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Xenobiotica
the fate of foreign compounds in biological systems
Volume 50, 2020 - Issue 10
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General Xenobiochemistry

Preference for O-demethylation reactions in the oxidation of 2′-, 3′-, and 4′-methoxyflavones by human cytochrome P450 enzymes

Haruna NagayoshiOsaka Institute of Public Health, Osaka, Japan; View further author information
,
Norie MurayamaLaboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, Tokyo, Japan; View further author information
,
Masaki TsujinoOsaka Institute of Public Health, Osaka, Japan; View further author information
,
Shigeo TakenakaGraduate School of Comprehensive Rehabilitation, Osaka Prefecture University, Habikino, Osaka, Japan; View further author information
,
Jun KatahiraLaboratory of Cellular and Molecular Biology, Veterinary Sciences, Osaka Prefecture University, Izumisano, Osaka, Japan; View further author information
,
Vitchan KimDepartment of Biological Sciences, Konkuk University, Seoul, Korea, and; View further author information
,
Donghak KimDepartment of Biological Sciences, Konkuk University, Seoul, Korea, and; ORCID Iconhttp://orcid.org/0000-0002-4421-7215View further author information
ORCID Icon,
Masayuki KomoriLaboratory of Cellular and Molecular Biology, Veterinary Sciences, Osaka Prefecture University, Izumisano, Osaka, Japan; View further author information
,
Hiroshi YamazakiLaboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, Tokyo, Japan; ORCID Iconhttp://orcid.org/0000-0002-1068-4261View further author information
ORCID Icon,
F. Peter GuengerichDepartment of Biochemistry, Vanderbilt University School of Medicine, Nashville, TN, USAORCID Iconhttp://orcid.org/0000-0002-7458-3048View further author information
ORCID Icon &
Tsutomu ShimadaLaboratory of Cellular and Molecular Biology, Veterinary Sciences, Osaka Prefecture University, Izumisano, Osaka, Japan; Correspondence[email protected]
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Pages 1158-1169 | Received 26 Mar 2020, Accepted 19 Apr 2020, Published online: 30 Apr 2020

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Tsutomu Shimada, Haruna Nagayoshi, Norie Murayama, Atsuki Sawai, Vitchan Kim, Donghak Kim, Hiroshi Yamazaki, F. Peter Guengerich & Shigeo Takenaka. (2022) Oxidation of 3’-methoxyflavone, 4’-methoxyflavone, and 3’,4’-dimethoxyflavone and their derivatives having 5,7-dihydroxyl moieties by human cytochromes P450 1B1 and 2A13. Xenobiotica 52:2, pages 134-145.
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Haruna Nagayoshi, Norie Murayama, Shigeo Takenaka, Vitchan Kim, Donghak Kim, Masayuki Komori, Hiroshi Yamazaki, F. Peter Guengerich & Tsutomu Shimada. (2021) Roles of cytochrome P450 2A6 in the oxidation of flavone, 4′-hydroxyflavone, and 4′-, 3′-, and 2′-methoxyflavones by human liver microsomes. Xenobiotica 51:9, pages 995-1009.
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Tsutomu Shimada, Haruna Nagayoshi, Norie Murayama, Shigeo Takenaka, Jun Katahira, Vitchan Kim, Donghak Kim, Masayuki Komori, Hiroshi Yamazaki & F. Peter Guengerich. (2021) Liquid chromatography-tandem mass spectrometry analysis of oxidation of 2′-, 3′-, 4′- and 6-hydroxyflavanones by human cytochrome P450 enzymes. Xenobiotica 51:2, pages 139-154.
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Ketan C. Ruparelia, Keti Zeka, Kenneth J. M. Beresford, Nicola E. Wilsher, Gerry A. Potter, Vasilis P. Androutsopoulos, Federico Brucoli & Randolph R. J. Arroo. (2024) CYP1-Activation and Anticancer Properties of Synthetic Methoxylated Resveratrol Analogues. Molecules 29:2, pages 423.
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Haruna Nagayoshi, Norie Murayama, Vitchan Kim, Donghak Kim, Shigeo Takenaka, Hiroshi Yamazaki, F. Peter Guengerich & Tsutomu Shimada. (2023) Oxidation of Naringenin, Apigenin, and Genistein by Human Family 1 Cytochrome P450 Enzymes and Comparison of Interaction of Apigenin with Human P450 1B1.1 and Scutellaria P450 82D.1. Chemical Research in Toxicology 36:11, pages 1778-1788.
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Alexandre Maciuk, Dominique Mazier & Romain Duval. (2023) Future antimalarials from Artemisia ? A rationale for natural product mining against drug-refractory Plasmodium stages . Natural Product Reports 40:6, pages 1130-1144.
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Lena Müller, Lucas Keuter, David Bücksteeg, Thomas Uebel, Markus Wilken, Lina Schürmann, Matthias Behrens, Hans-Ulrich Humpf & Melanie Esselen. (2022) Metabolic conjugation reduces in vitro toxicity of the flavonoid nevadensin. Food and Chemical Toxicology 164, pages 113006.
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Hernan Speisky, Fereidoon Shahidi, Adriano Costa de Camargo & Jocelyn Fuentes. (2022) Revisiting the Oxidation of Flavonoids: Loss, Conservation or Enhancement of Their Antioxidant Properties. Antioxidants 11:1, pages 133.
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