Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 49, 2019 - Issue 2
273
Views
15
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

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

, , , , , , , ORCID Icon, , & show all
Pages 131-142 | Received 18 Dec 2017, Accepted 07 Jan 2018, Published online: 29 Jan 2018

References

  • Akashi T, Aoki T, Ayabe S. (1998). Identification of a cytochrome P450 cDNA encoding (2S)-flavanone 2-hydroxylase of licorice (Glycyrrhiza echinata L.; Fabaceae) which represents licodione synthase and flavone synthase II. FEBS Lett 431:287–90
  • Akashi T, Fukuchi-Mizutani M, Aoki T, et al (1999). Molecular cloning and biochemical characterization of a novel cytochrome P450, flavone synthase II, that catalyzes direct conversion of flavanones to flavones. Plant Cell Physiol 40:1182–6
  • Arnqvist L, Persson M, Jonsson L, et al (2008). Overexpression of CYP710A1 and CYP710A4 in transgenic Arabidopsis plants increases the level of stigmasterol at the expense of sitosterol. Planta 227:309–17
  • Arct J, Pytkowska K. (2008). Flavonoids as components of biologically active cosmeceuticals. Clin Dermatol 26:347–57
  • Berim A, Gang DR. (2013). The roles of a flavone-6-hydroxylase and 7-O-demethylation in the flavone biosynthetic network of sweet basil. J Biol Chem 288:1795–805
  • Breinholt VM, Offord EA, Brouwer C, et al (2002). In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. Food Chem Toxicol 40:609–16
  • Broun P, Shanklin J, Whittle E, et al (1998). Catalytic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Science 282:1315–7
  • Broadwater JA, Whittle E, Shanklin J. (2002). Desaturation and hydroxylation. Residues 148 and 324 of Arabidopsis FAD2, in addition to substrate chain length, exert a major influence in partitioning of catalytic specificity. J Biol Chem 277:15613–20
  • Brown RE, Jarvis KL, Hyland KJ. (1989). Protein measurement using bicinchoninic acid: elimination of interfering substances. Anal Biochem 180:136–9
  • Das NP, Scott KN, Duncan JH. (1973). Identification of flavanone metabolites in rat urine by combined gas-liquid chromatography and mass spectrometry. Biochem J 136:903–9
  • Devore NM, Scott EE. (2012). Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone binding and access channel in human cytochrome P450 2A6 and 2A13 enzymes. J Biol Chem 287:26576–85
  • DeVore NM, Meneely KM, Bart AG, et al (2012). Structural comparison of cytochromes P450 2A6, 2A13, and 2E1 with pilocarpine. FEBS J 279:1621–31
  • Doostdar H, Burke MD, Mayer RT. (2000). Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 144:31–8
  • Du Y, Chu H, Chu IK, Lo C. (2010). CYP93G2 is a flavanone 2-hydroxylase required for C-glycosylflavone biosynthesis in rice. Plant Physiol 154:324–33
  • Fasco MJ, Dymerski PP, Wos JD, et al (1978). A new warfarin metabolite: structure and function. J Med Chem 21:1054–9
  • Fliegmann J, Furtwängler K, Malterer G, et al (2010). Flavone synthase II (CYP93B16) from soybean (Glycine max L.). Phytochemistry 71:508–14
  • Fujita K, Kamataki T. (2001). Screening of organosulfur compounds as inhibitors of human CYP2A6. Drug Metab Dispos 29:983–9
  • Guan X, Fisher MB, Lang DH, et al (1998). Cytochrome P450-dependent desaturation of lauric acid: isoform selectivity and mechanism of formation of 11-dodecenoic acid. Chem Biol Interact 110:103–21
  • Guengerich FP. (2001). Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol 14:611–50
  • Guengerich FP, Kim DH. (1991). Enzymatic oxidation of ethyl carbamate to vinyl carbamate and its role as an intermediate in the formation of 1,N6-ethenoadenosine. Chem Res Toxicol 4:413–21
  • Guengerich FP, Chun Y-J, Kim D, et al (2003). Cytochrome P450 1B1: a target for inhibition in anticarcinogenesis strategies. Mutat Res 523-524:173–82
