Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil

Hideo Kuwahara; Ayako Kanazawa; Daisuke Wakamatu; Shigeru Morimura; Kenji Kida; Takaaki Akaike; Hiroshi Maeda

doi:10.1021/jf040045+

Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil

Hideo Kuwahara, Ayako Kanazawa, Daisuke Wakamatu, Shigeru Morimura, Kenji Kida, Takaaki Akaike, Hiroshi Maeda

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

114 Citations (Scopus)

Abstract

A potent antioxidative compound in crude canola oil, canolol, was recently identified, and reported herein are studies of its scavenging capacity against the endogenous mutagen peroxynitrite (ONOO^-). ONOO^- is generated by the reaction between superoxide anion radical and nitric oxide, both of which are produced by inflammatory leukocytes. Among various antioxidative substances of natural or synthetic origin, canolol was one of the most potent antimutagenic compounds when Salmonella typhimurium TA102 was used in the modified Ames test. Its potency was higher than that of flavonoids (e.g., rutin) and α-tocopherol and was equivalent to that of ebselen. Canolol suppressed ONOO^--induced bactericidal action. It also reduced intracellular oxidative stress and apoptosis in human cancer SW480 cells when used at a concentration below 20 μM under H₂O₂-induced oxidative stress. In addition, canolol suppressed plasmid DNA (pUC19) strand breakage induced by ONOO^-, as revealed by agarose gel electrophoresis.

Original language	English
Pages (from-to)	4380-4387
Number of pages	8
Journal	Journal of Agricultural and Food Chemistry
Volume	52
Issue number	14
DOIs	https://doi.org/10.1021/jf040045+
Publication status	Published - 2004 Jul 14
Externally published	Yes

Keywords

Antioxidant
Canola oil
Canolol
DNA breaks
Mutagenicity
ONOO
Radical scavenger

ASJC Scopus subject areas

Chemistry(all)
Agricultural and Biological Sciences(all)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jf040045+

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title = "Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil",

abstract = "A potent antioxidative compound in crude canola oil, canolol, was recently identified, and reported herein are studies of its scavenging capacity against the endogenous mutagen peroxynitrite (ONOO-). ONOO- is generated by the reaction between superoxide anion radical and nitric oxide, both of which are produced by inflammatory leukocytes. Among various antioxidative substances of natural or synthetic origin, canolol was one of the most potent antimutagenic compounds when Salmonella typhimurium TA102 was used in the modified Ames test. Its potency was higher than that of flavonoids (e.g., rutin) and α-tocopherol and was equivalent to that of ebselen. Canolol suppressed ONOO--induced bactericidal action. It also reduced intracellular oxidative stress and apoptosis in human cancer SW480 cells when used at a concentration below 20 μM under H2O2-induced oxidative stress. In addition, canolol suppressed plasmid DNA (pUC19) strand breakage induced by ONOO-, as revealed by agarose gel electrophoresis.",

keywords = "Antioxidant, Canola oil, Canolol, DNA breaks, Mutagenicity, ONOO, Radical scavenger",

author = "Hideo Kuwahara and Ayako Kanazawa and Daisuke Wakamatu and Shigeru Morimura and Kenji Kida and Takaaki Akaike and Hiroshi Maeda",

year = "2004",

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T1 - Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil

AU - Kuwahara, Hideo

AU - Kanazawa, Ayako

AU - Wakamatu, Daisuke

AU - Morimura, Shigeru

AU - Kida, Kenji

AU - Akaike, Takaaki

AU - Maeda, Hiroshi

PY - 2004/7/14

Y1 - 2004/7/14

N2 - A potent antioxidative compound in crude canola oil, canolol, was recently identified, and reported herein are studies of its scavenging capacity against the endogenous mutagen peroxynitrite (ONOO-). ONOO- is generated by the reaction between superoxide anion radical and nitric oxide, both of which are produced by inflammatory leukocytes. Among various antioxidative substances of natural or synthetic origin, canolol was one of the most potent antimutagenic compounds when Salmonella typhimurium TA102 was used in the modified Ames test. Its potency was higher than that of flavonoids (e.g., rutin) and α-tocopherol and was equivalent to that of ebselen. Canolol suppressed ONOO--induced bactericidal action. It also reduced intracellular oxidative stress and apoptosis in human cancer SW480 cells when used at a concentration below 20 μM under H2O2-induced oxidative stress. In addition, canolol suppressed plasmid DNA (pUC19) strand breakage induced by ONOO-, as revealed by agarose gel electrophoresis.

AB - A potent antioxidative compound in crude canola oil, canolol, was recently identified, and reported herein are studies of its scavenging capacity against the endogenous mutagen peroxynitrite (ONOO-). ONOO- is generated by the reaction between superoxide anion radical and nitric oxide, both of which are produced by inflammatory leukocytes. Among various antioxidative substances of natural or synthetic origin, canolol was one of the most potent antimutagenic compounds when Salmonella typhimurium TA102 was used in the modified Ames test. Its potency was higher than that of flavonoids (e.g., rutin) and α-tocopherol and was equivalent to that of ebselen. Canolol suppressed ONOO--induced bactericidal action. It also reduced intracellular oxidative stress and apoptosis in human cancer SW480 cells when used at a concentration below 20 μM under H2O2-induced oxidative stress. In addition, canolol suppressed plasmid DNA (pUC19) strand breakage induced by ONOO-, as revealed by agarose gel electrophoresis.

KW - Antioxidant

KW - Canola oil

KW - Canolol

KW - DNA breaks

KW - Mutagenicity

KW - ONOO

KW - Radical scavenger

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Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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