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Xenobiotica
the fate of foreign compounds in biological systems
Volume 49, 2019 - Issue 2
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General Xenobiochemistry

Cytochrome P450 2A6 and other human P450 enzymes in the oxidation of flavone and flavanone

Kensaku KakimotoOsaka Institute of Public Health, Higashinari-ku, Osaka, Japan,
,
Norie MurayamaLaboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, Tokyo, Japan,
,
Shigeo TakenakaGraduate School of Comprehensive Rehabilitation, Osaka Prefecture University, Habikino, Osaka, Japan,
,
Haruna NagayoshiOsaka Institute of Public Health, Higashinari-ku, Osaka, Japan,
,
Young-Ran LimDepartment of Biological Sciences, Konkuk University, Seoul, Korea,
,
Vitchan KimDepartment of Biological Sciences, Konkuk University, Seoul, Korea,
,
Donghak KimDepartment of Biological Sciences, Konkuk University, Seoul, Korea,
,
Hiroshi YamazakiLaboratory of Drug Metabolism and Pharmacokinetics, Showa Pharmaceutical University, Machida, Tokyo, Japan, Correspondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-1068-4261
ORCID Icon,
Masayuki KomoriLaboratory of Cellular and Molecular Biology, Veterinary Sciences, Osaka Prefecture University, Izumisano, Osaka, Japan, and
,
F. Peter GuengerichDepartment of Biochemistry, Vanderbilt University School of Medicine, Nashville, TN, USA
&
Tsutomu ShimadaLaboratory of Cellular and Molecular Biology, Veterinary Sciences, Osaka Prefecture University, Izumisano, Osaka, Japan, and Correspondence[email protected]
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Pages 131-142 | Received 18 Dec 2017, Accepted 07 Jan 2018, Published online: 29 Jan 2018

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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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Haruna Nagayoshi, Norie Murayama, Masaki Tsujino, Shigeo Takenaka, Jun Katahira, Vitchan Kim, Donghak Kim, Masayuki Komori, Hiroshi Yamazaki, F. Peter Guengerich & Tsutomu Shimada. (2020) Preference for O-demethylation reactions in the oxidation of 2′-, 3′-, and 4′-methoxyflavones by human cytochrome P450 enzymes. Xenobiotica 50:10, pages 1158-1169.
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Supattra Boonruang, Khanistha Prakobsri, Phisit Pouyfung, Aruna Prasopthum, Pornpimol Rongnoparut & Songklod Sarapusit. (2020) Structure–activity relationship and in vitro inhibition of human cytochrome CYP2A6 and CYP2A13 by flavonoids . Xenobiotica 50:6, pages 630-639.
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Haruna Nagayoshi, Norie Murayama, Kensaku Kakimoto, Shigeo Takenaka, Jun Katahira, Young-Ran Lim, Vitchan Kim, Donghak Kim, Hiroshi Yamazaki, Masayuki Komori, F. Peter Guengerich & Tsutomu Shimada. (2019) Site-specific oxidation of flavanone and flavone by cytochrome P450 2A6 in human liver microsomes. Xenobiotica 49:7, pages 791-802.
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Articles from other publishers (9)

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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Navneet Goyal, Camilla Do, Jayalakshmi Sridhar, Shahensha Shaik, Anthony Thompson, Timothy Perry, Loren Carter & Maryam Foroozesh. (2023) Design, Synthesis, and Biological Studies of Flavone-Based Esters and Acids as Potential P450 2A6 Inhibitors. Chemical Research in Toxicology.
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Koichiro Adachi, Katsuhiro Ohyama, Yoichi Tanaka, Tasuku Sato, Norie Murayama, Makiko Shimizu, Yoshiro Saito & Hiroshi Yamazaki. (2023) High hepatic and plasma exposures of atorvastatin in subjects harboring impaired cytochrome P450 3A4∗16 modeled after virtual administrations and possibly associated with statin intolerance found in the Japanese adverse drug event report database. Drug Metabolism and Pharmacokinetics 49, pages 100486.
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Nico D. Fessner, Christopher Grimm, Matic Srdič, Hansjörg Weber, Wolfgang Kroutil, Ulrich Schwaneberg & Anton Glieder. (2021) Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4. ChemCatChem 14:1.
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Radim Vrzal. (2021) Genetic and Enzymatic Characteristics of CYP2A13 in Relation to Lung Damage. International Journal of Molecular Sciences 22:22, pages 12306.
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Siwaporn Boonyasuppayakorn, Thanaphon Saelee, Peerapat Visitchanakun, Asada Leelahavanichkul, Kowit Hengphasatporn, Yasuteru Shigeta, Thao Nguyen Thanh Huynh, Justin Jang Hann Chu, Thanyada Rungrotmongkol & Warinthorn Chavasiri. (2020) Dibromopinocembrin and Dibromopinostrobin Are Potential Anti-Dengue Leads with Mild Animal Toxicity. Molecules 25:18, pages 4154.
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Pallavi Sharma, Amit Kumar & Damanpreet Singh. (2019) Dietary Flavonoids Interaction with CREB-BDNF Pathway: An Unconventional Approach for Comprehensive Management of Epilepsy. Current Neuropharmacology 17:12, pages 1158-1175.
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Haruna Nagayoshi, Norie Murayama, Kensaku Kakimoto, Masaki Tsujino, Shigeo Takenaka, Jun Katahira, Young-Ran Lim, Donghak Kim, Hiroshi Yamazaki, Masayuki Komori, F. Peter Guengerich & Tsutomu Shimada. (2019) Oxidation of Flavone, 5-Hydroxyflavone, and 5,7-Dihydroxyflavone to Mono-, Di-, and Tri-Hydroxyflavones by Human Cytochrome P450 Enzymes. Chemical Research in Toxicology 32:6, pages 1268-1280.
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Ilona K. Jóźwik, Martin Litzenburger, Yogan Khatri, Alexander Schifrin, Marco Girhard, Vlada Urlacher, Andy-Mark W.H. Thunnissen & Rita Bernhardt. (2018) Structural insights into oxidation of medium-chain fatty acids and flavanone by myxobacterial cytochrome P450 CYP267B1. Biochemical Journal 475:17, pages 2801-2817.
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