Marine Natural Products. XXVII. Distribution of Lanostane-Type Triterpene Oligoglycosides in Ten Kinds of Okinawan Sea Cucumbers

Abstract

Triterpene-oligoglycoside constituents in ten sea cucumber species inhabiting Okinawan coral reefs were investigated. Several antifungal oligoglycosides were isolated from six species [stichlorosides A₁ (15), A₂ (16), B₁ (17), B₂ (18), C₁ (19), and C₂ (20) from Thelonota ananas (baika-namako in Japanese) and Stichopus hermanni; 15, 17, and 19 from Thelonota anax; bivittosides C (13) and D (14) from Bohadschia argus (janome-namako); holothurin A (6) from Holothuria edulis (akamishikiri); and 6 and echinoside A (10) from Bohadschia graeffei (kurote-namako)]. Furthermore, several oligoglycosides were isolated in their desulfated forms from four species [6 and 10 from Holothuria axiologa; holothurin B (4), 6, echinoside B (8), and 10 from Holothuria atra (kuro-namako); 6, 10, and 24-dehydroechinoside A (24) from Holothuria scabra (haneji-namako); and 8, 10, 24-dehydroechinoside B (22), and 24 from Actinopyga mauritiana (kuriiro-namako)]. 24-Dehydroechinoside B (22) is a new lanostane-type triterpene oligoglycoside.