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SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS

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Page 1: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

SOME REPRESENTATIVE

COMPOUNDS ISOLATED

FROM MARINE ORGANISMS

Page 2: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

AEROPLYSININ-1

from the sponge Aplysina aerophoba

Chem. Comm. 751 (1970)

1970

OCH3

Br

HO

Br

HO

CN

Page 3: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

AEROTHIONIN

from the sponge Aplysina aerophoba

Chem. Comm. 752 (1970)

1970

OCH3

Br

O

Br

HO

N CONHCH2CH2CH2CH2NHCO

O

N

OCH3

Br Br

OH

Page 4: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

NITENIN

from the sponge Spongia nitens

1971

Tetrahedron, 27, 309 (1971)

The first furanoterpene from marine organisms

O

CO

O

H

O

Page 5: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

OROIDINfrom the sponge Agelas oroides

The proposed uncorrect

structure

The first bromoalkaloid from marine organisms

Chem. Comm. , 1129 (1971)

1971

NH

CONH

N

NH

CH2NH2

Br

Br

NH

CONHBr

Br

NH

N NH2

CH2

Page 6: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

SCALARIN

from the sponge Cacospongia scalaris

The starting point

of the “scalarane” sesterpenes

Tetrahedron, 28, 5993 (1972)

1972

OOCOCH3

O

HO

Page 7: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

AXISONITRILE-1 – AXISOTHIOCYANATE-1from the sponge Axinella cannabina

The first isonitrile and

isothiocyanate

from marine organisms

Tetrahedron, 29 4259 (1973)

1973

N NCSC

Page 8: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

CALYSTEROL from the sponge Calyx nicaensis

A unique cyclopropene-containing

sterol

Tetrahedron, 31, 1715 (1975)

1975

HO

Page 9: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

CAULERPENYNEfrom the green alga Caulerpa prolifera

Tetrahedron Letters, 3593 (1978)

The well-known ecotoxin

of Caulerpa algae

1978

AcO

OAc

OAcH

Page 10: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

AN UNBELIEVABLE ARRAY OF NEW

DITERPENE SKELETONS FROM THE RED ALGA

Sphaerococcus coroponifolius

and a biogenetic hypothesis

Gazz. Chim. It. 106, 779 (1976)

Tetrahedron Letters, 4123 (1981)

Tetrahedron Letters 25, 3141 (1984)

J. Org. Chem. 50, 3982 (1985)

Tetrahedron 42, 4273 (1986).

Gazz. Chim. It. 117, 87 (1987).

Phytochemistry 27, 621 (1988).

1976/1988

o

Page 11: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

H

HH

HH

H

H2O

Br+

H

OH

Br

Br+

OH

Br

H

H

CH2Br

OPP

PROPOSED MECHANISM FOR THE BIOGENESIS OF

DITERPENES IN SPHAEROCOCCUS CORONOPIFOLIUS

Tetrahedron Letters 25, 3141 (1984)

Page 12: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

CLATHRIDINE

FROM THE SPONGE Clathrina clathrus

Tetrahedron, 45, 3873 (1989) ; 46, 4387 (1990)

The first marine

alkaloid Zn complex

1990

N

N

N

N

N

O

OO

O

N

N

HN

N

N

O

O

O

O

Zn

Page 13: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

INCISTEROLSfrom the sponge Dictyonella incisa

O

R

O

H3CO

H

R=

Unique sterols deriving

from a dramatic biodegradation

of the sterol nucleus

J. Am Chem Soc, 112, 3505 (1995)

1995

Page 14: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

PLAKOSIDE A and Bfrom the sponge Plakortis simplex

OOH

H

H

HO

H

HOH

O

OH

Plakoside A: R =

Plakoside B: R =

ROH

OOH

NH

C10H21

C10H21

C10H21

Unique prenylated glycolipids

with immunosuppressive activity

J. Am. Chem. Soc., 119,12465 (1997)

1997

Page 15: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

CARBOXYHOMOYESSOTOXINfrom contaminated Mytilus galloprovincialis

O

O

O

O

O

O

O

O

O

O

NaO3SO

NaO3SO Me

Me

Me

Me

Me

O

Me

40

( )n

41

COOH

OH

H

H

H H H HH

H

H

H

H

HH H

H

H

H

H

HO

A major toxin present in contaminated

Adriatic mussels

Chem Res. Tox.- 13, 770 (2000)

