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Chemical studies of marine invertebrates-XXI. Six triterpene genins artifacts from thelothurins A and B, toxic saponins of the sea cucumber Thelonota ananas Jaeger (echinodermata). Biosynthesis of the thelothurins

par Kelecom, Alphonse ;Daloze, Désiré ;Tursch, Bernard
Référence Tetrahedron, 32, 19, page (2353-2359)
Publication Publié, 1976

Article révisé par les pairs

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Résumé :

Aqueous hydrochloric acid hydrolysis of the mixture of thelothurins A and B, the saponins from the sea cucumber Thelonota ananas Jaeger, gave a complex mixture from which six sapogenins were isolated. Chemical and spectroscopic evidence led to the assignment of structures 3-8 to these genins which are correlated to the known seychellogenin acetate (9). It is also shown that compounds 1 and 2, obtained by mild aqueous acetic acid hydrolysis of the thelothurins, are the genuine aglycones, whereas 3-8 are artifacts. Their formation during the hydrolysis of the saponins is discussed. The aglycone moiety of thelothurins A (20A) and B (20B) was biosynthesized from the acetate. © 1976.