Iron-catalyzed reaction products of alpha-tocopherol with 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine (13S)-hydroperoxide

Chemistry and Physics of Lipids
R YamauchiK Kato

Abstract

Alpha-tocopherol was reacted with 1-palmitoyl-2-[(9Z,11E)-(S)-13-hydroperoxy-9,11-octadecadienoyl]-3-sn-phosphatidylcholine (13-PLPC-OOH) in the presence of a lipid-soluble iron chelate, Fe(III) acetylacetonate, in methanol at 37 degrees C. The reaction product was isolated and identified as a mixture of 1-palmitoyl-2-[(10E)-(12S,13S)-9-(8a-dioxy-alpha-tocopherone)-12,13-epoxy-10-octadecenoyl]-3-sn-phosphatidylcholine and 1-palmitoyl-2-[(9Z)-(12S,13S)-11-(8a-dioxy-alpha-tocopherone)-12,13-epoxy-9-octadecenoyl]-3-sn-phosphatidylcholine (TOO-epoxyPLPC), in which the 12,13-epoxyperoxyl radicals derived from 13-PLPC-OOH attacked the 8a-position of the alpha-tocopheroxyl radical. The iron and ascorbate-catalyzed reaction of 13-PLPC-OOH with alpha-tocopherol in phosphatidylcholine (PC) liposomes was assessed by measuring the reaction products of alpha-tocopherol. When 13-PLPC-OOH and alpha-tocopherol were added in saturated dimyristoyl-PC liposomes, the products were TOO-epoxyPLPC, alpha-tocopherylquinone, and epoxy-alpha-tocopherylquinones. In 1-palmitoyl-2-linoleoyl-PC (PLPC) liposomes, alpha-tocopherol could react with both the 13-PLPC-OOH derived 12,13-epoxyperoxyl radicals and the PLPC-derived peroxyl radicals and formed the add...Continue Reading

References

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Apr 1, 1996·Bioscience, Biotechnology, and Biochemistry·R YamauchiK Kato

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Citations

May 8, 2009·Bioscience, Biotechnology, and Biochemistry·Azzedine MazariRyo Yamauchi
Nov 5, 2005·Molecular Nutrition & Food Research·Wujuan Zhang, Robert G Salomon
Jul 31, 2007·American Journal of Kidney Diseases : the Official Journal of the National Kidney Foundation·Liang LuMiriam F Weiss
Sep 28, 2005·Japanese Journal of Ophthalmology·Nermin Serbecic, Sven Christoph Beutelspacher
May 20, 2004·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Junko AdachiYasuhiro Ueno

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