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Biosci Biotechnol Biochem ; 82(12): 2109-2117, 2018 Dec.
Article in English | MEDLINE | ID: mdl-30146952

ABSTRACT

We wished to search for the compounds contributing to the anti-inflammatory effects of the water extract of Curcuma longa (WEC). WEC was fractioned and the fractions were evaluated with regard to their inhibitory effect on the production of nitric oxide (NO) from the macrophage cell line stimulated by lipopolysaccharide. Compounds in the active fractions were isolated and identified. One isolated compound was identified as new: (6S)-2-methyl-5-hydroxy-6-(3-hydroxy-4-methylphenyl)-2-heptene-4-one (1). Four isolated compounds were identified as known: (6S)-2-methyl-6-(4-hydroxyphenyl)-2-heptene-4-one (4), bisabolone-4-one (5), curcumenone (6), and turmeronol A (8). Three isolated compounds were not identified their stereostructures but their planar structures: 2-methyl-6-(4-hydroxymethyl-phenyl)-2-heptene-4-one (2), 2-methyl-6-(2,3-epoxy-4-methyl-4-cyclohexene)-2-heptene (3), and 4-methylene-5-hydroxybisabola-2,10-diene-9-one (7). Compounds 1, 4, 7 and 8 inhibited production of prostaglandin E2 and NO. Others inhibited NO production only. These results (at least in part) show the active compounds contributing to the anti-inflammatory effects of WEC, and may be useful for elucidating its various beneficial physiologic effects.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Curcuma/chemistry , Dinoprostone/biosynthesis , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Nitric Oxide/biosynthesis , Plant Extracts/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Carbon-13 Magnetic Resonance Spectroscopy , Chromatography, High Pressure Liquid , Macrophages/metabolism , Mass Spectrometry/methods , Mice , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Proton Magnetic Resonance Spectroscopy , RAW 264.7 Cells , Water
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