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Antioxidative activities of furan- and thiophenethiols measured in lipid peroxidation systems and by tyrosyl radical scavenging assay

Author:
Eiserich, J.P., Wong, J.W., Shibamoto, T.
Source:
Journal of agricultural and food chemistry 1995 v.43 no.3 pp. 647-650
ISSN:
0021-8561
Subject:
free radicals, assays, fluorescence, lipid peroxidation, myoglobin, hydrogen peroxide, furans, tyrosine, oxygen, thiols, phospholipids
Abstract:
Malonaldehyde formation from dilinolenoylphosphatidylcholine liposomes was inhibited by 2-methyl-3-furanthiol, 2-thiophenethiol, and furfuryl mercaptan. 2-Methyl-3-furanthiol and 2-thiophenethiol showed strong and comparable inhibitory activities, whereas furfuryl mercaptan showed only slight activity. 2-Methyl-3-furanthiol possessed synergistic activity with alpha-tocopherol in the lower concentrations. Both 2-methyl-3-furanthiol and 2-thiophenethiol scavenged tyrosyl radicals formed from L-tyrosine in aqueous solutions with activity similar to that of ascorbic acid, whereas furfuryl mercaptan and L-cysteine did not scavenge them. 2-Methyl-3-furanthiol reacted readily with H2O2 in aqueous buffer solutions, resulting in bis(2-methyl-3-furyl) disulfide. Scavenging of myoglobin tyrosyl radicals and the decomposition of H2O2 are proposed as plausible antioxidative mechanisms for 2-methyl-3-furanthiol and 2-thiophenethiol.
Agid:
1369569