Abstract
A novel metabolite (-)-1 was isolated as its peracetylated derivative, (-)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran (2), from a strain of the phytopathogenic fungus Colletotrichum gloeosporioides CECT 20122. The synthesis of (-)-1 was carried out by ring-closing metathesis of diene 6 and stereoselective dihydroxylation of a dihydrofuran derivative 7 as key steps. The tetraol (-)-1 showed free radical scavenging activity comparable to that of BHT, caffeic acid or protocatechuic acid.
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetates / chemical synthesis
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Acetates / pharmacology*
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Antifungal Agents / chemical synthesis*
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Antifungal Agents / pharmacology
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Butylated Hydroxytoluene / pharmacology
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Caffeic Acids / pharmacology
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Colletotrichum / metabolism*
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Free Radical Scavengers / metabolism*
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Furans / chemical synthesis
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Furans / pharmacology*
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Hydroxybenzoates / pharmacology
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Peracetic Acid / analogs & derivatives
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Peracetic Acid / chemical synthesis
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Peracetic Acid / pharmacology*
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Plant Diseases / microbiology
Substances
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2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran
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Acetates
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Antifungal Agents
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Caffeic Acids
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Free Radical Scavengers
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Furans
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Hydroxybenzoates
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Butylated Hydroxytoluene
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protocatechuic acid
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Peracetic Acid
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caffeic acid