Canolol: A promising chemical agent against oxidative stress

Annia Galano, Misaela Francisco-Márquez, Juan R. Alvarez-Idaboy

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

The OOH radical scavenging activity of canolol (CNL) has been studied in aqueous and lipid solutions, using the density functional theory. CNL is predicted to react about 3.6 times faster in aqueous solution than in lipid media. The overall rate coefficients are predicted to be 2.5 × 10 6 and 6.8 × 105 M-1 s-1, respectively. The OOH radical scavenger activity of canolol is predicted to be similar to that of carotenes, higher than that of allicin, and much higher than that of melatonin. Branching ratios for the different channels of reaction are reported for the first time. It was found that the reactivity of canolol toward OOH radicals takes place almost exclusively by H atom transfer from the phenolic moiety in canolol, regardless of the polarity of the environment. Taking into account that the reactivity of peroxyl radicals is significantly lower than that of other reactive oxygen species, canolol is proposed to be a very good antioxidant. © 2011 American Chemical Society.
Original languageAmerican English
Pages (from-to)8590-8596
Number of pages7730
JournalJournal of Physical Chemistry B
DOIs
StatePublished - 7 Jul 2011
Externally publishedYes

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Oxidative stress
Lipids
Scavenging
Antioxidants
Density functional theory
lipids
reactivity
melatonin
aqueous solutions
carotene
Atoms
Oxygen
scavenging
antioxidants
polarity
Melatonin
Carotenoids
density functional theory
4-vinyl-2,6-dimethoxyphenol
Reactive Oxygen Species

Cite this

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abstract = "The OOH radical scavenging activity of canolol (CNL) has been studied in aqueous and lipid solutions, using the density functional theory. CNL is predicted to react about 3.6 times faster in aqueous solution than in lipid media. The overall rate coefficients are predicted to be 2.5 × 10 6 and 6.8 × 105 M-1 s-1, respectively. The OOH radical scavenger activity of canolol is predicted to be similar to that of carotenes, higher than that of allicin, and much higher than that of melatonin. Branching ratios for the different channels of reaction are reported for the first time. It was found that the reactivity of canolol toward OOH radicals takes place almost exclusively by H atom transfer from the phenolic moiety in canolol, regardless of the polarity of the environment. Taking into account that the reactivity of peroxyl radicals is significantly lower than that of other reactive oxygen species, canolol is proposed to be a very good antioxidant. {\circledC} 2011 American Chemical Society.",
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Canolol: A promising chemical agent against oxidative stress. / Galano, Annia; Francisco-Márquez, Misaela; Alvarez-Idaboy, Juan R.

In: Journal of Physical Chemistry B, 07.07.2011, p. 8590-8596.

Research output: Contribution to journalArticle

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AU - Francisco-Márquez, Misaela

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