psna newsletter 2 · arabidopsis thaliana, nicotiana tabacum, zea mays , oryza sativa , and others....

PSNA NEWSPhytochemical Society of North America

Sociedad Fitoquímica de América del Norte

Société Phytochimique de L’Amerique du Nord

Volume 43, Number 1 April 2003

PRESIDENT’S LETTER

IN THIS ISSUE

Invitation to Peoria

Will It Play in Peoria? - 2003 Annual Meeting Preview√

√

What Phytochemists Do When They’re Really Bored√

√ Annual Meeting Forms and Information

Hail to the Chief - Meet Our New Prez!√

Eric Conn - 50 Years of Plant Biochemistry

In August, our Society will have itsannual meeting in the city of Peoria,Illinois. This year’s topic is the use ofmodel systems to study secondary me-tabolism. As in recent years, the or-ganizers chose a hot and importanttopic for phytochemists. At the begin-ning of any research project or careerquestions emerge about the appropri-ate model system to study a specificproblem. In fact, we use several modelplants for studies in biochemistry, mo-lecular and cell biology, includingArabidopsis thaliana, Nicotianatabacum, Zea mays, Oryza sativa, andothers. The genome of some of theseplants has been sequenced and someproteomes are on the way. Choosinga model is not an easy task, particu-larly in the case of secondary metabo-lism. During the 1980s and 1990s,several groups developed severalmodels. Catharanthus roseus,Lithospermum erythrorhizon, Coptisjaponica and several tropane alkaloid-producing plants, such as Datura, At-ropa, Duboisia were among the most

used models. Today many are nolonger extensively used. Are therespecific criteria one should considerwhen choosing a model system? Fea-sibility, of course, is an important one.This is the reason why Arabidopsiswas adopted as a model. In severalcases, choosing the model will de-pend on who is funding the research.This is not a trivial issue. Today, it isharder than ever to fund and main-tain a productive research group. Of-ten, granting agencies expect that theproposal reports research objectivesas preliminary results. Few panels aredisposed to fund novel ideas and high-risk projects. Thus, few researchersare able to take this risk. I know sev-eral top scientists that are working onlight projects just to obtain fundingand, in parallel, they perform moreexciting, risky research. As a currentmember of a grant panel, my majorquestions are: (a) Is there an impor-tant question to answer? (b) Is there acontribution to knowledge? (c) Is theproject leader well trained? (d) Does

the project leader have a good trackrecord? e) For young scientists, dothey have the potential to carry out theproposed research? In reality, there isno single model system to use in thestudy of living organisms. A geneticapproach using Arabidopsis might al-low a breakthrough in one area, but abiochemical approach using a lilymight make a greater contribution inanother. The goal is to bring a diver-sity of approaches into play to solvefundamental plant problems (see R.Goldberg, Plant Cell, 8: 347, 1996).Plants share their metabolic pathwayswith many organisms. This is true insecondary metabolism even when thefinal product is different. Please cometo Peoria and share the experience ofthe model you are working on.

Victor Loyola-VargasCentro de Investigación

Cientifica de YucatánMérida, Yucatán, México

[email protected]

EXECUTIVE COMMITTEE

President

Victor Loyola-Vargas

Centro de Investigación

Cientifica de Yucatán

Mérida, Yucatán, México

01-9-981-39-43 (phone)

01-9-981-39-00 (fax)

[email protected]

President-ElectDaneel Ferreira

NCNPR, School of Pharmacy

The University of Mississippi

University, MS 38677, USA

662-915-1572 (phone)

662-915-7062 (fax)

[email protected]

Past-PresidentRichard A. Dixon

Sam Roberts Noble Foundation

2510 Sam Noble Parkway

Ardmore, OK 73401, USA

580-221-7301 (phone)

580-221-7380 (fax)

[email protected]

Secretary and Newsletter EditorPeter J. Facchini

Dept. of Biological Sciences

University of Calgary

Calgary, AB T2N 1N4, Canada

403-220-7651 (phone)

403-289-9311 (fax)

[email protected]

Treasurer

Charles L. Cantrell

Hauser Inc.

4161 Specialty Place

Longmont, CO 80504

720-652-7009 (phone)

303-772-8166 (fax)

[email protected]

Editor-in-ChiefJohn T. Romeo

Department of Biology

University of South Florida

Tampa, FL 33620, USA

813-974-3250 (phone)

813-974-3263 (fax)

[email protected]

ADVISORY COUNCIL

Peter Constabel (2003)

Jonathon Poulton (2003)

Margaret Essenberg (2004)

Felipe Vazquez-Flota (2004)

Vincenzo De Luca (2005)

Joe Chappell (2005)

Johnathan Gershenzon (2005)

CONTENTS

1 President’s Letter

Invitation to Peoria

3 Preview of the 2003

Annual Meeting

Secondary Metabolism

in Model Systems

5 Phytochemical

Pioneers

Eric Conn

12 Goodfellas

Meet Some Members of Your

Executive Committee

14 Annual Meeting Flyer

15 Will it Play in Peoria?

Get to Know Our Host City

16 2003 Annual Meeting

Symposia Speakers

18 Registration, Abstract

and Accommodation

Forms

21 Phytochemistry Word

Find

For Those Really Slow Days

22 New RAP Volume

23 Book Order Form

24 Membership Form

2003 PSNA

Annual Meeting

Secondary

Metabolism in

Model Systems

August 9 - 13, 2003

Peoria, Illinois

The Phytochemical Society ofNorth America (PSNA) is anonprofit scientific organizationwhose membership is open toanyone with an interest in phy-tochemistry and the role of plantsubstances in related fields. An-nual membership dues are U.S.$40 for regular members and $20for student members. Annualmeetings featuring symposiumtopics of current interest and con-tributed papers by conferenceparticipants are held throughoutthe United States, Canada, andMexico. PSNA meetings provideparticipants with exposure to thecutting-edge research of promi-nent international scientists, butare still small enough to offer in-formality and intimacy that areconducive to the exchange ofideas. This newsletter is circu-lated to members to keep theminformed of upcoming meetingsand developments within the so-ciety, and to provide a forum forthe exchange of information andideas. If you would like addi-tional information about thePSNA, or if you have materialthat you would like included inthe newsletter, please contact thePSNA Secretary and NewsletterEditor. Annual dues and changesof address should be sent to thePSNA Treasurer. Also check thePSNA website at www.psna-online.org for regular updates.

PSNA NEWS April 20033

lated human diseases. In addition, theincreasingly popular Art Neish YoungInvestigator Minisymposium will beanimated with 5 presentations on dif-ferent aspects of phytochemistry andplant-insect interactions.

Arabidopsis thaliana

Over the past ten years, genetic ap-proaches in Arabidopsis have providedinsights into aspects of phenyl-propanoid and glucosinolate biosyn-thesis that had eluded investigatorsusing conventional biochemical ap-proaches. Further, the Arabidopsisgenome was sequenced and research-ers interested in phytochemistry beganto realize that it contained a treasuretrove of genes involved in naturalproduct biosynthesis. As genes in-volved in exotic secondary metabo-lism pathways were being cloned inmedicinal plants like Catharanthusroseus, Atropa belladonna, Papaversomniferum and Taxus canadensis,several homologues of mostly un-known function were being discoveredin the growing Arabidopsis database.Recent attempts to functionally char-acterize the biosynthetic roles of thesehomologues have revealed thatArabidopsis displays a much greaterdiversity in secondary metabolitesthan had previously been imagined.This fact has prompted much moreintense efforts to study the secondarymetabolite chemistry and biochemis-try of this plant. The symposium, be-ing organized by Clint Chapple(Purdue University), will focus on thebiochemistry and molecular biology ofthree interesting classes of secondarymetabolites found in Arabidopsis. Theremarkable ability of Arabidopsis tomanufacture volatile terpenoids(Dorothea Tholl; Max-Planck-Insti-tute for Chemical Ecology), com-

plex glucosinolates (Jim Tokuhisa;Max-Planck-Institute for ChemicalEcology) and phenyl-propanoids(Clint Chapple) will be explored.Since many of these pathways alsoexist in the other model crops beingconsidered in this meeting, it will beinteresting to see how the Arabidopsismodel will continue to impact com-mercially important field crops likecorn, rice and soybean.

Legumes

Legumes are a rich source of protein,carbohydrate, and fat together with vi-tamins and minerals that have madethem ideal vegetable sources for hu-man and animal nutrition. The richand varied secondary product chem-istry of legumes like soybeans are alsoextremely important since they mayhelp prevent human diseases. In thecase of forage legumes the presenceor absence of different secondarymetabolites appears to be required toimprove their forage quality. Thesymposium being organized by MarkGijzen from the Agriculture CanadaResearch Station in London, Ontariowill include presentations by RichardDixon from the Noble Foundation onthe use of the model legume speciesMedicago truncatula, for investigat-ing natural product biosynthesis in re-lation to forage quality, by Lila Vodkinfrom the University of Illinois, whowill present her studies on the geneticand molecular control of the flavonoidpathway in soybean and by BrianMcGonigle from Dupont Company,who will provide an industrial per-spective on engineering the phenyl-propanoid pathway in soybeans forenhancing flavor and health. Thissymposium should provide fascinat-

continued on page 4

The increasing pace of genomic database development for numerous cropspecies has had an enormous impacton the approaches presently beingproposed for doing research on thecell biology, biochemistry, molecularbiology and metabolic engineering ofnatural product pathways. This isbased on the realization that there isa uniform message being transmittedfrom extensive sequencing ofgenomes from many different speciesof plants. This involves the repeatedidentification of identical classes ofgenes that are responsible for the di-verse secondary metabolism path-ways within different plant species.

Since information of thistype has begun to facilitate the rapidcloning and characterization of re-lated pathways in many more speciesof plants, the pace of discovery ofhow plants have evolved to manufac-ture their amazing diversity of sec-ondary products should increase rap-idly in the next few years. This trendhas certainly been apparent in the lastfew meetings held by the PSNAwhere symposia on diverse themeslike Regulation of Phytochemicals byMolecular Techniques, Phytochemis-try in the Genomics andPostgenomics Eras and most recentlyIntegrative Phytochemistry: fromEthnobotany to Molecular Ecologyall reported extensively how moderngenomics has impacted phytochem-istry. In this context, we have decidedto turn our attention to SecondaryMetabolism in Model Systems. Thisyear’s meeting will focus on how ge-nomic technology has improved ourunderstanding of secondary metabo-lism in such model plant systems asArabidopsis, corn, rice, and soybean.An additional timely symposium willdiscuss how secondary metabolism infungal models (Fusarium and As-pergillus) cause plant disease and re-

PREVIEW OF THE 2003 ANNUAL MEETING

Secondary metabolism in model systems


rational analysis of the large amountsof information being generated frommicroarray, proteomic and meta-bolomic experiments. The rice sym-posium being organized by Tom Okitafrom Washington State University willfocus on how these tools are beingused to investigate metabolic path-ways in rice (Mark Lange fromDiversa Inc.), on the use of this infor-mation to create a rice cell in silicoand the use of such a computerizedcell to do experiments that will pre-dict how a living cell would behaveunder a given set of parameters(Masuru Tomita from Keio Univer-sity). Predictable results obtained in aset of in silico experiments can thenbe tested in vivo to see how such acomputerized could be used in practi-cal improvement of rice.

Fungi

The fungal symposium will focus ontwo model systems, Aspergillus andFusarium, whose genetics are wellcharacterized and that cause importantplant and human diseases, respec-tively. It has been established thatmany of the secondary metabolismgenes for the biosynthesis ofmycotoxins such as aflatoxins,fumonisins and trichothecenes areclustered in Aspergillus and Fusarium.Aspergillus nidulans has been a use-ful model organism for studies of cellbiology and gene regulation. Plasmid,cosmid, EST and BAC genomic li-braries are publicly available. It hasa well-characterized, conventional ge-netic system. It undergoes DNA me-diated transformation and genes fromother Aspergilli as well as some mam-malian genes function in A. nidulans.In addition it is closely related to otherspecies with medical, agricultural andindustrial significance such as A. fla-vus, A. niger, A. oryzae, and A.fumigatus. It has been used as a modelfor penicillin and aflatoxin biosynthe-sis, sharing most of the aflatoxin gene

cluster with A. flavus and A.parasticus. Fusarium graminearumcauses wheat and barley head blightand diseases of corn and rice. F.graminearum produces a group ofsesquiterpene mycotoxins, thetrichothecenes which are inhibitors ofeukaryotic protein synthesis,estrogenic compounds the zearalen-ones and cyclic peptides enniatins.Cosmid and BAC, EST libraries havebeen available. Susan McCormick(USDA) has invited DeepakBhatnagar (USDA), Nancy Keller(Texas A&M) and Frances Trail(Michigan State University) to speakabout genomics in Aspergillus flavus,Aspergillus nidulans, and Fusareumgraminearum, respectively.

Art Neish Young InvestigatorMinisymposium

This year the minisymposium will fo-cus on the chemistry of insect controland how secondary metabolites affectplant-insect interactions. With theslowly increasing number of bannedpesticides, the comprehensive under-standing of how insects interact withplant chemicals and the mode of ac-tion of plant phytochemicals in deter-ring insect predation has become moreimportant. The research advances inthis field promise to greatly increasecommercial demand for natural insectcontrols. Mark Berhow (USDA,Peoria, Illinois) with advice from col-laborators, May Berenbaum (Univer-sity of Illinois) and Renee Wagner(USDA Biocontrol Lab in Columbia,Missouri), has assembled an excellentlist of young investigators who will re-port their studies on phytochemicalsand plant-insect interactions. Severalinteresting subjects will be covered, in-cluding the roles played by secondarymetabolites as inducible defenses inArabidopsis (Brian Taw, University ofChicago) and various roles played by

continued on page 17

ing discussions in relation to manipu-lating secondary metabolism in othercrop species.

Corn

The development of genomic tools forcorn and rice are allowing major newdevelopments in our knowledge tofurther improve corn yields and nutri-tional value, to increase disease, pest,cold and drought resistance, and to usecorn as a factory for production of alarge diversity of products tailor madeto fit industrial and medical uses. Inaddition to its role as a primary sourceof starch, oil and protein, corn has beenstudied extensively to elucidate flavo-noid chemistry, biochemistry and mo-lecular biology. The symposium or-ganized by Erich Grotewold fromOhio State University will focus onadvances made in the biosynthesis ofthree other classes of natural products.The symposium will include a seriesof presentations by Eleanore Wurtzelfrom Lehman College in New York onthe use of genomics to study the ge-netics and biochemistry of carotenoidbiosynthesis in maize, by Alfons Gierlfrom the Technische UniversitaetMuenchen who will speak about theevolution of DIMBOA biosynthesisand indole production in corn, and byBasil Nikolau from Iowa State Uni-versity who will discuss epicuticularwax biosynthesis using a combinationof genomic and metabolomic ap-proaches.

Rice

The complete sequencing of the ricegenome has generated intense inter-est in using it for improvement of riceand other cereals with respect to nu-tritional value and environmentaladaptability to biotic and abiotic fac-tors. This promising new tool has gen-erated intense efforts to produce as-sociated computing capabilities for


My career as a biochemist began whenI started graduate work at the Univer-sity of Chicago in September 1946.The subject was not unknown to meas I’d had a course in biochemistryduring my last year as a chemistrymajor at the University of Colorado. Iwas assigned by the department chairto work with Professor BirgitVennesland and since her interestswere in carbon dioxide fixation asmediated by malic enzyme and othersuch dark fixation enzymes, I wasquickly introduced to higher plants asexperimental material. My first yearin her lab was spent attempting to iso-late Coenzyme II, or TPN+, as NADP+

was called in those days, from 50pounds of hog liver! I followed a pro-cedure published in 1935 by Warburg(the discoverer of TPN+) inBiochemische Zeitschrift. The proce-dure involved such steps as precipi-tating the coenzyme as a mercury salt,and then removing the mercury withhydrogen sulfide; further purificationas a barium salt, followed by remov-ing the barium with sulfate! Not sur-prisingly the first attempt failed; thesecond resulted in about 150 milli-grams of TPN+ that was only 15%pure. Another student and I devised amakeshift counter current purificationto increase its purity to 77%.

