The modulation of carbonyl reductase 1 by polyphenols

References

• Aggarwal BB, Harikumar KB. (2009). Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. Int J Biochem Cell Biol 41:40–59
   PubMed Web of Science ®Google Scholar
• Aherne SA, O'brien NM. (2002). Dietary flavonols: Chemistry, food content, and metabolism. Nutrition 18:75–81
   PubMed Web of Science ®Google Scholar
• Aleksunes LM, Klaassen CD. (2012). Coordinated regulation of hepatic phase I and II drug-metabolizing genes and transporters using AhR-, CAR-, PXR-, PPAR alpha-, and Nrf2-null mice. Drug Metab Disp 40:1366–1379
   PubMed Web of Science ®Google Scholar
• Anand P, Thomas SG, Kunnumakkara AB, et al. (2008). Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature. Biochem Pharmacol 76:1590–1611
   PubMed Web of Science ®Google Scholar
• Arai Y, Endo S, Miyagi N, et al. (2015). Structure–activity relationship of flavonoids as potent inhibitors of carbonyl reductase 1 (CBR1). Fitoterapia 101:51–56
   PubMed Web of Science ®Google Scholar
• Bains OS, Karkling MJ, Grigliatti TA, et al. (2009). Two nonsynonymous single nucleotide polymorphisms of human carbonyl reductase 1 demonstrate reduced in vitro metabolism of daunorubicin and doxorubicin. Drug Metab Disp 37:1107–1114
   PubMed Web of Science ®Google Scholar
• Barski OA, Tipparaju SM, Bhatnagar A. (2008). The aldo-keto reductase superfamily and its role in drug metabolism and detoxification. Drug Metab Rev 40:553–624
   PubMed Web of Science ®Google Scholar
• Blanco JG, Sun C-L, Landier W, et al. (2012). Anthracycline-related cardiomyopathy after childhood cancer: Role of polymorphisms in carbonyl reductase genes – A report from the Children's Oncology Group. J Clin Oncol 30:1415–1421
   PubMed Web of Science ®Google Scholar
• Boeijinga PH, Galvan M, Baron BM, et al. (1992). Characterization of the novel 5-HT3 antagonists MDL 73147EF (dolasetron mesilate) and MDL 74156 in NG108-15 neuroblastoma × glioma cells. Eur J Pharmacol 219:9–13
   PubMed Web of Science ®Google Scholar
• Boušová I, Skálová L. (2012). Inhibition and induction of glutathione S-transferases by flavonoids: Possible pharmacological and toxicological consequences. Drug Metab Rev 44:267–286
   PubMed Web of Science ®Google Scholar
• Breyer-Pfaff U, Nill K. (2000). High-affinity stereoselective reduction of the enantiomers of ketotifen and of ketonic nortriptyline metabolites by aldo-keto reductases from human liver. Biochem Pharmacol 59:249–260
   PubMed Web of Science ®Google Scholar
• Breyer-Pfaff U, Nill K. (2004). Carbonyl reduction of naltrexone and dolasetron by oxidoreductases isolated from human liver cytosol. J Pharm Pharmacol 56:1601–1606
   PubMed Web of Science ®Google Scholar
• Busbee PB, Rouse M, Nagarkatti M, Nagarkatti PS. (2013). Use of natural AhR ligands as potential therapeutic modalities against inflammatory disorders. Nutr Rev 71:353–369
   PubMed Web of Science ®Google Scholar
• Carlquist M, Frejd T, Gorwa-Grausund MF. (2008). Flavonoids as inhibitors of human carbonyl reductase 1. Chem Biol Interact 174:98–108
   PubMed Web of Science ®Google Scholar
• Catalano RD, Wilson MR, Boddy SC, Jabbour HN. (2011). Comprehensive expression analysis of prostanoid enzymes and receptors in the human endometrium across the menstrual cycle. Mol Hum Reprod 17:182–192
   PubMed Web of Science ®Google Scholar
• Chang WH. (1992). Reduced haloperidol: A factor in determining the therapeutic benefit of haloperidol treatment? Psychopharmacology (Berl) 106:289–296
   PubMed Web of Science ®Google Scholar
• Chao H-M, Chuang M-J, Liu J-H, et al. (2013). Baicalein protects against retinal ischemia by antioxidation, antiapoptosis, downregulation of HIF-1 alpha, VEGF, and MMP-9 and upregulation of HO-1. J Ocular Pharmacol Ther 29:539–549
   PubMed Web of Science ®Google Scholar
