Raocyclamides A and B, novel cyclic hexapeptides isolated from the cyanobacterium Oscillatoria raoi

被引：49

作者：

Admi, V

Afek, U

Carmeli, S

机构：

[1] TEL AVIV UNIV,RAYMOND & BEVERLY SACKLER FAC EXACT SCI,SCH CHEM,IL-69978 TEL AVIV,ISRAEL

[2] AGR RES ORG,VOLCANI CTR,DEPT POSTHARVEST & FRESH PROD,IL-50250 BET DAGAN,ISRAEL

来源：

JOURNAL OF NATURAL PRODUCTS | 1996年 / 59卷 / 04期

关键词：

D O I：

10.1021/np960115+

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Raocyclamides A and B, two novel oxazole- and thiazole-containing cyclic hexapeptides, were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). The gross structures of raocyclamides A (1) and B (2) were elucidated by homonuclear and inverse-heteronuclear 2D-NMR techniques and HREIMS. The absolute stereochemistry of compounds 1 and 2 was determined by Marfey's HPLC Method. Raocyclamide A (1) was established as cyclo-thiazole-D-Ile-oxazole-L-Ala-D-oxazoline-D-Phe and raocyclamide B (2) as cyclo-thiazole-D-Ile-oxazole-L-Ala-D-Ser-D-Phe. Raocyclamide A (1) exhibits a moderate cytotoxicity against sea urchin embryos.

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页码：396 / 399

页数：6

相关论文

共 18 条

[1] TANTAZOLES - UNUSUAL CYTOTOXIC ALKALOIDS FROM THE BLUE-GREEN-ALGA SCYTONEMA-MIRABILE [J].

CARMELI, S ;

MOORE, RE ;

PATTERSON, GML ;

CORBETT, TH ;

VALERIOTE, FA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8195-8197

[2] REVISED STRUCTURES AND BIOSYNTHETIC-STUDIES OF TANTAZOLES-A AND TANTAZOLES-B [J].

CARMELI, S ;

PAIK, S ;

MOORE, RE ;

PATTERSON, GML ;

YOSHIDA, WY .

TETRAHEDRON LETTERS, 1993, 34 (42) :6681-6684

[3] CYANOBACTERIA SECONDARY METABOLITES - THE CYANOTOXINS [J].

CARMICHAEL, WW .

JOURNAL OF APPLIED BACTERIOLOGY, 1992, 72 (06) :445-459

[4]

DEGAN BM, 1989, J MED CHEM, V32, P1354

[5]

Desikachary TV, 1956, CYANOPHYTA

[6] BISTRATAMIDE-C AND BISTRATAMIDE-D - 2 NEW OXAZOLE-CONTAINING CYCLIC HEXAPEPTIDES ISOLATED FROM A PHILIPPINE LISSOCLINUM-BISTRATUM ASCIDIAN [J].

FOSTER, MP ;

CONCEPCION, GP ;

CARAAN, GB ;

IRELAND, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6671-6675

[7] 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

[8] RAPID AND CONVENIENT PROCEDURE FOR THE DETECTION OF INHIBITORS OF DNA-SYNTHESIS USING STARFISH OOCYTES AND SEA-URCHIN EMBRYOS [J].

IKEGAMI, S ;

KAWADA, K ;

KIMURA, Y ;

SUZUKI, A .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1979, 43 (01) :161-166

[9] 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

[10] DOLASTATIN-E, A NEW CYCLIC HEXAPEPTIDE ISOLATED FROM THE SEA HARE DOLABELLA-AURICULARIA [J].

OJIKA, M ;

NEMOTO, T ;

NAKAMURA, M ;

YAMADA, K .

TETRAHEDRON LETTERS, 1995, 36 (28) :5057-5058