In order to follow the yieldof the coenzyme during purification,I had to use the manometric proceduredescribed by Warburg, again fromBiochemische Zeitschrift, involvingglucose-6-phosphte dehydrogenaseand old yellow enzyme. Both enzymeswere obtained from spent brewer’syeast, and this necessitated visits to abrewery on Halsted Street behind theChicago stockyards to collect the yeastwe needed. When the coenzyme wassufficiently pure, it could be easily as-sayed by the characteristic absorptionof the reduced form at 340 nm

PHYTOCHEMICAL PIONEERS

Eric Conn - 50 years of plant biochemistry

and during that period, discovered thatoxidative phosphorylation was cou-pled to the oxidation of DPNH (i.e.NADH) in animal mitochondria. Allof this work was performed in a coldroom in the basement of Abbot Hallthat contained a tabletop Serval cen-trifuge that was enclosed inside ametal cage. On one occasion, the headcame off that centrifuge while runningand nearly demolished the interior ofthe cold room. Fortunately no one wasinjured as we were warned not to re-main in the cold room when the fugewas operating. Lehninger was an out-standing lecturer and later wrote aclassic text in biochemistry. His lec-turing skills were just as good as hiswriting.

My thesis research was notparticularly distinguished; it was en-titled Triphosphopyridine NucleotideEnzymes in Higher Plants, and mainlyconcerned the properties of malic en-zyme in several species. The thesisalso described the enzymatic reduc-tion of oxidized glutathione in wheatgerm extracts by TPNH. Since I hadthe only supply of TPN+ in the UnitedStates, I was probably the first to learnthat plant homogenates contain en-zymes (nucleotidases) that degradeTPN+ as well as oxidases that oxidizethe reduced form, TPNH. This is notsurprising now, but in those days wehad little experience with this cofac-tor. While a crude preparation ofCoenzyme I or DPN+ (i.e. NAD+) wascommercially available from PabstBrewing, I recall little published workon that cofactor at that time.

Vennesland’s laboratory at-tracted many visitors at that time, andshe arranged for them to meet her stu-dents. I recall in particular HansKrebs, Severo Ochoa and his youngpost-doc Arthur Kornberg, Alexander

continued on page 6

(Vennesland’s lab had a new BeckmanDU spectrophotometer, commerciallyavailable only after the war; its powersupply consisted of two 6-volt car bat-teries.) I mention all these things be-cause this was a time when much bio-chemical research involved a lot oftime and effort just to obtain the rea-gents needed for the experiments.

The University of Chicagowas an exciting place in those years,and the Biochemistry Department hada distinguished faculty that includedVennesland, Konrad Bloch and AlbertLehninger, with Frank Westheimer

and Henry Taube nearby in the De-partment of Chemistry. The biochem-istry graduate students at Chicagoconsidered Vennesland the role modelfor faculty supervisors, and I was ex-tremely fortunate to have been ableto work with her. Her biography canbe found on the Web site of the Ameri-can Society of Plant Biology, whereshe is listed in section on Women Pio-neers in Plant Biology. Bloch wasdeep into his work on cholesterol bio-synthesis, for which he later receiveda Nobel Prize. Lehninger’s studentswere studying the oxidation of pyru-vic acid by animal mitochondria,


Todd, Robert Burris and RutherfordNess (Bob) Robertson. I learned manythings from Vennesland, the mostimportant being open, not secretive,about one’s research, and being gen-erous in collaboration with others.She stressed that one usually advancesa project by collaborating with oth-ers who have different but applicableskills and knowledge.

After finishing my Ph. D. Istayed on at Chicago for two years atthe urging of Vennesland who wantedme to co-supervise her graduate stu-dents while she met other commit-ments. This allowed me to acquiresome valuable experience, and I alsotaught the introductory biochemistrycourse in the Biological Sciences Sur-vey, an integrated biology sequenceof five courses in the University Col-lege. Helen Stafford, who came toChicago in 1951 as a post-doc to workwith Vennesland, also taught botanyin that sequence. This gave us valu-able teaching experience that was im-portant later when we applied for fac-ulty positions. It also was the start ofa long friendship with Helen, anotherWoman Pioneer in Plant Biology.

During those two postdocyears in Vennesland’s lab, I was privi-leged to participate at the beginning

of a research problem that has becometextbook material. This was the dem-onstration of the direct enzymatictransfer of hydrogen atoms betweensubstrates and pyridine nucleotidescatalyzed by alcohol dehydrogenase(ADH). This was Harvey Fisher’s re-search project initiated underVennesland. Fisher had to synthesizedideuteroethanol (CH

3CD

2OH) to use

as a substrate, and sought FrankWestheimer’s advice concerning itssynthesis. I provided the crystallineADH and helped Harvey with the MSmeasurements. The results were un-ambiguous (J. Biol. Chem. 202, 687(1953)) and initiated a decade of col-laboration between Westheimer andVennesland that has significantly im-pacted our knowledge of the stere-ochemistry of pyridine nucleotidedehydrogenases. Frank Loewus, whocame to Chicago just as I was leav-ing, joined that project and contrib-uted a major share of the experimen-tal design.

I went to the Soils and PlantNutrition Department in the Collegeof Agriculture at UC Berkeley as anInstructor on September 1, 1992. Mybiochemical interests were welcomedin that department, made famous forstudies on plant nutrition by Dennis

Hoagland. However, two years later,an exchange suggested by PaulStumpf, chair of the small Plant Bio-chemistry Department in the sameCollege resulted in my moving intothat department. I had met Paul whenhe visited Vennesland in Chicago, andhe warmly welcomed me to theBerkeley campus where our relation-ship developed into a life-long per-sonal friendship. We collaborated inwriting the Outlines of Biochemistry,and editing the Biochemistry of Plantstreatise, but never collaborated in re-search because of our different re-search interests.

In Berkeley, I initially con-tinued with work involving pyridinenucleotide enzymes and in one projectdemonstrated that lupine mitochon-dria could carry out oxidative phos-phorylation with the same efficiency(i.e. same P:O ratios) as animal mito-chondria. I also had the great goodfortune to have, as my first graduatestudent, Tsune Kosuge, who had amaster’s degree in plant pathologyfrom Washington State, and soughttraining in plant biochemistry in or-der to apply that discipline to plantpathology. Tsune was familiar withthe role of coumarin as a precursor ofdicoumarol in spoiled sweet cloverhay, studied by the legendary K. P.Link at Wisconsin, and proposed in-vestigating the enzymes involved inthe biosynthesis of coumarin.Kosuge’s thesis research, and papersresulting from it, together with workcarried out after he joined the PlantPathology Department at UC Davis,is probably the first example of amulti-step biosynthetic pathway fora plant natural product described atthe enzymatic level. A series ofKosuge’s papers documents the evi-dence that coumarin is formed insweet clover as follows: phenyla-lanine → trans-cinnamic acid →ortho-coumaric acid → trans-ortho-coumaroyl-β-glucoside → cis-ortho-coumaroyl-β-glucoside → cis-ortho-coumaric acid (coumarinic acid) →


coumarin.The first evidence for PAL,

to my knowledge, is Kosuge’s thesisresearch when he observed formationof trans-cinnamic acid from pheny-lalanine in dialyzed extracts of sweetclover. These experiments eventuallywere discussed with Arthur Neish, adistinguished Canadian plant bio-chemist who, in the 1950s, had al-ready completed an impressive bodyof work on the biosynthesis of ligninfrom phenylalanine and tyrosine. Inhis 1960 review in Annual Review ofPlant Physiology (11:55 (1960)), Artproposed that trans-cinnamic acidmight be formed by transaminationof phenylalanine, reduction of theketo acid to phenyllactic acid, anddehydration to form cinnamic acid.The first two reactions presumablywould require stoichiometric amountsof keto acids and reducing agents(DPNH or TPNH) to accomplish theover-all conversion. Since Tsune’sdialyzed extracts catalyzed detectableamounts of cinnamic acid formedfrom phenylalanine, we believedthere had to be another reaction, andproposed a single enzyme catalyzingthe deamination, analogous to bacte-rial aspartase. In 1958 I visited Art atthe Prairie Regional Lab (PRL) inSaskatoon and we had a good discus-sion. I also met Stewart Brown, whodid some of the early labeling experi-ments on coumarins at PRL, and hascontributed greatly to the literature inthat subject.

One result of this visit wasArt coming to Davis in September,1959 on study leave to look for thedeamination of tyrosine in grasses andphenylalanine in a wider range of spe-cies. Art brought his supply of labeledcompounds as standards, and we pro-vided our new lab facilities for en-zyme work, as well as Kosuge, whowas located in an adjacent depart-ment. Art started looking for TAL inrice, and other grasses, and JaneKoukol, a postdoc from Vennesland,arrived and started working on PAL

in sweet clover. Eventually their workon TAL and PAL was published inPhytochemistry 1:1 (1961)) and J.Biol. Chem. 236: 2692 (1962)) re-spectively. An amusing problem ofnomenclature should be mentioned.We had decided to call these enzymestyrase and phenylalanase, after theenzyme aspartase. However, the edi-tors at JBC insisted that Jane and Iuse the newly agreed-upon nomencla-ture of phenylalanine ammonia-lyasefor PAL.

I’ve been queried occasion-ally about our lack of follow-up onthe discovery of PAL as the enzymegained prominence in plant second-ary metabolism. Because it wasTsune’s finding initially, I urged thathe continue with PAL. However, hewas keen to wind up his work on cou-marin and start looking at problemsin plant pathology that might be ame-nable to biochemical approaches. Hedid just that, in such quantity andquality, that he was elected to ourNational Academy of Sciences in1988. Tragically, this was shortly be-fore he died prematurely from coloncancer. Later I learned that he was tolda few days before his death that bothof us were elected that year.

As Tsune took leadership onthe coumarin problem, my intereststurned to the biosynthesis of cyano-genic glycosides and I concentratedmy efforts and limited resources

studying those compounds. With thehelp of Takashi Akazawa, a younggraduate student from Uritani’s lab inJapan, we soon showed that sorghumseedlings should be an ideal tissue tostudy the biosynthesis of dhurrin, theβ-glucoside of p-hydroxy-(S)-mandelonitrile, the cyanogen in sor-ghum. While sorghum seed containsonly traces of dhurrin, the 3-5 day oldetiolated seedlings contain about 5-10% (dry weight) dhurrin. Since ty-rosine was the obvious precursor, wefed C14 tyrosine to such seedlingsovernight and observed a relativelylarge incorporation (5-10% of the ac-tivity fed) into the glycoside.

We reported these results atthe Federation Meetings in April1998, and were surprised, and some-what chagrined, to hear John Gander,University of Minnesota, describe al-most the same experiments in the fol-lowing paper. Since John had the fol-lowing summer free, I invited him outto Berkeley where we worked hard toidentify intermediates between theamino acid fed and the cyanogen.With that large amount of incorpora-tion, we both thought that it would bea simple matter to find a few spots onchromatograms, identify them andsort out the pathway. Such was not thecase, and it eventually took anotherdecade to establish such intermedi-ates. At the end of the summer Johnreturned home and continued to workon the problem for a few months. But,as success was slow and he had otherinterests, he stopped working on theproblem.

At this point, I decided on adual approach, namely (a) to deter-mine whether the tyrosine moleculewas incorporated intact except for lossof the carboxyl carbon into dhurrin,and (b) to postulate possible interme-diates, label them with C14 and feedthem to seedlings. However, progresswas delayed by my move to the Daviscampus that fall and a delayed sab-

continued on page 8


batical in England in 1960.I’d applied for and received

a 3-yeaar USPHS grant in 1957 (for$12,000 per year) entitled Metabolismof Aromatic Compounds in Plants. Itwas subsequently renewed in 5-yearintervals for a total of 29 years; thefinal year was $120,000, some ofwhich had to accommodate inflationover those 3 decades. About 15 yearsinto those years, when NIH decidedthat it would no longer fund plant re-search, someone at NIH deleted thelast two words in the grant title. Iwanted to complain about that action,but since I had some people on salaryin that grant, I took the coward’s wayout, and accepted the renewal. In 1973NSF started funding our research usu-ally in 3-year grants.

In the mid 1950s, the Uni-versity regents approved a major ex-pansion of the university system thatincluded conversion of Davis to ageneral campus. Paul Stumpf wasasked to set up a general biochemis-try department in Davis, and I wasinvited to go with him. The promi-nence of plant sciences at Davis, andthe fact that the campus was enteringa rapid period of growth was very at-tractive to us. So, in September 1958,Paul and I moved to Davis to initiateour teaching program. We left our stu-dents in Berkeley, since the depart-ment’s facilities would not be readyuntil the following summer. That fallI had about 60 students in the intro-ductory course. The following fall,there were over 100. By the end ofthat decade, we were lecturing toclasses approaching 400. I describethis increase because it was primarilyresponsible for allowing us to hire 8or 9 additional faculty and offer awell-rounded selection of courses.The students and postdocs moved upfrom Berkeley in July 1959. Art Neishand his family arrived in August, andhe and Jane Koukol initiated work onTAL and PAL.

My sabbatical leave wasspent in the Low Temperature Re-

search Station in Cambridge withTony Swain, hoping to learn moreabout plant phenolics. I did a few ex-periments on a project of Swain’s andwe published a brief note indicatingthat gallic acid can also be formedwithout phenylalanine as an interme-diate. I met Tony’s boss, the fabled E.C. Bate Smith, Jeff Harborne, ArthurBell, Leslie Fowden, and TrevorGoodwin, among others, and attendedan early meeting of the Phytochemi-cal Society. These contacts resultedeventually in visits by Fowden andGoodwin to Davis where they taughtin our graduate course in plant bio-chemistry when either Stumpf or my-self was absent on sabbatical. Anotherfortuitous event in Tony’s lab was avisit from Alan Johns, a New Zea-lander I had met in Chicago years ear-lier. I invited Alan to our flat for din-

ner and learned that evening thatGraham Butler was working on cya-nogenesis in flax seedlings in Johns’department in Palmerston North. I im-mediately initiated correspondencewith Graham, and this resulted in hisspending a year’s leave in Davis withus in 1961-1962, and my taking mynext sabbatical in his lab.

My wife and I left England inJune 1960 to spend the summer vaca-tion on the continent, visiting friendsshe made while working in Paris dur-ing the 4 years preceding our marriagein 1959. In Germany I called on HansGrisebach in Freiburg; this was the

first of numerous visits in later yearsto that beautiful city. I’d met Hans inBerkeley when he was a post-doc withMelvin Calvin getting experience inthe use of radiotracers in metabolism.He often attended seminars in our De-partment and was aware of Kosuge’senzyme work on coumarin. When hereturned to Freiburg he suggested thatwe keep in touch. In 1960, he was stilla docent in the Chemistry Institute, butsoon had his own institute where hetrained an entire generation of plantbiochemists. I’ve often lectured in ourgraduate plant biochemistry course onthe elegant research done in Hans’Institute, and am sad that he did notlive to see the many current applica-tions of molecular biology to his field.I’m also indebted to Hans for advis-ing some of his students to obtainsome experience with enzymes in ourgroup. The first person to do so wasKlaus Hahlbrock who came to Davisin 1967.