• Chen J, Li Z, Chen AY, et al. (2013). Inhibitory effect of baicalin and baicalein on ovarian cancer cells. Int J Mol Sci 14:6012–6025
   PubMed Web of Science ®Google Scholar
• Cicerale S, Lucas L, Keast R. (2010). Biological activities of phenolic compounds present in virgin olive oil. Int J Mol Sci 11:458–479
   PubMed Web of Science ®Google Scholar
• Costa G, Francisco V, Lopes MC, et al. (2012). Intracellular signaling pathways modulated by phenolic compounds: Application for new anti-inflammatory drugs discovery. Curr Med Chem 19:2876–2900
   PubMed Web of Science ®Google Scholar
• Dewick PM. (2001). Medicinal natural products, a biosynthetic approach. Chichester (UK): John Wiley & Sons
   Google Scholar
• Dow J, Berg C. (1995). Stereoselectivity of the carbonyl reduction of dolasetron in rats, dogs, and humans. Chirality 7:342–348
   PubMed Web of Science ®Google Scholar
• Du G, Lin H, Wang M, et al. (2010). Quercetin greatly improved therapeutic index of doxorubicin against 4T1 breast cancer by its opposing effects on HIF-1 alpha in tumor and normal cells. Cancer Chem Pharmacol 65:277–287
   PubMed Web of Science ®Google Scholar
• Du G-J, Song Z-H, Lin H-H, et al. (2008). Luteolin as a glycolysis inhibitor offers superior efficacy and lesser toxicity of doxorubicin in breast cancer cells. Biochem Biophys Res Comm 372:497–502
   PubMed Web of Science ®Google Scholar
• Egert S, Rimbach G. (2011). Which sources of flavonoids: Complex diets or dietary supplements? Adv Nutr 2:8–14
   PubMed Web of Science ®Google Scholar
• Ellis EM. (2007). Reactive carbonyls and oxidative stress: Potential for therapeutic intervention. Pharmacol Ther 115:13–24
   PubMed Web of Science ®Google Scholar
• Endo S, Matsunaga T, Kitade Y, et al. (2008). Human carbonyl reductase 4 is a mitochondrial NADPH-dependent quinone reductase. Biochem Biophys Res Comm 377:1326–1330
   PubMed Web of Science ®Google Scholar
• Fajardo AM, Bisoffi M. (2014). Chapter 18 – Curcumin analogs, oxidative stress, and prostate cancer. In: Preedy V, ed. Cancer. San Diego: Academic Press
   Google Scholar
• Fernando W, Rupasinghe HPV, Hoskin DW. (2015). Regulation of hypoxia-inducible factor-1 alpha and vascular endothelial growth factor signaling by plant flavonoids. Mini-Rev Med Chem 15:479–489
   PubMed Web of Science ®Google Scholar
• Filling C, Berndt KD, Benach J, et al. (2002). Critical residues for structure and catalysis in short-chain dehydrogenases/reductases. J Biol Chem 277:25677–25684
   PubMed Web of Science ®Google Scholar
• Forrest GL, Gonzalez B. (2000). Carbonyl reductase. Chem Biol Interact 129:21–40
   PubMed Web of Science ®Google Scholar
• Freeland MM, Angulo J, Davis AL, et al. (2012). Sex differences in improved efficacy of doxorubicin chemotherapy in Cbr1+/− mice. Anticancer Drugs 23:584–589
   PubMed Web of Science ®Google Scholar
• Giudice A, Arra C, Turco M. (2010). Review of molecular mechanisms involved in the activation of the Nrf2-ARE signaling pathway by chemopreventive agents. In: Higgins PJ, ed. Transcription factors. Methods in Molecular Biology. New York City: Humana Press
   Google Scholar
• Gonzalez-Covarrubias V, Ghosh D, Lakhman SS, et al. (2007). A functional genetic polymorphism on human carbonyl reductase 1 (CBR1 V88I) impacts on catalytic activity and NADPH binding affinity. Drug Metab Dispos 35:973–980
   PubMed Web of Science ®Google Scholar
• Gonzalez-Covarrubias V, Kalabus JL, Blanco JG. (2008). Inhibition of polymorphic human carbonyl reductase 1 (CBR1) by the cardioprotectant flavonoid 7-monohydroxyethyl rutoside (monoHER). Pharm Res 25:1730–1734
   PubMed Web of Science ®Google Scholar
• Gonzalez-Covarrubias V, Zhang J, Kalabus JL, et al. (2009). Pharmacogenetics of human carbonyl reductase 1 (CBR1) in livers from black and white donors. Drug Metab Dispos 37:400–407
