Chain-breaking activity of carotenes in lipid peroxidation: A theoretical study

Jian Jhih Guo; Hong Yi Hsieh; Ching-Han Hu

doi:10.1021/jp907822h

Chain-breaking activity of carotenes in lipid peroxidation: A theoretical study

Jian Jhih Guo, Hong Yi Hsieh, Ching-Han Hu

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

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 (LȦ). Formation of the addition adduct radical ROO-CAṘ is energetically favorable, and it has an even smaller tendency to react with O₂ than CAR(-H)̇. Comparatively, ROO-β-CAṘ is less likely to react with O₂ than ROO-LYĊ. Both the hydrogen abstraction and addition radicals (CAR(-H)̇ and ROO-CAṘ) react readily with a second ROȮ radical via either hydrogen abstraction or addition.

Original language	English
Pages (from-to)	15699-15708
Number of pages	10
Journal	Journal of Physical Chemistry B
Volume	113
Issue number	47
DOIs	https://doi.org/10.1021/jp907822h
Publication status	Published - 2009 Nov 26

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Surfaces, Coatings and Films
Materials Chemistry

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title = "Chain-breaking activity of carotenes in lipid peroxidation: A theoretical study",

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 (LȦ). Formation of the addition adduct radical ROO-CAṘ is energetically favorable, and it has an even smaller tendency to react with O2 than CAR(-H{\.)}. Comparatively, ROO-β-CAṘ is less likely to react with O2 than ROO-LYĊ. Both the hydrogen abstraction and addition radicals (CAR(-H{\.)} and ROO-CAṘ) react readily with a second ROȮ radical via either hydrogen abstraction or addition.",

author = "Guo, {Jian Jhih} and Hsieh, {Hong Yi} and Ching-Han Hu",

year = "2009",

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T2 - A theoretical study

AU - Guo, Jian Jhih

AU - Hsieh, Hong Yi

AU - Hu, Ching-Han

PY - 2009/11/26

Y1 - 2009/11/26

N2 - 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 (LȦ). Formation of the addition adduct radical ROO-CAṘ is energetically favorable, and it has an even smaller tendency to react with O2 than CAR(-H)̇. Comparatively, ROO-β-CAṘ is less likely to react with O2 than ROO-LYĊ. Both the hydrogen abstraction and addition radicals (CAR(-H)̇ and ROO-CAṘ) react readily with a second ROȮ radical via either hydrogen abstraction or addition.

AB - 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 (LȦ). Formation of the addition adduct radical ROO-CAṘ is energetically favorable, and it has an even smaller tendency to react with O2 than CAR(-H)̇. Comparatively, ROO-β-CAṘ is less likely to react with O2 than ROO-LYĊ. Both the hydrogen abstraction and addition radicals (CAR(-H)̇ and ROO-CAṘ) react readily with a second ROȮ radical via either hydrogen abstraction or addition.

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