Back in Davis, I was eagerto continue with my teaching and re-search. Although I performed myshare of service on university commit-tees, my primary commitment was tothe students and post-docs in my lab,and the undergraduates in my courses.Progress was made on the cyanogenproblem; Jane Koukol showed that thecarbon bond between the α and β car-bons in the side chain of tyrosine wasnot severed during the conversion ofthe amino acid to the cyanogen. Shealso showed that the α carbon atomof tyrosine, labeled with C14, gave riseto labeled HCN, while the β carbonremained in the p-hydroxyben-zaldehyde moiety of the cyanogen.Several years later, my graduate stu-dent Ernie Uribe, using tyrosinelabeled with C14 in the α position andN15 in the amino nitrogen, showed thatthe bond between those two atomswas not severed during the synthesis.This important result of course meantthat all intermediates in the pathwayhad to contain nitrogen. However, westill did not know their nature. A later


experiment by Harold Zilg fromFreiburg showed that the oxygenatom involved in the glucosyl link-age was derived from molecular O

2.

This early result implicated a mixedfunction oxidase.

Graham Butler made severalimportant contributions during hisstudy leave. Since Gander had shownthat dhurrin undergoes metabolicturnover in sorghum seedlings, wewondered whether this involved therelease of HCN in the atmosphere. Inan off-the–wall experiment, Grahamand Shula Blumenthal fed C14 HCNto sorghum seedlings in a closed sys-tem for several hours and then exam-ined extracts for any labeled products.To our great surprise, a single, heav-ily labeled compound, quickly iden-tified as asparagine, was observed.Later work by Heinz Floss, LeeHadwiger and Jackie Miller showedthat many (and probably all) plantscontain a mitochondrial synthase thatcatalyzes the replacement of the –SHgroup of cysteine with –CN to formβ-cyanoalanine. While it was easy tounderstand why cyanogenic speciesmight have this enzyme, it was sur-prising to find that non-cyanogenicspecies contained lower amounts ofthe enzyme. This anomaly was prob-ably solved when Shang-fa Yang andhis student Galen Peiser showed thatone molecule of HCN is formed inthe last step of ethylene biosynthesiswhen ACC (1-aminocyclopropyl-1-carboxylic acid) is oxidized by ACCoxidase. In their experiments, theycould not detect HCN, but showed theC14 labeled carbon atom bearing thenitrogen atom in ACC was convertedto labeled asparagine in nearly stoi-chiometric amounts (70% yield).

While in Davis, Grahamdemonstrated the remarkable effi-ciency of tops of flax seedlings inconverting labeled valine to the cya-nogenic glucoside linamarin. The topscould convert 35% of the labeled va-line fed in experiments lasting only 7hours! (Intact seedlings converted

at most 5% under similar conditions.)Various experiments were also de-signed to detect conversion interme-diates, but none were found. Experi-ments with N15 showed that the nitro-gen atom in valine is retained as va-line is converted to linamarin. Sincesorghum shoots were also more ef-fective in dhurrin biosynthesis, thetwo experimental systems were rela-tively equivalent, and when I was inGraham’s group (1965-1966), weworked exclusively on flax.

Butler’s student, Brian Tap-per, was the first to show that oximesare intermediates in the biosynthesisof cyanogenic glucosides. A labeledcompound that had the properties ofan oxime glycoside accumulated inflax seedlings fed C14-valine and O-methylthreonine, a metabolic inhibi-tor of valine. He prepared the oximeof C14 labeled isobutyraldehyde, ad-ministered it to flax shoots and foundthat it was converted to linamarinnearly as efficiently as labeled valine;isobutyraldehyde itself was not con-verted. (Arch. Biochem. Biophys.119:593 (1967). Because oximes canbe dehydrated to form nitriles, and thelatter might be oxygenated to formcyanohydrins, Brian’s results sug-gested this biosynthetic sequence:amino acid → aldoxime → nitrile →α-hydroxynitrile (i.e. cyanohydrin)→ cyanogenic glycoside.

When Klaus Hahlbrock ar-rived in Davis, he prepared the nitrilesand cyanohydrins corresponding topossible intermediates in the biosyn-thesis of linamarin and prunasin, thecyanogen derived from phenyla-lanine. When fed to appropriate tis-sues (flax shoots and petioles ofcherry laurel leaves, respectively)Klaus found that the nitriles were in-corporated, although not as efficientlyas the amino acids. The aliphatic cy-anohydrin was readily converted tolinamarin, but the aromatic cyanohy-drin was toxic to leaves. In a joint notewith Tapper and Butler (Arch.Biochem. Biophys. 125: 1013 (1968)),

the plausible biosynthetic pathwaycited above was put in writing.

Hahlbrock soon demon-strated the last step in the pathway.He detected a UDPG-ketone cyano-hydrin glucosyltransferase in flaxseedlings and purified it 120 fold freefrom β-glucosidase activity. It wasequally active on the cyanohydrins ofacetone and butanone, forminglinamarin and lotaustralin respec-tively. In subsequent work, he con-cluded that the flax enzyme is respon-sible for formation of both cyanogenicglucosides in flax, a fact confirmedyears later using cloned enzyme. LaterPeter Reay purified and characterizedthe glucosyltransferase in sorghumseedlings.

From 1966 on, my researchcentered on several different aspectsof cyanogenesis, with two importantexceptions. The first was work per-formed on cinnamic-4-hydroxylase(C4H) by David Russell. In his thesisresearch with Arthur Galston, Davidhad studied the increase inkaemperferol derivatives mediated byphytochrome in pea seedlings. Heproposed using microsomes fromsuch tissue to look for C4H, and wasquickly successful (Arch. Biochem.Biophys. 122:256 (1967). In an impor-tant but seldom cited paper (J. Biol.Chem. 246:3870(1971)), David re-ported numerous properties of theenzyme including its light-reversibleinhibition by carbon monoxide (CO),and feed-back inhibition of its activ-ity by the product formed, p-coumaricacid. David concluded that his en-zyme had all the properties of a P-450type of cytochrome but that this re-quired studies of the action spectrumfor light reversal of the CO-inhibition.My graduate student Rowell Pottssubsequently measured the spectrum(J. Biol. Chem. 249:5019 (1975)). Hisspectrum, together with action spec-tra obtained in Charles West’s labo-ratory in 1969 for two enzymes

continued on page 10


involved in gibberellin biosynthesisare the only such data concerning themany P-450s now described in plants.Although I co-authored the originalnote in Archives with David, I insistedthat he be the sole author on the JBCpaper, as he had originally proposedthe research and had been completelyself-sufficient in his work in the lab.

A major advance in the cyano-gen biosynthetic work occurred whenIan McFarlane arrived from MichaelSlaytor’s lab in Sydney. By that time,aldoximes, nitriles and α-hydroxynitriles were consideredlikely intermediates because of feed-ing experiments. Since numerousstudies in animal tissues, and some inplants, had shown that microsomalenzyme systems catalyzed C-hydroxylation reactions, I suggestedto Ian that he see if sorghum micro-somes could catalyze the oxidation ofp-hydroxyphenylacetonitrile to p-hydroxymandelonitrile in the pres-ence of NADPH and oxygen. He iso-lated microsomes from etiolated seed-lings in the presence of thiol reagents,and in an early experiment includedtyrosine as a control, not expecting itto be acted upon. Astonishingly, hefound that tyrosine was oxidized bythe particles to form p-hydroxyben-zaldehyde and HCN. Moreover, thisreaction was more rapid than oxida-tion of p-hydroxyphenylacetonitrile.The particles also utilized the al-doxime as a substrate about as wellas the amino acid. The properties ofthis microsomal system were thenextensively studied by Ian and EdithLees, a faculty member on study leavefrom Sydney (J. Biol. Chem.250:4708 (1975)).

Since the conversion of ty-rosine to p-hydroxyphenylacetal-doxime constitutes a 4-electronoxidative decarboxylation, an inter-mediate in that conversion was likely.Earlier work on glucosinolate biosyn-thesis in Ted Underhill’s group inSaskatoon had indicated N-hydroxyaminoacids as intermediates

between amino acids and aldoximesin the biosynthesis of glucosinolates.The next step was the synthesis of N-hydroxytyrosine (NHT).

Birger Moller arrived fromCopenhagen, just as Ian and Edithwere finishing up this work, and de-cided to work on this problem. Heperfected a synthesis of NHT initiatedby Ian, and prepared the C14-labeledcompound. Its efficacy as a substratewas compared with five other com-pounds that, on paper, could be inter-mediates between tyrosine and its al-doxime (e.g. tyramine, N-hydroxy-tyramine, p-hydroxyphenylpyruvicacid oxime). Only NHT was metabo-lized to p-hydroxymandelo-nitrile bythe particles. Moreover, NHT wasproduced from [UC14-C]-tyrosine intracer experiments when unlabeledNHT was added as a trap (J. Biol.Chem. 254: 8575 (1979)).

Another major contributionBirger made to the problem while inDavis was to show that thebiosynthetic sequence catalyzed bythe microsomes is highly channeled(J. Biol. Chem. 255:3059 (1980)). Hisexperiments explain why, in the earlywork done both in Butler’s and ourlabs, we never easily detected anyintermediates. Helen Stafford wasamong the first to propose metabolicchanneling in the synthesis of natu-ral products, and she has discussed thecriteria that need to be met in herchapter in Volume 7 of The Biochem-istry of Plants. While this first papermet many of those criteria, recent re-search from Birger’s group in Copen-hagen has gone on to show that thethree enzymes involved in the biosyn-thesis form an organized complex.Recently, Meinhart Zenk told me hewas skeptical of that early paper un-til Birger presented his recent workon channeling at a seminar in Munichtwenty years later.

Birger returned to Denmarkafter two years and initially workedat the Carlsberg Institute on aspectsof photosynthesis. In 1985, when he

was appointed to the chair in PlantBiochemistry at the Royal Agricul-tural and Veterinary University, heproposed returning to the cyanogen-esis field, and I strongly encouragedhim to continue with his biosyntheticwork. Applying the tools of molecu-lar biology to that and related prob-lems, he and his group have greatlyadvanced our understanding of thesubject. He reviewed their progress atthe PSNA meeting in Montreal (Rec.Advan. Phytochem. 34:191(2002)),and numerous other papers have ap-peared since then.

Other problems, usually re-lated to cyanogenesis, attracted theinterest of workers in my lab from1970 until I retired in 1993. HaroldZilg, Kevin Farnden and Mark Rosen,an undergraduate student, studiedvarious stereochemical aspects of cya-nogen biosynthesis. Adrian Cutlerexamined metabolic channeling dur-ing biosynthesis in arrow grass andflax. Wendy Swenson and JoeOlechno described new cyanogensfrom Acacia sutherlandin andNandina. Mary Seely, Gary Kurokiand Lang-lai Xu studied the proper-ties of α-hydroxynitrile lyases in sev-eral species while Dirk Selmar con-centrated on the physiological role ofthat enzyme. The β-cyanoalanine syn-thase of lupine was studied by HarlandHendrickson, and Peter Castric andKevin Farnden discovered a new en-zyme that hydrolyzes β-cyanoalanineto asparagine, thereby explaining howthe nitrogen in cyanogens is retainedby plants rather than being lost asHCN. Compartmentation of cyano-genic glycosides and their catabolicenzymes attracted the interest of JimSaunders, Jonathan Poulton, SusanThayer, Eve Wurtele, Mineo Kojimaand Marco Frehner. Poulton, KazukoOba and Alain Boudet extended suchwork to enzymes and intermediates ofcoumarin biosynthesis in sweet clo-ver. Wolfgang Hosel and Ingrid Tobercharacterized β-glucosidases in sor-ghum, and Hosel emphasized the

reported.While testing acacias in Cali-

fornia gardens, I also started lookingat eucalyptus. Because there was onlyone documented report of cyanogen-esis in that large genus - prunasin inE. cladocalyx - I reasoned thereshould be some additional cyanogenicspecies. Initially I found two addi-tional cyanogenic species in Califor-nia, and this led to my last sabbaticalin Australia in 1981-1982.

My family and I flatted inAdelaide where I had space in thelaboratory of Brian Coombe at theWaite Institute. (I’d met Brian in 1955when he was getting his Ph. D. inplant physiology at Davis.) The Waitehas over 300 species of eucalyptus intheir botanic garden and that kept meoccupied for several weeks. We thenstarted visiting botanic gardens inAdelaide, Brisbane, Canberra, Mel-bourne, Hobart, Sydney and Perthwhere I arranged permission to exam-ine both eucalyptus and acacias. Ex-cept for Canberra and Perth, it wassurprising to see that the other gar-dens usually had more specimens ofnorthern hemispheric plants than Aus-tralian species. However, Canberra’sNational Botanic Garden is restrictedto Australian species and proved es-pecially useful.

While in Perth, I met BruceMaslin, an expert on the 800-plusAustralian species of acacia, many ofwhich are native to Western Australia.Bruce was interested in my project,and I mentioned one species I’d de-cided was cyanogenic after testing itin several gardens earlier. Because ofhis taxonomic knowledge, he quicklynamed several related species andproduced herbarium specimens thatwe tested. During that first afternoon,we identified more cyanogenic spe-cies than I had managed to find dur-ing several months of work in gar-dens. Such results from herbaria re-quire that live specimens be locatedin the field, tested for cyanogenesis,and if positive, sampled and pro-

specificity of plant β-glucosidases ina review in TIBS.

Another study, not involvingcyanogenesis, examined the role ofthe non-aromatic amino acid, arogenicacid, in the biosynthesis of tyrosineand phenylalanine in sorghum. Ear-lier studies by Roy Jensen had shownthat tyrosine is formed in mung bean,maize and tobacco by transaminationof prephenic acid to form arogenicacid (pre-tyrosine), followed byoxidative aromatization of the 6-membered ring to form tyrosine. JimConnelly and Dan Siehl showed thatsorghum contains prephenic transami-nase that utilizes glutamate as aminodonor forming arogenate, togetherwith arogenate dehydratase and dehy-drogenase required for aromatizationof arogenate and formation of pheny-lalanine and tyrosine. They could notdetect the dehydratase and dehydro-genase that aromatize prephenic acid.Bijay Singh and Gary Kuroki exam-ined the regulatory properties ofchorismate mutase in several species.

Starting in 1974, my re-search interests broadened because ofcollaboration with David Seigler. Itold David at the 1972 PSNA meet-ing of older literature showing thatsome South African species of acaciacontained cyanogens derived fromvaline and isoleucine, while those inAustralian species are derived fromphenylalanine. This was the only ex-ample at that time of aliphatic and aro-matic cyanogens occurring in thesame genus. David, who teaches planttaxonomy at Illinois although his Ph.D. is in physical organic chemistry, in-formed me of the taxonomic complex-ity of the genus, and we decided tocheck out the earlier work. After con-firming those studies, I started testingacacias in the UCD arboretum for cya-nogenesis, as well as herbarium speci-mens. Leaf material of any positivespecies were then obtained, extractedand worked up to identify the cyano-gen. This project resulted in severalnew cyanogenic glycosides being

cessed for identification of the cya-nogen. This led to several collectingtrips with Bruce in subsequent years.

Papers in Phytochemistry,Kingia, and the Western AustralianHerbarium Research Notes, presentresults of tests on 96% of the de-scribed species of the genus. Thiswork showed that cyanogenic speciesin subgenus Acacia contain onlyaliphatic cyanogens, while cyano-genic species in the two othersubgenera Phyllodineae andAculeiferum contain aromaticcyanogens. These data support tradi-tional taxonomic evidence thatsubgenus Aculeiferum, distributedmainly in Africa and Asia, is moreclosely related to the predominantlyAustralian subgenus Phyllodineaethan to the pan-tropical subgenus Aca-cia. The work on eucalyptus involvedtesting about 1400 individual plantsrepresenting 348 species, 22 of whichwere cyanogenic. (R)-prunasin, de-rived from phenylalanine, was iden-tified as the cyanogen in 10 of thosespecies.

I appreciate the invitation toprepare a description of my researchcareer. I’ve intentionally overempha-sized the early part to let youngerphytochemists know how differentresearch was then without the tech-niques, equipment and biochemicalsavailable now. As always, it’s a greatpleasure to acknowledge the essentialcontributions of all who have workedwith me.

