New cytotoxic sterol glycosides from the octocoral Carijoa (Telesto) riisei

被引:30
作者
Maia, LF
Epifanio, RD
Fenical, W
机构
[1] Univ Fed Fluminense, Inst Quim, Dept Quim Organ, BR-24020150 Niteroi, RJ, Brazil
[2] Univ Fed Rio de Janeiro, BR-21941590 Rio De Janeiro, Brazil
[3] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2000年 / 63卷 / 10期
关键词
D O I
10.1021/np9906323
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new steroidal glycosides, 3 beta -O-(3'-O-acetyl-beta -D-arabinopyranosyl)-25 xi -cholestane-3 beta ,5 alpha ,6 beta ,26-tetrol-26-acetate (riisein A, 2) and 3 beta -O-(4'-O-acetyl-beta -D-arabinopyranosyl)-25 xi -cholestane-3 beta ,5 alpha ,6 beta ,26-tetrol-26-acetate (riisein B, 3), were isolated from extracts of the Brazilian telestacean octocoral Carijoa (Telesto) riisei collected near Rio de Janeiro. The new glycosides co-occur with the polyhydroxy sterol, 25 xi -cholestane-3 beta ,5 alpha ,6 beta ,26-tetrol-26-acetate (1), an inseparable diastereomeric mixture previously reported from Telesto riisei collected in Micronesia. The structures of the new glycosides were assigned by spectroscopic methods and by comparison with spectral data for sterol 1. Riiseins A and B showed in vitro cytotoxicity toward HCT-116 human colon adenocarcinoma with IC50 values of 2.0 mug/mL.
引用
收藏
页码:1427 / 1430
页数:4
相关论文
共 13 条
[1]   PUNAGLANDINS - HALOGENATED ANTITUMOR EICOSANOIDS FROM THE OCTOCORAL TELESTO-RIISEI [J].
BAKER, BJ ;
OKUDA, RK ;
YU, PTK ;
SCHEUER, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (10) :2976-2977
[2]   THE PUNAGLANDINS - 10-CHLOROPROSTANOIDS FROM THE OCTOCORAL TELESTO-RIISEI [J].
BAKER, BJ ;
SCHEUER, PJ .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (10) :1346-1353
[3]  
Castro C.B., 1990, THESIS U SAO PAULO S
[4]  
Epifanio RD, 1998, J BRAZIL CHEM SOC, V9, P187
[5]   Chemical defenses against fish predation in three Brazilian octocorals:: 11β, 12β-epoxypukalide as a feeding deterrent in Phyllogorgia dilatata [J].
Epifanio, RD ;
Martins, DL ;
Villaça, R ;
Gabriel, R .
JOURNAL OF CHEMICAL ECOLOGY, 1999, 25 (10) :2255-2265
[6]  
Faulkner DJ, 1999, NAT PROD REP, V16, P155
[7]   DETERMINATION OF D AND L CONFIGURATION OF NEUTRAL MONOSACCHARIDES BY HIGH-RESOLUTION CAPILLARY GLC [J].
GERWIG, GJ ;
KAMERLING, JP ;
VLIEGENTHART, JFG .
CARBOHYDRATE RESEARCH, 1978, 62 (02) :349-357
[8]  
LYANAGE GK, 1996, J NAT PRODUCTS, V59, P148
[9]   New fish feeding deterrents, including a novel sesquiterpenoid heterogorgiolide, from the Brazilian gorgonian Heterogorgia uatumani (Octocorallia, Gorgonacea) [J].
Maia, LF ;
Epifanio, RD ;
Eve, T ;
Fenical, W .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09) :1322-1324
[10]  
Maia LF, 1998, BOL SOC CHIL QUIM, V43, P39