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Sphinxolide, a 26‐Membered Antitumoral Macrolide Isolated from an Unidentified Pacific Nudibranch
Author(s) -
Guella Graziano,
Mancini Ines,
Chiasera Giuseppe,
Pietra Francesco
Publication year - 1989
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.19890720207
Subject(s) - nudibranch , chemistry , stereochemistry , formamide , moiety , gastropoda , zoology , organic chemistry , biology
It is shown that an unidentified nudibranch of Hawaiian waters contains a 26‐membered macrolide, sphinxolide ((−)‐ 1 ) with potent activity against the KB cell line. The structure of sphinxolide, a 2:1 mixture of ( E / Z )‐isomers at the formamide moiety, is established to be (–)‐ 1 on the basis of extensive NMR and FAB‐MS analysis, in combination with data for the products of mono‐ (→(−)‐ 2 ) and diacetylation (→(+)‐3).