Eric ConnUniversity of California, Davis

Davis, California, [email protected]

Editor’s note: We are priviledged tohave the opportunity to read about thepersonal and professional events thatshaped the lives and careers of emi-nent scholars, such as Eric Conn.Nominations are still welcome forPhytochemical Pioneers who havemade an outstanding impact on theirfield. Please contact the Editor.


I DON’T GET NO RESPECT! NO RESPECT, I TELL YOU!


Peter Facchini - PSNA Secretary and Newsletter Editor

Daneel Ferreira - PSNA President-Elect

Daneel Ferreira graduated from theUniversity of Pretoria, South Africain 1964. He completed the B.Sc.(Hons.) and M.Sc. programs inChemistry at the University of the Or-ange Free State, Bloemfonteinthrough part time studies, whileteaching Mathematics and PhysicalSciences at a local high school. In1969 he was appointed as TechnicalAssistant in the Chemistry Depart-ment at UOFS, obtained the D.Sc.degree in Organic Chemistry in 1973and progressed through the ranks toProfessor of Organic Chemistry in1985, serving as chairperson of theChemistry Department from 1994 -1997. He spent 1977 as a VisitingLecturer at Imperial College, Londonwhere he worked under the supervi-sion of the Nobel laureate, the late SirDerek Barton, and was awarded theDiploma of Imperial College for hiswork on aminoglycoside antibioticsynthesis. While at UOFS he servedas supervisor/co-supervisor for 42M.Sc. and 27 Ph.D. students. He is arecipient of the Gold Medal of theSouth African Chemical Institute, andthe Havenga Prize of the South Afri-can Academy for Arts and Sciences

for longterm, sustained excellence inOrganic Chemistry.

Daneel has worked on thechemistry of flavonoids and proan-thocyanidins focusing on structureelucidation via physical methods, es-pecially NMR and circular dichroism,semisynthesis of oligomers, stereo-selective syntheses of monomericprecursors, and the development ofgeneral methodologies to manipulatethe C6-C3-C6 molecular backbone.He established a research unit forpolyphenol- and synthetic chemistryat UOFS by the Foundation for Re-

search Development in South Africa,and was appointed Director in 1990.In 1999 he joined the Thad CochranNational Center for Natural ProductsResearch as a Visiting Scholar.

He is currently a PrincipalScientist in the Center, where he con-tinues with the synthetic and semi-synthetic work on proantho-cyanidins, focusing in part on solu-tions toward the many unsolvedproblems in this complex field ofstudy. He collaborates with Dr. RickDixon of the Noble Foundation,Ardmore, Oklahoma in an effort toestablish the biosynthetic sequenceto proanthocyanidins (condensedtannins). In addition he works on thestructure elucidation and synthesis ofbiologically active natural products,with special emphasis on structure/activity relationships and selected ra-dio labeling synthetic sequences. Heis the author/co-author of more than220 papers in leading internationaljournals. Besides serving on the edi-torial board of Phytochemistry, heregularly reviews manuscripts for avariety of scientific journals, and alsoresearch proposals for several federalfunding agencies.

Ever wish you knew a little moreabout the next PSNA President? Doyou wonder who collects your hard-

earned cash for the priviledge of be-longing to this esteemed society?Most of all, wouldn’t you like to get

inside the mind of the crazy dude re-sponsible for this newsletter? Now’syour chance, kids. Read on!

Peter Facchini was born and raisedin the great city of Toronto, Canada.He obtained a B.Sc. in Biology in1987 and a Ph.D. in Plant Biochem-istry in 1991 from the University ofToronto. During the course of his doc-toral research, he began to cultivatean interest in plant natural productmetabolism. Peter pursued his firstpostdoctoral research followship

under the supervision of Joe Chappellat the University of Kentucky. In1992, they reported, for the first time,the cloning and characterization of aplant terpene synthase, 5-epi-aristolochene synthase from tobacco.Peter continued his postdoctoral re-search with Vincenzo De Luca at theUniversité de Montréal where theyreported the cloning of tyrosine/dopa

decarboxylase from opium poppy in1994. Peter headed to WesternCanada in 1995 and was appointed aProfessor in the Department of Bio-logical Sciences at the University ofCalgary. In 2002, he was awardedthe Canada Research Chair in PlantBiotechnology. His research programis focused on understanding the regu-lation of alkaloid biosynthesis in

opium poppy and related species at thebiochemical, molecular and cellularlevels. A major interest is the relation-ship between cellular differentiationand secondary metabolism. He is alsoactively engaged in the application ofgenomics technologies to the study ofalkaloid biosynthesis in plants. He hasbeen honoured over the past few yearswith invitations to contribute chaptersto the Annual Review of Plant Physi-ology and Plant Molecular Biology aswell as the Recent Advances in Phy-tochemistry series offered through thePSNA. He currently supervises fivegraduate students, two postdoctoralfellows and a research assistant in hislaboratory. He teaches a number of un-dergraduate and graduate courses in-cluding everything from first yearplant biology (to ~700 students) tojunior-level plant physiology and

senior-level plant biochemistry andplant molecular biology. He is also anassociate editor for the CanadianJournal of Botany. As if he didn’thave enough to do, Peter has servedas your PSNA Secretary and News-

letter Editor for the last three years.Peter is a life-long and avid hockeyplayer although, due to his somewhataverage size, in-yo’-face style andcocky on-ice attitude, he tends to getbeat up a lot. He also enjoys variousoutdoor activities in the nearby RockyMountains especially now that he candistinguish between a black bear anda grizzly. As he enters adulthood, Pe-ter is learning to appreciate the finerthings in life. Like most Canadians,he is particularly fond of whale blub-ber, carribou jerky, and snow cones.His greatest ambition is to haveenough money to buy some newclothes. Although he knows this is pie-in-the-sky on a professor’s salary, hetakes comfort in the fact that all hisold pairs of acid-washed jeans, high-top runners, and Van Halen T-shirts arefinally back in fashion.


Charles Cantrell - PSNA Treasurer

Charles Cantrell is currently a SeniorChemist with Hauser, Inc. inLongmont, Colorado. He was born inBaton Rouge, Louisiana and receiveda B.S. in Zoology and Physiology witha minor in Chemistry from LouisianaState University in 1994. He obtaineda Ph.D. in Chemistry from LSU in1998 under the direction of NikolausFischer. His thesis work focused oninvestigations of crude plant extractspossessing potent activity against My-cobacterium tuberculosis, the gram-positive bacterium species responsi-ble for the disease tuberculosis. Thisresearch led to the isolation of numer-ous terpenoids possessing remarkableactivity against M. tuberculosis. From1998 to 2000 he conductedpostdoctoral research in the Labora-tory of Drug Discovery Research andDevelopment, National Cancer Insti-tute, in Frederick, MD. His researchconsisted of the isolation and struc-ture elucidation of cytotoxic constitu-ents isolated from marine plants andanimals. This research led to the dis-

covery of the chondropsins, a newclass of cytotoxic macrolides from themarine sponge Chondropsis sp. Af-ter this short postdoctoral position, hespent two years as a Research Chem-ist with the Agricultural ResearchService in Peoria, Illinois where hisresearch focused on investigations ofcrude extracts from plant seedshoused within the NCAUR Oilseed

Repository. Charles left ARS in 2001to pursue a career in the private sectoras Associate Director of Research andDevelopment for Tanical Therapeu-tics, Inc. His research at Tanical fo-cused on the identification of smallmolecule drug candidates from plantswith a history of traditional usageagainst such diseases as cancer, rheu-matoid arthritis, and benign prostatehyperplasia. As is true of so manystart-up companies, Charles’s tenurewas cut short when Tanical was un-able to find additional venture capi-tal. Within a few months of leavingTanical, he settled into a Senior Chem-ist position at Hauser, Inc. He has beenPSNA Treasurer since 2002 and willserve a three-year term. He also servesas editor of The Cornucopia, the news-letter for the American Chemical So-ciety (ACS) Division of Agriculturaland Food Chemistry (AGFD). He wasthe recipient of the James G.Traynham Award for Excellence inTeaching and Research in Chemistryin 1998.

Peoria in the Summer of 2003

2003 ANNUAL MEETING PREVIEW


I know what you are thinking. Ithought the same things (and worse)some eight years ago when I firstmoved to the mid-west. Peoria? Flatlandscapes, corn and soy fields, andsome big company that makes yellowearthmoving equipment. Hot and hu-mid in the summer and cold andwindy in the winter. Why would any-body go there on purpose!?

But, it did not take long for meto grow to really appreciate the townand its people. Of all the places I havelived in my life, this was the one placewhere the majority of people I havemet have lived most of their liveshere. Sure some left for a while, butoften they come back.

all the amenities of the larger cities,but few of the hassles—no trafficjams and accessible parking. Localand Broadway theater, a symphony or-chestra, ballet, and all types of livemusic. For the evening out, Peoria of-fers everything from fine dining tolocal pubs and everything in between.The Peoria area has a gambling ca-sino, a superb collection of public golfcourses, and several nearby parks. Iask that you come, visit, and find outfor yourself what plays in Peoria. Ithink you’ll have a wonderful time.

Peoria has a major regional air-port and transportation can be easilyarranged from the airport to the hotel.The meeting hotel is the Hotel PereMarquette, a historic hotel located inheart of downtown Peoria. Just oneblock from the hotel is the PeoriaConvention Center where the sympo-sia, poster sessions, and banquet willbe held. Within easy walking distanceof the hotel are a number of restau-rants and night clubs for lunch andevening entertainment. Four blocksfrom the hotel is the waterfront area—with a newly developed park and foodand entertainment complex. We havea full schedule of symposia for thismeeting, and ample space for posterdisplays—hopefully all posters can be

displayed for the entire meeting. Atentative schedule includes a mixer onSaturday night, scheduled poster ses-sions on Sunday evening and Mon-day afternoon with the banquet onMonday evening. We are going to ar-range some activities for the afternoonoff—tours to local sites as we get vol-unteers in place.

Oh, and by the way, what aboutheading out to the old (new actually)ballpark with the PSNA? The City ofPeoria has just built a new state of theart minor league baseball stadium forthe hometown Peoria Chiefs a merefive blocks from the hotel. The PepsiPicnic Plaza has been reserved for thePSNA for the Tuesday August 12thgame at 7PM. Eat, drink, socialize,and watch the game with your fellowconference attendees, as well as thefolks from the USDA Lab (or the AgLab as the locals call it). We have gotplenty of room.

So, now I hope you are think-ing, “why not!” Come and enjoy themeeting, relax and take in some mid-west hospitality.

Mark BerhowUSDA. ARS, NCAUR

Peoria, Illinois, [email protected]

There really is something tothe place. Peoria is the second largestmetropolitan area in the state afterChicago. The City of Peoria is locatedin central Illinois—within three hoursdriving time of both Chicago and St.Louis. Peoria is located on the IllinoisRiver, a major waterway connectingthe Great Lakes with the MississippiRiver. It has a rich history, sophisti-cation, and diversity. While heavyindustry and agriculture are key partsof the commercial hub that surroundsthe area, there are other reasons thatpeople come and stay here. Peoria has

Arabidopsis Symposium

Dr. Dorothea ThollMax-Planck-Institute for Chemical EcologyJena, GermanyTitle: Terpenoid metabolism

Dr. Jim TokuhisaMax Planck Inst for Chemical EcologyJena, GermanyTitle: Glucosinolate biosynthesis

Dr. Clint ChappleDepartment Of BiochemistryPurdue University,West Lafayette, IN, USATitle: Phenylpropanoid metabolism

Rice Symposium

Dr. Mark LangeTorrey Mesa Research InstituteSan Diego, CA, USATitle: A genomic survey of metabolic pathways in rice

Dr. Masuru TomitaInstitute of Advanced BiosciencesKeio UniversityJapanTitle: Rice E-cells

Speaker TBA

Fungi Symposium

Jiujiang YuFood and Feed Safety Research Unit,USDA/ARS, Southern Regional Research CenterNew Orleans, LA, USATitle: Aspergillus flavus EST library

Dr. Nancy KellerUniversity of Wisconsin-MadisonDepartment of Plant PathologyMadison, WI, USATitle: Aflatoxin biosynthesis gene cluster inAspergillus

Dr Frances TrailDepartment of Plant BiologyMichigan State UniversityEast Lansing, MI, USATitle: Fusarium graminearum genome project.


PHYTOCHEMICAL SOCIETY OF NORTH AMERICA2003 ANNUAL MEETING

August 9-13, 2003

The Hotel Pere Marquette and Peoria Convention Center, PEORIA, ILLINOIS, USA

Secondary Metabolism in Model Systems

Symposium Speakers

Maize Symposium

Dr. Eleanore WurtzelDepartment of Biological SciencesLehman College CUNYBronx, NY, USATitle: Genomics, genetics, and biochemistry ofmaize carotenoid biosynthesis.

Dr. Alfons GierlLehrstuhl fuer GenetikWissenschaftszentrum WeihenstephanTechnische Universitaet MuenchenFreising, GermanyTitle: Evolution of DIMBOA Biosynthesis andIndole Production in Zea mays.

Dr. Basil J. NikolauDepartment of Biochemistry, Biophysics andMolecular Biology,Iowa State University,Ames, IA, USATitle: Genetic and metabolomic analysis ofepicuticular wax biosynthesis in maize


Dr. Benedict HollisterUSDA, ARSBeltsville Agricultural Research CenterBeltsville, MD, USATitle: TBA

Legume Symposium

Dr. Richard DixonNoble FoundationArdmore, OK, USATitle: Medicago truncatula: A model legume for thestudy of natural products and forage quality

Dr. Lila VodkinDepartment of Crop SciencesUniversity of Illinois at Urbana-ChampaignUrbana, IL, USATitle: Genetic and molecular control of the flavonoidpathway in soybean

Dr. Brian McGonigleNutrition and Health, The DuPont Co.Wilmington, DE, USATitle: Engineering of the soybean phenylpropanoidpathway for improved flavor and health benefits

Art Niesh Young InvestigatorMinisymposium

Dr. Eva CasellsDepartment of EntomologyUniversity of Illinois at Urbana-ChampaignUrbana, IL, USATitle: Secondary chemistry of Poison Hemlock and itsassociate herbivores

John TookerDepartment of EntomologyUniversity of Illinois at Urbana-ChampaignPlant defensive compounds as host plant and materecognition cues of gall wasps

Dr. Brian TrawDept. Ecology and EvolutionUniversity of ChicagoChicago, IL, USATitle: Glucosinolates as an induced defense inArabidopsis

Dr. Eric JohnsonUSDA, ARS, NCAURPeoria, IL, USATitle: Plant phenolic insect feeding deterrents

Don’t Be LocoWrite for PSNA News

For more informationcontact the Editor

Hey Pussygato!Annual meeting preview

continued from page 4

certain classes of secondarymetabolites that defend plants againstinsects (Eric Johnson, USDA, Peoria)or that affect insect behaviour in sys-tems like poison hemlock (EvaCassels, University of Illinois) and ininsect galls (Larry Hanks, Universityof Illinois).

Summary

With an original theme and impres-sive list of speakers, we are sure thisyear’s meeting will be interesting andsuccessful. Young scientists in all ar-eas of plant biology who wish to learnabout the functional side of genomicsshould be encouraged to attend. Whatyou learn here may help you develop

new ideas to define the function of thenumerous plant genes that remain tobe characterized. The PhytochemicalSociety of North America invites youto join us in Peoria, Illinois from Au-gust 9 - 13, 2003 for an interesting andproductive gathering.