2000

Page 16: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

HEXADECANOIC ACID 5’,6’,9’,10’,12’,13’,14’,16’,18’,18’,21’-UNDECACHLORO-

11’,15’,17’,22’,23’-PENTHYDROXY-1’-METHYL-7’-SULFOOXYTRICOS-2’-ENYL

ESTER

from contaminated Mytilus galloprovincialis

OH

O Cl

Cl

OSO3Cl

Cl

OH

Cl

Cl

Cl

OH

Cl

OH

Cl Cl

Cl

OH

C

O

(CH2)14

CH3

A unique chlorosulfolipid with a dense

functionalization of the alkenyl chain with

eleven chlorine atoms

J. Am. Chem. Soc., 124,13114 (2002)

2002

Page 17: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

CLIONASTATIN A - Bfrom the burrowing sponge Cliona nigricans

OO

Cl Cl

Cl

H

OO

Cl Cl

Cl

H

Cl

•First polyhalogenated steroids found in nature•First halogenated androstanes found in nature

Org. Letters, 6, 1633 (2004)

From the comment of a Organic Letters REFEREE :

“Short of marinating the marine sponge in bleach after collection and before

extraction, I cannot see how this structure can arises, biosynthetically. It

challenges the conventional wisdoms of both the nature of halogenases

responsible for introduction of Cl into isoprenoid carbon skeletons and the

locus and detailed steps of nor-side-chain sterol biosynthesis within

invertebrates”.

2004

Page 18: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

O

NH

S

O

O

OH

OOO

NH

S

O

O

OH

OO

A

B C D

ThiaplidiaquinonesThiaplidiaquinones AA--BB maymay targettarget thethe plasmaplasma membranemembrane redoxredox systemsysteminin thethe samesame wayway thatthat capsaicincapsaicin andand resiniferatoxinresiniferatoxin.. TheyThey produceproduce bothboth aadramaticdramatic increaseincrease inin thethe reactivereactive oxygenoxygen speciesspecies (ROS)(ROS) generationgeneration andand aafallfall inin thethe transmembranetransmembrane mitochondrialmitochondrial potentialpotential inducinginducing cellcell deathdeath bybyapoptosisapoptosis..

THIAPLIDINONE A – Bcytotoxic quinones from the marine

tunicate Aplidium conicum

J. Med Chem., 48, 3410-3416 (2005)

2004

Page 19: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

O

H

HO

H

HO

H

OHH

O

O

OH

O

OH

NH OH

H

C13H27

C19H39

OHO

H

H

HO

H

OH

H H

O

OH

HO

H

OHH

HO

H

H

O

H

O

H2

O

H

HHO

H OH

OH

H

OH

OH

H

OH H

OH

HO

H

HO

HO

HO

OH

Vesparioside B Vesparioside B

from the spongefrom the sponge Spheciospongia vespariaSpheciospongia vesparia

The most complex

glycosphingolipid

isolated from

a marine

sponge to date

J. Org. Chem. 2008, 73, 6158–6165

2008

Page 20: SOME REPRESENTATIVE COMPOUNDS ISOLATED … representative-2.pdf · SOME REPRESENTATIVE COMPOUNDS ISOLATED FROM MARINE ORGANISMS. ... CLATHRIDINE FROM THE SPONGE Clathrina clathrus

42-Hydroxy Palytoxin

O

OH

O

O

OH

O

OH

HO

OH

OHMe

O

HO

O

HO

Me

O

HO

O

O

OHHO

O

O

HN

O

NH

H2N

OH

HO

OH

OH

OH

OH

OH

OH

OH

OH

OH

OHOHHO

OH

OH

Me

MeOH

OHHO

OHOH

OH Me HO

OH

OH

OH

Me

Me

OH

HO

OH

HO

OH

OH

da

27

28

34

85

85' 84

86115

b

c

e

f

3948

2009

Chem. Res. in Toxicol, 22, 1851 (2009)

Hawaiian

Palythoa toxica