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Issue 32, 2018
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Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense

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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.

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

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Publication details

The article was received on 30 May 2018, accepted on 31 Jul 2018 and first published on 31 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01280F
Citation: Org. Biomol. Chem., 2018,16, 5913-5919
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    Tsavoenones A–C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense

    T. Duong, M. A. Beniddir, G. Genta-Jouve, T. Aree, M. Chollet-Krugler, J. Boustie, S. Ferron, A. Sauvager, H. Nguyen, K. Nguyen, W. Chavasiri and P. Le Pogam, Org. Biomol. Chem., 2018, 16, 5913
    DOI: 10.1039/C8OB01280F

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