Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense

Literature Information

Publication Date 2018-07-31
DOI 10.1039/C8OB01280F
Impact Factor 3.876
Authors

Mehdi A. Beniddir, Grégory Genta-Jouve, Thammarat Aree, Marylène Chollet-Krugler, Joël Boustie, Solenn Ferron, Aurélie Sauvager, Huu-Hung Nguyen, Kim-Phi-Phung Nguyen, Warinthorn Chavasiri, Pierre Le Pogam


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Abstract

New racemic dispiranic polyketides, tsavoenones A (1), B (2) and C (3), having a novel 1,7-dioxadispiro[4.0.4.4]tetradecane scaffold were isolated from the foliose lichen Parmotrema tsavoense. These compounds were structurally elucidated by extensive NMR analyses, comparison between experimental and theoretical 13C NMR data and X-ray crystallography. A putative biosynthetic scenario for the formation of 1–3 from parmosidone D, a meta-depsidone previously isolated from the same lichen material, was proposed. Tested for its cytotoxicity, 1 displayed a moderate activity against human myelogenous leukemia K562 cell line with an IC50 value of 66 μg mL−1.

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Organic & Biomolecular Chemistry
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