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Apralactone A and a New Stereochemical Class of Curvularins from the Marine Fungus Curvularia sp.
Author(s) -
Greve Hendrik,
Schupp Peter J.,
Eguereva Ekaterina,
Kehraus Stefan,
Kelter Gerhard,
Maier Armin,
Fiebig HeinzHerbert,
König Gabriele M.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800522
Subject(s) - chemistry , stereochemistry , fungus , curvularia , cytotoxic t cell , strain (injury) , marine fungi , in vitro , botany , penicillium , biology , biochemistry , food science , anatomy
Abstract Chemical investigations of the cytotoxic extract of the marine fungus Curvularia sp. (strain no. 768), isolated from the red alga Acanthophora spicifera , yielded the novel macrolide apralactone A ( 1 ), as well as the antipodes of curvularin macrolides 2 – 7 . Compound 8 , a dimeric curvularin was recognised as an artefact. The structures of 1 – 8 were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, CD, MS, UV and IR). Apralactone A ( 1 ) is a 14‐membered phenyl acetic acid macrolactone, and the first such compound with a 4‐chromanone substructure. Compounds 1 , 2 , 4 , 5 and 6 were found to be cytotoxic towards human tumor cell lines with mean IC 50 values in the range of 1.25 to 30.06 μ M . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)