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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 Curvularia 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 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). Apralacton ...[more]

PMID: 24260014

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