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Epoxyfocardin and Its Putative Biogenetic Precursor, Focardin, Bioactive, New‐Skeleton Diterpenoids of the Marine Ciliate Euplotes focardii from Antractica
Author(s) -
Guella Graziano,
Pietra Francesco,
Dini Fernando
Publication year - 1996
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.19960790211
Subject(s) - ciliate , chemistry , terpenoid , temperate climate , skeleton (computer programming) , stereochemistry , terpene , marine ecosystem , ecosystem , botany , ecology , biology , anatomy
From the ciliate Euplotes focardii , collected from Ross Sea coastal waters, Antarctica, a new‐skeleton diterpenoid, epoxyfocardin, was isolated as a 85:15 mixture of hemiacetals 8a and 8b . The absolute configuration of 8a/8b was determined from Mosher 's esters 11a/11b and 12a/12b . Focardin 9a/9b , most likely a biogenetic precursor of 8a/8b , was also isolated as a minor component. Focardin, and particularly epoxyfocardin, proved to be toxic towards representatives of ciliate communities from Antarctic, temperate, tropical, and equatorial environments, constituting the first example of ecologically relevant metabolites from ciliate species that inhabit polar ecosystems.