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Oceanapins A–F, Unique Branched Ceramides Isolated from the Haplosclerid Sponge Oceanapia cf. tenuis of the Coral Sea
Author(s) -
Mancini Ines,
Guella Graziano,
Pietra Francesco,
Debitus Cécile
Publication year - 1994
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.19940770108
Subject(s) - sponge , chemistry , sphingosine , coral , stereochemistry , fatty acid , branching (polymer chemistry) , ceramide , hydrolysis , sphingolipid , biochemistry , organic chemistry , botany , ecology , biology , receptor , apoptosis
A series of ceramides, called oceanapins A–F ( 2–7 ), which are unique for branching at both the sphingosine and fatty‐acid chains, have been isolated as pure compounds from the haplosclerid sponge Oceanapia cf. tenuis of the Coral Sea. Following acid hydrolysis, both the fatty‐acid and the sphingosine portions were obtained separately, which allowed their unequivocal structural definition. The absolute configuration was secured via protection of C(1′)–OH and Mosher's esterification at C(3′)–OH of the oceanapins.