-Methyloreophiline saltD-MethylorientalinoneN-MethylovigerineN-Methyloxoh ydrasteineD-MethyloxopukateineN-MethylpachycereineN-MethylpachypodanthineN-Methylpachypodanthine N-oxideN-Methylpalaudium quat

27876

396292292228454452

288,36918473

371450201310339273457256256197

23

394385

901759696

18919727628612473

195196324

66395276444450


O-MethylpallidineO-Methylpallidine N-oxideO-Methylpallidinine13-MethylpalmatineN-MethylpapaveraldineN-Methylpapaverine quatN-MethylpavineO-MethylpellotineN-Methylpellotine quat0-Methylpeyomvic acid0-Methylpeyoxylic acid0- MethylplatycerineN-Methylplatycerinium quat0-Methylprechilenine0-Methylpreocoteine0-Methyl przewalskiinone8a-Methylpseudoanibacanine8~-MethylpseudoanibacanineN-Methylpseudolaudanine0-MethylpukateineN-MethylputerineN-Methylsecoglaucine0-MethylseverzineN-MethylsinactineN-MethylsparsiflorineN-MethylstenantherineN-Methylstepharine0-MethylstepharinosineN-Methylstylopinium quata-N-Methylstylopinium quat~-N-Methylstylopinium quatN-Methyltetrahydrocolumbamine1-Methyl-1,2,3,4-tetrahydroisoquinolineN-MethyltetrahydropalmatineN-MethyltetrahydropapaverineN-Methylthaicanine0-MethylthaicanineN-Methylthalbaicaline0-MethylthalicmidineN-Methylthalidaldine0-MethylthalisopavineN-Methyl-2,3,6-trimethoxymorphinandien-7 -one N-oxide

147149149221220217213442435441441

212,371197,367

332402220

949478

26726721924122810339817918731331331315139

218207380402380214408214149


N-MethylushinsunineG-MethylvelucryptineN-MethylviguineN-MethylxylopineN-Methylxylopine N-oxideN-MethylzenkerineMichelalbineMichelanugineMicheline AMicheline BMichepressineMiltanthalineMilthanthineMocrispatineMollinedineMoschatolineMunitagineMuramineNandazurineNandigerineNandinineNantenineNarceimineNarceineNarceine imideNarceinoneNarcosineNarcotinea-Narcotinep-NarcotineNarcotinediolNarcotine hemiacetalNarcotolineNarcotolinolNarlumicineNarlurnidineNeocaryachineNeolitsineNigellimineNigellimine N-oxideNokoensineNoramurine

25518624526826810625327025425727643617950

307383

117,362222156290285226345454454454452452452453451452446446345345

286,368312164164437153


NoranicanineNorannuradhapurineNorargemonineNorarmepavineN-NorarmepavineNoratherosperminineNorboldineNorbracteolineNorbulbocapnineN orcanelillineNorcarnegineNorcinnamolaurineNorcoclaurineNorcorydineNorcorypallineNorcularicineNorcularidineNordelporphineNordicentrineN ordomesticineNorfissilandioneNorfumaritineNorglaucineN orgorchacoineNorguattevalineNorimeluteineNorisoboldineNorisocorydineN orisocorydioneN orisocorytuberineNorisocularineNorisodomesticineNorjusiphineNorjuziphineN-NorlaudanosineNorlaurelineNorleucoxylonineNorliridinineNorlirioferineNornantenineN ornarceineNorneolitsine

174280

147,20317617617164

134284

93163274

47139

88352350377295153325157206358376393111189237134363

80354354205277421383201223453307

NomuciferidineNomuciferineNomuciferine IO-NomuciferineNoroconovineNoroliveridineNoroliverineNoroliverolineNororientalineNororientinineNoroxyhydrastinineNorpachyconfineNorpachystaudineNorpallidineNorphoebineNorpredicentrineNorpreocoteineNorprotosinomenineNorpurpureineNorreframidineNorreticulineNorrufescineNorsalutaridineNorsarcocapnineNorsarcocapnidineNorsecocularidineNorsecocularineNorsecosarcocapnidineNorsecosarcocapnineNorsinoacutineNorsonodioneNorstephalagineNorstephanineNortehuanineNorthalicmineNorthalicthuberineNorthalifolineNorushinsunineNoruvariopsarnineNorweberineNoryuziphineNoscapalin


1731699255

40027027225313395

33258

256111405

73389

63401307109392110363359351366360364110237409260391416227159253186455354452


Noscapineu-NoscapineNoscopine hemiacetalNuciferidineNuciferinNuciferineNuciferolineNudaurineNummularineOblongineObovanineOchotensidineOchotensimineOchotensineOcobotrineOcokryptineOcominarineOcominaroneOconovineOcopodineOcoteineOcotominarineOcoxylonineOduocineOliveridine •Oliveridine N-oxideOliverineOliverine N-oxideOliverolineOliveroline P-N-oxideOphiocarpineOphiocarpinoneOpianOpianineOreobeilineOreolineOreophilineOridineOrientalineOrientalinoneOrientidineOrientine

45245245217417017018115553

35626232723887

12042332542240132341742242041827027027227225425430530645245212499

45099

135135183184


OrientinineOureguattidineOvigerineOxoanolobineOxoasimilobine7-oxobaicaline8-oxoberberrubineOxobuxifoline8-0xocanadineOxocompostelline8-0xocoptisineOxocrebanine13-0xocryptopineOxocularidineOxocularicineOxocularine7-0xodehydroasimilobineOxodicentrineOxoduocineOxoglaucineOxohydrastinineOxoisocalycinine8-0xoisocorypalmineOxolaurelineOxolaurenine 'Oxo-N -methylhydrasteine13-0xomuramineOxonantenineOxonuciferineOxophoebine8-0xopolyalthiaine13-0xoprotopineOxopukateineOxopurpureineOxoputerineOxosarcocapnidineOxosarcocapnineOxosarcophyllineOxostephanineOxostephanosine8-0xotetrahydropalmatine8-0xotetrahydrothalifendine

96386306266

58425285414297369310283233352353368

58306419220333319142279279339223231170407158331266404273362367352261259209291


8-0xothaicanineOxoushinsunineOxoxylopineOxyberberineN-Oxycodamine8-0xycoptisineOxydehydrocorybulbineN-OxyduguexineN-OxyguatterineOxyhydrastinineN-OxyoliveridineOxynarcotineN-OxypachyconfineOxypalmatine13-0xyprotopineN-Oxyspixianine8-0xythalifendinePachycereinePachyconfinePachyconfine N-oxidePachypodanthinePachystaudinePacodinePalaudinePallidinePallidinine'Palma tinePalmatrubinePancoridinePancorininePapaveraldinePapaveraldinium quatPapaverinePapaveroxidinePapaveroxinePapaveroxinolinePapracinePapracininePaprafuminePaprainePapralineParfumidine

379257273299141310

8026441033327045359

2113313192924565959

25625714019012312421019214014021922020645245145133910734651

245166

ParfuminePavinePecteninePellotinePeruvianinePeshawarinePessoinePetalinePetaline methinePeyoglutamPeyophorinePeyorovic acidPeyotine quatPeyotlinePeyoxylic acidPhanosteninePhellodendrinePhoebe basePhoebe base IIPhoebinePhyllocryptinePhyllocryptoninePilocereinePlatycerinePolyalthinePolyberbinePolycarpinePolygosperminePolysigninePolysuavinePrechileninePredicentrinePreocoteinePreocoteine N-oxidePrepseudopalmanineProaporphinePromucosinePronuciferineProtopineProtosinomenineProtothalipinePseudoanibacanine

Trivial Name Index

1072051644341763451093583574384454344354344342931326662

406288289240

192,365413321235405186265329

77389389223

40182179329

65200

94

31


PseudoberberinePseudocheilanthifolinePseudocolumbaminePseudocoptisinePseudojatrorrhizinePseudolaudaninePseudomanibacaninePseudopalmatinePseudoprotopinePseudorinePseudoroninePsilopinePterocereinePukateinePulchinePurpureinePuterinePycnarrhineQuettamineRaddeanamineRaddeanidineRaddeanineRaddeanoneRefractamideReframidineReframineReframine methiodideReframolineRehybrineRemerinRemerineRemerine N-oxideRemerolineRemrefidineRemrefineReticulineReticuline N-oxideRhopalotineRoefractineRoehybrineRoemecarineRoemecarine N-oxide

3001541463117673

175213331

7878

411372263106402266

88357232232231232307311226228

8313524824824926325022811111414562

1357474


n-RoemehybrineRoemeramineRoemerialinoneRoemerineRoemerine N -oxideRoemerolidineRoemerolineRoemrefidineRoemrefineRogersineRomneine (also see under Escholinine)RomucosineRomucosine GRomucosine HRotundineRufescineRugosinoneRurrebanidineRurrebanineSalSalsolidineSalsolineSalsolinolSalutaridineSalutaridine N-oxideSalutarineSanjoinine IaSanjoinine IbSanjoinine ESanjoinine KSarcocapnidineSarcocapnidine N-oxideSarcocapninecis-Sarcocapinine N-oxideSarcophyllineSauvagnineSaxoguattineSchefferineScoulerineSebiferineSecocularidineSecocularine

136275201248249264263250228195295252404199

71,122,20739332237539647

1635247

11811911816918917097

359360364364350323200202114147351367


SecoglaucineSecophoebineSecoquettamineSecosarcocapnineSecosarcocapnidineSecoxanthoplanineSendaverineSendaverine N-oxideSetigeridineSetigerineSevanineSeverzineSewerzineSiamineSiaminineASiaminine BSibiricineSinactineSinacutineSinoacutineSinococulineSinomendineSinomenineSonodioneSparsiflorineSpermatheridineSpiduxineSpinosineSpixianineSpixianine N-oxideSplendabolineSplendidineSrilankineStenantherineStephabinamineStephabineStephadiolamine 13-N-oxideStephalagineStephanineStepharanineStepharineStepharinosine

2174063573673611988989

231222153160160347347347317224118118426

4165

23810025723618831931939817478

398436438255409260136177187


StephenanthrineStephenanthrine N-oxideStephodelineStepholidineSteporphineStesakineStesakine-9-0-l3- D-glucopyranosideStipitatineStylophyllineStylopineSuavedolSuaveolineSubsessilineSukhodianineSukhodianine-~-N-oxideTakatonineTannagineTaxilamineTehuanineTehuanine N-oxideTelazolineTeliglazineTelikovineTelitoxineTembetarineTepenineTetradehydrocapaurineTetradehydrocheilanthifolineTetradehydroscoulerineTetrahydroberberineTetrahydroberberrubineTetrahydrocolumbarnineTetrahydrocoptisineTetrahydrocorysarnineTetrahydrojatrorrhizineTetrahydropalmatineTetrahydropalmatrubineTetrahydropapaverineTetrahydroprotoberberineTetrahydropseudoberberineTetrahydrosinacutineTetrahydrostephabine

251251429136249280280372337307102188398282282400429234391392

92386174167127371437

81117296285141307315

7420719120540

300120438


ThaicanineThailandineThaipetalineThalactamineThalbaicalidineThalbaicalineThalflavineThalicmidineThalicmidine methineThalicmidine N-oxideThalicmineThalicminineThalicsimidineThalicpureineThalicthuberineThalicthuberine N-oxideThalictricavineThalictricineThalictrimineThalictrineThalictrisineThalictuberineThalidastineThalidicineThalidineThalifaurineThalifendineThalifendlerineThalifolineThalihazineThalimicrinoneThalimonineThalimonine N-oxideThaliporphineThaliporphine methineThalisopavineThalisopynineThaliphendineThalphenineThalprzewalskiinoneTrichoguattineTriclisine

37926137840838037942514915215041741840240322822930429432712929422829113812382

291399160407400

237,424237,424

149152194401291159200252166

Trivial Name Index

Tridictyophylline3,10,11-Trihydroxy-l,2-methylenedioxynoraporphineTrilobinine2,3,7-Trimethoxy-8,9-methylenedioxy-N -methyl pavinane5,6,7-Trimethoxy-N-methylisoquinolinium quat1,2,11-Trimethoxy-6a-noraporphine2,3,6-Trimethoxy-N -normorphinandien-7 -one1,2,3-Trimethoxy-5-oxonoraporphineN,O,O- TrimethyllaurelliptineN,O,O- TrimethylsparsiflorineTritopineTuduranineTuliferolineTurcamineTurcomanidineTurcomanineUberineUmbellatinUshinsunineUshinsunine l3-N-oxideUthongineUvariopsamineUvariopsamine N-oxideUvariopsineVaillantineVelucryptineVeronamineViguineWeberidineWeberineWilsonirineWorenineXanthalineXanthopetalineXanthoplanineXanthopuccineXyloguyellineXylopineXylopinineXylopinine N-oxideYenhusomidineYenhusomine

438382158

235,41639218313939421418519117839635418810946

29725425428318718726851

10639924544

456139316219292198296384266212213234234

37


Yuanhunine 205Yuzirine 100Yuziphine 355Zanoxyline 185Zanthoxyphylline 184Zenkerine 105Zijinlongine 449Zippelianine 428Zizyphusine 51

Structural Index - Unsubstituted 39

UNSUBSTITUTED ISOQUINOLINES

IsoquinolineLeucoline

2-Benzazine

Cistanche salsa (Orobanchaceae) yh 8, 522 '88Nicotiana tabacum cv (Solanaceae) abc 41, 377 '77Papaver somniferum (Papaveraceae) abf 21, 201 '84Spigelia anthelmia (Loganiaceae) pm 52, 378 '86

OQHI-Methy l-l,2,3,4-tetrah y droisoq uinoline

Pachycereus weberi (Cactaceae) ac 57, 109 '85

I-Benzylisoquinoline

\ benzyl IH IQ

Thalictrum spp. (Ranunculaceae) yfz 10,72 '90


benzylMe THIQ

8,8a-SecoberbineNot a natural product.syn 9, 887 '92

Iwith a (2,N-Me) attack: ITetrahydroprotoberberine

Berbine

Berberis beaniana (Berberidaceae) tl25, 951 '84Fumaria officina lis (Papaveraceae) abs 4

4-HO-benzylMe THIQ

Compound unknown

Iwith a (1,8) attack: IProaporphine

Phoebe formosan a (Lauraceae) pptp 27, 65 '93

Structural Index - Monosubstituted

5-SUBSTITUTED lSOQUINOLINES

Compound unknown5-MeO2,3-MeO ,MeO-u,u- M e,HO-benzylH IQ

Iwith a (6,8) attack: I

Sinomendine

Sinomenium acutum (Menispermaceae)jnp 57, 1033 '94

6-SUBSTITUTED ISOQUINOLINES

6-HOHMe THIQ

H0Yi(l~NCH3

Longimammosine

Dolichothele longimamma (Cactaceae) joe 41,319 '76

OH

HO~

~~CH3

Iwith a 4-hydroxy group: I4,6-Dihydroxy-2-

methyltetrahydroisoquinoline

Theobroma cacao (Sterculiaceae) llyd 41, 130 '78

41


6-HO Compound unknown4-HO-benzyl, HOMe THIQ

with a (2,N-Me) attackand loss of hydrogen:

HO

OH

5,6-Dihydroconstrictosine

Aristolochia constricta (Aristoloehiaeeae)aa 13, 737 '83

Iwith a 3,4-ene: I HO

OH

Constrictosine

Aristolochia constricta (Aristolochiaceae)aa 13, 737 '83

6-MeOHH THIQ

Longimammatine

Dolichothele longimamma (Cactaceae) joe 41, 319 '76Dolichothele uberiformis (Cactaceae) joe 41, 319 '76


Not a natural product.tet 37, 3175 '81

6-MeO4-HO-benzyl, HOMe THIQ

with a (2,N-Me) attack,loss of hydrogen,and a 3,4-ene:

3-0-Methylconstrictosine

Aristolochia constricta (Aristolochiaceae) aa 13, 737 '83

Not a natural product.joc 44, 3730 '79

6-MeO4-MeO-benzyl, HOMe THIQ

with a (2,N-Me) attackand loss of hydrogen:

5,6-Dihydro-3,5-di-O-meth ylconstrictosine


Iand a 3,4-ene: I

3,5-Di-O-methylconstrictosine


43

OH



7-HO4-HO-benzylH THIQ

Compound unknown

with a 1,2 seco,with an N-carbomethoxy:

Gusanlung C

Arcangelisia gusanlung (Menispermaceae)phy 39, 439 '95

HO

Weberidine7-MeOHH THIQ

Pachycereus weberi (Cactaceae) ac 57, 109 '85

Compound unknown7-MeO3,4-MeO,HO-benzylMe THIQ


2,9-Dimethoxy-3-hydroxypavinane

CH30

Argemone munita (Papaveraceae) joe 38, 3701 '73

also under: 6,7 MeO HO R Me THIQR= 4-MeO-benzyl (2,3) attack



Longimammidine8-HOHMe THIQ

Dolichothele longimamma (Cactaeeae) joe 41, 319 '76Dolichothele uberiformis (Cactaeeae) llyd 40, 173 '77Theobroma cacao (Sterculiaceae) llyd 41, 130 '78

Iwith a 4-hydroxy group: I

Longimammamine

Dolichothele longimamma (Cactaeeae) joe 41, 319 '76Dolichothele uberiformis (Cactaeeae) llyd 40, 173 '77