  • Guengerich FP. (2015) Human cytochrome P450 enzymes. In: Ortiz de Montellano PR, ed. Cytochrome P450: structure, mechanism, and biochemistry. 4th ed. New York: Springer, 523–785
  • Han S, Choi S, Chun YJ, et al (2012). Functional characterization of allelic variants of polymorphic human cytochrome P450 2A6 (CYP2A6*5, *7, *8, *18, *19, and *35). Biol Pharm Bull 35:394–9
  • Hodek P, Trefil P, Stiborová M. (2002). Flavonoids-potent and versatile biologically active compounds interacting with cytochromes P450. Chem Biol Interact 139:1–21
  • Johnson KM, Phan TT, Albertolle ME, et al (2017). Human mitochondrial cytochrome P450 27C1 is localized in skin and preferentially desaturates trans-retinol to 3,4-dehydroretinol. J Biol Chem 292:13672–85
  • Kagawa H, Takahashi T, Ohta S, et al (2004). Oxidation and rearrangements of flavanones by mammalian cytochrome P450. Xenobiotica 34:797–810
  • Kakimoto K, Nagayoshi H, Inazumi N, et al (2015). Identification and characterization of oxidative metabolites of 1-chloropyrene. Chem Res Toxicol 28:1728–36
  • Kale A, Gawande S, Kotwal S. (2008). Cancer phytotherapeutics: role for flavonoids at the cellular level. Phytother Res 22:567–77
  • Kaminsky LS, Fasco MJ, Guengerich FP. (1980). Comparison of different forms of purified cytochrome P-450 from rat liver by immunological inhibition of regio- and stereoselective metabolism of warfarin. J Biol Chem 255:85–91
  • Kelly SL, Lamb DC, Baldwin BC, et al (1997). Characterization of Saccharomyces cerevisiae CYP61, sterol delta22-desaturase, and inhibition by azole antifungal agents. J Biol Chem y 272:9986–8
  • Kim H-J, Lee SB, Park S-K, et al (2005). Effects of hydroxy group numbers on the B-ring of 5,7-dihydroxyflavones on the differential inhibition of human CYP 1A and CYP1B1 enzymes. Arch Pharm Res 28:1114–21
  • Kitada C, Gong Z, Tanaka Y, et al (2001). Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens. Plant Cell Physiol 42:1338–44
  • Lam PY, Zhu FY, Chan WL, et al (2014). Cytochrome P450 93G1 is a flavone synthase II that channels flavanones to the biosynthesis of tricin O-linked conjugates in rice. Plant Physiol 165:1315–27
  • Martens S, Mithöfer A. (2005). Flavones and flavone synthases. Phytochemistry 66:2399–407
  • Moon YJ, Wang X, Morris ME. (2006). Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol In Vitro 20:187–210
  • Morikawa T, Mizutani M, Aoki N, et al (2006). Cytochrome P450 CYP710A encodes the sterol C-22 desaturase in Arabidopsis and tomato. The Plant Cell 18:1008–22
  • Nagata K, Liberato DJ, Gillette JR, et al (1986). An unusual metabolite of testosterone. 17 beta-Hydroxy-4,6-androstadiene-3-one. Drug Metab Dispos 14:559–65
  • Nikolic D, van Breemen RB. (2004). New metabolic pathways for flavanones catalyzed by rat liver microsomes. Drug Metab Dispos 32:387–97
  • Omura T, Sato R. (1964). The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370–8
  • Parikh A, Gillam EMJ, Guengerich FP. (1997). Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat Biotechnol 15:784–8
  • Rettie AE, Rettenmeier AW, Howald WN, et al (1987). Cytochrome P-450-catalyzed formation of delta 4-VPA, a toxic metabolite of valproic acid. Science 235:890–3
  • Sandhu P, Baba T, Guengerich FP. (1993). Expression of modified cytochrome P450 2C10 (2C9) in Escherichia coli, purification, and reconstitution of catalytic activity. Arch Biochem Biophys 306:443–50
  • Sandhu P, Guo Z, Baba T, et al (1994). Expression of modified human cytochrome P450 1A2 in Escherichia coli: Stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch Biochem Biophys 309:168–77
  • Sasaki S, Itagaki Y, Kurokawa T, et al (1966). The mass spectra of flavonoids. J Mass Spectro Soc Japan 14:82–92 (in Japanese)