Vincenzo De LucaBrock University

St. Catharines, Ontario, [email protected]

Susan McCormickand Mark Berhow

USDA. ARS, NCAURPeoria, Illinois, USA

[email protected]@ncaur.usda.gov


PHYTOCHEMICAL SOCIETY OF NORTH AMERICA 2003 ANNUAL MEETING

August 9-13, 2003 The Hotel Pere Marquette/Peoria Convention Center Peoria , Illinois , USA

Registration Form (Please Type or Print Clearly)

Name: ________________________________________________________________________

Business Address: _______________________________________________________________

City: ______________________________ State or Province_____________________________

Country:___________________________ Zip or Postal Code: ___________________________

Telephone: ___________________________ Fax: _____________________________________

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REGISTRATION FEES (Includes admission to all scientific sessions, reception, banquet and book ofabstracts): Due by June 30, 2003 .

Regular Registration US $250.00 ______________

Non-member Registration (includes membership fee) US $300.00 ______________

Student Registration (see Part A below) US $100.00 ______________

Late Registration Fee (after June 7, 2003) US $50.00 ______________

Additional Banquet Tickets US $25.00 ______________

Recent Advances in Phytochemistry - Symposium Proceedings (50% Discount) US $110 ______________

TOTAL ENCLOSED $______________

PART A:

The above named registrant is a graduate student working under my supervision.

Supervisor’s Printed Name: ______________________ Supervisor’s Signature: _______________________

REGISTRATION PAYMENT METHODS:

Credit Card - accepted through meeting website only: http://www.ncaur.usda.gov/psna2003

Check or Money orders in US funds payable to: PSNA 2003 Meeting

Send registration form and payment to: PSNA 2003 MeetingAttention: Mark BerhowUSDA. ARS, NCAUR1815 North University StreetPeoria, IL 61604 USAPhone: (309) 681-6347Fax: (309) 681-6524email: [email protected]




Abstract Submission Form (Please Type or Print Clearly)

Name: ________________________________________________________________________

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City: ______________________________ State or Province : ____________________________

Country:___________________________ Zip or Postal Code: ___________________________

Telephone: ___________________________ Fax: _____________________________________

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Graduate Students and Recent Ph.D. graduates: To encourage participation of young investigators in thismeeting, every effort will be made to provide travel assistance to graduate students and recent Ph.D.s to offseta portion of their travel costs. Please check below if you would like to be considered for financial assistance.Abstracts submitted by graduate students are also eligible for various awards.

Please check if you wish to be considered for a Best Student Paper or Poster Award.

_______ Best Paper or Poster Award _______ Travel Assistance

___________________________________________ Date of Ph.D

Abstracts must be received by June 1, 2003. Send two hard copies of the abstract and a copy on dis-kette (MS-Word) by post to:

PSNA 2003 Meeting

Attention: Mark BerhowUSDA. ARS, NCAUR1815 North University StreetPeoria, IL 61604 USAPhone: (309) 681-6347Fax: (309) 681-6524email: [email protected]

or e-mail (Microsoft Word or WordPerfect format) to: [email protected]

ABSTRACT FORMAT: Typed on plain paper in 12 point Times New Roman font and not exceeding 16.5cm x 7.5 cm (6.5 in x 3.0 in).

INVITED SPEAKERS: (Symposia and Plenary talks): Typed on plain paper in 12 point Times New Romanfont and not exceeding 16.5 cm x 12.5 cm (6.5 in x 5.0 in). Please submit abstracts by June 1, 2003.




Lodging Information

Participants are requested to contact the hotel directly for all room reservations.

All rooms must be guaranteed with a credit card or deposit for at least the first night by July 1st,

2003 to qualify for the block rate. Rooms are subject to availability.

HOTEL RATE: $83 for double or single, plus applicable taxes and fees. Please mention you are

attending the Phytochemical Society of North America Meeting to get the block room rate.

The Hotel Pere Marquette

501 Main Street

Peoria, Illinois 61602

USA

Telephone: (309) 637-6500 or 1-800-447-1676 (Reservations Only)

E-mail: www.hotelperemarquette.com

Other Hotels within walking distance of meeting site:

Holiday Inn City Center Mark Twain Hotel

500 Hamilton Blvd. 225 N.E. Adams Street

Peoria, Illinois 61602 Peoria, Illinois 61602

Telephone: 309-674-2500 Telephone: 309-676-3600

Fax: 309-674-8705 Fax: 309-676-3159

There are several other hotels located with in a short commute to the downtown area.

The City of Peoria is located in central Illinois, with a major regional airport and it is within three

hours driving time of both Chicago and St. Louis. Peoria is located on the Illinois River, a major

waterway connecting the Great Lakes with the Mississippi River, it is home to the USDA National

Center for Agricultural Utilization Research and Caterpillar, Inc. Peoria has a gambling casino, a

supurb collection of public golf courses, and several nearby parks with restored prairies. Downtown

Peoria has a number of restaurants, a newly developed river waterfront park and entertainment com-

plex, and a new minor league baseball park for evening entertainment. The meeting will be co-spon-

sored by the Peoria Regional BioCollaborative (PRB), whose objective is to build a strong biological

research park in Peoria over the next few years.

HOLY SESQUITERPENE LACTONE, BATMAN!

Its the amazing phytochemistry word find - for the chronically bored

Circle each of the letters in each word as you find them.

The uncircled letters reveal the secret message:

_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

P H E N Y L A L A N I N E S G ME H C M M A M I N O A C I D E LE P Y U P E P T I D E E S I N AP I L T R E T O M O R P O O E BY P O A O N D S A C L S R M N AT R A N S C R I P T I O N I A NO O O T L M H Y R S G A T C H TN T M O A E I E I E N T N R P HE E A N T C G D M R I E A O O O

H I D I L O C E E I N B L A T C P N P O L Y M E R O S L P R P Y

G E N O M I C S T B E T O R Y AL E M Y Z N E S I C L S R A R NT O C I D M I E N I S O R Y T IH E A T S H O C K P R O T E I N

AMINO ACID HEAT SHOCK PROTEIN PLANTANTHOCYANIN HISTONE PLASMIDBLOT HOMOLOG POLYMERCELL ION PRIMERCLONE LAB PROMOTERCODON LIGNIN PROTEINDICOT MEIOSIS RNADNA MICROARRAY ROOTE COLI MUTANT SEED (X2)ENZYME PEPTIDE STEMGEL PHENOTYPE TRANSCRIPTIONGENE PHENYLALANINE TRYPTOPHAN

GENOMICS PHYTOCHEMISTRY TYROSINE


Volume 36 of Recent Advances in Phytochemistry - Phytochemistry in the Genomics

and Post-Genomics Eras, the symposium volume resulting from the 2001 PSNA An-

nual Meeting in Oklahoma City, OK is the third volume in this series published byElsevier. Volume 36 centers on the role of phytochemistry in the rapid developments inbiology brought about by the application of large-scale genomics approaches.

Elsevier Publishes Volume 36 ofRecent Advances in Phytochemistry

Genomics has altered the way in which weview plant biology by providing a globalview of cellular processes. Sequencing pro-grams are documenting expressed genes inmany species, but we must still identify thefunction of most genes. Several functionalgenomic approaches can address plant genefunction on a large scale. Plants are combi-natorial chemists par excellence, and under-standing the principles that relate enzymestructure to function will create unlimitedpossibilities to generate novel biologicallyactive natural products. Knowledge of themolecular genetics of plant natural productbiosynthesis will also facilitate pathway en-gineering for plant improvement and humanbenefit. Phytochemistry truly has a great fu-ture in the genomics and post-genomics eras.

The PSNA, under terms of our contract, can sell this volume at almost a 50%

discount. To purchase Volume 36 please contact the Treasurer, Charles Cantrell.

Contributors to this timely volume explore a wide range of topics that include:4 4 4 4 4 Bioinformatics and computational biology4 4 4 4 4 Metabolomics as a component in functional genomic studies4 4 4 4 4 Metabolite profiling4 4 4 4 4 Biopanning by activation tagging4 4 4 4 4 Functional genomics of Cytochromes P450 and their role in biosynthesis4 4 4 4 4 Sequence-based approaches to alkaloid biosynthesis gene identification

4 4 4 4 4 Structurally guided alteration of biosyntheses

Recent Advances in Phytochemistry SeriesPSNA members receive a 40% discount on the following titles

Volume 36 (2001)** Phytochemistry in the Genomics and Postgenomics Eras(List $210.00, PSNA $99.00)

Volume 35 (2000)** Regulation of Phytochemicals by Molecular Techniques(List $210.00, PSNA $102.00)

Volume 34 (1999)** Evolution of Metabolic Pathways(List $222.50, PSNA $122.00)

Volume 33 (1998) Phytochemicals in Human Health Protection, Nutrition, Plant Defense(List $165.00, PSNA $99.00)

Volume 32 (1997) Phytochemical Signals and Plant-Microbe Interactions(List $95.00, PSNA $57.00)

Volume 31 (1996) Functionality of Food Phytochemicals(List $114.00, PSNA $68.40)

Volume 30 (1995) Phytochemical Diversity and Redundancy in Ecological Interactions(List $89.50, PSNA $53.70)

Volume 29 (1994) Phytochemistry of Medicinal Plants(List $71.00, PSNA $42.60)

Volume 28 (1993) Genetic Engineering of Plant Secondary Metabolism(List $89.50, PSNA $53.70)

Volume 27 (1992) Phytochemical Potential of Tropical Plants(List $79.50, PSNA $47.70)

Volume 26 (1991) Phenolic Metabolism in Plants(List $89.50, PSNA $53.70)

Volume 25 (1990) Modern Phytochemical Methods(List $85.00, PSNA $51.00)

Volume 24 (1989) Biochemistry of the Mevalonic Acid Pathway to Terpenoids(List $85.00, PSNA $51.00)

Volume 23 (1988) Plant Nitrogen Metabolism(List $89.50, PSNA $53.70)

Volume 22 (1987) Opportunities for Phytochemistry in Plant Biotechnology(List $59.50, PSNA $35.70)

Volume 21 (1986) Phytochemical Effects of Environmental Compounds(List $75.00, PSNA $45.00)

**Volumes 34, 35, and 36 are available from our new publisher, Elsevier. Please contact the PSNATreasurer, Charles Cantrell, for information on ordering these volumes.

Please send the copy/copies marked above.NEW YORK AND NEW JERSEY RESIDENTS MUST INCLUDE APPLICABLE SALES TAX.

All offers must be prepaid. Major credit cards accepted.Make checks payable to Plenum Publishing Corporation.

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Phytochemical Society of North America

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Please fill in the following application and return to the Treasurer with your dues payment. We are also inthe process of updating the PSNA website, so please respond to the question regarding posting informa-tion on the website and give information on your personal web page if you wish it to be included. Once yourapplication has been processed, you will receive newsletters and special mailings. You are also eligible forPSNA member discounts on the Recent Advances in Phytochemistry series.

Please make check or money order payable to the Phytochemical Society of North America. Paymentmust be made in U.S. dollars, drawn on a U.S. bank. Traveler’s Checks or Canadian Postal Money Orders,payable in U.S. dollars, are also acceptable. We are unable to accept payment via credit card.

Dues schedule: Life (or emeritus) member - no chargeRegular member - $40.00 per yearStudent member - $20.00 per year

Return this statement along with your payment to:

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Research Interests (circle up to 4 items):A. Acetylenes S. Terpenoids stressB. Alkaloids T. Vitamins nn. Industrial applicationsC. Amino acids/proteins aa. Biochemistry/physiology of oo. Structure identificationD. Coumarins herbicides pp. Marine natural compoundsE. Cyanogenics bb. Enzymology qq. Medicinal chemistryF. Flavonoids cc. Cell wall chemistry rr. Membrane structure/functionG. Glucosinolates dd. Chemotaxonomy ss. Molecular/immunologicalH. Lignans ee. Biotechnology techniquesI. Lipids ff. Plant-insect interactions tt. Nitrogen fixation/metabolismJ Nitrogen compounds gg. Plant-microbe interactions uu. Pharmacology/pharmacognosyK. Nucleic acids hh. Plant-plant interactions vv. Plant pathologyL. Organic acids ii. Chemical reactions/organic ww. Plant geneticsM. Phenolics synthesis xx. Recognition-cell surfaceN. Pigments jj. Biochemistry of secondary interactionsO. Quinones metabolism yy. Tissue/cell cultureP. Stilbenes kk. Fungal metabolism zz. Toxicology of naturalQ. Sugars/polysaccharides ll. Growth regulators productsR. Sulfur compounds mm. Biochemistry/physiology of OTHER: _______________________

PSNA NEWSPhytochemical Society of North America

Sociedad Fitoquímica de América del Norte

Société Phytochimique de L’Amerique du Nord

Volume 43, Number 2 December 2003


IN THIS ISSUE

The Changing Face of Phytochemistry

Daneel Ferreira - Changing Faces√

√

Looking Ahead to Ottawa in 2004√

√ 2003 Annual Meeting Wrap-Up

√

Tom Mabry - The Wonderous World of Plant Chemistry

It is indeed a great honor to addressour members as President of PSNAfor 2003-2004. I am privileged andgrateful for the opportunity to servenot only the PSNA membership butalso the larger communities ofphytochemists and plant biologistsduring this short period of the excit-ing and challenging timeframe that wework in.

Our annual meeting (August9-13, 2003) in Peoria – SecondaryMetabolism in Model Systems – wasa resounding success. The programwas divided into several symposia,each focusing on fundamental issuesrelated to important agricultural areasof research, i.e., legumes, rice, maize,Arabidopsis, and fungi. In addition,time slots were reserved for an ex-tremely useful “new techniques” sym-posium as well as the popular ArthurNeish young investigator symposium.As a traditional Phytochemist I wastruly amazed to experience how thefundamental principles of MolecularBiology may be utilized not only to

enhance the beneficial characteristicsof certain crops but indeed also toeliminate some of the unwanted prop-erties, e.g. to improve the flavor andhealth benefits of soybean products.As usual it was a very rewarding ex-perience to witness the enthusiasm ofour five young investigators in theNeish symposium. Their supervisorscan be proud of the contributions theyhave made to the scientific develop-ment of these bright young individu-als. We as a Society are indeed privi-leged to have such talented youngmembers who have the added respon-sibility to launch us into the future.May we again use this opportunity tothank the individual symposia organ-izers for bringing together such astrong scientific contingent, and alsoto Mark Berhow for superbly organ-izing a first class meeting.

Reflecting on the scientificprogram of the Peoria meeting, how-ever, strongly brings to the fore theissue of the “factionalization” of re-cent meetings [see President’s Letter

(Richard A. Dixon), PSNA Newslet-ter, 2001, 41(2), 1]. The Peoria meet-ing clearly catered for the “biologicalgroup” within The Society, hence of-fering considerably less to the “chemi-cal group”. This is perhaps the directresult of the necessity to have a “pro-gram theme” for our prestige publica-tion, Recent Advances in Phytochem-istry. Keeping in mind the importanceof this publication to the financial vi-ability of The Society, we need to thinkvery hard of ways to set up and struc-ture a program that will still be accept-able and indeed marketable as an RAPtheme. Failure to regularly accommo-date both the “chemical” and “biologi-cal” factions at all of our meetings canonly be detrimental to our Society.Phytochemistry and plant biochemis-try should never be viewed as anythingbut different sides of the same coin.Careful scrutiny and analysis of ap-propriate journals indeed reveals thatthe top papers are those where a

continued on page 7

2003 Student Award Winners

EXECUTIVE COMMITTEE

President

Daneel Ferreira

NCNPR, School of Pharmacy

The University of Mississippi

University, MS 38677, USA

662-915-1572 (phone)

662-915-7062 (fax)

[email protected]

President-Elect

Clint Chapple

Department of Biochemistry

Purdue University

West Lafayette, IN, 47907, USA

765-494-0494 (phone)

765-496-7213 (fax)

[email protected]

Past-PresidentVictor Loyola-Vargas

Centro de Investigación

Cientifica de Yucatán

Mérida, Yucatán, México

01-9-981-39-43 (phone)

01-9-981-39-00 (fax)

[email protected]

Secretary and Newsletter EditorPeter J. Facchini

Dept. of Biological Sciences

University of Calgary

Calgary, AB T2N 1N4, Canada

403-220-7651 (phone)

403-289-9311 (fax)

[email protected]

Treasurer

Charles L. Cantrell

Hauser Inc.