~NCH3

OH

OH

q)NCH3

OH

45


5,6-DISUBSTITUTED ISOQUINOLINES

5-MeO 6-MeO4-HO-benzylMe,Me+ THIQ

5,6-Dimethoxy-2,2-dimethyl-l-(4-hydroxybenzy1)-l,2,3,4- THIQ quat

Desmos yunnanensis (Annonaceae) tcyyk 12, 1 '00


Uberine5-MeO 7-HOHMe THIQ

Dolichothele uberiformis (Cactaceae) jnp 40, 173 '77


None found in plants

Structural Index - 6,7-HO,HO-Substituted

6,7-DIHYDROXYSUBSTITUTED ISOQUINOLINES

H0:GQ~ I S NHHO

CH3

6-HO 7-HOMeH THIQ

SalsolinolSal

Aconitum carmichaeli (Ranunculaceae) yx 17, 792 '82Musa paradisiaca (Musaceae) jafc 24, 189 '76Theobroma cacao (Sterculiaceae) jafc 24, 900 '76

Compound unknown6-HO 7-HOa-keto-benzylH IQ

HO

Iwith a (2,8) attack: I LiriodendronineHO

Liriodendron tulipifera (Magnoliaceae)phy 16,2015 '77

HOHigenamineNorcoc1aurine

Demethylcoc1aurine

6-HO 7-HO4-HQ-benzylH THIQ HO

HO

Aconitum carmichaelii (Ranunculaceae) kjp 29, 129 '98Aconitum japonicum (Ranunculaceae) jnp 44, 53 '81Aconitum koreanum (Ranunculaceae) kjp 29, 129 '98Aconitum kusnezoffii (Ranunculaceae) kjp 29, 129 '98

47


Aconitum napiforme (Ranunculaceae) kjp 29,129 '98Annona reticulata (Annonaceae) tl28, 1251 '87Annona squamosa (Annonaceae) jnp 44, 53 '81Asiasarum heterotropoides (Aristolochiaceae) cpb 26, 2284 '78Asiasarum sieboldii (Aristolochiaceae) cpj 44, 211 '92Euodia rutaecarpa (Rutaceae) book 1Gnetum parvifolium (Gnetaceae) jnp 62, 1025 '99Nelumbo nucifera (Nymphaeaceae) cpb 18,2564 '70

HO6-HO 7-HO4-HO-benzylMe THIQ

(d1)-N-Methylhigenamine

Gnetum parvifolium (Gnetaceae) jnp 62, 1025 '99

I the N-oxide: I(-)-N-Methylhigenamine N-Oxide

Gnetum parvifolium (Gnetaceae) jnp 62, 1025 '99

with a (1,8) attack,and reduction of a double bond and ofthe carbonyl group in the benzyl ring:

Discolorine

Croton discolor (Euphorbiaceae) rlq 1, 140 '70Croton plumieri (Euphorbiaceae) rlq 1, 140 '70

I the glucoside at the 7-0H position: I

N-Methylhigenamine, 7-0-[3- D-glucopyranoside

Phellodendron amurense (Rutaceae) phy 35,209 '94

HO

HO

HO

HO

Structural Index - 6,7-HO,HO-Substituted 49

6-HO 7-HO4-MeO-benzylMe,Me+ THIQ

HOLuxandrine

HO

Pseudoxandra sclerocarpa (Annonaceae) phy 25,2693 '86

6-HO 7-HO3,4-HO,HO-benzylMe THIQ

HO

HOLaudanosoline

Papaver somniferum (Papaveraceae) book 4 HO

OH

6-HO 7-HO3,4-HO,MeD-benzylH THIQ

Compound unknown

Iwith a (2,4a)attack: I

Croton bonplandianus (Euphorbiaceae)phy 20, 683 '81

4,6-Dihydroxy-3-methoxymorphinandien-7-one

o


Compound unknown6-HO 7-HO3,4-HO,MeO-benzylMe THIQ

Iwith a (2,4a) attack: I Mocrispatine

Monodora crispata (Annonaceae) aua 17, 105 '81

o

TetrahydroprotopapaverineNot a natural product.jcspt 2, 1696 '80

6-HO 7-HO3,4-MeO,MeO-benzylMe THIQ

with a (2,N-Me) attackand aromatization of the c-ring:

HO

OCH3

HO

Demethyleneberberine OCH3

Stephania venosa (Menispermaceae) zh 30, 250 '99Thalictrum javanicum (Ranunculaceae) jnp 46, 454 '83

Iwith a (6,8) attack: ILastourvilline

Artabotrys lastourvillensis (Annonaceae)jnp 48, 460 '85

Fumaria indica (Papaveraceae)phy 31, 2869 '92

Glaucium leiocarpum (Papaveraceae)pm 65, 492 '99

Structural Index - 6,7-HO,HO-Substituted

Compound unknown6-HO 7-HO3,4-MeO,MeO-benzylMe,Me+ THIQ

Iwith a (2,8) attack IZizyphusine

Nandina domestica (Berberidaceae)nmt 50, 427 '96

Ziziphus fructus (Rhamnaceae)apr10,208'87

Ziziphus jujuba (Rhamnaceae)apr 12,263'89

Ziziphus spinosa (Rhamnaceae) kjp 16,44 '85

HO6-HO 7-HO6',7'-MOO-isobenzofuranone, 3'-ylMe THIQ

Papraine

Fumaria indica (Papaveraceae) het 29,1091 '89

HO

6-HO 7-HO3,4-MeO,MeO-benzyl, HOMe,Me+ THIQ

Compound unknown

Iwith a (2,N-Me) attack I

Vaillantine

Fumaria vaillantii (Papaveraceae) kps 476 '74

Theassigned structure of this compound has beenchallenged:jnp 45,241 '82

HO

HO

51


6,7-HO-MeO-ISOQUINOLINES

Isocorypalline6-HO 7-MeOHMe THIQ

Berberis oblonga (Berberidaceae) cnc 11,563 '75Corydalis stricta (Papaveraceae) kps 19,461'83Stephania cepharantha (Menisperrnaceae) nrn 52, 541'98

Isopycnarrhine HOmI +::::::..... /: NCHa

CHaO

6-HO 7-MeOHMe+ DHIQ

Popowia pisocarpa (Annonaceae) jnp 49,1028 '86

HOmI NCHaO ::::::.....

6-HO 7-MeOH4-MeO-benzyl THIQ

Isosendaverine

Corydalis sp. (Papaveraceae) phy 36, 241 '94Ceratocapnos heterocarpa (Papaveraceae) phy 36, 241'94 OCHa

Salsoline H0x:QI NHCHaO::::::"'" S

CHa

6-HO 7-MeOMeH THIQ

Alangium lamarckii (Alangiaceae) prns 5 '80Corispermum leptopyrum (Chenopodiaceae) app 34, 421'77Desmodium tiliaefolium (Fabaceae) phy 12, 193'73

Structural Index - 6,7-HO,MeO-Substituted

Echinocereus merkerii (Cactaceae) jps 58, 1413 '69Genista purgens (Fabaceae) nrPachycereus pecten-aboriginum (Cactaceae) aps 15, 127 '78Salsola arbuscula (Chenopodiaceae) ber 67, 878 '34Salsola kali (Chenopodiaceae) book 6Salsola pestifera (Chenopodiaceae) iant 2, 86 '85Salsola richteri (Chenopodiaceae) rr 16, 86 '80

6-HO 7-MeOMe3,4-HO,MeO-benzyl THIQ

Nummularine

Berberis nummularia (Berberidaceae) cnc 33,70 '97

6-HO 7-MeOMe3,4-MeO,MeO-benzyl THIQ

Bemumicine

Berberis nummularia (Berberidaceae) kps 3, 397 '93

6-HO 7-MeOMe3,4-MDO-benzyl THIQ

Bemumine

Berberis nummularia (Berberidaceae) kps 3, 394 '93

53


Not a natural product.joc 49,581 '84

6-HO 7-MeObenzylH THIQ

Iwith a (2,8) attack: I (-)-Asimilobine

Anaxagorea spp. (Annonaceae) pm 41, 48 '81Annona cherimolia (Annonaceae) jccs 44, 313 '97Annona squamosa (Annonaceae) cpj 46, 439 '94Annona spp. (Annonaceae) fit 65,87 '94Anomianthus spp. (Annonaceae) bs&e 26, 139 '98Artabotrys spp. (Annonaceae) jbas 15,59 '91Asimina spp. (Annonaceae) yz 85, 77'65Cananga odorata (Annonaceae) jccs 46, 607 '99Cardiopetalum spp. (Annonaceae) pm 57, 581 '91Cymbopetalum spp. (Annonaceae) pm 50,517'84Desmos spp. (Annonaceae) jnp 45, 617'82Disepalum spp. (Annonaceae) phy 29, 3845 '90Fissistigma spp. (Annonaceae) abs 3Glossocalyx spp. (Monimiaceae) jnp 48, 833 '85Goniothalamus spp. (Annonaceae) abs 3Guatteria spp. (Annonaceae) jnp 46, 335 '83Hexalobus spp. (Annonaceae) lac 1982,1623'82Laurelia philippiana (Monimiaceae) phy 21, 773 '82Liriodendron spp. (Magnoliaceae) cnc 13, 602 '77Magnolia spp. (Magnoliaceae) phy 23, 188 '84Meiogyne spp. (Annonaceae) phy 26, 537 '87Melodorum spp. (Annonaceae) ajc 24, 2187 '71Monocyclanthus spp. (Annonaceae) jnp 54, 1331'91Nelumbo spp. (Nymphaeaceae) jnp 50, 773 '87Ocotea spp. (Lauraceae) fes 30, 479 '75Oncodostigma spp. (Annonaceae) pmp 20, 251'86Orophea spp. (Annonaceae) bs&e 27, 111'99Phoebe spp. (Lauraceae) jccs 40, 209 '93Polyalthia suberosa (Annonaceae) jbas 16, 99 '92Popowia spp. (Annonaceae) jnp 49, 1028 '86Rollinia spp. (Annonaceae) jnp 49,1028 '86

HO

CH30


Siparuna spp. (Monimiaceae) pm 59,100 '93Stephania spp. (Menispermaceae) yhhp 21, 223 '86Talauma spp. (Magnoliaceae) apf 43, 189 '85Uvaria spp. (Annonaceae) nm 51, 272 '97Xylopia spp. (Annonaceae) pmp 16,253 '82Ziziphus spp. (Rhamnaceae) pjsr 3D, 81 '78

Iglucoside at the 6-HO position: I(-)-Asimilobine- 2-0-/3-D-gI ucoside

Stephania pierrei (Menispermaceae) jnp 56, 1468 '93

6-HO 7-MeObenzylMe THlQ

Not a natural product.jhc 4, 417 '67


N-MethylasimilobineO-Nomuciferine

Annona cherimolia (Annonaceae) jccs 44, 313 '97Annona spp. (Annonaceae) phy 49, 2015 '98Colubrina spp. (Rhamnaceae) pm 27, 304 '75Duguetia spp. (Annonaceae) jnp 50, 664 '87Monocyclanthus spp. (Annonaceae) jnp 54, 1331 '91Nelumbo spp. (Nymphaeaceae) jps 66, 1627 '77Oxymitra spp. (Annonaceae) phy 3D, 1265 '91Papaver spp. (Papaveraceae) dsa 7, 93 '83Stephania cepharantha (Menispermaceae) jnp 63, 477 'DOXylopia spp. (Annonaceae) jnp 44, 551 '81Ziziphus spp. (Rhamnaceae) apr 12, 263 '89

Iglucosideat the 6-HO position: I

(·)·N-Methylasimilobine-2-0-~-D-glucopyranoside

Stephania cepharantha (Menispermaceae) jnp 63, 477 'DO

HO

55


Irhamnoside at the 6-HO position: IFloripavidine

N-Methylasimilobine-2-0-a- L-rhamnopyranoside

Papaver armeniacum (Papaveraceae) dsa 7, 93 '83Papaver fugax (Papaveraceae) dsa 7, 93 '83Papaver tauricolum (Papaveraceae) dsa 7, 93 '83

Compound unknown6-HO 7-MeObenzylMe,Me+ THIQ

with a (2,8) attackand a 1,2 seco:

HO

Argentinine

Annona montana (Annonaceae)pnsc 3, 63 '79

Aristolochia argentina (Aristolochiaceae) aaqa 60, 309 '72Enantia chlorantha (Annonaceae) pm 9, 296 '75Guatteria discolor (Annonaceae) jnp 47, 353 '84Guatteria foliosa (Annonaceae) jnp 57, 890 '94Guatteria goudotiana (Annonaceae) phy 30, 2781 '91Monocyclanthus vignei (Annonaceae) jnp 57, 1033 '94Phaeanthus vietnam ens is (Annonaceae) fit 62, 315 '91Popowia pisocarpa (Annonaceae) jnp 49,1028 '86

I the N-oxide: IArgentinine N-Oxide

Monocyclanthus vignei (Annonaceae) jnp 57, 1033 '94


Compound unknown6-HO 7-MeObenzylAc THIQ

Iwith a (2/8)attack I

(-)-N-Acetylasimilobine

Liriodendron tulipifera (Magnoliaceae)phy 15/547 '76

Zanthoxylum simulans (Rutaceae)phy 36/237 /94

6-HO 7-MeObenzylCONH2 THIQ

Compound unknown

Iwith a (2/8)attack I

N-Carbamoylasimilobine

Hexalobus crispiflorus (Annonaceae)jnp 46/761/83

HO

CH30

6-HO 7-MeObenzylC02Et THIQ

Compound unknown

witha (2/8)attack,glucosideat the 6-HO position:

Kamaline

Stephania venosa (Menispermaceae)phy 36/1053/94

Glu-O

CH30

57


6-HO 7-MeO Compound unknowna-keto-benzylH IQ

Iwith a (2,8) attack: I HO

Oxoasimilobine7-0xodehydroasimilobine

Annona cherimolia (Annonaceae) jccs 46, 77 '99Dasymaschalon rostra tum (Annonaceae) zzz 26, 39 '01Monocyclanthus vignei (Annonaceae) jnp 57, 1033 '94

6-HO 7-MeOa-Me-benzylCHO THIQ

Compound unknown

with a (2,8) attackand an a,l-ene:

HO

Duguespixine

Duguetia spixiana (Annonaceae) jnp 51, 389 '88Guatteria sagotiana (Annonaceae) jnp 51, 389 '88

6-HO 7-MeOa-HO-benzylH THIQ

Compound unknown

Norpachyconfine


Duguetia spixiana (Annonaceae) jnp 50, 664 '87


(-)-Anaxagoreine

Anaxagorea sp. (Annonaceae) pm 41,48 '81Cananga odorata (Annonaceae) jccs 46, 607 '99

CH30

HO

6-HO 7-MeOa-HO-benzylMe THIQ

Compound unknown


Pachyconfine

HO

Duguetia spixiana (Annonaceae) jnp 50, 664 '87Guatteria sagotiana (Annonaceae) jnp 49, 1078 '86Pachypodanthium confine (Annonaceae) apf 35, 65 '77

Ithe N-oxide: IN-Oxypachyconfine

Pachyconfine N-oxide

Duguetia spixiana (Annonaceae) jnp 50, 664 '87

6-HO 7-MeO4-HO-benzylH THIQ

(+)-Isocodaurine

Desmos yunnanensis (Annonaceae) tcyyk 12, 1 '00

59



CrotonosineCH30

Croton cumingii (Euphorbiaceae) llyd 32, 1 '69Croton discolor (Euphorbiaceae) llyd 32, 1 '69Croton linearis (Euphorbiaceae) llyd 32, 1 '69

0Croton plumieri (Euphorbiaceae) phy 8, 777 '69

and reduction of the 2,3 double bond HO

and of the carbonyl groupin the benzyl ring: CH30

jaculadine

Croton discolor (Euphorbiaceae) rlq 1, 140 '70HO

Croton plumieri (Euphorbiaceae) rlq 1, 140 '70

HOIwith a (2,8) attack: I

Apocrotonosine CH30

Croton sp. (Euphorbiaceae) jnp 38, 275 '75

HO

N-Methylisococlaurine

6-HO 7-MeO4-HO-benzylMe THIQ

(+)-isomer:Desmoe yunnanensis (Annonaceae) tcyyk 12,1 '00


(-)-isomer:Phoebe minutiflora (Lauraceae) cpj 49, 217 '97

isomernot specified:Nelumbo nucifera (Nymphaeaceae) phy 12, 699 '73

Iwith a (l,8) attack: I HO

N-Methylcrotonosine

(-)-isomer:Croton discolor (Euphorbiaceae) rlq 1, 140 '70Croton plumieri (Euphorbiaceae) phy 8,777 '69Meconopsis cambrica (Papaveraceae) jnp 44,67 '81Papaver triniaefolium (Papaveraceae) pm 63, 575 '97

o

isomernot specified:Anomianthus dulcis (Annonaceae) bs&e 26, 139 '98Croton cumingii (Euphorbiaceae) llyd 32, 1 '69Croton linearis (Euphorbiaceae) llyd 32, 1 '69Orophea hexandra (Annonaceae) bs&e 27, 111 '99Papaver fugax (Papaveraceae) pm 41, 105 '81

Theearliest isolation of this base from the Croton species (pes 261 '64)wasa mixture of alkaloids that was given the name Homolinearisine.Subsequentpurification showed it to be N-Methylcrotonosine(jcs 1676 '66).

and reduction of a doublebondin the benzyl ring:

HO

Linearisine

Croton discolor (Euphorbiaceae) rlq 1, 140 '70Croton linearis (Euphorbiaceae) llyd 32,1 '69 0Croton plumieri (Euphorbiaceae) phy 8,777 '69