   PubMed Web of Science ®Google Scholar
• Gonzalez-Gallego J, Sanchez-Campos S, Tunon MJ. (2007). Anti-inflammatory properties of dietary flavonoids. Nutr Hosp 22:287–293
   PubMed Web of Science ®Google Scholar
• Gupta SC, Kismali G, Aggarwal BB. (2013). Curcumin, a component of turmeric: From farm to pharmacy. Biofactors 39:2–13
   PubMed Web of Science ®Google Scholar
• Halliwell B. (2008). Are polyphenols antioxidants or pro-oxidants? What do we learn from cell culture and in vivo studies? Arch Biochem Biophys 476:107–112
   PubMed Web of Science ®Google Scholar
• Han SG, Han S-S, Toborek M, Hennig B. (2012). EGCG protects endothelial cells against PCB 126-induced inflammation through inhibition of AhR and induction of Nrf2-regulated genes. Toxicol Appl Pharmacol 261:181–188
   PubMed Web of Science ®Google Scholar
• Hayes JD, Dinkova-Kostova AT. (2014). The Nrf2 regulatory network provides an interface between redox and intermediary metabolism. Trends Biochem Sci 39:199–218
   PubMed Web of Science ®Google Scholar
• Henry LA, Witt DM. (2006). Effects of neonatal resveratrol exposure on adult male and female reproductive physiology and behavior. Dev Neurosci 28:186–195
   PubMed Web of Science ®Google Scholar
• Hintzpeter J, Hornung J, Ebert B, et al. (2015). Curcumin is a tight-binding inhibitor of the most efficient human daunorubicin reductase – Carbonyl reductase 1. Chem Biol Interact 234:162–168
   PubMed Web of Science ®Google Scholar
• Hlavac V, Brynychova V, Vaclavikova R, et al. (2014). The role of cytochromes P450 and aldo-keto reductases in prognosis of breast carcinoma patients. Medicine 93:e255
   PubMedGoogle Scholar
• Hoffmann F, Maser E. (2007). Carbonyl reductases and pluripotent hydroxysteroid dehydrogenases of the shortchain dehydrogenase/reductase superfamily. Drug Metab Rev 39:87–144
   PubMed Web of Science ®Google Scholar
• Huang W, Ding L, Huang Q, et al. (2010). Carbonyl reductase 1 as a novel target of (−)-epigallocatechin gallate against hepatocellular carcinoma. Hepatology 52:703–714
   PubMed Web of Science ®Google Scholar
• Ito Y, Mitani T, Harada N, et al. (2013). Identification of carbonyl reductase 1 as a resveratrol-binding protein by affinity chromatography using 4′-amino-3,5-dihydroxy-trans-stilbene. J Nutr Sci Vitaminol 59:358–364
   PubMed Web of Science ®Google Scholar
• Jang M, Kim Y, Won H, et al. (2012). Carbonyl reductase 1 offers a novel therapeutic target to enhance leukemia treatment by arsenic trioxide. Cancer Res 72:4214–4224
   PubMed Web of Science ®Google Scholar
• Jordheim LP, Ribrag V, Ghesquieres H, et al. (2015). Single nucleotide polymorphisms in ABCB1 and CBR1 can predict toxicity to R-CHOP type regimens in patients with diffuse non-hodgkin lymphoma. Haematologica 100:e204–e208
   PubMedGoogle Scholar
• Jornvall H, Persson B, Krook M, et al. (1995). Short chain dehydrogenases reductases (SDR). Biochemistry 34:6003–6013
   PubMed Web of Science ®Google Scholar
• Kaiserova H, Simunek T, Van Der Vijgh WJF, et al (2007). Flavonoids as protectors against doxorubicin cardiotoxicity: Role of iron chelation, antioxidant activity and inhibition of carbonyl reductase. Biochim Biophys Acta-Molecular Basis of Disease 1772:1065–1074
   PubMed Web of Science ®Google Scholar
• Kalabus JL, Cheng QY, Blanco JG. (2012). MicroRNAs differentially regulate carbonyl reductase 1 (CBR1) gene expression dependent on the allele status of the common polymorphic variant rs9024. PLoS One 7:e48622
   PubMed Web of Science ®Google Scholar
• Kassner N, Huse K, Martin HJ, et al. (2008). Carbonyl reductase 1 is a predominant doxorubicin reductase in the human liver. Drug Metab Dispos 36:2113–2120
   PubMed Web of Science ®Google Scholar
