Abstract
Three new rearranged prenylated C(6)-C(3) compounds, named illioliganones A, B, and C (1-3), and a new highly oxygenated seco-prezizaane-type sesquiterpene, oligandriortholactone (7), together with three known prenylated C(6)-C(3) compounds (4-6) and a known sesquiterpene lactone (8), have been isolated from the stem bark of Illicium oligandrum. The structures of 1-3 and 7 were elucidated by spectroscopic methods including 1D and 2D NMR, HRMS, and CD experiments. The absolute configuration of the 11,12-diol moiety in 2 and 3 was determined on the basis of observing the induced circular dichroism after addition of Mo(2)(OAc)(4) in DMSO solution. The anti-inflammatory and cytotoxic activities of 1-8 were evaluated.
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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Benzodioxoles
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Drugs, Chinese Herbal / chemistry*
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Drugs, Chinese Herbal / isolation & purification*
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Drugs, Chinese Herbal / pharmacology
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Glucuronidase / drug effects
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Illicium / chemistry*
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Lactones / chemistry
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Molecular Structure
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Neutrophils / drug effects
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Neutrophils / enzymology
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Nuclear Magnetic Resonance, Biomolecular
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Plant Bark / chemistry
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Plant Stems / chemistry
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Plants, Medicinal / chemistry*
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Platelet Activating Factor / pharmacology
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Rats
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Sesquiterpenes / chemistry*
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
Substances
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Anti-Inflammatory Agents
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Benzodioxoles
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Drugs, Chinese Herbal
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Lactones
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Platelet Activating Factor
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Sesquiterpenes
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illioliganone A
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illioliganone B
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illioliganone C
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oligandriortholactone
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Glucuronidase