Isolation, identification, and structure of a potent alkyl-peroxyl radical scavenger in crude canola oil, canolol

Daisuke Wakamatsu, Shigeru Morimura, Tomohiro Sawa, Kenji Kida, Chiaki Nakai, Hiroshi Maeda

Research output: Contribution to journalArticlepeer-review

91 Citations (Scopus)

Abstract

Alkylhydroperoxides in oxidized oil are undesirable components because they become alkylperoxyl radicals (ROO) in the presence of heme, hemoglobin, or myoglobin in red meat. ROO are biochemically reactive and damage nucleic acids and proteins, thereby harming living cells. We isolated a component, a highly potent ROO• scavenger, from crude canola oil (rapeseed), which we designated canolol, and identified its chemical structure, 4-vinyl-2,6-dimethoxyphenol. The canolol content of crude canola oil greatly increased after the seed was roasted as compared with that from unroasted seed, but it decreased in highly purified oil. This anti-ROO• activity was highest in crude oil, deceased after each refining step, and was lowest in highly purified refined oil. Canolol was thus generated during roasting. As shown previously, canolol is one of the most potent anti-ROO• components in crude canola oil and its potency is much greater than that of well-known antioxidants, including α-tocopherol, vitamin C, β-carotene, rutin, and quercetin.

Original languageEnglish
Pages (from-to)1568-1574
Number of pages7
JournalBioscience, Biotechnology and Biochemistry
Volume69
Issue number8
DOIs
Publication statusPublished - 2005 Aug 23

Keywords

  • Antimutagenic
  • Antioxidants
  • Canolol
  • Oil refining process
  • Seed oil

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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