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Biological Activities and Syntheses of Steroidal Saponins: the Shark‐Repelling Pavoninins
Author(s) -
Williams John R.,
Gong Hua
Publication year - 2007
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-006-1002-3
Subject(s) - starfish , diosgenin , steroid , glycosyl , chemistry , moiety , lipidology , glycoside , glycosylation , antifungal , saponin , sea cucumber , biological activity , stereochemistry , biochemistry , clinical chemistry , biology , organic chemistry , in vitro , ecology , microbiology and biotechnology , hormone , medicine , alternative medicine , pathology
Abstract Steroidal saponins are complex compounds that have a steroid attached to a carbohydrate moiety. They are natural surfactants and detergents and exhibit a number of biological effects. Steroidal saponins have shown membrane‐permeabilizing, hypocholesterolemic, immunostimulant, and anticancer properties. They have also been found to affect the growth, food intake and reproductive capabilities of animals. Furthermore, they have been shown to act as antiviral and antifungal agents. They have been isolated from many plants and some animals, especially sea cucumbers and starfish. Fish belonging to the species Pardachirus pavoninus excrete a mixture of six steroidal N ‐acetylglucosaminides, pavoninins 1–6, with shark‐repelling properties. We report syntheses of the C‐15α pavoninin‐4 by both direct synthesis from diosgenin and by remote functionalization. A general solution for the glycosylation of hindered alcohols was developed using glycosyl fluorides as good glycosyl donors. The syntheses of two C‐16β structural analogs of OSW‐1 are described.