Isolation and stereostructure of dolastatin I, a cytotoxic cyclic hexapeptide from the Japanese sea hare Dolabella auricularia

被引:46
作者
Sone, H [1 ]
Kigoshi, H [1 ]
Yamada, K [1 ]
机构
[1] NAGOYA UNIV,FAC SCI,DEPT CHEM,NAGOYA,AICHI 464,JAPAN
基金
日本学术振兴会;
关键词
D O I
10.1016/S0040-4020(97)00504-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dolastatin I(1), a cyclic hexapeptide containing three kinds of five-membered heterocycles (oxazole, thiazole, and oxazoline), has been isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated by spectroscopic analysis. The absolute stereostructure of 1 was determined by chiral HPLC analysis of the amino acid components obtained by acid hydrolysis of 1. Dolastatin I(1) exhibited cytotoxicity against HeLa S-3 cells with an IC50 value of 12 mu g/mL. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8149 / 8154
页数:6
相关论文
共 24 条
[1]   Raocyclamides A and B, novel cyclic hexapeptides isolated from the cyanobacterium Oscillatoria raoi [J].
Admi, V ;
Afek, U ;
Carmeli, S .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (04) :396-399
[2]   ASCIDIANS - PRODUCERS OF AMINO-ACID DERIVED METABOLITES [J].
DAVIDSON, BS .
CHEMICAL REVIEWS, 1993, 93 (05) :1771-1791
[3]   NOVEL CYTO-TOXIC COMPOUNDS FROM THE ASCIDIAN LISSOCLINUM-BISTRATUM [J].
DEGNAN, BM ;
HAWKINS, CJ ;
LAVIN, MF ;
MCCAFFREY, EJ ;
PARRY, DL ;
WATTERS, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1354-1359
[4]   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
[5]   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
[6]   ISOLATION AND STEREOSTRUCTURE OF DOLICULIDE, A CYTOTOXIC CYCLODEPSIPEPTIDE FROM THE JAPANESE SEA HARE DOLABELLA-AURICULARIA [J].
ISHIWATA, H ;
NEMOTO, T ;
OJIKA, M ;
YAMADA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4710-4711
[7]  
Kobayashi J. I, 1992, The Alkaloids: Chemistry and Pharmacology, V41, P41
[8]   PATELLAMIDE-E - A NEW CYCLIC PEPTIDE FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].
MCDONALD, LA ;
IRELAND, CM .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (03) :376-379
[9]  
MUTOU M, 1996, J ORG CHEM, V61, P6340
[10]   STEREOCHEMISTRY AND TOTAL SYNTHESIS OF DOLASTATIN-E [J].
NAKAMURA, M ;
SHIBATA, T ;
NAKANE, K ;
NEMOTO, T ;
OJIKA, M ;
YAMADA, K .
TETRAHEDRON LETTERS, 1995, 36 (28) :5059-5062