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Volumn 23, Issue 10, 2011, Pages 891-896

Enantiomers of naringenin as pleiotropic, stereoselective inhibitors of cytochrome P450 isoforms

Author keywords

CYP19; CYP2C19; CYP2C9; CYP3A; drug metabolism; enantioselectivity; flavonoid; food drug interaction

Indexed keywords

AROMATASE; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 INHIBITOR; ISOENZYME; NARINGENIN; RECOMBINANT ENZYME; CYTOCHROME P450; FLAVANONE DERIVATIVE;

EID: 80053928122     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.21005     Document Type: Article
Times cited : (57)

References (33)
  • 1
    • 23444456926 scopus 로고    scopus 로고
    • Stereospecific high-performance liquid chromatographic analysis of naringenin in urine
    • DOI 10.1016/j.jpba.2005.02.025, PII S0731708505001329
    • Yanez JA, Davies NM,. Stereospecific high-performance liquid chromatographic analysis of naringenin in urine. J Pharm Biomed Anal 2005; 39: 164-169. (Pubitemid 41112133)
    • (2005) Journal of Pharmaceutical and Biomedical Analysis , vol.39 , Issue.1-2 , pp. 164-169
    • Yanez, J.A.1    Davies, N.M.2
  • 2
    • 0025685663 scopus 로고
    • In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids
    • Guengerich FP, Kim DH,. In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis 1990; 11: 2275-2279.
    • (1990) Carcinogenesis , vol.11 , pp. 2275-2279
    • Guengerich, F.P.1    Kim, D.H.2
  • 3
    • 0033786069 scopus 로고    scopus 로고
    • Effects of citrus phytochemicals on liver and lung cytochrome P450 activity and on the in vitro metabolism of the tobacco-specific nitrosamine NNK
    • Bear WL, Teel RW,. Effects of citrus phytochemicals on liver and lung cytochrome P450 activity and on the in vitro metabolism of the tobacco-specific nitrosamine NNK. Anticancer Res 2000; 20: 3323-3329.
    • (2000) Anticancer Res , vol.20 , pp. 3323-3329
    • Bear, W.L.1    Teel, R.W.2
  • 4
    • 0035734306 scopus 로고    scopus 로고
    • Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds
    • Ho PC, Saville DJ, Wanwimolruk S,. Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins, and related compounds. J Pharm Pharm Sci 2001; 4: 217-227. (Pubitemid 34305597)
    • (2001) Journal of Pharmacy and Pharmaceutical Sciences , vol.4 , Issue.3 , pp. 217-227
    • Ho, P.-C.1    Saville, D.J.2    Wanwimolruk, S.3
  • 5
    • 66149151048 scopus 로고    scopus 로고
    • Naringenin: A potential immunomodulator for inhibiting lung fibrosis and metastasis
    • Du G, Jin L, Han X, Song Z, Zhang H, Liang W,. Naringenin: a potential immunomodulator for inhibiting lung fibrosis and metastasis. Cancer Res 2009; 69: 3205-3212.
    • (2009) Cancer Res , vol.69 , pp. 3205-3212
    • Du, G.1    Jin, L.2    Han, X.3    Song, Z.4    Zhang, H.5    Liang, W.6
  • 6
    • 0035001464 scopus 로고    scopus 로고
    • Biological properties of citrus flavonoids pertaining to cancer and inflammation
    • Manthey JA, Grohmann K, Guthrie N,. Biological properties of citrus flavonoids pertaining to cancer and inflammation. Curr Med Chem 2001; 8: 135-153. (Pubitemid 32421562)
    • (2001) Current Medicinal Chemistry , vol.8 , Issue.2 , pp. 135-153
    • Manthey, J.A.1    Guthrie, N.2    Grohmann, K.3
  • 7
    • 0026713228 scopus 로고
    • The relevance of chirality to the study of biological activity
    • Crossley R,. The relevance of chirality to the study of biological activity. Tetrahedron 1992; 48: 8155-8178.
    • (1992) Tetrahedron , vol.48 , pp. 8155-8178
    • Crossley, R.1
  • 8
    • 34547710450 scopus 로고    scopus 로고
    • Drug chirality and its pharmacological consequences
    • Smith H. editor. Boca Raton FL: CRC Press;. p.
    • Hutt A,. Drug chirality and its pharmacological consequences. In:, Smith H, editor. Introduction to the principles of drug design and action. Boca Raton FL: CRC Press; 2006. p 117-183.
    • (2006) Introduction to the Principles of Drug Design and Action , pp. 117-183
    • Hutt, A.1
  • 9
    • 0025935197 scopus 로고
    • Quinidine but not quinine inhibits in man the oxidative metabolic routes of methoxyphenamine which involve debrisoquine 4-hydroxylase
    • Muralidharan G, Hawes EM, McKay G, Korchinski ED, Midha KK,. Quinidine but not quinine inhibits in man the oxidative metabolic routes of methoxyphenamine which involve debrisoquine 4-hydroxylase. Eur J Clin Pharmacol 1991; 41: 471-474.
    • (1991) Eur J Clin Pharmacol , vol.41 , pp. 471-474
    • Muralidharan, G.1    Hawes, E.M.2    McKay, G.3    Korchinski, E.D.4    Midha, K.K.5
  • 10
    • 16244384507 scopus 로고    scopus 로고
    • Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro
    • DOI 10.1080/00498250400026472