61


HOLotusine6-HO 7-MeO4-HO-benzylMe,Me+ THIQ

CHsO

Nelumbo nucifera (Nymphaeaceae)zzz 16, 673 '91

Tiliacora racemosa (Menispermaceae)jics 57, 773 '80

HO

HO(+)-Roefractine6-HO 7-MeO4-MeO-benzylMe THIQ CHsO

Roemeria refracta (Papaveraceae)jnp 53, 666 '90

CHsO


Phoebe base II CHsO

Phoebe sp. (Lauraceae) jnp 38, 275 '75CHsO

6-HO 7-MeO Isovelucryptine4-MeO-a-keto-benzylH DHIQ

Cryptocarya velutinosa (Lauraceae)jnp 52, 516 '89


6-HO 7-MeO Compound unknown3,4-HO,HO-benzylMe THIQ

HO

Iwith a (2,8) attack: I Glaufine

Glaucium fimbrilligerum (Papaveraceae)kps 4, 493 '83

CHsO

HO

HO

HOIwith a (6,N-Me) attack: I

(-)-Artavenustine CHsO

Artabotrys venustus (Annonaceae)jnp 49, 602 '86

OHand a glucoside on the 3-HOof the original benzyl group:

Dauricoside

Menispermum dauricum (Menispermaceae) cpb 41, 1866 '93

HO6-HO 7-MeO3,4-HO,MeQ-benzylH THIQ

(+)-Norprotosinomenine

CHsO

HO

Erythrina lithosperma (Fabaceae) ajc 24, 2733 '71

63


Iwith a (2,8) attack I HOLindcarpine

Hernandia voyronii (Hernandiaceae)pm64,58'98

Illigera pentaphylla (Hernandiaceae)jnp 48, 835 '85

Lindera pipericarpa (Lauraceae) het 9, 903 '78Lindera reflexa (Lauraceae) cty 25, 565 '94Litsea acuminata (Lauraceae) cpj 46, 299 '94Phoebe grandis (Lauraceae) phy 45, 1543 '97Stephania sp. (Menispermaceae) jnp 38, 275 '75

Iwith a (6,8) attack I HOLaurolitsineNorboldine

Cryptocarya longifolia (Lauraceae)ajc 34, 195 '81

Dehaasia kurzii (Lauraceae)fit 62,261 '91

Illigera pentaphylla (Hernandiaceae)jnp 48, 835 '85

Lindera reflexa (Lauraceae) cty 25,565 '94Litsea rotundifolia (Lauraceae) ryz 8,324 '00Litsea spp. (Lauraceae) pm 48, 52 '83Machilus duthei (Lauraceae) jcp 2, 157 '80Monimia roiundiiolia (Monimiaceae) apf 38,537 '80Nectandra saliciiolia (Lauraceae) jnp 59, 576 '96Neolitsea aurata (Lauraceae) jccs 22, 349 '75Neolitsea buisanensis (Lauraceae) jccs 22, 349 '75Peumus boldus (Monimiaceae) phy 32, 897 '93Phoebe clemensii (Lauraceae) jnp 46,913 '83Phoebe formosana (Lauraceae) jnp 46,913 '83Phoebe grandis (Lauraceae) phy 45,1543 '97Phoebe minutiflora (Lauraceae) cpj 49, 217 '97Retanilla ephedra (Rhamnaceae) rlq 5, 158 '74

OH


HO6-HO 7-MeO3,4-HO,MeQ-benzylMe THIQ CHsO

Protosinomenine

Erythrina lithosperma (Fabaceae)ajc24, 2733 '71

Litsea glutinosa (Lauraceae)jcspt I, 1477 '88

Polyalthia nitidissima (Annonaceae) pm 49, 20 '83Stephania cepharantha (Menispermaceae) cpb 45, 470 '97

CHsO

Iwith a (2,N-Me) attack: I HO

IsoscoulerineCHsO

(-)-isomer:Corydalis ambigua (Papaveraceae)

daib 45, 2160 '85

isomer not specified:Stephania hainanensis (Menispermaceae) cty 18, 146 '87

Iwith a (2,4a) attack: I CHsO

the l,8a trans isomer:Sinomenine

CucolineKukoline

Stephania cepharantha (Menispermaceae)cpb 45, 470 '97

Stephania epigaea (Menispermaceae)nyx 5, 203 '85

Stephania micrantha (Menispermaceae)nyx 7,13 '87

OH

OH

OCHs

HO

oOCHs

65


the 1,8a cis isomer: CHsO

14-Episinomenine HO

Ocotea brachybotra (Lauraceae)fes 32, 767 '77

Stephania cepharantha (Menispermaceae)cpb 45, 470 '97 o

OCHs


N-MethyllindcarpinePhoebe base CHsO

HO

Dehaasia triandra (Lauraceae)tet 52, 6561 '96

Glaucium paucilobum (Papaveraceae)jsiri 10, 229 '99

Glaucium spp. (Papaveraceae) jnp 61, 1564 '98Illigera pentaphylla (Hernandiaceae) jnp 48, 835 '85Litsea cubeba (Lauraceae) jccs 39, 453 '92Magnolia acuminata (Magnoliaceae) daib 32, 2312 '71Menispermum canadense (Menispermaceae) llyd 34, 292 '71Phoebe clemensii (Lauraceae) jnp 46,913 '83Strychnopsis thouarsii (Menispermaceae) pm 58, 540'92

CHsO

I with a (6,N-Me) attack: I HO

OCHs

CHsO(S)(-)-Isocoreximine

ll-O-Demethyldiscretine

Toddalia asiatica (Rutaceae) phy 48, 1377 '98Xylopia vieillardi (Annonaceae) jnp 54,466 '91

OH



BoldineCHsO

Actinodaphne spp. (Lauraceae)ajc 22, 2257 '69

Artabotrys lastouroillensis (Annonaceae) CHsOjnp 48, 460 '85 OH

Cocculus spp. (Menispermaceae)jics56, 1020 '79

Dehaasia kurzii (Lauraceae) fit 58, 430 '87Desmos tieoaghiensis (Annonaceae) jnp 45, 617 '82Hedycarya angustifolia (Monimiaceae) het 26, 447 '87Illigera pentaphylla (Hernandiaceae) jnp 48, 835 '85Laurelia novae-zelandiae (Monimiaceae) hca 50, 1583 '67Laurus nobilis (Lauraceae) jnp 45, 560 '82Lindera spp. (Lauraceae) jnp 48, 160 '85Litsea spp. (Lauraceae) cpj 46, 299 '94Machilus duihei (Lauraceae) jcp 2, 157 '80Monimia rotundifolia (Monimiaceae) apf 38, 537 '80Nectandra grandiflora (Lauraceae) ijp 31, 189 '93Neolitsea spp. (Lauraceae) jccs 45, 103 '98Peumus spp. (Monimiaceae) jc 612, 315 '93Phoebegrand is (Lauraceae) phy 45,1543 '97Polyalthia cauliflora var. beccarii (Annonaceae) jnp 47, 504 '84Retanilla ephedra (Rhamnaceae) rlq 5, 158 '74Sassafras albidum (Lauraceae) llyd 39, 473a '76Trivalvaria macrophylla (Annonaceae) jnp 53, 862 '90

landan a,l-ene:1 HO

Dehydroboldine CHsO

Peumus boldus (Monimiaceae)jnp51,389 '88 CHsO

OH

67


Compound unknown6-HO 7-MeO3,4-HO,MeO-benzylMe,Me+ THIQ


N,N-Dimethyllindcarpine

Aristolochia triangularis (Aristolochiaceae)jcps 6, 8 '97

Caltha leptosepala (Ranunculaceae)phy 16, 500 '77

Coscinium fenestratum (Menispermaceae) pm 38, 24 '80Magnolia spp. (Magnoliaceae) jnp 38, 275 '75

CHsO

HOIwith a (6,8) attack: IN-Methylboldine

Boldine methiodideCHsO

Cocculus sp. (Menispermaceae)jnp 46, 761 '83 CHsO

OH

Compound unknown6-HO 7-MeO3,4-HO,MeO-benzylAc THIQ

HOIwith a (6,8) attack: IN-Acetyllaurolitsine CHsO

Litsea rotundifolia (Lauraceae)ryz 8, 324 '00

Litsea sp. (Lauraceae) ajc 22, 2259 '69 CHsOOH


6-HO 7-MeO3,4-MeO,HO-benzylH THIQ

Not a natural product.jcspt I, 1531 '75

Iwith a (2,8) attack: I (+)-Hemovine

Croton linearis (Euphorbiaceae)llyd 32, 1 '69

Croton wilsonii (Euphorbiaceae)rlq 1, 140 '70

Hernandia guianensis (Hemandiaceae)pm 50, 20 '84

Hernandia nymphaeifolia (Hemandiaceae) pm 63,154 '97Hernandia ovigera (Hemandiaceae) apf 42,317 '84Illigera luzonensis (Hemandiaceae) jnp 60, 645 '97Illigera parviflora (Hemandiaceae) cty 22, 393 '91Lindera myrrha (Lauraceae) phy 35, 1363 '94Neolitsea variabillima (Lauraceae) het 9, 903 '78Ocotea teleiandra (Lauraceae) rlq 23,18 '92

HO

HO

(Thename Hemovine is used as a synonym for Ovigerine. See pg. 306)

lwith a (6,8)attack: I Laetanine

Hernandia voyronii (Hernandiaceae)pm 64,58 '98

Litsea leata (Lauraceae) phy 18, 910 '79Ocotea teleiandra (Lauraceae) rlq 23, 18 '92 HO

HO

OCHs

6-HO 7-MeO3,4-MeO,HO-benzylMe THIQ

Not a natural product.dmd 14,703 '86

69



(S)(-)DiscretamineAequaline CHsO

Annona cherimolia (Annonaceae) pmp 23, 159 '89Annona reticulata (Annonaceae) zzz 17,295 '92Anomianthus dulcis (Annonaceae) bs&e 26,139 '98Artabotrys maingayi (Annonaceae) jnp 53, 503 '90Artabotrys venustus (Annonaceae) jnp 49, 602 '86Desmos longiflorus (Annonaceae) fit 66, 463 '95Desmos tiebaghiensis (Annonaceae) jnp 45, 617 '82Duguetia calycina (Annonaceae) pmp 12, 259 '78Fissistigma glaucescens (Annonaceae) phy 24, 1829 '85Fissistigma oldhamii (Annonaceae) abs 3Goniothalamus amuyon (Annonaceae) abs 3Guatteria discolor (Annonaceae) jnp 47, 353 '84Meiogyne virgata (Annonaceae) phy 26, 537 '87Nandina domestica (Berberidaceae) phy 27, 2143 '88Oncodostigma monosperma (Annonaceae) jnp 52, 273 '89Polyalthia stenopetala (Annonaceae) phy 29, 3845 '90Rollinia leptopetala (Annonaceae) pb138, 318 '00Saccopetalum prolificum (Annonaceae) ccl Tl, 129 '00Schefferomitra subaequalis (Annonaceae) joe 42, 3588 '77Stephania intermedia (Menispermaceae) yhtp 16, 1 '85Stephania succifera (Menispermaceae) zx 31, 544 '89Uvaria lucida (Annonaceae) nm 51, 272 '97Xylopia buxifolia (Annonaceae) jnp 44, 551 '81Xylopia discreta (Annonaceae) bull I

HOIand aromatization of the c-ring: I

Dehydrodiscretamine CHsO

Fissistigma balansae (Annonaceae) phy 48, 367 '98Nandina domestica (Berberidaceae) phy 27, 2143 '88Stephania intermedia (Menispermaceae) yhtp 16, 1'85Thalictrum foliolosum (Ranunculaceae) daib 45, 520 '84Tinospora capillipes (Menispermaceae) pm 50, 88 '84

OCHs

OH

OCHs

OH


Iwith a (2,8) attack: I N-Methylhemovine HO

Croton linearis (Euphorbiaceae)llyd 32,1 '69

Croton wilsonii (Euphorbiaceae)llyd 32,1 '69

Hernandia guianensis (Hernandiaceae)pm 50, 20 '84

Hernandia nymphaeifolia (Hernandiaceae) pm 63,154 '97Hernandia peltata (Hernandiaceae) pm 46, 119 '82Lindera megaphylla (Lauraceae) jnp 57, 689 '94Lindera oldhamii (Lauraceae) het 9, 903 '78Neolitsea variabillima (Lauraceae) het 9, 903 '78

OH

Iwith a (6,N-Me) attack: IHO

lO-O-Demethyldiscretine

Artabotrys venustus (Annonaceae)jnp 49, 602 '86

Caryomene olivascens (Menispermaceae) afb 6, 163 '87Guatteria discolor (Annonaceae) jnp 47, 353 '84Xylopia vieillardi (Annonaceae) jnp 54, 466 '91

OH

OCHs

OHIwith a (6,3)attack: I HO

OCHsBisnorargemonineDinorargemonine

Rotundine

CHsO

Argemone spp. (Papaveraceae) jnp 46,293 '83Chasmanthera dependens (Menispermaceae) pm 49,17 '83Cocculus laurifolius (Menispermaceae) tet 40, 1591 '84Corydalis decumbens (Papaveraceae) jca 6691/2,225 '94Cryptocarya longifolia (Lauraceae) jnp 46, 293 '83Eschscholzia spp. (Papaveraceae) jnp 46,293 '83

71


Fumaria bastardii (Papaveraceae) nps 4, 257 '98Thalictrum dasycarpum (Ranunculaceae) jnp 46, 293 '83

also under: 6,7 MeO HO R Me THIQR= 3,4-HO,MeO-benzyl (6,3) attack

(The name Rotundine has been used for two unrelated alkaloids; the onein this section, and one which is a synonym for Tetrahydropalmatine.The literature shows that (-)-Rotundine (Tetrahydropalmatine) comesfrom Stephania sp., whereas this Rotundine comes from Argemone sp.)


Liriotulipiferine

Artabotrys lastourvillensis (Annonaceae)jnp 48, 460 '85

Liriodendron tulipifera (Magnoliaceae)jnp 42, 325 '79

Litsea cubeba (Lauraceae) jca 667, 322 '94Strychnopsis thouarsii (Menispermaceae) pm 58, 540 '92

HO

6-HO 7-MeO3,4-MeO,HO-a- Me-benzylMe THIQ

Compound unknown

HOIwith a (2,N-Me) attack: I

Corydalidzine

Corydalis caucasica (Papaveraceae)ijcd 27, 161 '89 OH

Corydalis koidzumiana (Papaveraceae) cpb 23, 313 '75Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89Corydalis solida ssp. brachyloba (Papaveraceae) jcsp 13, 63 '91


6-HO 7-MeO3,4-MeO,MeO-benzylH THIQ

Not a natural product.sh 17,49 '86

Iwith a (2,8) attack: I lO-O-Methylhernovine

Croton wilsonii (Euphorbiaceae) rlq 1, 140 '70

Iwith a (6,8) attack: INorpredicentrine

9-0- Methyllaurolitsine9-0-Methylnorboldine

Guatteria scandens (Annonaceae)jnp46, 335 '83

Hernandia voyronii (Hemandiaceae)pm 64, 58'98

Isopacodine HO6-HO 7-MeO3,4-MeO,MeO-benzylH IQ

Papaver somniferum var. noordster (Papaveraceae)jcspt I, 1531 '75 CH30

(+)-Pseudolaudanine HO6-HO 7-MeO3,4-MeO,MeO-benzylMe THIQ

Arctomecon merriami (Papaveraceae)bse 18,45 '90


73


Iand a (+)-trans 4-hydroxy group: IOH

Roemecarine

Roemeria carica (Papaveraceae)het 24, 1227 '86


I the N-oxide: IRoemecarine N-Oxide

Roemeria carica (Papaveraceae) het 24, 1227 '86

Iwith a (2,N-Me) attack: I

(-)-Corypaimine(+Tetrahydrojatrorrhizine

3-Hydroxy-2,9,lO-trimethoxy-tetrahydroprotoberberine

Annona cherimolia (Annonaceae) pmp 23,159 '89Argemone grandiflora (Papaveraceae) phy 11, 461 '72Berberis julianae (Berberidaceae) cz 29, 265 '75Coptis teeta (Ranunculaceae) ijcs 28, 97 '51Corydalis lutea (Papaveraceae) phy 33, 943 '93Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89Duguetia stelichantha (Annonaceae) rlq 16,107 '85Enantia chlorantha (Annonaceae) pmp 9, 296 '75Fibraurea chloroleuca (Menispermaceae) pw 113, 1153 '78Glaucium grandiflorum (Papaveraceae) jnp 49,1166 '86Guatteria discolor (Annonaceae) jnp 47, 353 '84Hydrastis canadensis (Ranunculaceae) gci 110, 539 '80Pachypodanthium confine (Annonaceae) apf 35,65 '77Pachypodanthium staudtii (Annonaceae) pw 113, 1153 '78Rollinia leptopetala (Annonaceae) pbI 38, 318 '00Stephania mashanica (Menispermaceae) cty 14, 249 '83Stephania micrantha (Menispermaceae) yhhp 16,557 '81


