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Title: Chain-Breaking Activity of Carotenes in Lipid Peroxidation: A Theoretical Study
Authors: Guo, Jian-Jhih;Hsieh, Hong-Yi;Hu, Ching-Han
Contributors: 化學系
Date: 2009-11
Issue Date: 2012-05-03T06:18:11Z
Publisher: American Chemical Society
Abstract: Chain-breaking reactions against lipid peroxidation performed by carotenes, including β-carotene (β-CAR) and lycopene (LYC), have been studied using density functional theory. We chose linoleic acid (LAH) as the lipid model and examined two mechanisms: hydrogen abstraction and addition. Our computed reaction diagrams reveal that the addition mechanism is able to offer a larger extent of chain-breaking protection than hydrogen abstraction. In the case of hydrogen abstraction, the resulting carotene radical CAR(−H)• has a smaller O2 affinity than the linoleic acid radical (LA•). Formation of the addition adduct radical ROO−CAR• is energetically favorable, and it has an even smaller tendency to react with O2 than CAR(−H)•. Comparatively, ROO−β-CAR• is less likely to react with O2 than ROO−LYC•. Both the hydrogen abstraction and addition radicals (CAR(−H)• and ROO−CAR•) react readily with a second ROO• radical via either hydrogen abstraction or addition.
Relation: J. Phys. Chem. B, 113(47): 15699-15708
Appears in Collections:[Department of Chemistry] Periodical Articles

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