  • Shimada T. (2017). Inhibition of carcinogen-activating cytochrome P450 enzymes by xenobiotic chemicals in relation to antimutagenicity and anticarcinogenicity. Toxicol Res 33:79–96
  • Shimada T, Kakimoto K, Takenaka S, et al (2016c). Roles of human CYP2A6 and monkey CYP2A24 and 2A26 cytochrome P450 enzymes in the oxidation of 2,5,2′,5′-Tetrachlorobiphenyl. Drug Metab Dispos 44:1899–909
  • Shimada T, Kim D, Murayama N, et al (2013). Binding of diverse environmental chemicals with human cytochromes P450 2A13, 2A6, and 1B1 and enzyme inhibition. Chem Res Toxicol 26:517–28
  • Shimada T, Takenaka S, Kakimoto K, et al (2016b). Structure-function studies of naphthalene, phenanthrene, biphenyl, and their derivatives in interaction with and oxidation by cytochromes P450 2A13 and 2A6. Chem Res Toxicol 29:1029–40
  • Shimada T, Takenaka S, Murayama N, et al (2015). Oxidation of acenaphthene and acenaphthylene by human cytochrome P450 enzymes. Chem Res Toxicol 28:268–78
  • Shimada T, Takenaka S, Murayama N, et al (2016a). Oxidation of pyrene, 1-hydroxypyrene, 1-nitropyrene and 1-acetylpyrene by human cytochrome P450 2A13. Xenobiotica 46:211–24
  • Shimada T, Tanaka K, Takenaka S, et al (2010). Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol 23:1921–35
  • Skaggs BA, Alexander JF, Pierson CA, et al (1996). Cloning and characterization of the Saccharomyces cerevisiae C-22 sterol desaturase gene, encoding a second cytochrome P-450 involved in ergosterol biosynthesis. Gene 169:105–9
  • Tanaka Y, Brugliera F, Kalc G, et al (2010). Flower color modification by engineering of the flavonoid biosynthetic pathway: practical perspectives. Biosci Biotechnol Biochem 74:1760–9
  • Tanaka Y, Brugliera F. (2013). Flower colour and cytochromes P450. Philos Trans R Soc Lond B Biol Sci 368:1–14
  • Tsujimoto M, Horie M, Honda H, et al (2009). The structure-activity correlation on the inhibitory effects of flavonoids on cytochrome P450 3A activity. Biol Pharm Bull 32:671–6
  • Uno T, Obe Y, Ogura C, Goto T, et al (2013). Metabolism of 7-ethoxycoumarin, safrole, flavanone and hydroxyflavanone by cytochrome P450 2A6 variants. Biopharm Drug Dispos 34:87–97
  • Uno T, Ogura C, Izumi C, et al (2015). Point mutation of cytochrome P450 2A6 (a polymorphic variant CYP2A6.25) confers new substrate specificity towards flavonoids. Biopharm Drug Dispos 36:552–63
  • Walle T. (2007). Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? Semin Cancer Biol 17:354–62
  • Walle T, Ta N, Kawamori T, Wen X, et al (2007). Cancer chemopreventive properties of orally bioavailable flavonoids-methylated versus unmethylated flavones. Biochem Pharmacol 73:1288–96
  • Walle UK, Walle T. (2007). Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones. Drug Metab Dispos 35:1985–9
  • Wang RW, Kari PH, Lu AY, et al (1991). Biotransformation of lovastatin. IV. Identification of cytochrome P450 3A proteins as the major enzymes responsible for the oxidative metabolism of lovastatin in rat and human liver microsomes. Arch Biochem Biophys 290:355–61
  • Yamazaki H, Nakamura M, Komatsu T, et al (2002). Roles of NADPH-P450 reductase and apo- and holo-cytochrome b5 on xenobiotic oxidations catalyzed by 12 recombinant human cytochrome P450s expressed in membranes of Escherichia coli. Protein Expr Purif 24:329–37
  • Yano JK, Denton TT, Cerny MA, et al (2006). Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization. J Med Chem 49:6987–7001
  • Zhang S, Yang X, Coburn RA, et al (2005). Structure activity relationships and quantitative structure activity relationships for the flavonoid-mediated inhibition of breast cancer resistance protein. Biochem Pharmacol 70:627–39

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.