Oxidation products of quercetin catalyzed by mushroom tyrosinase

Bioorganic & Medicinal Chemistry
Isao KuboKuniyoshi Shimizu

Abstract

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.

References

Dec 20, 1999·Journal of Agricultural and Food Chemistry·J C Espín, H J Wichers

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Citations

Sep 19, 2009·Applied Biochemistry and Biotechnology·Shu-Bai LiLi-Min Zhu
Apr 10, 2013·Bioorganic & Medicinal Chemistry·Shrikant S GawandeChandrahasya N Khobragade
Jan 15, 2014·Bioorganic & Medicinal Chemistry·Yan WangKi Hun Park
Apr 30, 2011·Chemical Reviews·Daniela MontiSergio Riva
Jul 15, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Dae Wook KimByoung Seob Ko
Aug 9, 2015·International Journal of Biological Macromolecules·Hemachandran HridyaRamamoorthy Siva
Feb 21, 2006·Biochemical and Biophysical Research Communications·Egor M CherviakovskySergey A Usanov
Aug 26, 2015·ACS Applied Materials & Interfaces·Yi LiuJun-Jie Yin
Sep 14, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Igor G ZenkevichViktor A Utsal
Sep 18, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Isao KuboKen-ichi Nihei
Dec 18, 2013·Bioorganic & Medicinal Chemistry Letters·Takehiro IwadateKen-Ichi Nihei
Mar 12, 2017·Bioorganic & Medicinal Chemistry Letters·Takehiro Iwadate, Ken-Ichi Nihei
Jun 28, 2017·The Journal of Physical Chemistry. B·Romana SokolováVladimír Křen
Jun 21, 2008·Phytotherapy Research : PTR·Teruhiko NitodaIsao Kubo
Aug 24, 2010·Chemistry & Biodiversity·Tae Joung HaIsao Kubo
Jul 9, 2008·Journal of Enzyme Inhibition and Medicinal Chemistry·Y B RyuK H Park
Mar 8, 2006·Phytotherapy Research : PTR·Noriyoshi MasuokaIsao Kubo
Mar 7, 2013·Chemical Biology & Drug Design·Jinbing LiuLiangzhong Zhao
Jan 31, 2020·Phytochemical Analysis : PCA·Randolph R J ArrooDidem Şöhretoğlu
Dec 13, 2019·Frontiers in Chemistry·Alejandro Vásquez-EspinalWilliam Tiznado
Jun 20, 2018·Carbohydrate Research·Takashi MatsumotoKen-Ichi Nihei
Jun 25, 2016·Journal of Agricultural and Food Chemistry·Beata Gąsowska-Bajger, Hubert Wojtasek
Dec 3, 2008·Bioorganic & Medicinal Chemistry·Yoon Su BaekKi Hun Park

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