Stephania succifera (Menispermaceae) zx 31, 544 '89Xylopia vieillardii (Annonaceae) jnp 54, 466 '91

land aromatization of the c-ring: I HO

Jatrorrhizine

Arcangelisia flava (Menispermaceae) jnp 45, 582 '82Berberis erataegina (Berberidaceae) kps 106, '96Berberis spp. (Berberidaceae) jnp 58, 1100 '95Burasaia australis (Menispermaceae) bse 19, 433 '91Burasaia congesta (Menispermaceae) bse 19, 433 '91Burasaia gracilis (Menispermaceae) bse 19, 433 '91Chasmanthera dependens (Menispermaceae) pm 46, 228 '82Coptis spp. (Ranunculaceae) phy 21,1419 '82Corydalis spp. (Papaveraceae) jca 669 1/2, 225 '94Coscinium fenestratum (Menispermaceae) pm 38, 24 '80Dioscoreophyllum cumminsii (Menispermaceae) phy 22, 1671 '83Enantia chlorantha (Annonaceae) pmp 9, 296 '75Fagara chalybea (Rutaceae) kdr 23, 153 '90Fibraurea chloroleuca (Menispermaceae) pw 113, 1153 '78Fibraurea recisa (Menispermaceae) ncyh 2, 77 '82Glaucium arabicum (Papaveraceae) duj 17, 185 '90Hydrastis canadensis (Ranunculaceae) sz 46, 42 '92Jatrorrhiza palmata (Menispermaceae) llyd 28, 73 '65Jeffersonia dubia (Berberidaceae) pm 51,52 '85Mahonia aquifolium (Berberidaceae) pm 61, 372 '95Mahonia spp. (Berberidaceae) pm 57, 505 '91Nandina domestica (Berberidaceae) phy 27, 2143 '88Penianthus zenkeri (Menispermaceae) phy 30,1957 '91Phellodendron spp. (Rutaceae) pm 59,557 '93Sphenocentrum jollyanum (Menispermaceae) phy 15, 2027 '76Stephania glabra (Menispermaceae) jnp 45, 407 '82Stephania intermedia (Menispermaceae) yhtp 16, 1'85Stephania miyiensis (Menispermaceae) zh 30, 250 '99Stephania viridiflavens (Menispermaceae) cty 12, 1 '81Thalictrum spp. (Ranunculaceae) jnp 43, 372 '80Tinospora spp. (Menispermaceae) pm 48, 275 '83Xanthorhiza simplicissima (Ranunculaceae) llyd 26, 254 '63Zanthoxylum chalybeum (Rutaceae) jnp 59, 316 '96

75



N,O-DimethylhernovineN-Methyl-lO-O-methylhernovine

Croton linearis (Euphorbiaceae)llyd 32,1 '69

Croton wilsonii (Euphorbiaceae)rlq 1,140 '70

Iwith a (6,N-Me) attack: IHO

Discretine

Caryomene olivascens (Menispermaceae) afb 6,163 '87Duguetia obovata (Annonaceae) jnp 46, 862 '83Guatteria discolor (Annonaceae) jnp 46, 862 '83Guatteria scandens (Annonaceae) jnp 46, 335 '83Pachypodanthium staudtii (Annonaceae) pmp 11, 315 '77Stephania suberosa (Menispermaceae) phy 26, 547 '87Xylopia discreta (Annonaceae) bull 1Xylopia vieillardi (Annonaceae) jnp 54, 466 '91

Iand aromatization of the c-ring: I HO

DehydrodiscretinePseudojatrorrhizine

Fibraurea chloroleuca (Menispermaceae) pw 113, 1153 '78Heptacyclum zenkeri (Menispermaceae) phy 22, 321 '83Penianthus zenkeri (Menispermaceae) phy 22, 321 '83Sinomenium acutum (Menispermaceae) nm 48, 287 '94Thalictrum [auriei (Ranunculaceae) jps 69, 1061 '80Xylopia vieillardii (Annonaceae) jnp 54, 466 '91


Iwith a (6,3)attack: I

Isonorargemonine

Argemone gracilenta (Papaveraceae) jnp 46, 293 '83Argemone munita (Papaveraceae) jnp 46, 293 '83Eschscholzia californica (Papaveraceae) ecce 51, 1743 '86Eschscholzia douglasii (Papaveraceae) ecce 51,1743 '86Eschscholzia glauca (Papaveraceae) ecce 51, 1743 '86Thalictrum minus (Ranunculaceae) pm 63, 533 '97Thalictrum revolutum (Ranunculaceae) jnp 46, 293 '83

alsounder: 6,7 MeO MeO R Me THIQR= 3,4-HO,MeO-benzyl (6,3) attack

HOIwitha (6,8) attack: I

(+)-Predicentrine

Annona purpurea (Annonaceae)jnp 61,1457 '98

Aromadendron elegans (Magnoliaceae) CH30phy 31,2495 '92 OCH

3Beilschmiedia podagrica (Lauraceae)het 9,903 '78

Cassytha [iliformis (Lauraceae) prs 12, 39 '98Corydalis cava (Papaveraceae) zpn 69, 99 '85Corydalis spp. (Papaveraceae) pm 50,136 '84Dicentra peregrina (Papaveraceae) cnc 20, 74 '84Glaucium leiocarpum (Papaveraceae) pm 65, 492 '99Glaucium spp. (Papaveraceae) cnc 19, 714 '83Liriodendron tulipifera (Magnoliaceae) cnc 13, 602 '77Litsea trif/ora (Lauraceae) aqsc 76, 171 '80Dcotea spp. (Lauraceae) fes 32, 767 '77Platycapnos spicata (Papaveraceae) phy 32, 1055 '93PolyaIthia caulif/ora var. beccarii (Annonaceae) jnp 47, 504 '84Strychnopsis thouarsii (Menispermaceae) pm 58, 540 '92

77


land an a,1-ene: I

Dehydropredicentrine

Polyalthia cauliflora (Annonaceae)jnp 51, 389 '88

OH

Iwith a 4-hydroxy group: ISrilankine

Alseodaphne semicarpifolia (Lauraceae)jnp 42, 325 '79

HO6-HO 7-MeO3,4-MeO,MeO-benzylMe,Me+ THIQ

PseudorineN-Methylpseudolaudanine

CH30

Fagara mayu (Rutaceae) pm 48, 77 '83 OCH3

Papaver pseudo-orientale (Papaveraceae) ecce 51, 1752 '86Popowia pisocarpa (Annonaceae) jnp 49,1028 '86

the seco-compound was also isolated from this plant,the substitution positions were not determined:

Pseudoronine

Papaver pseudo-orientale (Papaveraceae) ecce 51, 1752 '86



N-Methylcorypalminen-Hainanine

Berberis iliensis (Berberidaceae) cnc 29,69 '93Cyclea hainanensis (Menispermaceae) cwhp 23, 216 '81

6-HO 7-MeO Compound unknown3,4-MeO,MeO-a-Me-benzylMe THIQ

Iwitha (2,N-Me) attack: I HO

Corybulbine

GJrydalis ambigua (Papaveraceae)5Z 42,214 '88

Corydalis cava (Papaveraceae) sz 40, 61 '86Corydalis koidzumiana (Papaveraceae) yz 94, 844 '74GJrydalis platycarpa (Papaveraceae) jnp 51, 262 '88GJrydalis nobilis (Papaveraceae) ecce 54, 2009 '89GJrydalis nokoensis (Papaveraceae) yz 96, 527 '76GJrydalis remota (Papaveraceae) jnp 51, 262 '88GJrydalis tuberosa (Papaveraceae) book 2GJrydalis turtschaninovii (Papaveraceae) yx 21, 447 '86

landaromatization of the c-ring: I HO,

DehydrocorybulbineCH30

Berberis baluchistanica (Berberidaceae)daib 38, 686 '77 H3C

GJrydalis ambigua (Papaveraceae)daib 45, 2160 '85

GJrydalis nokoensis (Papaveraceae) yz 96, 527 '76

79


Iand a carbonyl on the original N-Me group: IHO

Oxydehydrocorybulbine

Corydalis ambigua (Papaveraceae)daib 45, 2160 '85

6-HO 7-MeO3,4-MOO-benzylH THIQ

Not a natural product.cpb 16, 953 '68

Iwith a (2,8) attack: ILaetine

Hernandia peltata (Hernandiaceae) cjc 64, 123 '86Litsea laeta (Lauraceae) phy 19, 998 '80Ocotea teleiandra (Lauraceae) rlq 23, 18 '92

Iwith a (6,8) attack: INorisodomesticine

Glossoealyx brevipes (Monimiaceae) jnp 48, 833 '85Guatteria goudotiana (Annonaceae) phy 30, 2781 '91Laurus nobilis (Lauraceae) jnp 45, 560 '82Xylopia danguyella (Annonaceae) jnp 44, 551 '81

HO

6-HO 7-MeO3A-MOO-benzylMe THIQ

Not a natural product.het 1, 223 '73



Cheilanthifoline

(5)(-)-isomer:Argemone grandiflora (Papaveraceae) phy 11, 461 '72Argemone mexicana (Papaveraceae) ecce 40, 1576 '75Argemone ochroleuca (Papaveraceae) ecce 38, 2307 '73Corydalis koidzumiana (Papaveraceae) yz 94, 844 '74Corydalis spp. (Papaveraceae) phy 13,2620 '74Fumaria bella (Papaveraceae) jnp 49,178 '86Fumaria capreolata (Papaveraceae) jnp 49, 178 '86Fumaria parviflora (Papaveraceae) jnp 44, 475 '81Fumaria uaillantii (Papaveraceae) phy 22, 2073 '83Papaver commutatum (Papaveraceae) pm 62, 483 '96

(d1):

Dactylicapnos torulosa (Papaveraceae) phy 36,519 '94Eschscholzia californica (Papaveraceae) pm 62, 188 '96

isomernot specified:Argemone hybrida (Papaveraceae) cnc 22, 189 '86Corydalis ochotensis (Papaveraceae) jccs 34, 157 '87Dicentra epeciabilis (Papaveraceae) cnc 20,74 '84Fumaria densiflora (Papaveraceae) jnp 49, 370 '86Menispermum dauricum (Menispermaceae) yz 91, 684 '71Papaver arenarium (Papaveraceae) cnc 20,71 '84Papaver cylindricum (Papaveraceae) pm 46, 175 '82Papaver fugax (Papaveraceae) cnc 24, 475 '89Papaver triniaefolium (Papaveraceae) pm 49, 43 '83

land aromatization of the c-ring: I HO

Dehydrocheilanthifoline*Groenlandicine CH30

Tetradehydrocheilanthifoline

Coptischinensis (Ranunculaceae) sz 37, 195 '83Coptisdeltoides (Ranunculaceae) sz 37, 195 '83Coptisgroenlandica (Ranunculaceae) pm 21, 313 '72

81

o)

o

o)

o


Copt is japonica (Ranunculaceae) jnp 47, 189 '84Coptis quinquefolia (Ranunculaceae) sz 46, 42 '92Coptis trifolia (Ranunculaceae) phy 31,717 '92Corydalis humosa (Papaveraceae) jcpu 20, 261 '89Corydalis ochotensis (Papaveraceae) jcspt I, 63 '76Corydalis ophiocarpa (Papaveraceae) yz 98, 1658 '78Fumaria capreolata (Papaveraceae) per 4, 96 '85Fumaria indica (Papaveraceae) phy 15, 545 '76Menispermum canadense (Menispermaceae) llyd 34, 292 '71Nandina domestica (Berberidaceae) phy 27, 2143 '88Thalictrum glandulosissimum (Ranunculaceae) pm 53, 498 '87

"This name has also been given to the 6-MeO 7-HO isomer.

with a (6,N-Me) attack,and aromatization of the c-ring:

HO

Thalifaurine

Copt is quinquefolia (Ranunculaceae) sz 43, 81 '89Thalictrum fauriei (Ranunculaceae) jps 69, 1061 '80

Iwith a (6,N) attack: I HO

Cryptowolidine CH30

Cryptocarya phyllostemon (Lauraceae)cjc 67, 947 '89

OH o>o

I with a (6,3) attack: I(-)-Caryachine CH30

Cryptocarya chinensis (Lauraceae) jnp 53, 1267 '90Eschscholzia californica (Papaveraceae) ecce 51, 1743 '86Eschscholzia douglasii (Papaveraceae) ecce 51, 1743 '86Eschscholzia glauca (Papaveraceae) ecce 51, 1743 '86

also under: 6,7 MDO R Me THIQR= 3,4-HO,MeO-benzyl (6,3) attack



Reframoline

Meconopsis speciosa (Papaveraceae) zh 27, 459 '96Roemeria refracta (Papaveraceae) jnp 46, 293 '83

Iwith a (6,8) attack: IHO

Guatteria goudotiana (Annonaceae) phy 30, 2781 '91Laurus nobilis (Laraceae) jnp 45, 560 '82Litsea spp. (Laraceae) jccs 39, 453 '92Nandina domestica (Berberidaceae) jnp 38, 275 '75Neolitsea villosa (Laraceae) cpj 47, 69 '95Platycapnos spicata (Papaveraceae) phy 32, 1055 '93

Isodomesticine CH30

6-HO 7-MeO3,4-MDQ-benzylMe,Me+ THIQ

Compound unknown

HO

Iwith a (2,N-Me) attack: ICH30

N-Methylcheilanthifoline quat

Dicentra spectabilis (Papaveraceae) sz 46, 109 '92

Iwith a (6,3) attack: I OH

Caryachine methiodideN-Methylcaryachinium quat CH30

Cryptocarya chinensis (Lauraceae) jnp 42, 163 '79Eschscholzia californica (Papaveraceae) ecce 51, 1743 '86

83

o>o

o)

o


Eschscholzia douglasii (Papaveraceae) ecce 51, 1743 '86Eschscholzia glauca (Papaveraceae) ecce 51, 1743 '86

also under: 6,7 MOO R Me,Me+ THIQR= 3,4-HO,MeO-benzyl (6,3) attack

HO

with a (6,8) attackand a 1,2 seco: CH30

3-0-Demethylthalicthuberine

Ocotea insularis (Lauraceae) jnp 57, 1033 '94

6-HO 7-MeO3,4-MOO-a-Me-benzylMe THIQ

Compound unknown

Isoapocavidineo>o


Dactylicapnos torulosa (Papaveraceae)phy 36,519 '94

6-HO 7-MeO2,3,4-MDO,MeO-benzylMe THIQ

Compound unknown

HO OCH3

(-)-9-Demethylthalimonine


Thalictrum simplex (Ranunculaceae) pm 59, 262 '93

also under: 5,6,7 MOO MeO R Me THIQR= 3,4-HO,MeQ-benzyl (6,3) attack


6-HO 7-MeO Compound unknown3,4,5-MeO,MeO,MeO-benzylMe THIQ

Iwitha (2,8)attack: I Acutifolidine

CH30

CH30Thalicrum acutifolium (Ranunculaceae)

jnp 57,1033'94 CH30

HO

OCH3

6-HO 7-MeO~-(4-Ho-phenyl)ethylMe THIQ

(S)-Colchiethanamine

Colchicum szavitsii (Liliaceae) jnp 53,634 '90

CH30

HO

OH

HO6-HO 7-MeO13-(4-MeO-phenyl)ethylMe THIQ

(S)-Colchiethine

Colchicum szavitsii (Liliaceae) jnp 53,634 '90

CH30

OCH3

85


HO6-HO 7-MeO~-(3,4,5-HO ,MeO,MeO-phenyl)ethylMe THIQ CH30

(-)-Isoautumnaline

Colchicum ritchii (Liliaceae) jnp 50,684 '87 OHOCH3

HO6-HO 7-MeO6',7'-MDG-isobenzofuranone,3'-ylMe THIQ CH30

Corle dine6-0-Demethy ladlumine

Corydalis ledebouriana (Papaveraceae) jnp 45, 105 '82Fumaria parviflora (Papaveraceae) ojc 14, 217 '98Fumaria oaillaniii (Papaveraceae) tet 39, 577 '83

Corlumidine

CH30

(+)-isomer:Corydalis decumbens (Papaveraceae) jcps 4, 57 '95Corydalis linarioides (Papaveraceae) yhhp 16, 798 '81Corydalis scouleri (Papaveraceae) jnp 45, 105 '82Fumaria parviflora (Papaveraceae) ojc 14,217 '98

HO

6-HO 7-MeO Compound unknown3,4-MDO-a-(=CHz)-benzyl, MeMe THIQ


HO[witha (2,I-Me) attack: I

(+)-Ochotensine CH30

Corydalis ochotensis (Papaveraceae) jccs 34, 157 '87Corydalis solida (Papaveraceae) cjc 56, 383 '78Corydalis stewartii (Papaveraceae) jnp 51, 1136 '88Corydalis thyrsiflora (Papaveraceae) yx 26, 303 '91

Compound unknown6-HO 7-MeO3,4-MDO-benzyl, HOMe,Me+ THIQ

HOIwith a (2,N-Me) attack: IIzmirine CH30

Fumaria parviflora (Papaveraceae) jnp 46,934 '83

87

o>o


6,7-MeO,HO-ISOQUINOLINES

Norcorypalline CH30m~ I NH

HO

6-MeO 7-HOHH THIQ

Ziziphus rugosa (Rhamnaeeae) phy 27, 1915 '88

CH30~

HO~NCH3

6-MeOHMe

Corypalline7-HO

THIQ

Berberis nummularia (Berberidaeeae) cne 33, 70 '97Berberis tureomanniea (Berberidaeeae) cne 29, 63 '93Berberis valdiviana (Berberidaeeae) fit 64, 378 '93Corydalis ophioearpa (Papaveraceae) yz 98, 1658 '78Corydalis speeiosa (Papaveraeeae) yz 95, 838 '75Corydalis strieta (Papaveraeeae) kps 19,461 '83Doryphora sassafras (Monimiaeeae) llyd 37,493 '74Islaya minor (Cactaeeae) je 189, 79 '80Menispermum daurieum (Menispermaeeae) tcyyk 5,30 '93Papaver braetea tum (Papaveraeeae) phy 22, 247 '83Stephania eepharantha (Menispermaeeae) nm 52, 541 '98Thalietrum dasyearpum (Ranunculaeeae) joe 34, 1062 '69Thalietrum rugosum (Ranunculaeeae) jnp 43,143 '80Thalietrum uehiyamai (Ranunculaeeae) kjp 13, 132 '82Xylopia vieillardii (Annonaeeae) jnp 54, 466 '91