4161 Specialty Place

Longmont, CO 80504

720-652-7009 (phone)

303-772-8166 (fax)

[email protected]

Editor-in-ChiefJohn T. Romeo

Department of Biology

University of South Florida

Tampa, FL 33620, USA

813-974-3250 (phone)

813-974-3263 (fax)

[email protected]

ADVISORY COUNCIL

Margaret Essenberg (2004)

Felipe Vazquez-Flota (2004)

Vincenzo De Luca (2005)

Joe Chappell (2005)

Johnathan Gershenzon (2005)

Richard Dixon (2005)

CONTENTS

1 President’s Letter

The Changing Face of

Phytochemistry

3 Phytochemical

Pioneers

Tom Mabry

8 Student Award

Winners

Meet the winners of the Best

Student Presentations at the

2003 Annual Meeting


Announcement

11 Memories of Peoria

Images of the 2003 Annual

Meeting


Neish Symposium

Speakers

16 I Know What You Did

Last SummerOr, How I Spent My Summer

Vacation in Peoria

17 2002 PSNA Business

Summary

18 New RAP Volume

19 Book Order Form

20 Membership Form

2004 PSNA

Annual Meeting

a joint meeting with the

International

Society of

Chemical Ecology

July 24 - 28, 2004

Ottawa, Ontario

The Phytochemical Society ofNorth America (PSNA) is anonprofit scientific organizationwhose membership is open toanyone with an interest in phy-tochemistry and the role of plantsubstances in related fields. An-nual membership dues are U.S.$40 for regular members and $20for student members. Annualmeetings featuring symposiumtopics of current interest and con-tributed papers by conferenceparticipants are held throughoutthe United States, Canada, andMexico. PSNA meetings provideparticipants with exposure to thecutting-edge research of promi-nent international scientists, butare still small enough to offer in-formality and intimacy that areconducive to the exchange ofideas. This newsletter is circu-lated to members to keep theminformed of upcoming meetingsand developments within the so-ciety, and to provide a forum forthe exchange of information andideas. If you would like addi-tional information about thePSNA, or if you have materialthat you would like included inthe newsletter, please contact thePSNA Secretary and NewsletterEditor. Annual dues and changesof address should be sent to thePSNA Treasurer. Also check thePSNA website at www.psna-online.org for regular updates.

PSNA NEWS December 20033

PHYTOCHEMICAL PIONEERS

Tom Mabry: From the cotton fields of Texas to the wonderous world

of plant chemistry

Born and raised on a farm a few milesfrom Commerce, Texas, some 60miles northeast of Dallas, my child-hood was filled with many good timeseven when working in our cottonfields with my three siblings and myparents, farmer/County Commis-sioner Thomas Lee Mabry and house-wife/grade school teacher GraceCreamer Mabry. It was on the farmwhere I developed a curiosity aboutthe natural world, which led me tostudy biology and chemistry in highschool. Luckily, Commerce had asmall college, East Texas State (nowTexas A&M University-Commerce),which my mother, my siblings and Iall attended at very little cost. One ofmy proudest moments occurred inJune, 1952 when I walked across thegraduation stage to receive B.S. andM.S. degrees in Chemistry and a 2nd

Lt. commission in the Air Force viaan ROTC program.

Following college and sixmonths before reporting for activeduty in the Air Force, I worked as achemist for Chance Vought Aircraft,located near Dallas. My induction intothe Air Force began in San Antonioat Lackland Air Force Base, butwithin two months I was assigned asa Research Scientist to Wright-Patterson Air Development Center,Dayton, Ohio. During my two yearsin the Air Force, I evaluated newequipment for aerial photography,married my high school sweetheartMyra Butler, and enjoyed private fly-ing lessons; the latter led me to signup for pilot training for what I envi-sioned would be a long, exciting mili-tary career.

Just after I was notified therewould be a one-year delay before Icould enter the pilot training program,I visited with one of my collegefriends Mark Norwood who was com-

pleting his two years in the Air Force.Mark mentioned that he had been ac-cepted for graduate study in physicsat Rice University in Houston. Mydisappointment with the delay for pi-lot training turned to joy when I tooksteps necessary to leave the Air Forceand study chemistry at Rice in a Ph.D.program. Although in college I hadbeen an honor student in chemistry, I

had no knowledge of reaction mecha-nisms and struggled during my first se-mester in graduate school. Neverthe-less, with the guidance of my outstand-ing supervisor Prof. Martin Ettlinger,I completed a dissertation on the modeof vitamin action of ascorbic acid. Forthese studies, I synthesized many ana-logs of ascorbic acid and comparedtheir vitamin C activity with theirstructural and enzymatic properties.These studies suggested an enzymaticcofactor role for ascorbate’s vitaminactivity. For characterization of thesecarbohydrate-type analogs of ascorbicacid, I often converted them to deriva-tives that were soluble in organic sol-

vents. Thus, derivatization (under verymild conditions) of various classes ofwater-soluble natural products forNMR and GC analyses became a pow-erful analytical procedure I utilized formany of my later phytochemical in-vestigations: for example, studies ofthe beet pigment betanidin (methyla-tion using diazomethane), flavonoidglycosides (forming trimethylsilylethers using hexamethyldisilazane/trimethylchlorosilane), and non-pro-tein amino acids (to N-ethoxycarbonylethyl esters using ethylchloroformate/ethanol). My friend Gene Mitch fin-ished his Ph.D. in chemistry at Ricein 1959 and then accepted a post-doc-toral position with Professor AndreDreiding in the Organic Chemistry In-stitute, The University of Zürich, Swit-zerland. Gene encouraged me to alsojoin Dreiding’s group. With my Ph.D.degree in Organic Chemistry freshlyin hand, it was in great anticipation inJune 1960 when Myra and I boardedthe Queen Mary for our voyage fromNew York to England, and then bytrain from London to Paris to pick upa new Renault. Enroute to Zürichfrom Paris we detoured to Strasbourg,France and there crossed the RheinRiver into Germany in order to visitthe parents of Rice post-doctorate Dr.Heinz Gänshirt in the small BlackForest city of Lahr. When we crossedthe Rhein, we were less than 20 milesfrom the German village of Lichtenau,the home of my second wife Helga andher mother Elisabeth (Omi) Humm,both of whom I would meet only a fewyears later.

Thus, in the summer of 1960,Myra and I began our year and a halfsojourn in Zürich, and it was herewhere I became a “natural productschemist.” Dreiding, a brilliant, mod-ern organic chemist, suggested that Itackle his only natural products prob-


were readily resolved. During thenext few years, we determined thebiosynthesis and remarkable distribu-tion of these unusual pigments, whichDreiding and I named “betalains” in1966.

In 1962, I joined the Depart-ment of Botany at The University ofTexas at Austin to develop a programin phytochemistry determining struc-tures, distribution, and biologicalroles for flavonoids, terpenoids, andalkaloids as well as other smallerclasses of plant secondary com-pounds, all for biochemical system-atics studies being pursued by plantphysiologist Ralph Alston and plantsystematist Billie Turner. The firstkey analysis instrument I purchasedwas an NMR instrument; however,initially I used the spectrometer in theChemistry Department at Rice Uni-versity, and recorded there many ofthe spectra of trimethylsilyl ethers offlavonoids included in my 1970 vol-ume “The Systematic Identificationof Flavonoids” (with post-doctoratesKen Markham and Michael Thomas).

By 1968 I was a full Profes-sor and in the 1980s served for sev-eral years as Chairman of Botany, andsince 1999, following reorganizationof Biology at UT-Austin, I have beena member of the Section of Molecu-

lar Cell and Developmental Biologyin the School of Biological Sciences.A quote from a footnote in my 2001career review paper in the Journal ofNatural Products sums up the senti-ments I quickly felt upon starting mynew position in Austin. Once at UT-Austin, I soon recognized that I wasindeed fortunate to be one of the firstchemists in a group of biologists whowere excited to study, understand andenjoy the world of plants around usand at the same time were deeply con-cerned with preserving and protect-ing this green earth for future genera-tions. Within six years I was a fullprofessor envying no one as I cher-ished my continually challenging ex-traordinary position, which was sup-ported by several large fully equippedphytochemistry laboratories (GC,UV, NMR, MS, and GC-MS instru-ments), all staffed with excellentbotany Ph.D. students and remarkableinternational post-doctorates whowere organic chemists and biochem-ists.

I recognize Dr. Klaus Fischeras one the excellent post-doctoratesin my lab in the 1960s; Klaus recentlyretired to the Dallas area from theChairmanship of the Department ofPharmacognosy, University of Mis-sissippi. Of course, when Klaus and

lem, namely, the elusive pigments inthe red beet, compounds whose struc-tures had puzzled his group and oth-ers for many, many years. In my lastyears at Rice I had learned a new (atthat time) technique, NMRspectroscopy, and had become an op-erator of a Varian Associates instru-ment, the big cumbersome HR-60, aswell as a pretty good interpreter ofspectra. When I initiated my lab workin Zürich, there was no NMRspectrometer but within a few monthsVarian opened a European office inZürich with an HR-60. Soon there-after, I inquired of the American man-ager Les Procter if I could use theirHR-60 in the evenings and on week-ends, and to my delight he replied“okay” and handed me keys to the of-fices. Within a few months I hadstacks of NMR spectra of my newlyprepared methylated and acetylatedderivatives of neobetanidin, com-pounds that were not only soluble inorganic solvents but that also con-tained all the carbon atoms of the wa-ter-soluble betanidin, the aglycone ofthe main red beet pigment betanin.When my data were combined withthose of Dr. Hugo Wyler, Dreiding’soutstanding assistant who had eluci-dated key fragments of the pigment,the structures of the beet pigments

Professor Andre Dreiding and post-doctorate Tom Mabry, 1960.


his wife Helga first arrived from Ger-many in 1965, little did I expect Helgato become my second wife. Helga hadbeen trained as a Chemical Technicianat the Science Academy in Isny (insoutheastern Germany) and then

1962 to mid-1960’s Mabry research group (from left): Dr. Heinz Rösler (Ger-man, later American); Dr. Henri Kagan (French); Dr. Peter Seeligmann(Argentinean); Ph.D. students Walter Renold (Swiss), Gene Miller (American)and Al Wohlpart (German-American); Dr. Jacques Kagan (French, later Ameri-can); American Ph.D. students Morris Cranmer and Jim Pipkin; Mabry.

Mid to late 1960’s Mabry research group (from left); Christina Chang (Ph.D.student); Dr. Iain Taylor (Canadian); Dr. Ken Markham (New Zealander); Ph.D.students Al Wohlpart, Gene Miller and Julius “Bud” Kroschewsky; Mabry; Dr.Michael Thomas (English); lab assistant Helga Fischer (German, later Ameri-can); Dr. Klaus Fischer (German, later American); lab assistant Hanspeter Rüesch(Swiss).

worked as a chemistry laboratory as-sistant at the University of Tübingen,as well as in German industry. Withsuch a rigorous laboratory back-ground, including many invaluableanalytical skills, Helga easily became

one of my best lab assistants and co-edited with me and Jeffrey Harbornethe 1975 volume “The Flavonoids.”Since our marriage in 1971, Helga hasbeen a terrific partner not only for ourhome life but also in most of my sci-entific adventures in almost all coun-tries in the expanded European Un-ion, from the Canary Islands to War-saw, from London to Athens. In ad-dition, we spent almost a year inFreiberg, Germany during my tenureas a Guggenheim Fellow in the labsof Prof. Wolfgang Barz; here I learnedtechniques for manipulating andanalyzing plant cell cultures. We alsohad a half-dozen enormously stimu-lating stays in Heidelberg in the pe-riod 1983-2001 when Prof. DietmarBehnke hosted me during my Alex-ander von Humboldt Senior Scientistvisits. Moreover, the village home ofHelga’s mother has served every sum-mer since 1971 as our quiet Rhein val-ley retreat. Since his birth in 1974,our son Patrick has also spent all hisvacations in Germany. Still today, aspecial summer pleasure for me is tobicycle from Lichtenau to the RheinRiver where I take a ferry across toFrance to experience another culture,really another world, in the Alsatiancountryside. However, our greatestjoy is to have Helga’s mother with usin Austin every year from Decemberto April.

In my 2001 review paper, Icommented on only four of dozens ofresearch projects: 1) establishing thestructures, biosynthesis, and distribu-tion of the unique betalain pigments;2) the development of a chemical-structural basis for a biochemical sys-tematic program; 3) unraveling themechanism of action of the antiviralproteins in Phytolacca; and 4) show-ing how a non-protein amino acidfrom Guam cycad seeds may be in-volved in causing the Guamneurodisease ALS-PDC (amyotropiclateral sclerosis-Parkinson’s demen-tia complex), findings which supportthe hypothesis that substances in ourdiets and in the air we breathe may


cause major neurodiseases includingParkinson’s, Alzheimer’s, and ALS.To illustrate additional diversity of ourprogram, which has resulted in >600publications, titles of 27 of more than60 dissertations and theses supervisedfrom 1965 to 2002 are presented:

“Biochemical and BiosystematicStudies of Baptisia Alkaloids” (Mor-ris Cranmer, 1965)“The Ultraviolet Spectral Analysis ofCoumarins” (Genie Bracken-ridge,1968)“Origin of the Texas Gulf Coast Is-land Populations of Ambrosiapsilostachya DC.: a Biochemical andNumerical Systematic Investigation”(Janet Potter, 1970)“The Chemistry and InfraspecificVariation of Sesquiterpene Lactonesin Ambrosia confertiflora DC.(Compositae): ChemosystematicStudy at the Populational Level”(Walter Renold, 1970)“Nucleic Acid Studies amongCentrospermae Species” (ChristinaChang, 1971)“Betalamic Acid and Other Productsof the Biotransformations of L-Dopain Betalain Biogenesis” (LindaKimler, 1972)“Biochemical Systematic Investiga-tions of Western Hemisphere Speciesof the Genus Vernonia (Compositae)Emphasizing Flavonoid Chemistry”(Zeinab Abdel-Baset, 1973)“The Chemistry and Distribution ofNew Germacranolide-type Sesqui-terpene Lactones in the North Ameri-can Taxa of the Genus Vernonia(Compositae)” (William Padolina,1973)“The Distribution of Azoxy-glycosides, Amino Acids andBiflavonoids in the Order Cycadales:Their Taxonomic, Phylogenetic, andToxicological Significance” (SaifuDossaji, 1974)“The Chemistry and Distribution ofSesquiterpene Lactones andFlavonoids in Parthenium (Compo-sitae): Systematic and Ecological Im-

plications” (Eloy Rodriguez, 1975)“Sulfated and NonsulfatedFlavonoids from Flaveria, Sartwellia,and Haploesthes” (Munira Al-Khubaizi, 1977)“Phytochemical Investigations of theGenus Brickellia (Compositae) Em-phasizing Flavonoids” (BarbaraTimmermann, 1977)“Qualitative and Quantitative Natu-ral Products Chemistry of a DesertPlant Community, Andalgala Valley,Argentina: A Chemical-EcologicalStudy” (Daniel DiFeo, 1977)“Phytochemical Investigations of theGenus Larrea (Zygophyllaceae) Em-phasizing Volatile Constituents andSapogenins” (Charles Bohnstedt,1977)“Biochemical Investigations of Ma-rine Algae of the Texas Gulf CoastEmphasizing Amino Acids” (PaulaNeuman, 1978)“The Terpenoid Chemistry ofHelianthus series corona-solis and itsEcological and Systematic Applica-tions” (Jonathan Gershenzon, 1984)“ A Systematic Study of the GenusKrigia (Asteraceae Lactuceae), Em-phasizing Chloroplast DNA and Nu-clear Ribosomal DNA Variations”(Ki-Joong Kim, 1989)“Phytoalexin Aurone Induction inCephalocereus senilis (old-man cac-tus) Liquid Suspension Culture”(Paul Paré, 1991)“Pokeweed Antiviral ProteinInactivitates Pokeweed Ribosomes;Implications for the Antiviral Mecha-nism” (Maureen Bonness,, 1992)“Isolation and Biological Propertiesof Citrus Limonoids” (GeorgeMitchell-Tapping, 1992)“Protoplasts from Phytolaccadodecandra” (Patricia Koch, 1993)“Chemical and Enzymological Inves-tigations of the PhenylpropanoidPathway in Elicited Cultures ofCephalocereus senilus (“old man”cactus)” David Liu, 1994)“A Study of Known ExcitotoxicCompounds and Isolated NonproteinAmino Acids from Cycads” (Delia

Brownson,1996)“Pigment Dichotomy and MolecularEvolution in the Caryophyllales”(John Clement, 1997)“The Role of Root Exudates inArbuscular Mycorrhizal Initiation”(Carol Mandelbaum, 1997) “Estrogenic Activity of Flavonoidsfrom Cyperus alopecuroides Rottb.(Cyperaceae)” (Amy Bystrom, 2002)“Chitin-Induced Biosynthesis ofPhytoalexin 4β-Deoxyaurone in CellSuspension Cultures of “Old Man”Cactus, Cephalocereus senilis”(Isagani Padolina, 2002)

I acknowledge two very brightstudents, Gani Padolina (listed justabove) and his father WilliamPadolina (eighth from the top of thelist), as they are my only parent-childgraduate student combination. WhileI cannot individually express myheartfelt gratitude to all myhardworking, technically excellent,and very productive colleagues andco-workers, including the sixty-plusgraduate students and well over ahundred post-doctorates, I close withone more quote from a footnote in my2001 Journal of Natural Products re-view paper that testifies to the enor-mous joy I have experienced in mycareer through them. I proudly reportthat my role in complex biologicalchemistry investigations and mystimulating interactions with a largenumber of fascinating colleagues andspecial friends continues still todayto be a great, exhilarating forty-yearride!