• Kavanagh K, Jornvall H, Persson B, Oppermann U. (2008). The SDR superfamily: Functional and structural diversity within a family of metabolic and regulatory enzymes. Cell Mol Life Sci 65:3895–3906
   PubMed Web of Science ®Google Scholar
• Kelner MJ, Estes L, Rutherford M, et al. (1997). Heterologous expression of carbonyl reductase: Demonstration of prostaglandin 9-ketoreductase activity and paraquat resistance. Life Sci 61:2317–2322
   PubMed Web of Science ®Google Scholar
• Kim H-S, Wannatung T, Lee S, et al. (2012). Quercetin enhances hypoxia-mediated apoptosis via direct inhibition of AMPK activity in HCT116 colon cancer. Apoptosis 17:938–949
   PubMed Web of Science ®Google Scholar
• Kohle C, Bock KW. (2007). Coordinate regulation of Phase I and II xenobiotic metabolisms by the Ah receptor and Nrf2. Biochem Pharmacol 73:1853–1862
   PubMed Web of Science ®Google Scholar
• Krajka-Kuzniak V, Szaefer H, Stefanski T, et al. (2014). The effect of resveratrol and its methylthio-derivatives on the Nrf2-ARE pathway in mouse epidermis and HaCaT keratinocytes. Cell Mol Biol Lett 19:500–516
   PubMed Web of Science ®Google Scholar
• Krook M, Ghosh D, Stromberg R, et al. (1993). Carboxyethyllysine in a protein – Native carbonyl reductase/NADP+-dependent prostaglandin dehydrogenase. Proc Natl Acad Sci USA 90:502–506
   PubMed Web of Science ®Google Scholar
• Kudo S, Ishizaki T. (1999). Pharmacokinetics of haloperidol: An update. Clin Pharmacokinet 37:435–456
   PubMed Web of Science ®Google Scholar
• Lakhman SS, Chen X, Gonzalez-Covarrubias V, et al. (2007). Functional characterization of the promoter of human carbonyl reductase 1 (CBR1). Role of XRE elements in mediating the induction of CBR1 by ligands of the aryl hydrocarbon receptor. Mol Pharmacol 72:734–743
   PubMed Web of Science ®Google Scholar
• Lal S, Sandanaraj E, Wong ZW, et al. (2008). CBR1 and CBR3 pharmacogenetics and their influence on doxorubicin disposition in Asian breast cancer patients. Cancer Sci 99:2045–2054
   PubMed Web of Science ®Google Scholar
• Lim S, Shin JY, Jo A, et al. (2013). Carbonyl reductase 1 is an essential regulator of skeletal muscle differentiation and regeneration. Int J Biochem Cell Biol 45:1784–1793
   PubMed Web of Science ®Google Scholar
• Lund B, Wesolowska-Andersen A, Lausen B, et al. (2014). Host genome variations and risk of infections during induction treatment for childhood acute lymphoblastic leukaemia. Eur J Haematol 92:321–330
   PubMed Web of Science ®Google Scholar
• MacPherson L, Matthews J. (2010). Inhibition of aryl hydrocarbon receptor-dependent transcription by resveratrol or kaempferol is independent of estrogen receptor alpha expression in human breast cancer cells. Cancer Lett 299:119–129
   PubMed Web of Science ®Google Scholar
• Malatkova P, Maser E, Wsol V. (2010). Human carbonyl reductases. Curr Drug Metab 11:639–658
   PubMed Web of Science ®Google Scholar
• Malatkova P, Wsol V. (2014). Carbonyl reduction pathways in drug metabolism. Drug Metab Rev 46:96–123
   PubMed Web of Science ®Google Scholar
• Manach C, Scalbert A, Morand C, et al. (2004). Polyphenols: Food sources and bioavailability. Am J Clin Nutr 79:727–747
   PubMed Web of Science ®Google Scholar
• Maser E. (2006). Neuroprotective role for carbonyl reductase? Biochem Biophys Res Comm 340:1019–1022
   PubMed Web of Science ®Google Scholar
• Maser E, Stinner B, Atalla A. (2000). Carbonyl reduction of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by cytosolic enzymes in human liver and lung. Cancer Lett 148:135–144
   PubMed Web of Science ®Google Scholar
• Matsumoto K, Hasegawa T, Kamei T, et al. (2015). Reductive metabolism of nabumetone by human liver microsomal and cytosolic fractions: Exploratory prediction using inhibitors and substrates as marker probes. Eur J Drug Metab Pharmacokinet 40:127–135
   PubMed Web of Science ®Google Scholar