CH30ro I +~ ~ NCH3HO

6-MeO 7-HOHMe DHIQ

(+J-PycnarrhineDehydrocorypalline

Areangelisia flava (Menispermaeeae) jnp 45, 582 '82Corydalis ophioearpa (Papaveraeeae) yz 98, 1658 '78

Structural Index - 6,7-MeO,HO-Substituted

Corydalis stricta (Papaveraceae) kps 4, 490 '83Pycnarrhena longifolia (Menispermaceae) phy 20, 323 '81

6-MeO 7-HOHMe,Me+ THIQ

2-MethylcorypalliniumN-Methylcorypalline

Corydalis stricta (Papaveraceae) kps 4, 490 '83

CH30mI N

HO ~

6-MeO 7-HOH4-HO-benzyl THIQ

Corgoine

Ceratocapnos sp. (Papaveraceae) kps 7, 211 '70Corydalis sp. (Papaveraceae) kps 6, 638 '70

CH30mI N

HO ~

6-MeO 7-HOH4-MeQ-benzyl THIQ

Sendaverine

Corydalis gortschakovii (Papaveraceae) kps 6, 438 '70Ceratocapnos heterocarpa (Papaveraceae) phy 36, 241 '94Corydalis impatiens (Papaveraceae) patent 3Corydalis tashiroi (Papaveraceae) pm 41, 403 '81

OCH3

Ithe N-oxide: ISendaverine N-oxide

Corydalis gortschakovii (Papaveraceae) kps 6, 834 '77

89

OH


6-MeO 7-HOH3,4-HO,MeO-benzyl THIQ

Capnosine

Ceratocapnos heterocarpa (Papaveraceae)phy 36, 241 '94

Corydalis sp. (Papaveraceae) phy 36, 241 '94

CH30mI N

HO ~

HO

6-MeOMeH

Isosalsoline

OCH3

7-HO

THIQCH30:cy

I NHHO ~

CH3Hammada articulata (Chenopodiaceae) apf 48,219 '90Pachycereus pecten-aboriginum (Cactaceae) aps 15, 127 '78

6-MeO 7-HOMeH IQ

7-0-Desmethylisosalsolidine

CH30:cQ""::::::I NHO::::::"'" ~

CH3

Hernandia nymphaeifolia (Hernandiaceae) phy 42,1479 '96

7-HO6-MeOMeMe

I-MethylcorypallineN-Methylisosalsoline

THIQ

CH30Y(JHO~NCH,

CH3(R)(+)-isomer:Corydalis ambigua (Papaveraceae) phy 12, 3008 '73

(S)(-)-isomer:Arthrocnemum glaucum(Chenopodiaceae) phy 31,1023 '92

isomer not specified:Haloxylon articulatum (Chenopodiaceae) book 6


7-HO6-MeOi-BuMe

LophocereineLophocerine

THIQ

iopnocereus schottii (Cactaceae) phy 8,1481 '69Pachycereus marginatus (Cactaceae) book 6

7-HO Not a natural product.joc 41,443 '76

6-MeObenzylH THIQ

IWitha (2,8)attack: I CH30

Caaverine

Isolona pilosa (Annonaceae) pm 50, 23 '84Liriodendron tulipifera (Magnoliaceae) cnc 23, 521 '88Liriodendron sp. (Magnoliaceae) jnp 38, 275 '75Neostenanthera gabonensis (Annonaceae) jnp 51, 973 '88Ocoteaglaziovii (Lauraceae) fes 30, 479 '75Ocotea sp. (Lauraceae) jnp 38, 275 '75Papaver pseudo-orientale (Papaveraceae) paz 13, 50 '77Polyalthia acuminata (Annonaceae) jnp 45, 471 '82Symplocos celastrinea (Symplocaceae) llyd 33s, 1 '70Symplocos sp. (Symplocaceae) jnp 38, 275 '75Ziziphus jujuba (Rhamnaceae) apr 12, 263 '89Ziziphus spinosus (Rhamnaceae) sh 16, 233 '86

HO

7-HO Not a natural product.jhc 4, 417 '67

6-MeObenzylMe THIQ

lwitha (2,N-Me)attack: IBharatamine HO

Alangium lamarckii (Alangiaceae) tl24, 291 '83

91


Iwith a (2,8) attack: I CH30

LirinidineNomuciferine I HO

Lirinidine:Annona purpurea (Annonaceae) phy 49, 2015 '98Artabotrys venustus (Annonaceae) jnp 49,602 '86Guatteria sagotiana (Annonaceae) jnp 49,1078 '86Isolona zenkeri (Annonaceae) pm 50, 23 '84Liriodendron tulipifera (Magnoliaceae) cnc 23, 521 '88Nelumbo nucifera (Nymphaeaceae) jnp 50, 773 '87Neostenanthera gabonensis (Annonaceae) jnp 51,973 '88Ocotea macrophylla (Lauraceae) pptp 27, 65 '93Papaver spp. (Papaveraceae) pm 41,105 '81

Nornuciferine I:Croton bonplandianus (Euphorbiaceae) abs 10Croton sparsiflorus (Euphorbiaceae) tet 35, 2323 '79

Dehydrolirinidine HO

Iand an a.,1-ene: I

Annona purpurea (Annonaceae) jnp 61,1457 '98

6-MeO 7-HOa.-NH2-benzylH IQ

Compound unknown

with a (2,8) attackaromatization and oxidation:

Telazoline

Telitoxicum peruvianum (Menispermaceae)jnp 44, 320 '81


Compound unknown6-MeO 7-HOa-keto-benzylMe+ IQ


O,N-Dimethylliriodendronine HO

Guatteria chrysopetala (Annonaceae) pmp 18, 165 '84Stephania dinklagei (Menispermaceae) pm 66,478 '00

6-MeO 7-HO3-HO-benzylH THIQ

(-)-N orcanelilline

Aniba canelilla (Lauraceae) cjc 71, 1128 '93

6-MeO 7-HO3-HO-benzylMe THIQ

Canelilline

OH



Anibacanine

Aniba canelilla (Lauraceae)cjc 71,1128'93

OH

93

OH


land a methyl group on the original N-Me group: I

(-)-a-8-Methylanibacanine

Aniba canelilla (Lauraceae)cjc 71, 1128 '93


Isothebaidine

Papaver orientale (Papaveraceae)cnc 14, 402 '78


(-)-Pseudoanibacanine


HO

HO

land a methyl group on the original N-Me group: I

the cis isomer:(-)-8a-Methylpseudoanibacanine

Aniba canelilla (Lauraceae)cjc 71,1128 '93

the trans isomer:(-)-8~-Methylpseudoanibacanine

Aniba canelilla (Lauraceae)cjc 71, 1128 '93

OH

OH


6-MeO 7-HO3-MeO-benzylH THIQ

Compound unknown

Iwith a (6,8) attack: I Nororientinine

Ocotea caesia (Lauraceae) jnp 57, 1033 '94

CH30

HO

OCH3

6-MeO 7-HO3-MeO-benzylMe THIQ

Not a natural product.cpb 29, 1083 '81

Iwitha (2,8) attack: I CH30Isothebaine

HOCH30

Discaria serratifolia (Rhamnaceae)jnp47, 1040 '84

Papaver atlanticum (Papaveraceae)ecce 51, 2232 '86

Papaver bracteatum (Papaveraceae) pm 32, 60 '77Papaver nudicaule (Papaveraceae) zpf 114, 361'84Papaver orientale (Papaveraceae) jps 66, 1050 '77Papaver pseudo-orientale (Papaveraceae) paz 13, 50 '77Papaver setigerum (Papaveraceae) zpf 114, 361 '84Papaver somniferum (Papaveraceae) zpf 114, 361 '84

Iandan CJ.,1-ene:I

Dehydroisothebaine HO

CH30Papaver orientale (Papaveraceae)jnp51,389 '88

95



Orientinine

Papaver orientale (Papaveraceae) jnp 51, 389 '88

OCH3

6-MeO 7-HO Compound unknown3-MeO-benzylMe,Me+ THIQ

Iwith a (2,8) attack: I CH30

N-Methylisothebainium cationN-Methylisothebaine HO

CH30Papaver bracteatum (Papaveraceae)

jnp 51, 389 '88Papaver pseudo-orientale (Papaveraceae)

ecce 51, 1752 '86

Compound unknown6-MeO 7-HO3-MeO-a-keto-benzylMe IQ


Alkaloid PO-3HO

CH30Papaver orientale (Papaveraceae)

jnp 38, 275 '75


CH306-MeO 7-HO4-HQ-benzylH THIQ

CoclaurineMachiline

Sanjoinine K

(S)(-)-isomerof CoclaurineMachiline:Alseodaphne archboldiana (Lauraceae) het 9,903 '78Aniba canelilla (Lauraceae) cjc 71,1128 '93Annona montana (Annonaceae) pmp 16, 169 '82Annona reticulata (Annonaceae) jcspt I, 1515, '79Cocculus hirsutus (Menispermaceae) npl 2, 105 '93Cocculus pendulus (Menispermaceae) jpic 32, 250 '60Corydalis gortschakovii (Papaveraceae) kps 6, 638 '70Corydalis paniculigera (Papaveraceae) cnc 18, 689 '82Corydalis pseudoadunca (Papaveraceae) cnc 21, 807 '86Cryptocarya longifolia (Lauraceae) ajc 34, 195 '81Fumaria parviflora (Papaveraceae) cnc 18, 608 '82Fumaria vaillantii (Papaveraceae) cnc 17, 437 '81Litseaglutinosa (Lauraceae) abs 10Litsea lecardii (Lauraceae) pm 52, 74 '86Machilus acuminatissima (Lauraceae) het 9,903 '78Machilus kusanoi (Lauraceae) het 9,903 '78Magnolia salicifolia (Magnoliaceae) pm 48, 43 '83Mezilaurus synandra (Lauraceae) phy 22, 772 '83Nymphaea stellata (Nymphaeaceae) jics 63, 530 '86Pachygone ovata (Menispermaceae) daib 45, 567 '84Peumus boldus (Monimiaceae) fit 64, 455 '93Phoebe minutiflora (Lauraceae) cpj 49,217 '97Polyalthia macropoda (Annonaceae) phy 29, 3845 '90Retanilla ephedra (Rhamnaceae) rlq 5, 158 '74Stephania pierrei (Menispermaceae) jnp 52,846 '89Xylopia papuana (Annonaceae) npl6, 57 '95Ziziphus jujuba (Rhamnaceae) apr 12, 263 '89Ziziphus spinosus (Rhamnaceae) kjp 16, 44 '85Ziziphus vulgaris (Rhamnaceae) apr 10, 203 '87

(R)(+}-isomerof CoclaurineSanjoinineK:Abuta pahni (Menispermaceae) phy 26, 2136 '87

HO

HO

97


Alseodaphne archboldiana (Lauraceae) het 9, 903 '78Annona muricata (Annonaceae) pm 42, 37 '81Bongardia chrysogonum (Berberidaceae) jnp 52,818 '89Caryomene olivascens (Menispermaceae) afb 6, 163 '87Cassytha racemosa (Lauraceae) het 9, 903 '78Cocculus laurifolius (Menispermaceae) tet 36, 3107 '80Colubrina faralaotra ssp. sinuata (Rhamnaceael pm 30, 201 '76Corydalis severtzovii (Papaveraceae) cnc 11, 826 '75Cyclea barbata (Menispermaceae) jnp 56, 1989 '93Cyclea peltata (Menispermaceae) jnp 56,1989 '93Discaria pubescens (Rhamnaceae) pm 50, 454 '84Litsea triflora (Lauraceae) aqsc 76,171 '80Magnolia fargesii (Magnoliaceae) pm 48, 43 '83Magnolia liliflora (Magnoliaceae) yhtp 20, 522 '85Magnolia salicifolia (Magnoliaceae) pm 48, 43 '83Nectandra salicifolia (Lauraceae) jnp 59, 576 '96Neolitsea villosa (Lauraceae) cpj 47, 69 '95Peumus boldus (Monimiaceae) fit 64, 455 '93Polyalthia acuminata (Annonaceae) jnp 45,471 '82Popowia pisocarpa (Annonaceae) jnp 49, 1028 '86Roemeria refracta (Papaveraceae) hca 75, 260'92Sciadotenia eichleriana (Menispermaceae) jnp 48, 69 '85Sparattanthelium uncigerum (Hernandiaceae) jnp 48,333 '85Stephania cepharantha (Menispermaceae) cpb 45, 470 '97Stephania excentrica (Menispermaceae) jnp 60, 294 '97Ziziphus jujuba (Rhamnaceae) apr 12, 263 '89Ziziphus vulgaris (Rhamnaceae) apr 12, 263 '89

(d1)-Codaurine:Cocculus hirsutus (Menispermaceae) ijc 14b, 62 '76Cryptocarya konishii (Lauraceae) het 9, 903 '78Machilus acuminatissima (Lauraceae) het 9, 903 '78Machilus macrantha (Lauraceae) het 9,903 '78Peumus boldus (Monimiaceae) fit 64, 455 '93Polyalthia acuminata (Annonaceae) jnp 45,471 '82Retanilla ephedra (Rhamnaceae) rlq 5, 158 '74Talguenea quinquenervis (Rhamnaceae) aaqa 62, 361 '74Xylopia papuana (Annonaceae) llyd 33s, 1 '70Ziziphus jujuba (Rhamnaceae) kps 13,239 '77


Iwith a (l,8) attack: ICrotsparineCrotoflorine

Alphonsea sclerocarpa (Annonaceae) jnp 50, 518 '87Croton bonplandianus (Euphorbiaceae) jcspt 1659 '75Croton flavens (Euphorbiaceae) llyd 32, 1 '69Croton ruizianus (Euphorbiaceae) bse 24, 463 '96Croton sparsiilorus (Euphorbiaceae) llyd 32, 1'69Monodora brevipes (Annonaceae) phy 28,2489 '89Ocotea glaziovii (Lauraceae) het 9, 903 '78

with reduction of thebenzyl 2,3 double-bond:

(lS-cis) (+)-Crotsparinine

Croton bonplandianus (Euphorbiaceae) jcspt 1659 '75

(lR-trans) (-)-Jacularine

Croton discolor (Euphorbiaceae) rlq I, 140 '70Croton echinocarpus (Euphorbiaceae) llyd 32, 1'69Croton linearis (Euphorbiaceae) llyd 32, 1 '69Croton plumieri (Euphorbiaceae) rlq I, 140 '70Croton ruizianus (Euphorbiaceae) bse 24, 463 '96Croton sparsiflorus (Euphorbiaceae) exp 25, 354 '69

withreduction of both double bondsandof the carbonyl group in the benzyl ring:

OridineOreoline

(-)-isomer:Papaver lisae (Papaveraceae) cnc 14, 228 '78Papaveroreophilum (Papaveraceae) frm 29, 23 '80

CHsO

HO

CHsO

HO

R,S is CrotsparinineR,R is Jacularine

CHsO

HO

HO

99


SparsiflorineApocrotsparine


(-I-Isomer:Monodora tenuifolia (Annonaceae) pm 50, 455 '84

isomer not specified:Alphonsea sclerocarpa (Annonaceae) jnp 50,518 '87Croton bonplandianus (Euphorbiaceae) jcspt 1,1659 '75Croton flavens (Euphorbiaceae) llyd 32, 1 '69Thalicirum foliolosum (Ranunculaceae) jnp 45,252 '82

6-MeO 7-HO4-HO-benzylH IQ

JuzirineYuzirine

HO

Ziziphus jujuba (Rhamnaceae) iant 4,48 '87Magnolia fargesii (Magnoliaceae) pm 48, 43 '83Magnolia salicifolia (Magnoliaceae) ws 14, 101'81 HO

6-MeO 7-HO4-HO-a-keto-benzylH DHIQ

Longifolonine

Cryptocarya velutinosa (Lauraceae) ajc 34, 195 '81

6-MeO 7-HO N-Methylcoclaurine4-HO-benzylMe THIQ HO

(S)(+)-isomer:Aniba canelilla (Lauraceae) cjc 71, 1128 '93 HODesmos tiebaghiensis (Annonaceae) jnp 45,617 '82Stephania cepharantha (Menispermaceae) cpb 45, 470 '97

Structural Index - 6,7-MeO,HO-Substituted 101

Stephania pierrei (Menisperrnaceae) jnp 52, 846 '89Thalictrum revolutum (Ranunculaceae) llyd 40, 593 '77