Finally, although I still keepmy lab doors open for a few dedicatedand highly talented co-workers, I dobegin to feel increasing excitement asI expand my personal goals and cul-tivate my dreams for yet anotherphase of what has already been overforty “Golden Years.” I like the pros-pect of Helga and spending long-post-poned time with numerous kindredspirits and with many family mem-bers including Myra and Klaus, our


02-03) of Patrick (son) and Birgit.Lastly, I warmly acknowledge

the generous support of the NSF, NIH,and several private foundations in-cluding especially the Robert A.Welch Foundation, which has fundedour program for over 40 years. Also,I express my heartfelt thanks to D.J.Sibley Jr., Theo Weisser, Jimmy Gill,

first spouses, with whom we sharemany special bonds. We especiallyrelish the idea of finally impersonat-ing grandparents for the adorabletwins William Sumner Cooley (left)and Thomas Mabry Cooley (born 05-27-00) of Michele (daughter, far left)and Webb, and the charmingCassandra Caroline Mabry (born 03-

and Feng Gao.Tom J. Mabry

ProfessorMolecular Cell and

Developmental BiologyThe University of Texas at Austin

[email protected]


The changing face of phytochemistry

continued from page 1

fine balance has been struck betweenplant chemistry, plant biochemistryand a strong “molecular” approach.We must always keep in mind that itis the traditional strong chemicalcomponent that makes PSNA uniqueamongst related societies. If our so-ciety were to retain its individualidentity, it is of paramount importancethat the “chemical” componentshould not be neglected.

The changing face of Phyto-chemistry? My very first paper, basedon research done for a Masters de-gree, was published more than 30years ago (Synthesis of pterocarpananalogues: 6α,11α-dehydropterocar-pancoumestan conversion. D.Ferreira, C.v.d.M. Brink and D.G.Roux, Phytochemistry, 1971, 10,1141-1144). Even a superficial

comparison will demonstrate that con-temporary phytochemical research is,no doubt, vastly different from whatit was in those early days. The levelsof sophistication have been raised tosuch an extent that one is somewhatembarrassed by the standard of paperslike the one cited above, of course,always remembering the primitive sta-tus of the techniques we had availableat the time. Such quantum leaps in ourprogress could not have been realizedif it were not for the incredible suc-cesses that have been achieved at theinterface of chemistry and biology.Some of the topics covered at recentmeetings had not even been conceivedsome 10 to 15 years ago, and certainlymany of the topics of the 2015 PSNAmeeting, if we could peep into the fu-ture, would be virtually unrecogniz-able to us now. The very fact that weare dealing with a changed, and

ever changing, discipline exemplifiesits dynamic nature. Our membershave amply demonstrated that they areup to the challenges of the cutting-edge research that is necessary to en-sure our relevance in the broad scien-tific community and society at large.Let us not regard this dynamic andvery powerful momentum towardschange as a threat to our own self in-terest but let us rather embrace it aspart and parcel of the mystique thatstimulated our initial interest and luredus into this exciting and essential areaof research.

Daneel FerreiraNCNPR, School of PharmacyThe University of Mississippi

University, MS 38677, [email protected]


My interest in the sciences was firstkindled when I was forced to reviewan article in Junior High School enti-tled “Our Children’s Children MayLive Forever” from a source that I canno longer recall. My interpretation ofthe article at that time was that nor-mal human cells have a limited ca-pacity to proliferate. After a finitenumber of cell divisions, the cellswould “age” and stop dividing. Re-setting this biological clock could dra-matically extend the human lifespan.Until then, science to me had been anendless memorization of dry facts. Itwas refreshing to realize that little wasknown about the aging of cells andthat research in the area could poten-tially have a huge impact on our life-styles and on the treatment of somediseases.

My excitement about the sci-ences was once again squashed inHigh School when an aptitude test,designed to uncover my hidden tal-ents, suggested that I was most suitedto be a funeral director. New inspira-tion, however, came from my HighSchool chemistry teacher, Mr.Masaro. His enthusiasm about chem-istry and the sciences was contagiousand he offset the potentially devas-tating impact of my uni-browed phys-ics teacher who told me that womenwere incapable of excelling in sci-ence. Mr. Masaro if this articlereaches you, I’d like you to know thatI still remember fluorine is the mostelectronegative element becauseRudolf Fluorentino is the greatestlover of electrons (whatever works!).

When I first encountered theuse of Agrobacterium tumefaciens asa tool for plant transformation duringan undergraduate course, I was trulycaptivated. The premise that any gene

STUDENT AWARD WINNERS

Best Paper Presentations

Nailish Samanani from any organism could be trans-formed into a plant which would thenproduce the foreign protein soundedlike an episode out of a bad sciencefiction movie. My fascination withplants was magnified by successiverealizations of the complexity of plantperceptions and responses: their dis-cernment of day and night and the dif-ferent seasons, their ability to launchdefences against foreign invasions,their ability to “communicate” notonly with other parts of themselvesbut also with other plants (and possi-bly with insects!) and their ability toproduce a mind-boggling variety of

cell-specific separation of biosyntheticsteps all appear to play an importantrole in the regulation of alkaloidbiosynthetic pathways.

When I first started my pro-gram, sparse information existed inthe literature about the enzyme thatcatalyzes the first condensation stepin the biosynthesis of allbenzylisoquinoline alkaloids,norcoclaurine synthase (NCS). Ourdata suggests that the purified nativeprotein exhibits a dimeric quanternarystructure. Product inhibition kineticsusing the purified enzyme indicates aniso-ordered bi-uni mechanism with 4-HPAA binding before dopamine. Thelatter substrate binds cooperatively tothe two subunits of the enzyme. Theposition of the enzyme as first com-mitted catalytic step in the pathway,along with the displayed cooperativesubstrate binding kinetics, suggest thatNCS plays a regulatory or rate-limit-ing role in controlling the metabolicflux of benzylisoquinoline alkaloidbiosynthesis. NCS displays 35% iden-tity to the enzyme that catalyzes acomplex series of reactions followingan initial condensation reaction inhypericin biosynthesis in St. John’sWort (hyp-1). It also displays 28 to38% identity to the Bet v1 allergen andpathogenesis-related (PR)10 proteinfamilies. The NCS protein encodes aputative N-terminal signal peptide aswell as a C-terminal region that is notfound in the other related proteins.NCS and Hyp-1 infer novel enzymaticfunctions for the Bet v1 group of pro-teins.

After the condensation of twotyrosine derivatives by NCS to formnorcoclaurine, eight additional en-zymes convert norcoclaurine to theprotoberberine alkaloid berberine.Berberine has potent antimicrobialproperties, which suggest it functions

chemical compounds.Fittingly, I am currently pur-

suing a doctorate degree in plant bi-ology in Dr. Peter Facchini’s lab at theUniversity of Calgary. My research ison the metabolic regulation ofprotoberberine alkaloid biosynthesisin Thalictrum flavum. In planta, themetabolic regulation of alkaloids isachieved using several different strat-egies. Along with gene expression,sub-cellular compartmentation ofbiosynthetic enzymes, tissue- and cell-specific accumulation of alkaloids and


in the defence of plants against patho-gen challenge. In T. flavum, berber-ine accumulates in specific tissues asthe major alkaloid. In the rhizome, wedetected alkaloid accumulationthroughout the pith and, to a lesserextent, the cortex. In the roots, wedetected alkaloid accumulation onlyin the endodermis at the onset of sec-ondary growth. Alkaloid accumula-tion was also detected in the pericyclecells of older roots near the base ofthe stem. The cell type-specific ac-cumulation of the alkaloid in the roots

supports the putative role of berber-ine in plant defense.

Using in situ RNA hybridiza-tion of aerial organs we have local-ized transcripts for the intermediatebiosynthetic steps in the berberinebiosynthetic pathway primarily to theepidermis of young leaves. In theroots, transcript accumulation was re-stricted to the endodermis and adja-cent cortical cells. The continuationof our work will include the localiza-tion of gene transcripts for the entireberberine biosynthetic pathway.

The realization that theideas in science are fluid and subjectto continuous change is what first at-tracted me to graduate school. Thenotion that ultimately the scientificprocess will expose the “truth” con-tinues to motivate me as I near thecompletion of my doctorate program

Nailish SamananiDepartment of Biological Sciences

University of CalgaryCalgary, Alberta, [email protected].

Anusha Dias

I was born in Colombo, Sri Lanka,and did my undergraduate studiesspecializing in Botany at the Univer-sity of Colombo, Sri Lanka. I cameto the United States in 1998 to beginmy PhD studies in the Department ofPlant Biology at the Ohio State Uni-versity with Dr. Keith Davis. My ini-tial exposure to research and tech-niques in plant molecular biologycame from working with him until heleft OSU in the summer of 1999. Soonafter I joined Dr. Erich Grotewold’slab, and was very excited in the re-search project given to me, dissect-ing the function of a recently dupli-cated R2R3 MYB transcription fac-tor in maize. My research project in-volved both molecular and functionalcharacterization of ZmMyb-IF35 andthe main objective was to find themechanisms by which plant MYB do-main transcription factors contributeto metabolic diversity. The functionalcharacterization of ZmMyb-IF35made me very much involved in theplant secondary metabolic pathwaysand the application of a number ofdifferent metabolite profiling tech-niques. Throughout the years, themore I learned about plantmetabolites, the more I appreciatedthe amazing roles played by thesesmall molecules.

As with any scientific endea-

vor, ZmMyb-IF35 gave me morequestions than answers and workingwith it for four years made it almosta part of me. Working in a lab likeErich’s, with his enormous experienceand knowledge on regulation of sec-ondary metabolic pathways, and agroup of people with similar interests,always made it a challenge, but ex-citing in every step of the way. Ourfindings that ZmMyb-IF35 might be

regulating novel metabolic pathwaysopened up new directions in our un-derstanding on the evolution of sec-ondary metabolic pathways. Lookingback I feel very fortunate to see howmuch I have learned working withphytochemicals and the experiencegained in facing challenges and the

training I got as a graduate student,which I consider to be invaluable.

On August 7, 2003 I had myfinal thesis defense and two days laterI was in Peoria IL attending the Phy-tochemical Society meeting. It wasmy first Phytochemical Society meet-ing and I was excited to be aroundwith all those phytochemists, some Ihave either heard or read about, finallyI got a chance to meet them. Theaward I won, I believe, was for thepassion I had and the struggles I facedin finding what my gene does. It came,in a way, as a reward for all my ef-forts and thoughts I had put in to mak-ing my gene an important playerabove thousands of others.

Three weeks later, I was readyto move on, to continue my adven-ture in the wonderful world of science.This time I took a different path, a pathI did not cross before. It was time toleave my gene behind, let somebodyelse take over. As I was cleaning upmy bench, my cold room space, myfreezer space, emptying those boxesfilled with eppendorfs, I felt tears inmy eyes. I was amazed to see howmuch I have got myself attached tothese materialistic things - to aneppendorf tube! I guess it shows howmuch you loved what you did and howdifficult it is to be apart from some-thing so close to you. Who would haveever thought it could be a piece ofDNA.


Now in a different city with so manynew things surrounding me I keepthinking about my gene, and my lifeas a graduate student in Erich’s lab,how much I have grown as a personand as a scientist. Although I am leav

ing plants for now to explore the restof the world, the experiences I gainedas a graduate student working withphytochemicals would surely lead myway as a guiding star throughout myfuture endeavors.

2004 Annual PSNA MeetingJuly 24 - 28, 2004Ottawa, Canada

held jointly with the

International Society of Chemical Ecology

Tentative Scientific Program

Chemical Ecology and Phytochemistry in Forests and Forest Ecosystems

Confirmed SpeakersJorg Bohlmann,Department of Botany, University of British Columbia

Peter Constabel, Department of Biology, University of Victoria,Johnathan Gershenzon, Max-Plank-Institute for Chemical Ecology

Murray Isman, Department of Plant Science,University of British ColumbiaNorman Lewis, Institute of Biological Chemistry, Washington State University

Hanna Mustaparta, Norwegian University of Science and TechnologyErika Plettner, Department of Chemistry, Simon Fraser UniversityKen Raffa, Department of Entomology,University of Wisconsin

Claus Tittinger, Department of Biochemistry, University of Nevada RenoGeraldine Wright, Oxford University

Takashi Yoshida, Faculty of Pharmaceutical Sciences, Okayama University

Mini SymposiaB. Kimball and D.Nolte: Chemically Mediated Behavior in Wildlife

C. Keeling: Hymenoptera SemiochemicalsV. De Luca: Aurthur Niesh Young Investigator Minisymposium

S. MacKinnon: Marine Chemical EcologyJ. McNeill: Pheremones

Posters and Contributed Oral PresentationsInvited in all areas of phytochemistry and chemical ecology. The organizers

reserve the right to limit the number of oral presentations due to time constraints.

Online registration will be available after January 15 on the meeting website:http://www.isce-psna2004ottawa.ca/

Anusha DiasHarvard University

Boston, [email protected]


IMAGES OF PEORIA - PSNA 2003


2003 ANNUAL MEETING - HEY, MY PICTURE’S IN THE NEWSLETTER!


ARTHUR NEISH SYMPOSIUM

Profile of Invited Speakers

Brian Traw

Brian Traw is currently a DropkinPostdoctoral Fellow working with JoyBergelson in the Department of Ecol-ogy and Evolution at the Universityof Chicago. He is exploring howplants in the mustard family defendthemselves against enemies, such asherbivores and bacterial pathogens.He has focused on leaf trichomes andglucosinolates, which are induceddefenses of mustard plants.

