Tsavoenones A-C: unprecedented polyketides with a 1,7-dioxadispiro[4.0.4.4]tetradecane core from the lichen Parmotrema tsavoense
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...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2018, Vol.16 (32), p.5913-5919 |
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| creator | Duong, Thuc-Huy Beniddir, Mehdi A Genta-Jouve, Grégory Aree, Thammarat Chollet-Krugler, Marylène Boustie, Joël Ferron, Solenn Sauvager, Aurélie Nguyen, Huu-Hung Nguyen, Kim-Phi-Phung Chavasiri, Warinthorn Le Pogam, Pierre |
| description | 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. |
| doi_str_mv | 10.1039/c8ob01280f |
| format | Article |
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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. 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| ispartof | Organic & biomolecular chemistry, 2018, Vol.16 (32), p.5913-5919 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical Sciences Crystallography Cytotoxicity Leukemia Myeloid leukemia NMR Nuclear magnetic resonance Polyketides Tetradecane Toxicity testing X-ray crystallography |
| title | 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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