• Matsunaga T, Endo S, Soda M, et al. (2009). Potent and selective inhibition of the tumor marker AKR1B10 by bisdemethoxycurcumin: Probing the active site of the enzyme with molecular modeling and site-directed mutagenesis. Biochem Biophys Res Comm 389:128–132
   PubMed Web of Science ®Google Scholar
• Matsunaga T, Shintani S, Hara A. (2006). Multiplicity of mammalian reductases for xenobiotic carbonyl compounds. Drug Metab Pharmacokinet 21:1–18
   PubMed Web of Science ®Google Scholar
• Melstrom LG, Salabat MR, Ding XZ, et al. (2011). Apigenin down-regulates the hypoxia response genes: HIF-1alpha, GLUT-1, and VEGF in human pancreatic cancer cells. J Surg Res 167:173–181
   PubMed Web of Science ®Google Scholar
• Mesia-Vela S, Kauffman FC. (2003). Inhibition of rat liver sulfotransferases SULT1A1 and SULT2A1 and glucuronosyltransferase by dietary flavonoids. Xenobiotica 33:1211–1220
   PubMed Web of Science ®Google Scholar
• Miao W, Hu L, Scrivens PJ, Batist G. (2005). Transcriptional regulation of NF-E2 p45-related factor (NRF2) expression by the aryl hydrocarbon receptor-xenobiotic response element signaling pathway: Direct cross-talk between phase I and II drug-metabolizing enzymes. J Biol Chem 280:20340–20348
   PubMed Web of Science ®Google Scholar
• Mitani T, Ito Y, Harada N, et al. (2014). Resveratrol reduces the hypoxia-induced resistance to doxorubicin in breast cancer cells. J Nutr Sci Vitaminol 60:122–128
   PubMed Web of Science ®Google Scholar
• Miura T, Nishinaka T, Terada T. (2008). Different functions between human monomeric carbonyl reductase 3 and carbonyl reductase 1. Mol Cell Biochem 315:113–121
   PubMed Web of Science ®Google Scholar
• Miura T, Taketomi A, Nishinaka T, Terada T. (2013). Regulation of human carbonyl reductase 1 (CBR1, SDR21C1) gene by transcription factor Nrf2. Chem Biol Interact 202:126–135
   PubMed Web of Science ®Google Scholar
• Modesto JL, Hull A, Angstadt AY, et al. (2015). NNK reduction pathway gene polymorphisms and risk of lung cancer. Mol Carcinog 54:E94–E102
   PubMed Web of Science ®Google Scholar
• Mohammadi-Bardbori A, Bengtsson J, Rannug U, et al. (2012). Quercetin, resveratrol, and curcumin are indirect activators of the aryl hydrocarbon receptor (AHR). Chem Res Toxicol 25:1878–1884
   PubMed Web of Science ®Google Scholar
• Molnari JC, Myers AL. (2012). Carbonyl reduction of bupropion in human liver. Xenobiotica 42:550–561
   PubMed Web of Science ®Google Scholar
• Mordente A, Meucci E, Silvestrini A, et al. (2009). New developments in anthracycline-induced cardiotoxicity. Curr Med Chem 16:1656–1672
   PubMed Web of Science ®Google Scholar
• Murakami A, Fukushima C, Yoshidomi K, et al. (2011). Suppression of carbonyl reductase expression enhances malignant behaviour in uterine cervical squamous cell carcinoma: Carbonyl reductase predicts prognosis and lymph node metastasis. Cancer Lett 311:77–84
   PubMed Web of Science ®Google Scholar
• Murakami A, Yakabe K, Yoshidomi K, et al. (2012). Decreased carbonyl reductase 1 expression promotes malignant behaviours by induction of epithelial mesenchymal transition and its clinical significance. Cancer Lett 323:69–76
   PubMed Web of Science ®Google Scholar
• Na H-K, Surh Y-J. (2008). Modulation of Nrf2-mediated antioxidant and detoxifying enzyme induction by the green tea polyphenol EGCG. Food Chem Toxicol 46:1271–1278
   PubMed Web of Science ®Google Scholar
• Newsome BJ, Petriello MC, Han SG, et al. (2014). Green tea diet decreases PCB 126-induced oxidative stress in mice by up-regulating antioxidant enzymes. J Nutr Biochem 25:126–135
   PubMed Web of Science ®Google Scholar
• Nishiumi S, Yoshida K-I, Ashida H. (2007). Curcumin suppresses the transformation of an aryl hydrocarbon receptor through its phosphorylation. Arch Biochem Biophys 466:267–273
   PubMed Web of Science ®Google Scholar
