Abstract
A triterpenoid, 3beta-cis-p-coumaroyloxy-2alpha,23-dihydroxyolean-12-en-28-oic acid (1), and two natural products, 3beta-trans-p-coumaroyloxy-2alpha,23-dihydroxyolean-12-en-28-oic acid (2) and 23-trans-p-coumaroyloxy-2alpha,3beta-dihydroxyolean-12-en-28-oic acid (3), were isolated from a chloroform-soluble extract of the stems of Eugenia sandwicensis, along with 10 known compounds. Of these compounds, 2 showed significant inhibitory activity (79.2% at 4 microg/ml) in a 7,12-dimethylbenz[a]anthracene-induced mouse mammary organ culture assay system of relevance to cancer chemoprevention. Gallic acid was isolated as an antioxidative constituent of an ethyl acetate-soluble extract of E. sandwicensis stems. Isolates 1-3 were characterized on the basis of spectral and chemical evidence.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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9,10-Dimethyl-1,2-benzanthracene / toxicity
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Animals
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Anticarcinogenic Agents / chemistry
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Anticarcinogenic Agents / isolation & purification*
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Anticarcinogenic Agents / pharmacology
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Biological Factors / chemistry
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Biological Factors / isolation & purification*
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Biological Factors / pharmacology
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Boraginaceae / chemistry*
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Coumaric Acids / chemistry
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Coumaric Acids / isolation & purification
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Female
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Magnetic Resonance Spectroscopy
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Mammary Glands, Animal / drug effects
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Mammary Glands, Animal / pathology
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Mice
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Mice, Inbred BALB C
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Models, Molecular
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Molecular Conformation
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Organ Culture Techniques
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Plant Stems / chemistry
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Plants, Medicinal / chemistry*
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Spectrometry, Mass, Electrospray Ionization
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Spectrometry, Mass, Fast Atom Bombardment
Substances
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Anticarcinogenic Agents
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Biological Factors
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Coumaric Acids
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9,10-Dimethyl-1,2-benzanthracene