STUDIES OF AUSTRALIAN ASCIDIANS .4. MOLLAMIDE, A CYTOTOXIC CYCLIC HEPTAPEPTIDE FROM THE COMPOUND ASCIDIAN DIDEMNUM MOLLE

被引：62

作者：

CARROLL, AR

BOWDEN, BF

COLL, JC

HOCKLESS, DCR

SKELTON, BW

WHITE, AH

机构：

[1] JAMES COOK UNIV N QUEENSLAND,DEPT MOLEC SCI,TOWNSVILLE,QLD 4811,AUSTRALIA

[2] UNIV CENT QUEENSLAND,CHANCELLORY,ROCKHAMPTON,QLD 4702,AUSTRALIA

[3] UNIV WESTERN AUSTRALIA,DEPT CHEM,NEDLANDS,WA 6009,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1994年 / 47卷 / 01期

关键词：

D O I：

10.1071/CH9940061

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new cytotoxic cyclic heptapeptide, mollamide, has been isolated from the compound ascidian Didemnum molle. The structure of mollamide was initially deduced from one-dimensional and two-dimensional n.m.r. experiments at 300 MHz. The structure was confirmed by an X-ray crystallographic study, which showed the relative stereochemistry of the cyclic peptide. Hydrolysis of mollamide, and characterization of the amino acids by derivatization with N alpha-(5-fluoro-2,4-dinitrophenyl)-L-alanina (FDAA; Marfey's reagent) gave the absolute stereochemistry; all constituent amino acids were the L-isomers. Cytotoxicity data are reported.

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页码：61 / 69

页数：9

相关论文

共 14 条

[1] NEW CYCLIC-PEPTIDES WITH CYTO-TOXIC ACTIVITY FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].

DEGNAN, BM ;

HAWKINS, CJ ;

LAVIN, MF ;

MCCAFFREY, EJ ;

PARRY, DL ;

VANDENBRENK, AL ;

WATTERS, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1349-1354

[2] NAIRAIAMIDE-A AND NAIRAIAMIDE-B - 2 NOVEL DI-PROLINE HEPTAPEPTIDES ISOLATED FROM A FIJIAN LISSOCLINUM-BISTRATUM ASCIDIAN [J].

FOSTER, MP ;

IRELAND, CM .

TETRAHEDRON LETTERS, 1993, 34 (18) :2871-2874

[3]

HALL SR, 1990, XTAL 3 0 REFERENCE M

[4] CYCLOXAZOLINE - A CYTOTOXIC CYCLIC HEXAPEPTIDE FROM THE ASCIDIAN LISSOCLINUM-BISTRATUM [J].

HAMBLEY, TW ;

HAWKINS, CJ ;

LAVIN, MF ;

VANDENBRENK, A ;

WATTERS, DJ .

TETRAHEDRON, 1992, 48 (02) :341-348

[5] ANTI-NEOPLASTIC CYCLIC-PEPTIDES FROM THE MARINE TUNICATE LISSOCLINUM-PATELLA [J].

IRELAND, CM ;

DURSO, AR ;

NEWMAN, RA ;

HACKER, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1807-1811

[6] ISOLATION AND STRUCTURE DETERMINATION OF DIAZONAMIDE-A AND DIAZONAMIDE-B, UNUSUAL CYTOTOXIC METABOLITES FROM THE MARINE ASCIDIAN DIAZONA-CHINENSIS [J].

LINDQUIST, N ;

FENICAL, W ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2303-2304

[7] DETERMINATION OF D-AMINO ACIDS .2. USE OF A BIFUNCTIONAL REAGENT, 1,5-DIFLUORO-2,4-DINITROBENZENE [J].

MARFEY, P .

CARLSBERG RESEARCH COMMUNICATIONS, 1984, 49 (06) :591-596

[8] TAWICYCLAMIDES-A AND TAWICYCLAMIDES-B, NEW CYCLIC-PEPTIDES FROM THE ASCIDIAN LISSOCLINUM-PATELLA - STUDIES ON THE SOLUTION-STATE AND SOLID-STATE CONFORMATIONS [J].

MCDONALD, LA ;

FOSTER, MP ;

PHILLIPS, DR ;

IRELAND, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4616-4624

[9] WESTIELLAMIDE, A BISTRATAMIDE-RELATED CYCLIC PEPTIDE FROM THE BLUE-GREEN-ALGA WESTIELLOPSIS-PROLIFICA [J].

PRINSEP, MR ;

MOORE, RE ;

LEVINE, IA ;

PATTERSON, GML .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (01) :140-142

[10] DIDEMNINS AND TUNICHLORIN - NOVEL NATURAL-PRODUCTS FROM THE MARINE TUNICATE TRIDIDEMNUM-SOLIDUM [J].

RINEHART, KL ;

KISHORE, V ;

BIBLE, KC ;

SAKAI, R ;

SULLINS, DW ;

LI, KM .

JOURNAL OF NATURAL PRODUCTS, 1988, 51 (01) :1-21