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

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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 27. Compound 8, a dimeric curvularin was recognised as an artefact. The structures of 18 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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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