(R)(-)-isomer:Aniba burchellii (Lauraceae) bse 8, 51 '80Aniba cylindriflora (Lauraceae) bse 8, 51 '80Aniba simulans (Lauraceae) bse 8, 51 '80Berberis lycium (Berberidaceae) daib 44, 1458 '83Ceratocapnos palaestinus (Papaveraceae) jnp 53, 1006 '90Cryptocarya longifolia (Lauraceae) ajc 34,195 '81Cyclea peltata (Menispermaceae) jnp 56, 1989 '93Discaria serratifolia var. discolor (Rhamnaceae) jnp 42, 430 '79Discaria toumatou (Rhamnaceae) jnp 45,777 '82Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177 '80Glaucium leiocarpum (Papaveraceae) pm 65, 492 '99Cuaiteria sagotiana (Annonaceae) jnp 49, 1078 '86Litsea triflora (Lauraceae) aqsc 76,171 '80Magnolia fargesii (Magnoliaceae) pm 48, 43 '83Magnolia salicifolia (Magnoliaceae) pm 48, 43 '83Thalictrum dioicum (Ranunculaceae) llyd 41, 169 '78Xylopia pancheri (Annonaceae) pm 30, 48 '76Xylopia vieillardii (Annonaceae) jnp 54, 466 '91Ziziphus mucronata (Rhamnaceae) phy 13, 2328 '74

(dl):Berberis actinacantha (Berberidaceae) daib 45,2160 '85Berberis boliviana (Berberidaceae) jnp 52, 81 '89Bongardia chrysogonum (Berberidaceae) jnp 52, 818 '89Polyalthia acuminata (Annonaceae) jnp 45, 471 '82Roemeria refracta (Papaveraceae) hca 75, 260 '92Tiliacora racemosa (Menispermaceae) cc 226 '78

isomer not specified:Aniba muca (Lauraceae) rbq 13, 19 '96Annona squamosa (Annonaceae) cpj 46, 439 '94Artabotrys odoratissimus (Annonaceae) fit 65, 92 '94Berberisiliensis (Berberidaceae) cnc 29, 69 '93Berberisnummularia (Berberidaceae) cnc 29, 335 '93Berberisvaldiviana (Berberidaceae) fit 64, 378 '93Cocculus laurifolius (Menispermaceae) ijc 26b, 24 '87Corydalis gortschakovii (Papaveraceae) cnc 20, 245 '84Discariacrenata (Rhamnaceae) phy 12, 954 '73


Fumaria capreolata (Papaveraceae) per 4, 96 '85Glaucium oxylobum (Papaveraceae) cnc 20, 244 '84Gyrocarpus american us (Hernandiaceae) jnp 49,101 '86Litsea acuminata (Lauraceae) cpj 46, 299 '94Nectandra salicifolia (Lauraceae) jnp 59, 576 '96Retanilla ephedra (Rhamnaceae) rlq 5, 158 '74Stephania excentrica (Menispermaceae) zh 27, 586 '96Thalictrum longistylum (Ranunculaceae) jnp 62, 1410 '99

!xyloside at the 7-HO position: ILatericine

Papaver californicum (Papaveraceae) svs 55, 23 '93

CH30Iwith a (1,8) attack: IN-Methylcrotsparine

GlaziovineSuavedol

HO

(R)(+)-isomer:N-MethylcrotsparineGlaziovine: 0Annona cherimolia (Annonaceae) pmp 23,159 '89

(5)(-)-isomer:N-MethylcrotsparineGlaziovineSuavedol:Aniba canelilla (Lauraceae) cjc 71, 1128 '93Annona purpurea (Annonaceae) jnp 61, 1457 '98Aristolochia chilensis (Aristolochiaceae) fit 61, 190 '90Berberis lycium (Berberidaceae) daib 44, 1458 '83Corydalis claviculata (Papaveraceae) jnp 53, 1280 '90Croton bonplandianus (Euphorbiaceae) tet 37,3175 '81Desmos tiebaghiensis (Annonaceae) jnp 45, 617 '82Guatteria sagotiana (Annonaceae) jnp 49, 1078 '86Isolona zenkeri (Annonaceae) pm 50, 23 '84Liriodendron tulipifera (Magnoliaceae) cnc 11, 829 '75Litsea cubeba (Lauraceae) jca 667, 322 '94


Litsea laurifolia (Lauraceae) pmp 13, 262 '79Meeanopsis cambrica (Papaveraceae) jpps 27, 84p '75Neetandra membranacea (Lauraceae) pptp 27, 65 '93Neetandra salicifolia (Lauraceae) jnp 59, 576 '96Neostenanthera gabonensis (Annonaceae) jnp 51, 973 '88Ocotea brachybotra (Lauraceae) pptp 27, 65 '93Deotea glaziovii (Lauraceae) het 9,903 '78Deotea variabilis (Lauraceae) pptp 27, 65 '93Paehygone ovata (Menispermaceae) jnp 42, 399 '79Papaver caucasicum (Papaveraceae) phzi 23, 267 '68Stephania eepharantha (Menispermaceae) cpb 45, 470 '97Uvaria ehamae (Annonaceae) pmp 14, 143 '80

isomernot specified:Neolitsea konishii (Lauraceae) phzi 45, 442 '90

CH30Iwith the reduction of a double bond: IN-Methylcrotsparinine HO

Croton bonplandianus (Euphorbiaceae)jcspt I, 1659 '75

Iwitha (2,8)attack: I CH30

ApoglaziovineN-Methylsparsiflorine

N-MethylapocrotsparineHO

(5)(+l-isorner:Aniba canelilla (Lauraceae) cjc 71, 1128 '93 HOBerberis brandisiana (Berberidaceae) jnp 49, 538 '86Croton bonplandianus (Euphorbiaceae) jnp 38, 275 '75Croton sparsiflorus (Euphorbiaceae) tet 37, 3175 '81Liriodendron tulipifera (Magnoliaceae) cnc 27,516 '92Deotea sp_(Lauraceae) jnp 38, 275 '75

(R)(-)-isomer(Apoglaziovine only):Neetandra membranacea (Lauraceae) fit 60, 474 '89Stephania venosa (Menispermaceae) jnp 50, 1113 '87

103


6-MeO 7-HO4-HO-benzylMe,Me+ THIQ

Magnocurarine CH30

HO

(5)(+)-isomer:Euodia trichotoma (Rutaeeae) pm 59, 290 '93Lindera oldhamii (Lauraeeae) jnp 49, 726 '86Litsea cubeba (Lauraeeae) het 9, 903 '78

HO

(R)(-)-isomer:Colletia hystix (Rhamnaeeae) aaqa 59, 343 '71Colletia spinosissima (Rhamnaeeae) llyd 335, 1 '70Dicentra spectabilis (Papaveraeeae) sz 46, 109 '92Leontice leontopetalum (Berberidaeeae) jnp 49, 726 '86Litsea cubeba (Lauraeeae) jnp 56, 1971 '93Magnolia acuminata (Magnoliaeeae) llyd 335, 1 '70Magnolia obovata (Magnoliaeeae) pm 58, 137 '92Magnolia officinalis var. biloba (Magnoliaeeae) nm 50, 413 '96Magnolia rostrata (Magnoliaeeae) ety 12, 10 '81Tiliacora racemosa (Menispermaeeae) jic 57, 773 '80

isomer not specified:Magnolia anglietia (Magnoliaeeae) yhhp 23, 383 '88Magnolia sprengeri (Magnoliaeeae) yhhp 23, 383 '88Magnolia szechuanica (Magnoliaeeae) yhhp 23, 383 '88Magnolia wilsonii (Magnoliaeeae) yfz 2, 95 '82Manglietia chingii (Magnoliaeeae) yhhp 24, 295 '89Manglietia duclouxii (Magnoliaeeae) yhhp 24, 295 '89Manglietia insignis (Magnoliaeeae) yhhp 24, 295 '89Manglietia szechuanica (Magnoliaeeae) yhhp 24, 295 '89Manglietia yuyuanensis (Magnoliaceae) yhhp 24, 295 '89

6-MeO 7-HO4-HO-a-HD-benzylH IQ

Annocherine ACH30

HO

Annona cherimolia (Annonaeeae) phy 56,753 '01HO


6-MeO 7-HO Annocherine B4-HO-a-MeO-benzylH IQ

Annona cherimolia (Annonaceae) phy 56, 753 '01

CH30

HO

HO

6-MeO 7-HO4-HO-a-HO-benzylMe,Me+ THIQ

(+)-la-Hydroxymagnocurarine

Cryptocarya konishii (Lauraceae)jnp 56,1971 '93

6-MeO 7-HO4-MeO-benzylH THIQ

Not a natural product.Is 30, 1747 '82

Iwith a (2,8)attack: I ZenkerinelO-Methoxycaaverine

(-)-isomer:Dcotea caesia (Lauraceae) jnp 42, 325 '79

isomernot specified:Iso/ana pi/osa (Annonaceae) era 285, 447 '77Iso/ana zenkeri (Annonaceae) pm 50, 23 '84

CH30

HO

CH30

6-MeO 7-HO N-DemethyIcoIIetine4-MeO-benzylMe THIQ

(R)-isomer:Aconitum /eucostomum (Ranunculaceae)

kps6,805'80

CH30

CH30

HO

105


Discaria serratifolia (Rhamnaceae) jnp 42, 430 '79Xylopia pancheri (Annonaceae) pm 30, 48 '76

CH30Iwith a (2,3) attack: I

2,9-Dimethoxy-3-hydroxypavinane HO

Argemone munita (Papaveraceae) joe 38, 3701 '73

also under: 7 MeO R Me THIQR= 3,4-MeO,HO-benzyl (6,3) attack

CH30

Iwith a (2,8) attack: IN-MethyIzenkerine

PulchineHO

Ocotea caesia (Lauraceae) jnp 42, 325 '79 CH30

6-MeO 7-HO4-MeO-benzylMe,Me+ THIQ

Colletine

HO

Colchicum luteum (Liliaceae) kpr 12, 359 '76Colletia spinosissima (Rhamnaceae)

llyd 335, 1 '70Cymbopetalum brasiliense (Annonaceae) pm 50,517 '84Zanthoxylum sarasinii (Rutaceae) pm 54, 189 '88

CH30

6-MeO 7-HO4-MeO-a-keto-benzylH DHIQ

VeIucryptine CH30

HO

Cryptocarya velutinosa (Lauraceae) jnp 52, 516 '89

CH30


6-MeO 7-HO Compound unknown2,3-MeO,MeO-a-keto-benzylH IQ

Iwith a (6,8) attack: I Annolatine

Annona montana (Annonaceae) phy 33, 497 '93

CH30

HO

6-MeO 7-HO Compound unknown2,3-MOO-benzyl,MeMe THIQ

witha (6,1-Me)attack,theN-oxide:

(+)-Papracinine

Fumaria indica (Papaveraceae) phy 31,2869 '92

HO

6-MeO 7-HO Compound unknown2,3-MOO-a-keto-benzyl,MeMe THIQ

lwitha (6,1-Me)attack: I (+)-Parfumine

Corydalis rutifolia (Papaveraceae) ijcdr 26, 155 '88Corydalis solida (Papaveraceae) guefd 5, 9 '88Fumaria densiflora (Papaveraceae) cccc 61, 1064 '96Fumaria indica (Papaveraceae) phy 31, 2869 '92Fumaria mural is (Papaveraceae) jpps 33, 16 '81

HO

107


Fumaria officina lis (Papaveraceae) jnp 46, 433 '83Fumaria parviflora (Papaveraceae) pm 45,120 '82Fumaria rostellata (Papaveraceae) dban 25, 345 '72

Compound unknown6-MeO 7-HO2,3-MDO-a-HO-benzyl, MeMe THIQ

CH30Iwith a (6,I-Me) attack: I FumaritineFumarophycinol

(+)-isomer:Corydalis caucasica (Papaveraceae) ijcdr 27, 161 '89Corydalis solida (Papaveraceae) jcsp 13, 63 '91

(-)-isomer:Corydalis rutifolia (Papaveraceae) ijcdr 26, 155 '88Fumaria bastardii (Papaveraceae) nps 4, 257 '98Fumaria densiflora (Papaveraceae) ecce 61, 1064 '96Fumaria macrosepala (Papaveraceae) aqse 83, 119 '87Fumaria muralis (Papaveraceae) jpps 33, 16 '81Fumaria officina lis (Papaveraceae) jnp 46, 433 '83Fumaria spp. (Papaveraceae) nps 4, 257 '98

I the N-oxide: IFumaritine N-oxide

Alkaloid Fk-5

Fumaria indica (Papaveraceae) phy 31, 2869 '92Fumaria kralikii (Papaveraceae) cjc 57, 53 '79

HO

CH306-MeO 7-HO2,5-MeO ,HO-benzylMe THIQ

Dehassiline

Dehassia kurzii (Lauraceae) fit 62, 261 '91

HO

HO


CH306-MeO 7-HO3,4-HO,HO-benzylH IQ HO

Turcomanine

Berberis turcomanica (Berberidaceae) cnc 32, 59 '96HO

OH

6-MeO 7-HO Compound unknown3,4-HO,HO-benzylMe THIQ

Iwitha (6,N-Me) attack: IHO

(-)-Pessoine

Annona spinescens (Annonaceae) jnp 59, 438 '96

OH

6-MeO 7-HO Norreticuline3,4-HO,MeO-benzylH THIQ

(R)(+)- isomer:Ficus pachyrrachis (Moraceae) pm 59, 286 '93

(S)(-)-isomer: OHAnnona reticulata (Annonaceae) phy 26, 3235 '87Argemone platyceras (Papaveraceae) phy 26, 3235 '87Berberis aggregata (Berberidaceae) phy 26,3235 '87Berberisaristata (Berberidaceae) phy 26, 3235 '87Berberis beaniana (Berberidaceae) phy 26, 3235 '87Berberiskoetineana (Berberidaceae) phy 29,3491'90Berberisstolonifera (Berberidaceae) phy 26,3235 '87Berberiswilsoniae var. subcaulialata (Berberidaceae) phy 26, 3235 '87

109

OH


Chelidonium majus (Papaveraceae) phy 26, 3235 '87Cissampelos pareira (Menispermaceae) phy 26, 3235 '87Corydalis cava (Papaveraceae) phy 26, 3235 '87Corydalis meifolia (Papaveraceae) tet 42,675 '86Eschscholzia californica (Papaveraceae) phy 26,3235 '87Eschscholzia lobbii (Papaveraceae) phy 26, 3235 '87Fumaria parviflora (Papaveraceae) phy 26,3235 '87Papaver somniferum (Papaveraceae) phy 26,3235 '87Thalictrum dipterocarpum (Ranunculaceae) phy 26, 3235 '87Thalictrum flavum (Ranunculaceae) phy 26, 3235 '87Thalictrum foetidum (Ranunculaceae) phy 26, 3235 '87Thalictrum rugosum (Ranunculaceae) phy 26, 3235 '87

Iwith a (2,4a) attack: INorsinoacutine

HOCroton balsamifera (Euphorbiaceae) llyd 32, 1 '69Croton bonplandianus (Euphorbiaceae) phy 20,683 '81Croton flavens (Euphorbiaceae) rlq 1, 140 '70Croton linearis (Euphorbiaceae) llyd 32, 1 '69 CH30Croton plumieri (Euphorbiaceae) phy 8, 777 '69 0

NorsalutaridineCH30

(+)-isomer:Papaver pseudo-orientale (Papaveraceae) HO

jnp 51, 802 '88

isomer not specified:Croton hemiargyreus (Euphorbiaceae) CH30

phy 47, 1445 '98 0

and a hydrogenated double bond CH30at the 8,8a-position :

8/14-Dihydronorsalutaridine HO

Croton echinocarpus (Euphorbiaceae) llyd 32, 1 '69Croton linearis (Euphorbiaceae) llyd 32, 1 '69

CH30Croton plumieri (Euphorbiaceae) phy 8, 777 '690


OH

Iwitha (6,4a) attack I CH30

H-Norpallidine

Fumaria vaillantii (Papaveraceae) phy 15, 1802 '76

CH30o

Iwitha (6,8)attackl CH30NorisoboldineLaurelli ptine

HOAnnona salzmanii (Annonaceae) je 36,39 '92Artabotrys monteiroae (Annonaceae) pa 4, 72 '93Beilschmiedia spp. (Lauraceae) het 9,903 '78Cassytha pubescens (Lauraceae) het 9,903 '78 CH30Cassytha racemosa (Lauraceae) het 9, 903 '78 OHCocculus laurifolius (Menispermaceae) cnc 27, 73 '91Illigera pentaphylla (Hemandiaceae) jnp 48,835 '85Litsea acuminata (Lauraceae) cpj 46, 299 '94Litsea triflora (Lauraceae) aqsc 76, 171 '80Litsea spp. (Lauraceae) ajc 22, 2259 '69Monodora tenuifolia (Annonaceae) daib 45, 520 '84Nectandra rigida (Lauraceae) jnp 43,353 '80Neolitsea zeylanica (Lauraceae) het 9,903 '78Ocoteacaesia (Lauraceae) phy 28, 3577 '89Ziziphus jujuba (Rhamnaceae) kps 13,239 '77

CH306-MeO 7-HO3,4-HO,MeD-benzylMe THIQ

HO

Reticuline

W~ CH~Argemonegracilenta (Papaveraceae) joe 34, 555 '69 OHMachi/us duthei (Lauraceae) jcp 2, 157 '80Ocoteavelloziana (Lauraceae) phy 39,815 '95Papaverbradeatum (Papaveraceae) phy 16, 1939 '77

