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

Jason P. Eiserich, Jon W. Wong, Takayuki Shibamoto

Research output: Contribution to journalArticle

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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 α-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.

Original languageEnglish (US)
Pages (from-to)647-650
Number of pages4
JournalJournal of Agricultural and Food Chemistry
Volume43
Issue number3
StatePublished - 1995

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Keywords

  • Antioxidant
  • Lipid peroxidation
  • Phospholipid
  • Thiols

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

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