Antioxidant activity of thiosulfinates derived from garlic.
Garlic extract significantly inhibited the oxidation of methyl linoleate in homogeneous acetonitrile solution, whereas the antioxidant effect of allicin-free garlic extract, prepared by removing allicin by prepared by removing allicin by preparative HPLC, was much lower than that of the garlic extract. These results suggest that the antioxidant properties are mostly attributed to the presence of allicin in the garlic extract. Allicin a major component of the thiosulfinates in garlic extract, was found to be effective for inhibiting methyl linoleate oxidation, but its efficiency was less than that of alpha-tocopherol. Next, the reactivity of allicin toward the peroxyl radical, which is a chain-propagating species, was investigated by direct ESR detection. The addition allicin to 2,2'-azobis(2,4-dimethylvaleronitrile)-peroxyl radical solution caused the signal intensity of the peroxyl radical to dose-dependently decrease, indicating that allicin is capable of scavenging the the peroxyl radical and acting as an antioxidant. Finally, we studied the structure-anioxidant activity relationship for thiosulfinates and suggested that the combination of the allyl group (-CH2CH=CH2) and the -S(O)S- group is necessary for the antioxidant action of thiosulfinates in the garlic extract. In addition, one of the two possible combinations, -S(O)S-CH2CH=CH2, was found to make a much larger contribution to the antioxidant activity of the thiosulfinates than the other, CH2=CH-CH2-S(O)S-.
Okada
Y
Y
Departments of Analytical Chemistry, School of Health Sciences, Kyorin University, Tokyo, Japan.
Tanaka
K
K
Fujita
I
I
Sato
E
E
Okajima
H
H
D000097:Acetonitriles / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D004220:Disulfides; D004305:Dose-Response Relationship, Drug; D004578:Electron Spin Resonance Spectroscopy; D005737:Garlic / Q000378:metabolism*; D008041:Linoleic Acids / Q000494:pharmacology; D008956:Models, Chemical; D004364:Pharmaceutical Preparations; D010936:Plant Extracts / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000378:metabolism*; D012997:Solvents; D013441:Sulfinic Acids / Q000737:chemistry; D013696:Temperature; D013885:Thiosulfates / Q000737:chemistry*
D000097:Acetonitriles; D000975:Antioxidants; D004220:Disulfides; D008041:Linoleic Acids; D004364:Pharmaceutical Preparations; D010936:Plant Extracts; D012997:Solvents; D013441:Sulfinic Acids; D013885:Thiosulfates; C005575:methyl linoleate; C006452:allicin; C032159:acetonitrile