• Ohara H, Miyabe Y, Deyashiki Y, et al. (1995). Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver. Biochem Pharmacol 50:221–227
   PubMed Web of Science ®Google Scholar
• Olson LE, Bedja D, Alvey SJ, et al. (2003). Protection from doxorubicin-induced cardiac toxicity in mice with a null allele of carbonyl reductase 1. Cancer Res 63:6602–6606
   PubMed Web of Science ®Google Scholar
• Olson RD, Mushlin PS, Brenner DE, et al. (1988). Doxorubicin cardiotoxicity may be caused by its metabolite, doxorubicinol. Proc Natl Acad Sci USA 85:3585–3589
   PubMed Web of Science ®Google Scholar
• Oppermann U. (2007). Carbonyl reductases: The complex relationships of mammalian carbonyland quinone-reducing enzymes and their role in physiology. Ann Rev Pharmacol Toxicol 47:293–322
   PubMed Web of Science ®Google Scholar
• Oppermann U, Filling C, Hult M, et al. (2003). Short-chain dehydrogenases/reductases (SDR): The 2002 update. Chem Biol Interact 143:247–253
   PubMed Web of Science ®Google Scholar
• Osawa Y, Yokoyama Y, Shigeto T, et al. (2015). Decreased expression of carbonyl reductase 1 promotes ovarian cancer growth and proliferation. Int J Oncol 46:1252–1258
   PubMed Web of Science ®Google Scholar
• Osman A-MM, Bayoumi HM, Al-Harthi SE, et al. (2012). Modulation of doxorubicin cytotoxicity by resveratrol in a human breast cancer cell line. Cancer Cell Internat 12:47
   PubMed Web of Science ®Google Scholar
• Ovaskainen ML, Torronen R, Koponen JM, et al. (2008). Dietary intake and major food sources of polyphenols in Finnish adults. J Nutr 138:562–566
   PubMed Web of Science ®Google Scholar
• Park SY, Jeong KJ, Lee J, et al. (2007). Hypoxia enhances LPA-induced HIF-1alpha and VEGF expression: Their inhibition by resveratrol. Cancer Lett 258:63–69
   PubMed Web of Science ®Google Scholar
• Perez-Jimenez J, Fezeu L, Touvier M, et al. (2011). Dietary intake of 337 polyphenols in French adults. Am J Clin Nutr 93:1220–1228
   PubMed Web of Science ®Google Scholar
• Perez-Jimenez J, Neveu V, Vos F, Scalbert A. (2010). Identification of the 100 richest dietary sources of polyphenols: An application of the Phenol-Explorer database. Eur J Clin Nutr 64:S112–S120
   PubMed Web of Science ®Google Scholar
• Petri N, Tannergren C, Holst B, et al. (2003). Absorption/metabolism of sulforaphane and quercetin, and regulation of phase II enzymes, in human jejunum in vivo. Drug Metab Dispos 31:805–813
   PubMed Web of Science ®Google Scholar
• Pietta PG. (2000). Flavonoids as antioxidants. J Nat Prod 63:1035–1042
   PubMed Web of Science ®Google Scholar
• Pilka ES, Niesen FH, Lee WH, et al (2009). Structural basis for substrate specificity in human monomeric carbonyl reductases. PLoS One 4:e7113
   PubMed Web of Science ®Google Scholar
• Piotrowska H, Kucinska M, Murias M. (2012). Biological activity of piceatannol: Leaving the shadow of resveratrol. Mutat Res 750:60–82
   PubMed Web of Science ®Google Scholar
• Pirolli D, Giardina B, Mordente A, et al. (2012). Understanding the binding of daunorubicin and doxorubicin to NADPH-dependent cytosolic reductases by computational methods. Eur J Med Chem 56:145–154
   PubMed Web of Science ®Google Scholar
• Plebuch M, Soldan M, Hungerer C, et al. (2007). Increased resistance of tumor cells to daunorubicin after transfection of cDNAs coding for anthracycline inactivating enzymes. Cancer Lett 255:49–56
   PubMed Web of Science ®Google Scholar
• Prochazkova D, Bousova I, Wilhelmova N. (2011). Antioxidant and prooxidant properties of flavonoids. Fitoterapia 82:513–523
   PubMed Web of Science ®Google Scholar
• Ramprasath T, Senthamizharasi M, Vasudevan V, et al. (2014). Naringenin confers protection against oxidative stress through upregulation of Nrf2 target genes in cardiomyoblast cells. J Physiol Biochem 70:407–415
   PubMed Web of Science ®Google Scholar
