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Apralactone A and a New Stereochemical Class of Curvularins from the Marine-Derived Fungus Curvularia sp.


ABSTRACT: Chemical investigations of the cytotoxic extract of the marine-derived 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 IC50 values in the range of 1.25 to 30.06 µM.

SUBMITTER: Greve H 

PROVIDER: S-EPMC3831275 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Apralactone A and a New Stereochemical Class of Curvularins from the Marine-Derived Fungus <i>Curvularia</i> sp.

Greve Hendrik H   Schupp Peter J PJ   Eguereva Ekaterina E   Kehraus Stefan S   Kelter Gerhard G   Maier Armin A   Fiebig Heinz-Herbert HH   König Gabriele M GM  

European journal of organic chemistry 20081001 30


Chemical investigations of the cytotoxic extract of the marine-derived fungus <i>Curvularia</i> sp. (strain no. 768), isolated from the red alga <i>Acanthophora spicifera</i>, yielded the novel macrolide apralactone A (<b>1</b>), as well as the antipodes of curvularin macrolides <b>2-7</b>. Compound <b>8</b>, a dimeric curvularin was recognised as an artefact. The structures of <b>1-8</b> were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, CD, MS, UV and IR). Apralacton  ...[more]

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