A novel group of polyhydroxycholanic acid derivatives from the deep water starfish Styracaster caroli

Tetrahedron Letters
1993.0

Abstract

Three novel polyhydroxysteroid constituents have been isolated from the starfish Styracaster caroli collected at a depth of 2000 m off New Caledonia. These, designated carolisterols A - C (1 - 3), are characterized by a polyhydroxycholanic acid moiety, in which the 24-carboxylic acid function is found as an amide derivative of D-cysteinolic acid. Extensive studies of starfishes steroid constituents have yielded a large number of steroidal oligoglycosides accompanied by numerous polyhydroxysteroids in both sulphated and non sulphated forms. More than eighty polyhydroxysteroids from starfishes have been reported so far. The large majority of them possess a 3β,6α (or β), 8,15α (or β), 16β-pentahydroxycholestane nucleus, sometimes with additional hydroxyl groups at one or more of positions 4β,5α, 7α (or β) and occasionally 14β. A 26-hydroxyl function is usually present in the side chain, less commonly the side chain is hydroxylated at C-24. All hydroxyl groups are disposed on one side of the tetracyclic nucleus inducing an amphiphilic character in the molecules². As a part of our continuing investigation of the New Caledonian marine species, we have examined the polar extracts of the starfish Styracaster caroli collected at a depth of 2000 m between the islands of Thio and Lifou and wish to report the isolation of three unique polyhydroxysteroids, carolisterols A - C (1 - 3). Separation of the polar steroids from the aqueous and acetone extracts of Styracaster caroli (2 Kg fresh) was achieved by chromatography on a column of Sephadex LH-20, followed by droplet countercurrent chromatography and reversed phase HPLC to yield carolisterol A (1, 6.0 mg), B (2, 3.3 mg) and C (3, 2.7 mg).

Knowledge Graph

Similar Paper