Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil.
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 alpha-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 microM under H(2)O(2)-induced oxidative stress. In addition, canolol suppressed plasmid DNA (pUC19) strand breakage induced by ONOO(-), as revealed by agarose gel electrophoresis.
Kuwahara
Hideo
H
Department of Microbiology, Graduate School of Medical Sciences, Kumamoto University, Honjo 1-1-1, Kumamoto 860-8556, Japan.
Kanazawa
Ayako
A
Wakamatu
Daisuke
D
Morimura
Shigeru
S
Kida
Kenji
K
Akaike
Takaaki
T
Maeda
Hiroshi
H
D000900:Anti-Bacterial Agents / Q000494:pharmacology; D016587:Antimutagenic Agents / Q000494:pharmacology*; D000975:Antioxidants / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D003110:Colonic Neoplasms; D004249:DNA Damage / Q000187:drug effects; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D006801:Humans; D009152:Mutagenicity Tests; D018384:Oxidative Stress / Q000187:drug effects; D030421:Peroxynitrous Acid / Q000037:antagonists & inhibitors; D010636:Phenols / Q000302:isolation & purification* / Q000494:pharmacology*; D000074262:Rapeseed Oil; D014407:Tumor Cells, Cultured; D014753:Vinyl Compounds / Q000302:isolation & purification* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D016587:Antimutagenic Agents; D000975:Antioxidants; D005229:Fatty Acids, Monounsaturated; D010636:Phenols; D000074262:Rapeseed Oil; D014753:Vinyl Compounds; D030421:Peroxynitrous Acid; C488411:4-vinyl-2,6-dimethoxyphenol