Abstract
Six new polyoxygenated triterpenoids, cannabifolins A-F (1-6), and eight known triterpenoids, 7-14, were isolated from the leaves of Vitex negundo var. cannabifolia. The absolute configuration of cannabifolin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 represent a class of rare natural pentacyclic triterpenoids bearing cis-fused C/D rings and are the first examples of 12,19-epoxy ursane- and oleanane-type triterpenoids. Compounds 3, 7, 8, and 14 exhibited inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values in the range 24.9-40.5 μM.
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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Crystallography, X-Ray
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Drugs, Chinese Herbal / chemistry
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Lipopolysaccharides / pharmacology
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Macrophages / drug effects
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Mice
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Molecular Conformation
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Molecular Structure
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Nitric Oxide / biosynthesis
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Oleanolic Acid / analogs & derivatives*
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Oleanolic Acid / chemistry
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Oleanolic Acid / isolation & purification
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Oleanolic Acid / pharmacology
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Plant Leaves / chemistry
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Vitex / chemistry*
Substances
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Anti-Inflammatory Agents
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Drugs, Chinese Herbal
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Lipopolysaccharides
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oleanane
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Nitric Oxide
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Oleanolic Acid