Abstract
Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellones A (2)-D (5). The benzo[c]chromene-7,10-dione scaffold contained within scabellones A-D is particularly rare among natural products. The structures were elucidated by interpretation of NMR data. Scabellone B was also identified as a moderately potent, nontoxic inhibitor of Plasmodium falciparum.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Inflammatory Agents / chemistry*
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Anti-Inflammatory Agents / isolation & purification*
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Anti-Inflammatory Agents / pharmacology*
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Antimalarials / chemistry*
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Antimalarials / isolation & purification*
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Antimalarials / pharmacology*
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Benzopyrans / chemistry*
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Benzopyrans / isolation & purification*
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Benzopyrans / pharmacology*
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Molecular Structure
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New Zealand
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Nuclear Magnetic Resonance, Biomolecular
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Plasmodium falciparum / chemistry
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Plasmodium falciparum / drug effects*
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Quinones / chemistry*
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Quinones / isolation & purification*
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Quinones / pharmacology
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Terpenes / chemistry*
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Terpenes / isolation & purification*
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Terpenes / pharmacology*
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Urochordata / chemistry*
Substances
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2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate
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Anti-Inflammatory Agents
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Antimalarials
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Benzopyrans
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Quinones
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Terpenes
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azo(c)chromene-7,10-dione