Abstract
A new beta-hydroxy-gamma-methyl-gamma-lactone bistetrahydrofuranic acetogenin, tucumanin, with the infrequent symmetrical threo/trans/threo/trans/threo relative configuration at the tetrahydrofuran rings was isolated from Annona cherimolia (Annonaceae) seeds. The inhibitory potency on the mitochondrial complex I of acetogenins with this relative configuration (tucumanin and asimicin)was compared with that shown by the corresponding pairs with an asymmetrical threo/trans/threo/trans/erythro relative configuration (laherradurin/rolliniastatin-2, and itrabin/molvizarin). All these compounds act as selective inhibitors of mitochondrial complex I in the 0.18 - 1.55 nM range.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Annona*
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Electron Transport Complex I / antagonists & inhibitors*
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Electron Transport Complex I / metabolism
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Enzyme Inhibitors / administration & dosage
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Enzyme Inhibitors / pharmacology*
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Enzyme Inhibitors / therapeutic use
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Furans / administration & dosage
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Furans / pharmacology*
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Furans / therapeutic use
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Humans
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Inhibitory Concentration 50
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Lactones / administration & dosage
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Lactones / pharmacology*
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Lactones / therapeutic use
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Mitochondria, Heart / drug effects
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Mitochondria, Heart / enzymology
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Phytotherapy*
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Plant Extracts / administration & dosage
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Plant Extracts / pharmacology*
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Plant Extracts / therapeutic use
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Seeds
Substances
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Enzyme Inhibitors
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Furans
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Lactones
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Plant Extracts
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tucumanin
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Electron Transport Complex I