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