Marine Natural Products. VII. Bioactive Triterpene-Oligoglycosides from the Sea Cucumber Holothuria leucospilota Brandt (1). Structure of Holothurin B

Abstract

Two lanostane-type triterpene oligoglycosides designated as holothurin A and holothurin B were isolated from the sea cucumber Holothuria leucospilota Brandt (=H. vagabnda Selenica). The chemical structure of holothurin B, which is contained mainly in the body walls, has been established as 3-O-(2′-O-β-d-quinovopyranosyl-β-d-xylopyranosyl)-holothurigenol 4′-O-sodium sulfate (6), on the basis of chemical, physicochemical, and biochemical evidence. The genuine aglycone of holothurin B was designated as holothurigenol (2) and the C-20 and C-22 configurations of 2 and the artifact aglycone 22,25-oxidoholothurinogenin (1) have been elucidated as S. © 1981, The Pharmaceutical Society of Japan. All rights reserved.