Oxidation products of quercetin catalyzed by mushroom tyrosinase

Isao Kubo, Ken Ichi Nihei, Kuniyoshi Shimizu

研究成果: Contribution to journalArticle

83 被引用数 (Scopus)

抄録

Quercetin was oxidized as a substrate catalyzed by mushroom tyrosinase to the corresponding o-quinone and subsequent isomerization to p-quinone methide type intermediate; followed by the addition of water on C-2 yielding a relatively stable intermediate, 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)- benzofuranone. Quercetin was oxidized as a substrate catalyzed by mushroom tyrosinase to the corresponding o-quinone and subsequent isomerization to p-quinone methide type intermediate; followed by the addition of water on C-2 yielding a relatively stable intermediate, 2-(3,4-dihydroxybenzoyl)-2,4,6- trihydroxy-3(2H)-benzofuranone. In the presence of a catalytic amount of l-DOPA as a cofactor, the rate of this oxidation was enhanced. Fisetin, which lacks the C-5 hydroxyl group, was also oxidized but the rate of oxidation was faster than that of quercetin, indicating that the C-5 hydroxyl group is not essential but is associated with the activity.

本文言語英語
ページ(範囲)5343-5347
ページ数5
ジャーナルBioorganic and Medicinal Chemistry
12
20
DOI
出版ステータス出版済み - 10 15 2004
外部発表はい

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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