• Rashid MA, Lee S, Tak E, et al. (2010). Carbonyl reductase 1 protects pancreatic beta-cells against oxidative stress-induced apoptosis in glucotoxicity and glucolipotoxicity. Free Rad Biol Med 49:1522–1533
   PubMed Web of Science ®Google Scholar
• Rodeiro I, Donato MT, Lahoz A, et al. (2008). Interactions of polyphenols with the P450 system: Possible implications on human therapeutics. Mini Rev Med Chem 8:97–106
   PubMed Web of Science ®Google Scholar
• Rodriguez-Mateos A, Vauzour D, Krueger CG, et al. (2014). Bioavailability, bioactivity and impact on health of dietary flavonoids and related compounds: An update. Arch Toxicol 88:1803–1853
   PubMed Web of Science ®Google Scholar
• Rothwell JA, Perez-Jimenez J, Neveu V, et al (2013). Phenol-Explorer 3.0: A major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database (Oxford) 2013:bat070
   PubMed Web of Science ®Google Scholar
• Russell PT, Eberle AJ, Cheng HC. (1975). Prostaglandins in clinical medicine – Developing role for clinical chemist. Clin Chem 21:653–666
   PubMed Web of Science ®Google Scholar
• Sawamura R, Sakurai H, Wada N, et al. (2015). Bioactivation of loxoprofen to a pharmacologically active metabolite and its disposition kinetics in human skin. Biopharm Drug Dispos 70:74–80
   Google Scholar
• Shen T, Wang XN, Lou HX. (2009). Natural stilbenes: An overview. Nat Prod Rep 26:916–935
   PubMed Web of Science ®Google Scholar
• Shimoda K, Shibasaki M, Inaba T, et al. (1998a). Carbonyl reduction of timiperone in human liver cytosol. Pharmacol Toxicol 83:164–168
   PubMedGoogle Scholar
• Shimoda K, Someya T, Morita S, et al. (1998b). Plasma concentrations of timiperone and its reduced metabolite in the patients on timiperone. Psychiatry Clin Neurosci 52:535–540
   PubMed Web of Science ®Google Scholar
• Shishodia S. (2013). Molecular mechanisms of curcumin action: Gene expression. Biofactors 39:37–55
   PubMed Web of Science ®Google Scholar
• Silvestrini A, Meucci E, Vitali A, et al. (2006). Chalcone inhibition of anthracycline secondary alcohol metabolite formation in rabbit and human heart cytosol. Chem Res Toxicol 19:1518–1524
   PubMed Web of Science ®Google Scholar
• Skarydova L, Nobilis M, Wsol V. (2013). Role of carbonyl reducing enzymes in the phase I biotransformation of the non-steroidal anti-inflammatory drug nabumetone in vitro. Xenobiotica 43:346–354
   PubMed Web of Science ®Google Scholar
• Skarydova L, Tomanova R, Havlikova L, et al. (2014). Deeper insight into the reducing biotransformation of bupropion in the human liver. Drug Metab Pharmacokinet 29:177–184
   PubMed Web of Science ®Google Scholar
• Slupe A, Williams B, Larson C, et al. (2005). Reduction of 13-deoxydoxorubicin and daunorubicinol anthraquinones by human carbonyl reductase. Cardiovasc Toxicol 5:365–376
   PubMed Web of Science ®Google Scholar
• Szaefer H, Cichocki M, Krajka-Kuzniak V, et al. (2014). The effect of resveratrol and its methylthio-derivatives on NF-kappa B and AP-1 signaling pathways in HaCaT keratinocytes. Pharmacol Rep 66:732–740
   PubMed Web of Science ®Google Scholar
• Szotakova B, Bartikova H, Hlavacova J, et al (2013). Inhibitory effect of anthocyanidins on hepatic glutathione S-transferase, UDP-glucuronosyltransferase and carbonyl reductase activities in rat and human. Xenobiotica 43:679–685
   PubMed Web of Science ®Google Scholar
• Tak E, Lee S, Lee J, et al. (2011). Human carbonyl reductase 1 upregulated by hypoxia renders resistance to apoptosis in hepatocellular carcinoma cells. J Hepatol 54:328–339
   PubMed Web of Science ®Google Scholar
• Tanaka M, Bateman R, Rauh D, et al. (2005). An unbiased cell morphology-based screen for new, biologically active small molecules. Plos Biol 3:764–776
   Web of Science ®Google Scholar
