Abstract
Two new compounds, (6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid (1) and 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]epicatechin (3), were isolated by bioassay-guided fractionation from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Compound 1 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC(50) 43.7 and 4.7 microM, respectively), while compound 3 was active in 1,1-diphenyl-2-picrylhydrazyl free-radical and cytochrome c reduction antioxidant assays (IC(50) 29.1 and 16.3 microM, respectively). Additionally, one further new compound was isolated, (3S,24S)-25-trihydroxy-9,19-cycloartane-29-oic acid (2), but this was inactive in the bioassay systems used. Compound 1 is based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Anticarcinogenic Agents / isolation & purification
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Anticarcinogenic Agents / pharmacology
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Antioxidants / isolation & purification*
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Antioxidants / pharmacology
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Bepridil / analogs & derivatives*
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Bepridil / metabolism
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Biphenyl Compounds
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Cyclooxygenase 1
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Cyclooxygenase 2
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors / isolation & purification*
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Cyclooxygenase Inhibitors / pharmacology
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Cytochrome c Group / metabolism
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Humans
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Inhibitory Concentration 50
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Isoenzymes / antagonists & inhibitors
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Membrane Proteins
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oxidation-Reduction
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Picrates*
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Plant Structures / chemistry
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Plants, Medicinal / chemistry*
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Prostaglandin-Endoperoxide Synthases
Substances
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Anticarcinogenic Agents
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Antioxidants
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Biphenyl Compounds
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors
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Cytochrome c Group
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Isoenzymes
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Membrane Proteins
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Picrates
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Bepridil
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1,1-diphenyl-2-picrylhydrazyl
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Cyclooxygenase 1
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Cyclooxygenase 2
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PTGS1 protein, human
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PTGS2 protein, human
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Prostaglandin-Endoperoxide Synthases