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Sparticolins A-G, Biologically Active Oxidized Spirodioxynaphthalene Derivatives from the Ascomycete Sparticola junci.
Phukhamsakda, Chayanard Macabeo, Allan Patrick G Huch, Volker Cheng, Tian Hyde, Kevin D
Phukhamsakda, Chayanard
Macabeo, Allan Patrick G
Huch, Volker
Cheng, Tian
Hyde, Kevin D
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2019-10-25
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Abstract
To explore the chemical diversity of metabolites from new species of Dothideomycetes, the ex-type strain of Sparticola junci was investigated. Seven highly oxygenated and functionalized spirodioxynaphthalene natural products incorporating carboxyalkylidene-cyclopentanoid (1-4), carboxyl-functionalized oxabicyclo[3.3.0]octane (5-6), and annelated 2-cyclopentenone/δ-lactone (7) units, sparticolins A-G, were isolated from submerged cultures of the fungus. Their chemical structures including their relative (and absolute) configurations were established through spectroscopic and X-ray crystallographic analyses. Sparticolin B (2) exhibited inhibitory activity against the Gram-positive bacteria Bacillus subtilis, Micrococcus luteus, and Staphylococcus aureus, while sparticolin G (7) showed antifungal activities against Schizosaccharomyces pombe and Mucor hiemalis. All other sparticolins were only weakly active against S. aureus and also showed weak activities against the nematode Caenorhabditis elegans. Compounds 2 and 7 also showed moderate cytotoxic activities against seven mammalian cell lines.
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J Nat Prod. 2019 Oct 25;82(10):2878-2885. doi: 10.1021/acs.jnatprod.9b00604. Epub 2019 Oct 10.
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en
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1520-6025
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Attribution-NonCommercial-ShareAlike 4.0 International