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Cacospongione A, cacospongienone A, and cacospongienone B, new C 21 difuran terpenoids from the marine sponge Cacospongia scalaris S CHMIDT of the Côte d' Azur
Author(s) -
Guella Graziano,
Amade Philippe,
Pietra Francesco
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690325
Subject(s) - terpenoid , sponge , chemistry , stereochemistry , absolute configuration , botany , biology
The sponge Cacospongia scalaris (family Thorectidae), collected at the Cap de Nice (Cǒte d'Azur), is shown to contain a series of truncated, linear C 21 difuran terpenoids comprising the known sponge products furospongin‐1 ((+)‐ 1 ), furospongin‐2 ( 2 ), and dihydrofurospongin‐2 ((−)‐( E )‐ 3 ), besides the new products cacospongione A ((−)‐ 4 ), cacospongienone A ((−)‐( Z )‐ 6 ), and cacospongienone B ((−)‐( E )‐ 6 ), whose absolute configurations have been assigned by chemical correlations with (+)‐ 1 . Possibly, one of the two cacospongienones is an artifact, as these two terpenoids interconvert on standing. This is the first finding of linear C 21 difuran terpenoids, which are typical of the Spongiidae, in a member of the family Thorectidae.