Chain-Breaking Activity of Carotenes in Lipid Peroxidation: A Theoretical Study

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

doi:10.1021/jp907822h

Cited by 36 publications

(36 citation statements)

References 52 publications

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“…More frequently, they act as direct radical scavengers of the lipid peroxidation chain reactions (chain breakers). Chain-breakers donate an electron to the free radical, neutralizing the radicals and themselves becoming stable (less reactive) radicals, thus stopping the chain reactions [43,44,45]. …”

Section: Biological Roles and Implications (Mainly On Antioxidant mentioning

confidence: 99%

Chemistry and Biochemistry of Dietary Polyphenols

2010

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Polyphenols are the biggest group of phytochemicals, and many of them have been found in plant-based foods. Polyphenol-rich diets have been linked to many health benefits. This paper is intended to review the chemistry and biochemistry of polyphenols as related to classification, extraction, separation and analytical methods, their occurrence and biosynthesis in plants, and the biological activities and implications in human health. The discussions are focused on important and most recent advances in the above aspects, and challenges are identified for future research.

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Section: Biological Roles and Implications (Mainly On Antioxidant mentioning

confidence: 99%

Chemistry and Biochemistry of Dietary Polyphenols

2010

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“…The reaction of carotenoids as scavengers of both short-lived and long-lived oxidizing radicals has been investigated. In homogeneous solutions reaction pathways have been found to depend on both the nature of the reacting free radical and the structure of carotenoid [ 18 , 36 , 37 , 38 , 39 , 40 ]. Three possible mechanism, shown as the reactions of Equations (6), (7) and (8), may be involved:…”

Section: Radical Scavenging Of Flavonoids and Carotenoidsmentioning

confidence: 99%

Reaction Dynamics of Flavonoids and Carotenoids as Antioxidants

2012

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Flavonoids and carotenoids with rich structural diversity are ubiquitously present in the plant kingdom. Flavonoids, and especially their glycosides, are more hydrophilic than most carotenoids. The interaction of flavonoids with carotenoids occurs accordingly at water/lipid interfaces and has been found important for the functions of flavonoids as antioxidants in the water phase and especially for the function of carotenoids as antioxidants in the lipid phase. Based on real-time kinetic methods for the fast reactions between (iso)flavonoids and radicals of carotenoids, antioxidant synergism during protection of unsaturated lipids has been found to depend on: (i) the appropriate distribution of (iso)flavonoids at water/lipid interface, (ii) the difference between the oxidation potentials of (iso)flavonoid and carotenoid and, (iii) the presence of electron-withdrawing groups in the carotenoid for facile electron transfer. For some (unfavorable) combinations of (iso)flavonoids and carotenoids, antioxidant synergism is replaced by antagonism, despite large potential differences. For contact with the lipid phase, the lipid/water partition coefficient is of importance as a macroscopic property for the flavonoids, while intramolecular rotation towards coplanarity upon oxidation by the carotenoid radical cation has been identified by quantum mechanical calculations to be an important microscopic property. For carotenoids, anchoring in water/lipid interface by hydrophilic groups allow the carotenoids to serve as molecular wiring across membranes for electron transport.

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“…51,52 We found that the chain-terminating function of CAR is attributed to the trapping of the radical and the suppression of the addition of O 2 . Furthermore, a hydrogen abstraction mechanism also contributes to the protective function of CARs, although to a lesser extent.…”

Section: → • Initiation: Rh Rmentioning

confidence: 91%

Antioxidative Reaction of Carotenes against Peroxidation of Fatty Acids Initiated by Nitrogen Dioxide: A Theoretical Study

Chen

Huang

2015

J. Phys. Chem. B

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In this study, we investigated the antioxidative functions of carotenes (CARs) against the peroxidation of lipids initiated by nitrogen dioxide using density functional theory. The hydrogen-atom transfer (HAT), radical adduct formation (RAF), and electron transfer (ET) mechanisms were investigated. We chose β-carotene (β-CAR) and lycopene (LYC) and compared their NO2(•) initiations and peroxidations with those of linoleic acid (LAH), the model of the lipid. We found that for CARs ET is more likely to occur in the most polar (water) environment than are HAT and RAF. In less polar environments, CARs react more readily with NO2(•) via HAT and RAF than does the lipid model, LAH. Comparatively, reaction barriers for the RAF between CARs and NO2(•) are smaller than those for the HAT. The additions of O2 to the radical intermediates O2N-CAR(•) and CAR(-H)(•) involve sizable barriers and are endergonic. Other than HAT of LAH, we revealed that lipid peroxidation is likely to be initiated by -NO2 addition and the subsequent barrierless addition of O2. Finally, LYC is a more effective antioxidative agent against NO2(•)-initiated lipid peroxidation than is β-CAR.

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Chain-Breaking Activity of Carotenes in Lipid Peroxidation: A Theoretical Study

Cited by 36 publications

References 52 publications

Chemistry and Biochemistry of Dietary Polyphenols

Chemistry and Biochemistry of Dietary Polyphenols

Reaction Dynamics of Flavonoids and Carotenoids as Antioxidants

Antioxidative Reaction of Carotenes against Peroxidation of Fatty Acids Initiated by Nitrogen Dioxide: A Theoretical Study

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