• Tang X, Wang H, Fan L, et al. (2011). Luteolin inhibits Nrf2 leading to negative regulation of the Nrf2/ARE pathway and sensitization of human lung carcinoma A549 cells to therapeutic drugs. Free Rad Biol Med 50:1599–1609
   PubMed Web of Science ®Google Scholar
• Tanigawa S, Fujii M, Hou D-X. (2007). Action of Nrf2 and Keap1 in ARE-mediated NQO1 expression by quercetin. Free Rad Biol Med 42:1690–1703
   PubMed Web of Science ®Google Scholar
• Thony B, Auerbach G, Blau N. (2000). Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochem J 347:1–16
   PubMed Web of Science ®Google Scholar
• Usami N, Kitahara K, Ishikura S, et al. (2001). Characterization of a major form of human isatin reductase and the reduced metabolite. Eur J Biochem 268:5755–5763
   PubMedGoogle Scholar
• Vaiyapuri S, Roweth H, Ali MS, et al. (2015). Pharmacological actions of nobiletin in the modulation of platelet function. Br J Pharmacol 172:4133–4145
   PubMed Web of Science ®Google Scholar
• Vannozzi A, Dry IB, Fasoli M, et al. (2012). Genome-wide analysis of the grapevine stilbene synthase multigenic family: Genomic organization and expression profiles upon biotic and abiotic stresses. BMC Plant Biol 12:130
   PubMed Web of Science ®Google Scholar
• Varatharajan S, Abraham A, Zhang W, et al. (2012). Carbonyl reductase 1 expression influences daunorubicin metabolism in acute myeloid leukemia. Eur J Clin Pharmacol 68:1577–1586
   PubMed Web of Science ®Google Scholar
• Varma SD, Mikuni I, Kinoshita JH. (1975). Flavonoids as inhibitors of lens aldose reductase. Science 188:1215–1216
   PubMed Web of Science ®Google Scholar
• Volkova M, Russell IIIR. (2011). Anthracycline cardiotoxicity: Prevalence, pathogenesis and treatment. Curr Cardiol Rev 7:214–220
   PubMedGoogle Scholar
• Vrba J, Kren V, Vacek J, et al. (2012). Quercetin, quercetin glycosides and taxifolin differ in their ability to induce AhR activation and CYP1A1 expression in HepG2 cells. Phytotherapy Res 26:1746–1752
   PubMed Web of Science ®Google Scholar
• Wang X, Abdelrahman DR, Zharikova OL, et al. (2010). Bupropion metabolism by human placenta. Biochem Pharmacol 79:1684–1690
   PubMed Web of Science ®Google Scholar
• Wermuth B. (1981). Purification and properties of an NADPH-dependent carbonyl reductase from human brain – Relationship to prostaglandin 9-ketoreductase and xenobiotic ketone reductase. J Biol Chem 256:1206–1213
   PubMed Web of Science ®Google Scholar
• Williams CA, Grayer RJ. (2004). Anthocyanins and other flavonoids. Nat Prod Rep 21:539–573
   PubMed Web of Science ®Google Scholar
• Wirth H, Wermuth B. (1992). Immunohistochemical localization of carbonyl reductase in human tissues. J Histochem Cytochem 40:1857–1863
   PubMed Web of Science ®Google Scholar
• Zhang S, Qin CH, Safe SH. (2003). Flavonoids as aryl hydrocarbon receptor agonists/antagonists: Effects of structure and cell context. Environ Health Perspect 111:1877–1882
   PubMed Web of Science ®Google Scholar
• Zhang T, Kimura Y, Jiang S, et al. (2014). Luteolin modulates expression of drug-metabolizing enzymes through the AhR and Nrf2 pathways in hepatic cells. Arch Biochem Biophys 557:36–46
   PubMed Web of Science ®Google Scholar
• Zhang Q, Tang X, Lu QY, et al. (2005). Resveratrol inhibits hypoxia-induced accumulation of hypoxia-inducible factor-1alpha and VEGF expression in human tongue squamous cell carcinoma and hepatoma cells. Mol Cancer Ther 4:1465–1474
   PubMed Web of Science ®Google Scholar
• Zhao CR, Gao ZH, Qu XJ. (2010). Nrf2–ARE signaling pathway and natural products for cancer chemoprevention. Cancer Epidemiol 34:523–533
   PubMed Web of Science ®Google Scholar
• Zimmermann TJ, Niesen FH, Pilka ES, et al. (2009). Discovery of a potent and selective inhibitor for human carbonyl reductase 1 from propionate scanning applied to the macrolide zearalenone. Bioorg Med Chem 17:530–536
   PubMed Web of Science ®Google Scholar