Antioxidative activity of tetrahydrocurcuminoids.
In order to develop a new type of antioxidative compound which has both the phenolic and beta-diketone moiety in the same molecule, we converted three known curcuminoids, curcumin (diferuloylmethane, U1), (4-hydroxy-3-methoxycinnamoyl)methane (U2), and bis-(4-hydroxycinnamoyl)methane (U3), which are the natural antioxidants of Curcuma longa L. (tumeric), to tetrahydrocurcuminoids (THU1, THU2, and THU3, respectively) by hydrogenation, and evaluated their antioxidative activity by using linoleic acid as the substrate in an ethanol/water system. Further, we used the rabbit erythrocyte membrane ghost and rat liver microsome as in vitro systems and determined the antioxidative activity of these curcuminoids. When we evaluated their antioxidative activity by these assays, it was found that THU1 had the strongest antioxidative activity among all curcuminoids in each assay system. THU1 has been reported to be one of the main metabolites of U1 in vivo [Holder et al., Xenobiotica, 8, 761-768 (1978)]. These results suggest that THU1 must play an important role in the antioxidative mechanism of U1 in vivo by converting U1 into THU1.
Department of Applied Biological Sciences, Nagoya University, Japan.
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Osawa
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Sugiyama
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Inayoshi
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Kawakishi
D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D003474:Curcumin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D004910:Erythrocyte Membrane / Q000187:drug effects / Q000648:ultrastructure; D006865:Hydrogenation; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D008862:Microsomes, Liver / Q000187:drug effects; D010084:Oxidation-Reduction; D011817:Rabbits; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship; D013858:Thiobarbiturates / Q000737:chemistry; D013861:Thiocyanates / Q000737:chemistry
D000975:Antioxidants; D008041:Linoleic Acids; D013858:Thiobarbiturates; D013861:Thiocyanates; D019787:Linoleic Acid; D003474:Curcumin; C029684:thiobarbituric acid; C031760:thiocyanate; D008697:Methane