INVESTIGATION OF THE POLAR STEROIDS FROM AN ANTARCTIC STARFISH OF THEFAMILY ECHINASTERIDAE - ISOLATION OF 27 POLYHYDROXYSTEROIDS AND STEROIDAL OLIGOGLYCOSIDES, STRUCTURES AND BIOLOGICAL-ACTIVITIES

Citation
M. Iorizzi et al., INVESTIGATION OF THE POLAR STEROIDS FROM AN ANTARCTIC STARFISH OF THEFAMILY ECHINASTERIDAE - ISOLATION OF 27 POLYHYDROXYSTEROIDS AND STEROIDAL OLIGOGLYCOSIDES, STRUCTURES AND BIOLOGICAL-ACTIVITIES, Tetrahedron, 52(33), 1996, pp. 10997-11012
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
52
Issue
33
Year of publication
1996
Pages
10997 - 11012
Database
ISI
SICI code
0040-4020(1996)52:33<10997:IOTPSF>2.0.ZU;2-1
Abstract
An investigation of the extracts from a starfish collected in the Anta rctic Sea, Echinasteridae family, has led to the isolation of thirteen glycosides of polyhydroxysteroids (1-13), fourteen polyhydroxysteroid s (14-27), which are the subject of this report, and seven asterosapon ins (penta-and hexa-saccharides), described in a previous paper. Glyco sides 1-13 are composed of the same 3 beta,4 beta,6 alpha,8,15 beta,26 -hexahydroxysteroidal aglycone with small variations in the side chain s, and a carbohydrate portion made up of one or two monosaccharide uni ts attached at C-26, except 11, which has a steroidal aglycone with a 24,28-dihydroxylated side chain and the monosaccharide unit attached a t C-24. The structures of the polyhydroxysteroids (14-27) have the hyd roxyl groups typically disposed on one side of the steroid nucleus, i. e. 3 beta,4 beta,6 beta (or alpha),8,15 alpha (or beta) and 16 beta an d the majority of them possess a 26-hydroxyl function. A selection of fifteen compounds were tested against human non-small-cell lung carcin oma cells and found to be moderately cytotoxic. Copyright (C) 1996 Els evier Science Ltd