His work with Joy Bergelson hasyielded the first evidence that appli-cation of jasmonic acid increases plantproduction of trichomes, a defenseagainst herbivores, whereas applica-tion of salicylic acid actually inhibitstrichome production. Furthermore, hehas found that application of salicylicacid increases defenses against abiotrophic pathogen, whereas appli-cation of jasmonic acid inhibitsdefenses against this same pathogen.Collectively, these results suggest thatmustards have surprising complexityin their regulation of defenses, includ-ing substantial negative crosstalk be-tween the major defense pathways,which is a novel finding for mustards.

Before arriving in Chicago, Brianwas a graduate student in the Depart-ment of Ecology and Evolutionary Bi-ology at Cornell University under theco-direction of Paul Feeny, a chemi-cal ecologist, and Todd Dawson, aplant ecophysiologist. Brian spent agreat deal of time outdoors observingherbivore activity in wild populationsof the black mustard, Brassica nigra.His dissertation research showed thatblack mustard responds differently todamage by different herbivores, sug-gesting that these plants have anuanced perception of damage. In-duced plants supported lower per-formance of two major herbivores,revealing important benefits of an in-

duction response. However, half-sibfamilies with higher constitutivedefense allocation took longer toflower, suggesting important costs ofresistance, which may explain whynatural populations of black mustardtypically lack high constitutivedefense.

Brian can trace his interest innatural history and entomology to hischildhood, but owes his current fas-cination with plant defenses to his un-dergraduate experience in the lab ofFahkri Bazzaz at Harvard University.In collaboration with David Ackerly,a graduate student in the lab, he as-sessed the relationship betweenherbivory and leaf nitrogen concen-trations in five rainforest pioneertrees. Later, his honors thesis showedthat an elevated CO

2 atmosphere

would decrease leaf nitrogen concen-trations and thereby alter the effectsof an economically important pest, thegypsy moth, on two of its host plants.

In the future, Brian hopes toidentify broad patterns in the regula-tion of plant defense and to determinehow these patterns have influencedthe coevolution of plants and theirenemies, particular at the geneticlevel. In this direction, he is nowworking with Joy Bergelson to iden-tify novel genes involved in the in-duction of plant defenses, using a va-riety of mapping techniques.

John Tooker

John Tooker is currently a post-doc-toral scholar in the lab of ConsueloDeMoraes in the Department of En-tomology at Pennsylvania State Uni-versity in State College, PA. His re-search at Penn State is focusing onthe influence of gall-forming insects

on the chemistry of their host plants.He developed his interest in in-

sects while earning his Bachelor’sdegree in biology from Bates Collegein Lewiston, ME. After graduatingand working in the business world fora couple years, he joined the Depart-ment of Entomology at the Universityof Illinois at Urbana-Champaign tostudy the behavior and ecology of in-sect parasitoids. Under the supervi-sion of Dr. Lawrence Hanks, he com-pleted his Master’s studying the con-servation biological control of a scaleinsect that is a pest of pine trees inornamental landscapes and Christmastree farms.

For his PhD, he continued towork with Larry Hanks but switchedto a native prairie system to study theinfluence of native insect herbivoreson their co-evolved host plants. Thesystem he studied was comprised oftwo prairie perennials, Silphiumlaciniatum L. and S. terebinthinaceumJacquin (Asteraceae), the gall waspAntistrophus rufus Gillette, whose lar-vae feed in galls formed in the flow-ering stems of both plant species, andthe hymenopteran parasitoids that killthe gall wasp larvae. John determinedthat these two sibling plant speciesemit the same five monoterpenes butin different ratios and that sub-populations of A. rufus have special-ized on each plant species, using char-acteristic blends of the fivemonoterpenes to find their preferredhost plant. John also found that feed-ing by gall wasp larvae during thegrowing season results in a change inthe ratios of enantiomers of two of themonoterpenes (alpha- and beta-pinene) that the host plant emits. Thischange appears significant because itpersists into the next spring whenmale gall wasps use this altered blendof enantiomers on dead stems to as-sist their search for emerging female


gall wasps. Whether this change isactively caused by the gall wasp lar-vae or is a response made by the plantis unclear, but an additional trophiclevel may provide some insight.Plants with gall wasp larvae feedingin their stems produce significantlysmaller seeds than ungalled plants andthese smaller seeds are much lesslikely to germinate. However, thedominant hymenopteran parasitoid inthe system, Eurytoma lutea Bugbee,is able to salvage plant reproductiveoutput by killing larvae of A. rufus.Therefore, plants in the populationthat can attract parasitoids should havea selective fitness advantage. Johnfound support for this theory by de-termining that E. lutea is attracted togalled plants via volatile mono-terpenes that act as a synomone.

Eva Castells

Eva Castells is a Fulbright postdoc-toral researcher at the University ofIllinois at Urbana-Champaign in Dr.May Berenbaum laboratory since

May 2002. She is interested in chemi-cal ecology, specifically in thecoevolution between plant chemicaldefenses and their specialist herbiv-ores. At present she is studying thegeographical variation of Coniummaculatum (poison hemlock) piperi-dine alkaloids under a variety ofherbivory exerted by the mothAgonopterix alstroemeriana in USand Europe to determine whether theselective pressure exerted by this her-bivore can determine changes of Co-nium maculatum chemical defenses.Her project also involves determiningthe enzymatic mechanisms involvedin alkaloid detoxification byAgonopterix alstroemeriana.

Eva studied Biology atUniversitat de Barcelona (Catalonia,Spain) and in 1996 became a gradu-ate student at the Ecophysiology Unitat CREAF (Center for Ecological Re-search and Forestry Applications), lo-cated at Universitat Autònoma de Bar-celona, under the supervision of Dr.Josep Peñuelas. Her dissertation fo-cused on the effects of elevated CO

2

on phenolic compounds from Medi-terranean plants growing in a commu-nity and competing for water, nutri-

ents and light. During her graduatestudies Eva was funded by the Euro-pean Science Foundation with a short-term fellowship to conduct the project“Genotypic variations in the produc-tion of antiherbivore phenolic com-pounds under elevated CO

2 levels” at

Centre d’Ecologie Fonctionelle etEvolutive, CEFE-CNRS (Montpellier,France). She got her Masters degreein 1998. After spending two summersat University of Alaska (Fairbanks,USA) she became highly interested inthe role of secondary metabolites inecological interactions. Eva com-pleted her PhD in April 2002 study-ing how phenolics released from theplant canopy may regulate the inter-action between plant and soil by modi-fying soil N mineralization and otherprocesses related to N cycling.

Eva was born in Barcelona andalthough she is excited about work-ing at University of Illinois in such ahighly rich intellectual environment,she would like in the future to con-tinue her research career in her favoritecity, combining coevolution with thepleasures of a Mediterranean lifestyle.

The 4th Tannin Conference – Plant Polyphenols: Chemistry, Biology, Function

American Chemical Society’s Fall Meeting, Philadelphia, 22-26 August, 2004

The 4th Tannin Conference – Plant Polyphenols: Chemistry, Biology, Function - will be organized as part of the 2004American Chemical Society’s (ACS) Fall Meeting (22-26 August, Philadelphia) in the “Cellulose and Renewable Materi-als” Division. Our objectives are to promote collaboration between chemists, biologists and human health related disci-plines in order to improve our understanding of the chemistry and the biological and physiological significance of polyphenols,and to focus on expanded possibilities for their applications in industry and in human health and nutrition. All prospectivecontributors to The 4th Tannin Conference are requested to submit an abstract describing the work they wish to present atthe meeting. Your abstract should be prepared according to ACS instructions (http://oasys.acs.org/acs/228pm/authorinstructions.cgi). This should then be sent electronically to the coordinator of the planning committee, Daneel Ferreira([email protected]) no later than January 15, 2004. This abstract will serve as the basis on which selections will bemade for oral presentations in each of the topic areas. You will be informed whether your contribution has been accepted asan oral presentation; all other contributions will be presented as posters. At a time that will be announced on the ACSwebsite (http://www.chemistry.org/portal/a/c/s/1/home.html) for the 228th National Meeting in Philadelphia, you may submityour abstract to ACS at the former website. Prospective participants may register and make hotel reservations online oncethese options become available on the latter website for the Philadelphia meeting. At this time we would also like to probeyour interest in attending a conference dinner at a cost of roughly $50/ticket. Please indicate your interest or otherwisewhen submitting your initial abstract to the coordinator of the planning committee.


I KNOW WHAT YOU DID LAST SUMMER

This sounded like a good idea... ...until I saw the place next door.

This fine establishment was next door to the hotel. If itwas good enough for Big Al, it’s good enough for me.

I hate when people leave their shopping carts in my parkingspace. I got the quarter back though.

Note to self...avoid using fire escapes in Peoria. “I’msaved...uhh, no, I’m not!

It was the top of the fifth before anyone noticed the otherteam hadn’t shown up...still no score though.


PHYTOCHEMICAL SOCIETY OF NORTH AMERICA

Financial Report (January 1 - December 31, 2002)

Assets: (12/31/02) (12/31/01) (12/31/00)

Checking account $ 5850.73 $ 4205.80 $ 2620.09Business Money Market 36319.58 41316.83 26951.12Neish Symposium account 23654.99 25258.39 24571.29

Fortis Money Market 114.10 113.50 109.60Fortis Advantage* 9077.46 10543.00 11476.74

TOTALS 75016.86 $81437.52 $65728.84

* Investment account, subject to fluctuation.

2002 Annual Meeting:

Expenditures:Meeting Advance $ 5000.00Travel and Awards $ 7267.70

Expenditure subtotal $ 12267.70

Receipts:Meeting Grant (H. Flores) $ 4750.00

Receipts subtotal $ 4750.00

Total cost to PSNA $ 7517.70

Membership Summary (as of 7/28/03):

2000 2001 2002 Country Members Members Members USA 227 224 236 Canada 63 46 45 Germany 23 23 Japan 18 16 Mexico 14 9 17 Other 104 51 49

TOTALS 408 371 386

Volume 37 of Recent Advances in Phytochemistry - Integrative Phytochemistry: from

Ethnobotany to Molecular Ecology, the symposium volume resulting from the 2002

PSNA Annual Meeting in Mérida, México is the fourth volume in this series publishedby Elsevier. Volume 37 is founded on the belief that biological complexity can be under-stood by incorporating many perspectives from a diversity of disciplines.

Elsevier Publishes Volume 37 ofRecent Advances in Phytochemistry

Integrative biology is the belief that biologi-cal complexity can be understood by incor-porating perspectives from diverse disci-plines. This volume includes chapters on thetraditional phytochemical topics of synthe-sis, enzymology, chemical diversity, andchemical ecology of secondary metabolites.They also include less frequently coveredtopics, such as the cellular localization ofmetabolites, levels of regulation, structure/function analyses, molecular genetics, andfunctional genomics. Papers in the volumecover: what compounds are produced; howthey are produced; why they are produced;and the regulation that might lead to moreefficient production. The chapters aregrouped, as they were in the symposia, ac-cording to chemical classes.

The PSNA, under terms of our contract, can sell this volume at almost a 50%

discount. To purchase Volume 37 please contact the Treasurer, Charles Cantrell.

Contributors to this timely volume explore a wide range of topics that include:• • • • • Flavonoid biodiversity• • • • • Methylation of small molecules• • • • • Anthocyanin pigmentation• • • • • Myrosinases and glucosinolates• • • • • Regulation of alkaloid biosynthesis• • • • • Chemical ecology of pyrrolizidine alkaloids

• • • • • Diversity of isoprenoid metabolism

Recent Advances in Phytochemistry SeriesPSNA members receive a 40% discount on the following titles

Volume 36 (2001)** Phytochemistry in the Genomics and Postgenomics Eras(List $210.00, PSNA $99.00)

Volume 35 (2000)** Regulation of Phytochemicals by Molecular Techniques(List $210.00, PSNA $102.00)

Volume 34 (1999)** Evolution of Metabolic Pathways(List $222.50, PSNA $122.00)

Volume 33 (1998) Phytochemicals in Human Health Protection, Nutrition, Plant Defense(List $165.00, PSNA $99.00)

Volume 32 (1997) Phytochemical Signals and Plant-Microbe Interactions(List $95.00, PSNA $57.00)

Volume 31 (1996) Functionality of Food Phytochemicals(List $114.00, PSNA $68.40)

Volume 30 (1995) Phytochemical Diversity and Redundancy in Ecological Interactions(List $89.50, PSNA $53.70)

Volume 29 (1994) Phytochemistry of Medicinal Plants(List $71.00, PSNA $42.60)

Volume 28 (1993) Genetic Engineering of Plant Secondary Metabolism(List $89.50, PSNA $53.70)

Volume 27 (1992) Phytochemical Potential of Tropical Plants(List $79.50, PSNA $47.70)

Volume 26 (1991) Phenolic Metabolism in Plants(List $89.50, PSNA $53.70)

Volume 25 (1990) Modern Phytochemical Methods(List $85.00, PSNA $51.00)

Volume 24 (1989) Biochemistry of the Mevalonic Acid Pathway to Terpenoids(List $85.00, PSNA $51.00)

Volume 23 (1988) Plant Nitrogen Metabolism(List $89.50, PSNA $53.70)

Volume 22 (1987) Opportunities for Phytochemistry in Plant Biotechnology(List $59.50, PSNA $35.70)

Volume 21 (1986) Phytochemical Effects of Environmental Compounds(List $75.00, PSNA $45.00)

**Volumes 34, 35, and 36 are available from our new publisher, Elsevier. Please contact the PSNATreasurer, Charles Cantrell, for information on ordering these volumes.

Please send the copy/copies marked above.NEW YORK AND NEW JERSEY RESIDENTS MUST INCLUDE APPLICABLE SALES TAX.

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Phytochemical Society of North America

Membership Application

Please fill in the following application and return to the Treasurer with your dues payment. We are also inthe process of updating the PSNA website, so please respond to the question regarding posting informa-tion on the website and give information on your personal web page if you wish it to be included. Once yourapplication has been processed, you will receive newsletters and special mailings. You are also eligible forPSNA member discounts on the Recent Advances in Phytochemistry series.

Please make check or money order payable to the Phytochemical Society of North America. Paymentmust be made in U.S. dollars, drawn on a U.S. bank. Traveler’s Checks or Canadian Postal Money Orders,payable in U.S. dollars, are also acceptable. We are unable to accept payment via credit card.

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Research Interests (circle up to 4 items):A. Acetylenes S. Terpenoids stressB. Alkaloids T. Vitamins nn. Industrial applicationsC. Amino acids/proteins aa. Biochemistry/physiology of oo. Structure identificationD. Coumarins herbicides pp. Marine natural compoundsE. Cyanogenics bb. Enzymology qq. Medicinal chemistryF. Flavonoids cc. Cell wall chemistry rr. Membrane structure/functionG. Glucosinolates dd. Chemotaxonomy ss. Molecular/immunologicalH. Lignans ee. Biotechnology techniquesI. Lipids ff. Plant-insect interactions tt. Nitrogen fixation/metabolismJ Nitrogen compounds gg. Plant-microbe interactions uu. Pharmacology/pharmacognosyK. Nucleic acids hh. Plant-plant interactions vv. Plant pathologyL. Organic acids ii. Chemical reactions/organic ww. Plant geneticsM. Phenolics synthesis xx. Recognition-cell surfaceN. Pigments jj. Biochemistry of secondary interactionsO. Quinones metabolism yy. Tissue/cell cultureP. Stilbenes kk. Fungal metabolism zz. Toxicology of naturalQ. Sugars/polysaccharides ll. Growth regulators productsR. Sulfur compounds mm. Biochemistry/physiology of OTHER: _______________________

psna newsletter 2 · arabidopsis thaliana, nicotiana tabacum, zea mays , oryza sativa , and others....

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