111


(+)(S)-isomer:Alseodaphne archboldiana (Lauraceae) het 9, 903 '78Aniba canelilla (Lauraceae) cjc 71, 1128 '93Annona cherimolia (Annonaceae) jnp 48, 151 '85Annona spp. (Annonaceae) jnp 48, 151 '85Argemone spp. (Papaveraceae) joe 34, 555 '69Artabotrys monteiroae (Annonaceae) pa 4, 72 '93Artabotrys venustus (Annonaceae) jnp 49, 602 '86Berberis spp. (Berberidaceae) phy 29, 3505 '90Bongardia chrysogonum (Berberidaceae) jnp 52,818 '89Cananga odorata (Annonaceae) jccs 46, 607 '99Ceratocapnos palaestinus (Papaveraceae) jnp 53, 1006 '90Cinnamomum spp. (Lauraceae) het 9, 903 '78Corydalis spp. (Papaveraceae) ijcdr 26, 155 '88Cryptocarya spp. (Lauraceae) het 9, 903 '78Cymbopetalum brasiliense (Annonaceae) pm 50, 517 '84Desmos tiebaghiensis (Annonaceae) jnp 45,617 '82Eschscholzia californica (Papaveraceae) lac 6, 555 '90Fumaria capreolata (Papaveraceae) per 4, 96 '85Glaucium grandiflorum (Papaveraceae) apt 43, 89 '01Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177 '80Glossocalyx brevipes (Monimiaceae) jnp 48, 833 '85Guatteria goudotiana (Annonaceae) phy 30,2781 '91Hernandia spp. (Hernandiaceae) bmnh 2, 387 '80Illigera parviflora (Hernandiaceae) cty 22, 393 '91Laurus nobilis (Lauraceae) jnp 45, 560 '82Leontice leontopetalum (Berberidaceae) jnp 49, 726 '86Lindera spp. (Lauraceae) jnp 47, 1066 '84Litsea spp. (Lauraceae) ajc 43, 1949 '90Magnolia spp. (Magnoliaceae) pm 48, 43 '83Monocyclanthus vignei (Annonaceae) jnp 54,1331 '91Nectandra salicifolia (Lauraceae) jnp 59, 576 '96Neolitsea spp. (Lauraceae) jnp 47, 1062 '84Papaver somniferum (Papaveraceae) kps 12, 750 '76Papaver spp. (Papaveraceae) phy 25, 2639 '86Peumus boldus (Monimiaceae) jps 57,1023 '68Phoebe minutiflora (Lauraceae) cpj 49, 217 '97Polyalthia acuminata (Annonaceae) jnp 45, 471 '82Rollinia emarginata (Annonaceae) jnp 49,717 '86Siparuna tonduziana (Monimiaceae) pm 56, 492 '90Sparattanthelium uncigerum (Hernandiaceae) jnp 48, 333 '85Stephania spp. (Menispermaceae) cpb 45, 470 '97


Thalictrum minus chemovar b (Ranunculaceae) llyd 41, 257 '78Thalictrum spp. (Ranuneulaeeae) jnp 45, 252 '82Uvaria spp. (Annonaeeae) nm 51, 272 '97Xylopia spp. (Annonaeeae) pm 30, 48 '76

(-)(R)-isomer:Aniba spp. (Lauraceae) bse 8, 51 '80Anomianthus dulcis (Annonaeeae) bse 26, 139 '98Croton celtidifolius (Euphorbiaeeae) pm 63, 485 '97Ficus pachyrrachis (Moraceae) pm 59, 286 '93Papaver spp. (Papaveraceae) phy 25, 2639 '86

isomernot specified:Aconitum zeravschanicum (Ranuneulaeeae) ene 20, 760 '84Aniba muca (Lauraeeae) rbq 13, 19 '96Annona squamosa (Annonaceae) epj 46, 439 '94Anomianthus dulcis (Annonaceae) bse 26, 139 '98Arctomecon humile (Papaveraceae) bse 18, 45 '90Chelidonium majus (Papaveraceae) jcspt I, 1140 '75Cinnamomum camphora (Lauraeeae) het 9, 903 '78Cocculus laurifolius (Menispermaeeae) tet 36, 3107 '80Corydalis spp. (Papaveraceae) ene 20, 245 '84Croton hemiargyreus var. gymnodiscus (Euphorbiaceae) pa 10, 254 '99Cryptocarya longifolia (Lauraeeae) abs 11Dicentra peregrina (Papaveraceae) ene 20, 74 '84Doryphora sassafras (Monimiaeeae) llyd 37, 493 '74Erythrina arborescens (Fabaeeae) yz 93,1617 '73Fumaria vaillantii (Papaveraceae) ene 17, 437 '81Glaucium spp. (Papaveraceae) cne 19, 714 '83Guatteria spp. (Annonaeeae) pmp 18, 165 '84Gyrocarpus american us (Hernandiaceae) jnp 49, 101 '86Hernandia guianensis (Hemandiaeeae) pm 50, 20 '84Hydrastis canadensis (Ranuneulaeeae) llyd 33s, 1 '70LAureliaphilippiana (Monimiaeeae) phy 21,773 '82LAurobasidium lauri (Exobasidiaeeae) jpp 40, 801 '88Litseaspp. (Lauraeeae) epj 46, 299 '94Machilus thunbergii (Lauraeeae) het 9, 903 '78Magnolia salicifolia (Magnoliaceae) pm 51, 291 '85Ocoteaspp. (Lauraeeae) rlq 11, 110 '80Oropheahexandra (Annonaeeae) bse 27, 111 '99Oxandra major (Annonaeeae) phy 26, 2093 '87Pachygone ovata (Menispermaeeae) jnp 42, 399 '79

113


Papaver spp. (Papaveraceae) cnc 24, 475 '89Phoebe spp. (Lauraceae) jca 667, 322 '94Phylica rogersii (Rhamnaceae) llyd 33s, 1 '70Polyalthia nitidissima (Annonaceae) pm 49,20 '83Sassafras albidum (Lauraceae) llyd 39, 473a '76Thalictrum pedunculatum (Ranunculaceae) izk 21, 246 '88Xylopia frutescens (Annonaceae) pmp 16, 253 '82Xylopia papuana (Annonaceae) npl 6, 57 '95

(Beware of the spelling without the final "e." Reticulin is a connectivetissue protein.)

I the N-oxide:1 Reticuline N-oxide

(+)-isomer:Corydalis pseudoadunca (Papaveraceae) cnc 21, 807 '86Magnolia saliciiolia (Magnoliaceae) pm 48, 43 '83

isomer not specified:Pachygone ovata (Menispermaceae) jnp 42, 399 '79

Iwith a 3,4-ene: I CH30

a-Dehydroreticuline HO

Croton hemiargyreus (Euphorbiaceae) pa 10, 254 '99Licaria armeniaca (Lauraceae) bps 8, 28 '85

CH30OH

I with a (2,N-Me) attack: I CH30

ScoulerineAurotensine HO

OH(d1)-ScoulerineAurotensine:Giaucium oxylobum (Papaveraceae) llyd 33s, 1 '70 OCHs

Structural Index - 6,7-MeO,HO-Substituted 115

(R)(+)-Scoulerine:Corydalis bulleyana (Papaveraceae) pm 52, 193 '83Corydalis caucasica (Papaveraceae) ijcd 27, 161 '89Corydalis incisa (Papaveraceae) cpb 24, 2859 '76Corydalis rutifolia (Papaveraceae) ijcdr 26, 155 '88Corydalis scouleri (Papaveraceae) bull 1Corydalis solida ssp. brachyloba (Papaveraceae) jcsp 13, 63 '91

(5)(-)-Scoulerine:Argemone albiflora (Papaveraceae) ecce 38, 3312 '73Argemone polyanthemos (Papaveraceae) ecce 39, 2491 '74Corydalis claviculata (Papaveraceae) phy 24, 585 '85Corydalis decumbens (Papaveraceae) jcps 4, 57 '95Corydalis gigantea (Papaveraceae) kps 12, 754 '76Corydalis hsuchowensis (Papaveraceae) pm 57, 156 '91Corydalis incisa (Papaveraceae) phy 13, 2620 '74Corydalis intermedia (Papaveraceae) ecce 54,2009 '89Corydalis koidzumiana (Papaveraceae) yz 94, 844 '74Corydalis majori (Papaveraceae) pmp 22, 219 '88Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89Corydalis ochroleuca (Papaveraceae) cjc 47, 1103 '69Corydalis omeiensis (Papaveraceae) tcyyk 4, 7 '92Corydalis saxicola (Papaveraceae) zx 24, 289 '82Corydalis severtzovii (Papaveraceae) cnc 11, 826 '75Corydalis stewartii (Papaveraceae) pm 58, 108 '92Corydalis vaginans (Papaveraceae) cnc 12, 118 '76Disepalum pulchrum (Annonaceae) phy 29, 3845 '90Eschscholzia californica strain bb (Papaveraceae) tet 47, 5945 '91Eschscholzia lobbii (Papaveraceae) ecce 41,2429 '76Eschscholzia oregana (Papaveraceae) ecce 40, 1095 '75Fumaria asepala (Papaveraceae) ijcdr 24, 105 '86Fumaria bella (Papaveraceae) jnp 49, 178 '86Fumaria capreolata (Papaveraceae) jnp 48, 670 '85Fumaria judaica (Papaveraceae) guefd 1, 15 '84Fumaria kralikii (Papaveraceae) ijcdr 26, 61 '88Fumaria petteri ssp. thuretii (Papaveraceae) ijcdr 26, 61 '88Fumaria vaillantii (Papaveraceae) phy 22, 2073 '83Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177 '80Hunnemannia fumariaefolia (Papaveraceae) ecce 45, 914 '79Hypecoum procumbens (Papaveraceae) jnp 46, 414 '83Sarcocapnos crassifolia speciosa (Papaveraceae) phy 28,251 '88Sarcocapnos enneaphylla (Papaveraceae) phy 30, 1005 '91


Sarcocapnos saetabensis (Papaveraceae) phy 30,2071 '91Stephania cepharantha (Menispermaceae) cpb 45, 470 '97

isomer not specified:Annona paludosa (Annonaceae) pmp 22, 159 '88Argemone alba (Papaveraceae) cnc 22, 189 '86Argemone albiflora (Papaveraceae) cnc 22,742 '87Argemone hybrida (Papaveraceae) cnc 22, 189 '86Argemone mexicana (Papaveraceae) cnc 22, 189 '86Argemone orchroleuca (Papaveraceae) kps 6, 798 '86Berberis valdiviana (Berberidaceae) fit 64, 378 '93Chelidonium majus (Papaveraceae) pm 60,380 '94Cop tis japonica (Ranunculaceae) phy 32, 659 '93Corydalis bungeana (Papaveraceae) pm 53,418 '87Corydalis gortschakovii (Papaveraceae) cnc 20, 245 '84Corydalis impatiens (Papaveraceae) patent 3Corydalis ochotensis (Papaveraceae) jcspt I, 390 '77Corydalis pseudoadunca (Papaveraceae) cnc 21, 807 '86Corydalis repens (Papaveraceae) yhtp 17, 3 '82Corydalis soiida (Papaveraceae) guefd 5, 9 '88Corydalis stricia (Papaveraceae) kps 19, 461 '83Corydalis tashiroi (Papaveraceae) pm 67, 423 '01Cryptocarya longifolia (Lauraceae) abs 11Dicentra peregrina (Papaveraceae) cnc 20,74 '84Dicentra speciabilis (Papaveraceae) cnc 20,74 '84Fumaria capreolata (Papaveraceae) ijcd 23, 161 '85Fumaria densiflora (Papaveraceae) ecce 61, 1064 '96Fumaria [udaica (Papaveraceae) ijcd 22, 181 '84Fumaria officinalis (Papaveraceae) cjc 47, 1103 '69Fumaria parviflora (Papaveraceae) cnc 18, 608 '82Fumaria oaillantii (Papaveraceae) cnc 17,437 '81Fumaria spp. (Papaveraceae) jnp 48, 670 '85Glaucium fimbrilligerum (Papaveraceae) cnc 19,464 '83Glaucium oxylobum (Papaveraceae) ecce 50, 854 '84Glaucium squamigerum (Papaveraceae) ecce 49, 1318 '84Glaucium spp. (Papaveraceae) ecce 50,854 '84Mahonia aquiiolium (Berberidaceae) cp 39,537 '85Nandina domestica (Berberidaceae) patent 1Papaver argemone (Papaveraceae) ecce 53,1845 '88Papaver atlanticum Ball (Papaveraceae) ecce 51, 2232 '86Papaver bracteatum (Papaveraceae) IT 24, 400 '88Papaver confine (Papaveraceae) ecce 54, 1118 '89


Papaver cylindricum (Papaveraceae) pm 46,175 '82Papaver fugax (Papaveraceae) kps 4, 559 '88Papaver lecoquii (Papaveraceae) ecce 46, 2587 '81Papaver litwinowii (Papaveraceae) ecce 46, 1534 '81Papaver orientale (Papaveraceae) ecce 56, 1534 '91Papaver pinnatifidum (Papaveraceae) ecce 59, 1879 '94Papaver rhoeas var. chelidonioides (Papaveraceae) ecce 54,1118 '89Papaver setigerum (Papaveraceae) ecce 61, 1047 '96Papaver stevenianum (Papaveraceae) ecce 55, 1812 '90Papaver tauricolum (Papaveraceae) phy 19, 2189 '80Papaver triniaejolium (Papaveraceae) pm 49, 43 '83Stylophorum lasiocarpum (Papaveraceae) ecce 56, 1116 '91Stylophorum diphyllum (Papaveraceae) ecce 49, 704 '84Thalictrum tuberosum (Ranunculaceae) phy 33,1431 '93

landaromatization of the c-ring: I CHsO

Tetradehydroscoulerine HOPseuduvaria indochinensis (Annonaceae)

phy 27, 4004 '88Thalictrum tuberosum (Ranunculaceae)

phy 33,1431 '93

OH!with a (2,3) attack: I CHsO

MunitagineHO

Argemone hybrida (Papaveraceae) cnc 22, 189 '86Argemone gracilenta (Papaveraceae) jnp 46, 293 '83Argemone munita (Papaveraceae) jnp 46, 293 '83Argemone platyceras (Papaveraceae) kfz 22, 580 '88Argemone pleiacantha (Papaveraceae) phy 8, 611 '69

alsounder: 7,8 MeO HO R Me THIQR=3,4-MeO,Ho-benzyl (6,3) attack

OH

OCHs

OCHs

117

(-)-Salutaridine(-)-SinoacutineSinacutine:Artabotrys uncinatus (Annonaceae) jnp 64, 1157 '01 HOBerberis buxifolia (Berberidaceae) daib 44,1458 '83Berberis ilieifolia (Berberidaceae) het 43,949 '96Cassytha pubescens (Lauraceae) het 9, 903 '78Ceraiocapnos palaestinus (Papaveraceae)

jnp 53, 1006 '90Cocculus carolinus (Menispermaceae) jps 61, 1825 '72Corydalis koidzumiana (Papaveraceae) yz 94,844 '74Corydalis majori (Papaveraceae) pmp 22, 219 '88Corydalis ochotensis var. raddeana (Papaveraceae) jcspt I, 390 '77Corydalis stewartii (Papaveraceae) pm 58, 108 '92Croton flavens (Euphorbiaceae) llyd 32, 1 '69Croton lechleri (Euphorbiaceae) pm 62, 90 '96


Iwith a (2,4a) attack: I SalutaridineFloripavineSalutarine

SinoacutineSinacutine

CHsO(+ )-SalutaridineFloripavine:Croton balsamifera (Euphorbiaceae) rlq 1,140 '70Croton plumieri (Euphorbiaceae) rlq 1,140 '70Croton spp. (Euphorbiaceae) llyd 32, 1 '69Glaucium fimbrilligerum (Papaveraceae)

jnp 61, 1564 '98Glaueium flavum (Papaveraceae) phy 27, 1021 '88Glaucium spp. (Papaveraceae) jnp 61, 1564 '98Papaver bracteatum (Papaveraceae) ecce 50, 1215 '85Papaver fugax (Papaveraceae) jsiri 7, 263 '96Papaver orientale (Papaveraceae) book 4Papaver pseudo-orientale (Papaveraceae) ecce 51, 1752 '86Papaver somniferum (Papaveraceae) book 4Papaver triniifolium (Papaveraceae) pm 49, 43 '83Papaver spp. (Papaveraceae) dsa 7, 93 '83Sarcocapnos crassifolia (Papaveraceae) phy 30, 1175 '91Sarcocapnos saetabensis (Papaveraceae) phy 30,1175 '91

CHsO

CHsO

CHsO

HO

o

o


Glaucium contortuplicatum (Papaveraceae) jps 65, 755 '76Nandina domestica (Berberidaceae) yz 94, 1149 '74Ocotea brachybotra (Lauraceae) tl1631 '76Peumus boldus (Monimiaceae) fit 54, 175 '83Platycapnos saxicola (Papaveraceae) phy 30,3315 '91Stephania brachyandra (Menispermaceae) tcyyk 4, 11 '92Stephania cepharaniha (Menispermaceae) bpb 22, 268 '99Stephania dicentzinifeza (Menispermaceae) zh 15, 8 '84Stephania dielsiana (Menispermaceae) zh 14, 57 '83Stephania elegans (Menispermaceae) ijnp 42, 147 '80Stephania epigaea (Menispermaceae) nyx 5,203 '85Stephania graciienia (Menispermaceae) ijnp 3,8 '87Stephania micrantha (Menispermaceae) yx 16, 557 '81Stephania officinarum (Menispermaceae) zx 32, 368 '90Stephania pierrei (Menispermaceae) jnp 56, 1468 '93Stephania yunnanensis (Menispermaceae) zx 31, 296 '89Strychnopsis thouarsii (Menispermaceae) bse 23, 679 '95

