Sparticolins A–G, Biologically Active Oxidized Spirodioxynaphthalene Derivatives from the Ascomycete Sparticola junci

Sparticolins A–G, Biologically Active Oxidized Spirodioxynaphthalene Derivatives from the Ascomycete Sparticola junci

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-functionaliz...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2019-10, Vol.82 (10), p.2878-2885
Hauptverfasser: Phukhamsakda, Chayanard, Macabeo, Allan Patrick G, Huch, Volker, Cheng, Tian, Hyde, Kevin D, Stadler, Marc
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container_issue 10
container_start_page 2878
container_title Journal of natural products (Washington, D.C.)
container_volume 82
creator Phukhamsakda, Chayanard
Macabeo, Allan Patrick G
Huch, Volker
Cheng, Tian
Hyde, Kevin D
Stadler, Marc
description 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.
doi_str_mv 10.1021/acs.jnatprod.9b00604
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title Sparticolins A–G, Biologically Active Oxidized Spirodioxynaphthalene Derivatives from the Ascomycete Sparticola junci
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