(dll-Salutaridine(dll-Salutarine: (structure the same as (+)-Salutaridine)Croton salutaris (Euphorbiaceae) phy 20, 543 '81

isomernot specified:Antizoma angustifolia (Menispermaceae) jnp 51, 584 '88Croton linearis (Euphorbiaceae) rlq 1, 140 '70Sinomenium acutum (Menispermaceae) llyd 33s, 1 '70Thalictrum foetidum (Ranunculaceae) pm 56,337 '90

(theN-oxide: I (+)-Salutaridine N-oxide

Papaverbracteatum (Papaveraceae) pm 58, 368 '92

anda hydrogenated double bondatthe8,8a-position :

CHsO

(-)-8,14-Dihydrosal utaridineHO

Crotondiscolor (Euphorbiaceae) llyd 32, 1 '69 CHsOCrotonechinocarpus (Euphorbiaceae) llyd 32, 1 '69 0Crotonlinearis (Euphorbiaceae) llyd 32, 1 '69

119


Croton plumieri (Euphorbiaceae) phy 8, 777 '69Croton stenophyllus (Euphorbiaceae) ref 16, 45 '82Sinomenium acutum (Menispermaceae) bydx 23, 235 '91Stephania brachyandra (Menispermaceae) cty 13, 1 '82

CH30

Hernandia voyronii (Hernandiaceae) pm 64, 58 '98Ocotea brachybotra (Lauraceae) tl 1631 '76Thalictrum [auriei (Ranunculaceae)

jnp 62, 803 '99

HO

(-)-Ocobotrine

CH30o

Iand hydrogenated double bonds: I CH30

HOTetrahydrosinacutine

Ocotea brachybotra (Lauraceae) fes 32, 767 '77

oIwith a (2,8) attack: I CH30

CorytuberineHOHOAconitum spp. (Ranunculaceae)

ecce 60, 1034 '95Actaea spicaia (Ranunculaceae)

ecce 60, 1034 '95Adonis spp. (Ranunculaceae) ecce 52, 804 '87Annona cherimolia (Annonaceae) jnp 48, 151 '85Aquilegia spp. (Ranunculaceae) ecce 52, 804 '87Aristolochia clematitis (Aristolochiaceae) ecce 52, 804 '87Caltha palustris (Ranunculaceae) ecce 52, 804 '87Chelidonium majus (Papaveraceae) pm 60, 380 '94Cissampelos pareira (Menispermaceae) fit 63, 282 '92Clematis recta (Ranunculaceae) ecce 52, 804 '87Consolida regalis (Ranunculaceae) ecce 52, 804 '87Corydalis dasyptera (Papaveraceae) tcyyk 9, 37 '97Corydalis gortschakovii (Papaveraceae) cnc 13, 702 '77Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89

CH30

616

CODE

aaaabcaajpsaaqaabbabcabfabsacaccacccacracreacsacssbacvadqafbaimajbajcajpsakzalapapfapjapnappaprapsaptapwaqaqsc

The Simple Plant Isoquinolines

Journal Names Appendix

JOURNAL NAME

Acta AmazonicaAnales Acad. Brasil Cienc.Al-Azhar Journal of Pharm. Sci.An. Asoc. Quimica ArgentinaArch. Biochem. Biophys.Agr. Biol, Chern.Ann. Bot. Fenn.(see ABSTRACTS below)Anal. Chern.Acta Crystallog., Commun.Acta Crystallog., Sec. C Commun.Anticancer ResearchAcgc Chern. Res. Commun.Acta Chimica Scandinav.Acta Chimica Scandinav., Ser. BActa Gent. Venze.Anales De QuimicaActa Farm. BonaerenseAnnals of Internal MedicineAmerican Journal of BotanyAustralian Journal of ChemistryAlexandria Journal of Pharm. Sci.Arm. Khim. Zh.Acta LeidensiaArch. Pharm. (Germany)Ann. Pharm. FranceActa Pharm. Jugosl.Acta Pharm. Nord.Acta Pol. Pharm. (Poland)Archives of Pharm. Res.Acta Pharm. SuecicaActa Pharm. Turc.Arch Pharm. (Weinheim)An.Quim.An. Quim. Ser. C

archauaaupbabfbbbbebemmbesjberbfsbgacbiobkcsbmelbmnhbookbpbpbbpsbrbsbscqbs&ebscfbscqbspbsrsbullbydxCAcbcccccccelcctcfchernchimchrchycicjccjr


Arch. Androl.Ann. Univ. Abidjan Ser. CActa Univ. Palacki. Olomuc., Fac. Rerum Nat., Chern.Bol. Assoc. Brasil Farm.Biosci. Biotech. Biosci.Biomed. ChromatographyBull. Chinese Materia MedicaBull. Chern. Soc. JapanChemische BerichteBull. Fac. Sci., Assiut UniversityBulletin Georgian Acad. Sci.BiokhimiyaBulletin Korean Chern. Soc.Bioorg. Med. Chern. LettersBull. Mus. Natl. Hist. Nat. Sect. B(see BOOKS below)Biochem. PharmacologyBioI. Pharm. BulletinBull. Pharm. Sci. Assiut Univ.Brain Res.BiosciencesBiol, Soc. Chil. Quim.Biochem. Systematics & Ecol.Bull. Soc. Chim. Fr.Bull. de la Soc. Chilena de QuimicaBull. Sci. PharmacologyBull. Soc. R. Sci. Leige(see BULLETINS below)Beijing Yike Daxue XuebaoChemical AbstractsChern. Ber.Chern. CommunicationsColl, Czee. Chern. Comm.Chinese Chern. LettersContrib. Gent. Teenol. (Univ, Tee. Estado, Santiago)Cesk. Farm.ChemicaChimiaChromatographiaChung-Hua Yao Hsueh Tsa ChiliChern. Ind. (London)Canadian Journal of ChemistryCanadian Journal of Research

617

618

clcnccpcpbcpjcracrabcrhscrtctctycwfcwhpcytpczdaibdantdbandissdmddsadujebejcpejpsexpfesffbdfitfmfrmfzsgcigogpguefdhcahethhhhhphkkuchuehx


Chern. LettersChern. Nat. CompoChern. Pap.Chern. Pharm. BulletinChinese Pharmaceut. Journalc. R. Acad. Sei., Ser. CC. R. Acad. Bulg. Sci.C. R. Hebd. Seances Acad. Sci., Ser. CChern. Res. Toxicol.Clinical ToxicologyChung Ts'ao YaoChih Wu Fen Lei Hsueh PaoChih Wu Hsueh PaoChung Yao Tung PaoChern. ZvestiDissertation Abstracts Int. b001<1.Akad. Nauk Tadzh. SSR001<1.Boig. Akad. Nauk(see DISSERTATIONS below)Drug Metab. Dispos.DogaSeriADirasat-Univ; Jordan Ser. bEconomic BotanyEur. J. Clin. PharmacologyEgypt Journal of Pharm. Sci.ExperientiaFarmaco Ed. Sci.Fabad. Farm. Bilimler Derg.FitoterapiaFolia Med.Farmatsiya (Moscow)Faming Zhuanli Shenqing Gongkai ShoumingshuGazetta Chimica ItalianaGarcia OrtaGeneral PharmacologyGazi. Univ. Eczacilik Fak. Derg.Helvetica Chimica ActaHeterocyclesHerbaHungHua Hsueh Hsueh PaoHwahak Kwa Kongop Ui ChinboHacettepe Univ. Eczacilik Fak. Derg.Huaxue Xuebao


hyziangiansiant

Huaxi Yaoxue ZazhiIzv. Akad. Nauk Gruz., Ser. Khim.Izv. Akad. Nauk SSSR Ser. Khim.Izv. Akad. Nauk Tadzh. SSR Otd. Fiz. Mat. Khirn. Geol.

NaukIndian DrugsIndian Journal of Chern. Sec. BInt. Journal of Crude Drug Res.Indian Journal of Chern. Soc.Indian Journal of Exp. Biol.Indian Journal of Heterocycl. Chern.Indian Journal of Natural ProductsInt. Journal of PharmacognosyIndian Journal Pharm. Sci.Iyakuhin KenkyuIzv. Khim.Journal of American Chemical SocietyJournal of Agric. & Food Chern.Journal of Amer. Pharm. Ass. Sci. Ed.Journal of Bangladesh Acad. Sci.Journal of ChromatographyJournal of Chromatography AJournal of Chern. Crystal.Journal of Chin. Chern. Soc. (Taipei)Journal of the Chern. Soc. of PakistanJournal of Chinese Pharm. ScienceJournal of Chinese Pharm. UniversityJournal of Chemical ResearchJournal of Chemical Research Synop.Journal of the Chemical Society-CJournal of the Chemical Society-Chern. CommunicationsJournal of Chern. Soc. PakistanJournal of the Chemical Society-Perkins TransactionsJournal of Crystallographic & Spectroscopic Res.Journal of EthnopharmacologyJournal of Fac, Pharm. Istanbul Univ.Journal of Heterocyclic Chern.Journal of Inst. Chern. (Calcutta)Journal of the Indian Chern. Soc.Journal of Natural ProductsJournal of Neuroscience ResearchJournal of Natl. Sci. Council Sri LankaJournal of Organic Chemistry

idijcijcdrijcsijebijhcijnpijpijpsikizkjacsjafcjapjbasjcjcajccjccsjcpjcpsjcpujcrjcrsjcscjcsccjcspjcsptjcsrjejfpjhcjicjicsjnpjnrjnscjoe

619

620

joejpjpicjppjppsipsjpsjjrimjscsjsirikdr

kfzkjpkpslacllydlrIsmjpsmjsnasbnatncyhneinlnmnmtnplnpsnrnyxoizojcornrpapatentpazpbpblpebrpcipel


Journal of EthnopharmacologyJournal of Pharm.Journal of Proc. Inst. Chern. (India)Journal of Pharm. Pharmacol.Journal of Pharm. Pharmacol. Suppl.Journal of Pharmaceutical ScienceJournal of Pharm. Society JapanJournal of Res. Indian Med, Yoga HomeopathyJournal of Serb. Chern. Soc.Journal of Sci. Islamic Repub. IranKagoshima Daigaku Rigakubu Kiyo Sugaku

Butsurigaku KagakuKhim. Farm. Zh.Korean Journal of PharmacognosyKhimiya Prirodnykh SoedineniiLiebigs Ann. Chern.LloydiaLekarstv. RasteniyaLife ScienceMansoura Journal of Pharm Sci.Malaysian Journal of ScienceNational Applied Science BulletinNatureNan-Ching Yao Hsueh Yuan Hsueh PaoNeirokhimiyaNeuroscience LettersNatural MedicineNatural Medicine, TokyoNatural Products LettersNatural Products of Scienceno referenceNanjing Yixueyuan XuebaoOkayama Igakkai ZasshiOrient. Journal of ChemistryOrg. Magn. Reson.Phytochemical Analysis(see PATENTS below)Pazhoohandeh(Tehran)Pharm. Bull.Pharm. Biol, (Netherlands)Prog. CIin. BioI. Res.Pharm. Chern. JournalPharmacologist

pcrpespet&ocpertphyphymedphzipjpspjsrpmpmjpmppmspnscpppptpprprspsjptnpwqnrbfrbprbqrefrcqrlqIT

ryzsanscishspsvssysynsyxsztaxontcdhtcyyktet


Plant Cell Rep.Proceedings of the Chemical SocietyPlant Cell Tissue & Organ CulturePertanikaPhytochemistryPhytomedicinePharmaziePakistan Journal of Pharm. Sci.Pakistan Journal of Sci. Res.Planta MedicaPahlavi Med. JournalPlanta Medica Phytother.Planta Medica Supp.Proceedeings of the National Sci. Council, Rep. ChinaPlant PhysiologyPhytochem. Potential Trop. PlantsPhytotherapy ResearchPhytotherapy Research Supp.Pharm. Soc. JapanPhyton (Horn, Austria)Pharm Weekbl. (Sci. Ed.)Quim.NovaRev. Brasil FarmRev. Brasil Plant Med.Rev. Boliv. QuimicaRev. Cubana Farm.Rev. Colomb. QuimicaRev. Latinoam. QuimicaRastit. Resur.Redai Yaredai Zhiwu XuebaoSoobshch. Akad. Nauk Gruz. SSRScienceSaengyak HakhoechiSci. Pharm.Sb. Vys. Sk. Zemed. Praze, Fak. Agron., Rada ASynth. Commun.SynthesisShenyang Yaoxueyuan XuebaoShoyakugaku ZasshiTaxonTap Chi Duoc HocTianran Chanwu Yanjiu Yu KaifaTetrahedron

621

622

tetatjctltoxtyhtcwsyfzygyhyhcyhhpyhtpytyxyzzhzkzpfzpnzxzydxzyhzzyzzzz

ABSTRACTS

abs 1

abs2

abs3

abs4

abs 5


Tetrahedron-AsymmetryTurkish Journal of ChemistryTetrahedron lettersToxiconTaiwan Yao Hsueh Tsa ChihWakanyaku ShinpojumuYaowu Fenxi ZazhiYiyao GongyeYouji HuaxueYakhak Hoe ChiYao Hsueh Hsueh PaoYao Hsueh Tung PaoYaoxue TongbaoYaoxue XuebaoYakugaku ZasshiZhongcaoyaoZhongyaocao KejiZ PflanzenphysiolZb. Prir. NaukeZhiwu XuebaoZhonggou Yaoke Daxue XuebaoZhonggou Yaowu Huaxue ZazhiZhonghua Yaoxue ZazhiZhongguo Zhongyao Zazhi

Abstr 23rd Annual Meeting American Society ofPharmacognosy, Aug. 1-5 (1982) Pittsburgh, PA: Abstr-26

Abstr Joint Meeting American Society of Pharmacognosyand Society for Economic Botany, July 13-17 (1981)Boston, MA :31-

Abstr Intemat Res Cong Nat Prod ColI Pharm UNCChapel Hill, NC, July 7-12 (1985):Abstr-19

Proc 1st Int Coni Chern Biotechnol Biol Act Nat Prod(1981) BAtanasova(Ed) Bulgarian Acad Sci Sofia, 31:74-

Proceedings of the 38th Asms Conference 'on MassSpectrometry and Allied Topics: (1990)

abs 6

abs 7

abs8

abs9

abs 10

abs 11

abs 12

abs 13

abs 14

abs 15

abs 16

BOOKS

book 1

Journal Names Appendix 623

Int Conf Chern Biotechnol Biol Act Nat Prod (Proc)1st 31:95-97 (1981)

Plant Tissue Cult Proc Int Congr Plant Tissue Cell Cult5th (1982) :315-316

Tezisy Dokl Molodezhnaya Konf Org Sint Bioorg Khim(1976):59-60

Abstr Internat Res Cong Nat Prod Coll Pharm, UNCChapel Hill, NC, July 7-12 (1985):Abstr-61

Proc Fifth Asian Symposium on Medicinal Plants andSpices, Seoul, Korea, Aug. 20-24 (1984)Bh Han Os Han Yn Han and Ws Woo(Eds) 5:509-518

Abstr 4th Asian Symp Med Plants Spices, Bangkok,Thailand, Sept. 15-19 (1980):170-

Proc Int Symp Recent Adv Nat Prod Res, Seoul, Korea,Dec. 14-16 (1979):18-23

Proc 25th Symp on the Chern of Nat Prod, Tokyo (1982)25:353-360

Biochem. Physiol. Alkaloide, Int. Symposium, 4th, (1972)Meeting Date 1969, 275-8. Publisher: Akad.-Verlag,Berlin, E. Germany.

Revista de la Facultad de Ciencias QuimicasUniversidad Nacional de la Plata 6, 75 (1930)

Abstr 27th Annual Meeting American Society ofPharmacognosy, July 27-30 (1986), Ann Arbor, MI:Abstr-49

Scientific Basis of Traditional Chinese Medicine, Y.Lau &J.P. Fowler (Eds) p. 45 (1982)

624

book 2

book 3

book 4

book 5

book 6

BULLETINS


Chinese Herbal Medicine. US Dept. of Health, Educationand Welfare, Publ. No. (NIH) 75-732, Washington,DCLi,Cp: Book (1974)

Adv Nat Prod Chern-Extraction & Isolation ofBiologically Active Compounds. S. Natori, N. Ikekawa,M. Suzuki (Eds.), Wiley, NY.:240-248 (1981)

Opium Poppy. Botany, Chemistry, and Pharmacology.Kapoor, L.D., Hayworth Press (1995)

Sacred Cacti. K. Trout, Better Days Publication (1999)

Cactus Alkaloids. K. Trout, Better Days Publication,in press

buIll Ars, Usda, Tech Bull 1234, Supt Documents,Govt Print Office, Washington DC (1961)

DISSERTATIONS

diss 1 Dissertation-Ph.D.-Univ Illinois Medical Center (1979):pp 171-

PATENTS

patent 1

patent 2

patent 3

patent 4

Patent-Japan Kokai Tokkyo Koho-08 208,651: 7pp-.(1996)Ca 125:257165y

Patent-USSR-721,1 01:1pp-(1980) Gindarine

Faming Zhuanli Shenqing Gongkai Shoumingshu (2001)CA 135:142208

Faming Zhuanli Shenqing Gongkai Shoumingshu (2000)CA 134:120918