    • Liu KH, Kim MJ, Shon JH, Moon YS, Seol SY, Kang W, Cha IJ, Shin JG,. Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro. Xenobiotica 2005; 35: 27-38. (Pubitemid 40459215)
    • (2005) Xenobiotica , vol.35 , Issue.1 , pp. 27-38
    • Liu, K.H.1    Kim, M.J.2    Shon, J.H.3    Moon, Y.S.4    Seol, S.Y.5    Kang, W.6    Cha, I.J.7    Shin, J.G.8
  • 11
    • 0030952696 scopus 로고    scopus 로고
    • Stereoselective inhibition of rat brain cyclooxygenase by dexketoprofen
    • DOI 10.1002/(SICI)1520-636X(1997)9:3<281::AID-CHIR13>3.0.CO;2-J
    • Carabaza A, Cabre F, Garcia AM, Rotllan E, Garcia ML, Mauleon D,. Stereoselective inhibition of rat brain cyclooxygenase by dexketoprofen. Chirality 1997; 9: 281-285. (Pubitemid 27242152)
    • (1997) Chirality , vol.9 , Issue.3 , pp. 281-285
    • Carabaza, A.1    Cabre, F.2    Garcia, A.M.3    Rotllan, E.4    Garcia, M.L.5    Mauleon, D.6
  • 12
    • 0035142516 scopus 로고    scopus 로고
    • Potent inhibition of CYP2D6 by haloperidol metabolites: Stereoselective inhibition by reduced haloperidol
    • DOI 10.1046/j.1365-2125.2001.01313.x
    • Shin JG, Kane K, Flockhart DA,. Potent inhibition of CYP2D6 by haloperidol metabolites: stereoselective inhibition by reduced haloperidol. Br J Clin Pharmacol 2001; 51: 45-52. (Pubitemid 32118819)
    • (2001) British Journal of Clinical Pharmacology , vol.51 , Issue.1 , pp. 45-52
    • Shin, J.-G.1    Kane, K.2    Flockhart, D.A.3
  • 13
    • 1642498267 scopus 로고    scopus 로고
    • Enantioselectivity of Inhibition of Cytochrome P450 3A4 (CYP3A4) by Ketoconazole: Testosterone and Methadone as Substrates
    • DOI 10.1002/chir.10294
    • Dilmaghanian S, Gerber JG, Filler SG, Sanchez A, Gal J,. Enantioselectivity of inhibition of cytochrome P450 3A4 (CYP3A4) by ketoconazole: testosterone and methadone as substrates. Chirality 2004; 16: 79-85. (Pubitemid 38134070)
    • (2004) Chirality , vol.16 , Issue.2 , pp. 79-85
    • Dilmaghanian, S.1    Gerber, J.G.2    Filler, S.G.3    Sanchez, A.4    Gal, J.5
  • 17
    • 0035126980 scopus 로고    scopus 로고
    • Effect of grapefruit juice on pharmacokinetics of microemulsion cyclosporine in African American subjects compared with caucasian subjects: Does ethnic difference matter?
    • DOI 10.1177/00912700122010131
    • Lee M, Min DI, Ku YM, Flanigan M,. Effect of grapefruit juice on pharmacokinetics of microemulsion cyclosporine in African American subjects compared with Caucasian subjects: does ethnic difference matter? J Clin Pharmacol 2001; 41: 317-323. (Pubitemid 32184984)
    • (2001) Journal of Clinical Pharmacology , vol.41 , Issue.3 , pp. 317-323
    • Lee, M.1    Min, D.I.2    Ku, Y.-M.3    Flanigan, M.4
  • 19
    • 77954945999 scopus 로고    scopus 로고
    • Methadone: A substrate and mechanism-based inhibitor of CYP19 (aromatase)
    • Lu WJ, Bies R, Kamden LK, Desta Z, Flockhart DA,. Methadone: a substrate and mechanism-based inhibitor of CYP19 (aromatase). Drug Metab Dispos 2010; 38: 1308-1313.
    • (2010) Drug Metab Dispos , vol.38 , pp. 1308-1313
    • Lu, W.J.1    Bies, R.2    Kamden, L.K.3    Desta, Z.4    Flockhart, D.A.5
  • 22
    • 36649036013 scopus 로고    scopus 로고
    • Polysaccharide derivatives as useful chiral stationary phases in high-performance liquid chromatography
    • Chen X, Yamamoto C, Okamoto Y,. Polysaccharide derivatives as useful chiral stationary phases in high-performance liquid chromatography. Pure Appl Chem 2007; 79: 1561-1573.
    • (2007) Pure Appl Chem , vol.79 , pp. 1561-1573
    • Chen, X.1    Yamamoto, C.2    Okamoto, Y.3
  • 23
    • 10944222281 scopus 로고    scopus 로고
    • Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power
    • DOI 10.1039/b411110a
    • Giorgio E, Parrinello N, Caccamese S, Rosini C,. Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power. Org Biomol Chem 2004; 2: 3602-3607. (Pubitemid 40010634)
    • (2004) Organic and Biomolecular Chemistry , vol.2 , Issue.24 , pp. 3602-3607
    • Giorgio, E.1    Parrinello, N.2    Caccamese, S.3    Rosini, C.4
  • 24
    • 19444363540 scopus 로고    scopus 로고
    • High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones
    • DOI 10.1016/j.chroma.2005.04.024, PII S0021967305007843
    • Caccamese S, Caruso C, Parrinello N, Savarino A,. High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones. J Chromatogr A 2005; 1076: 155-162. (Pubitemid 40725189)
    • (2005) Journal of Chromatography A , vol.1076 , Issue.1-2 , pp. 155-162
    • Caccamese, S.1    Caruso, C.2    Parrinello, N.3    Savarino, A.4
  • 25
    • 0035150315 scopus 로고    scopus 로고
    • Human nutrition and metabolism: Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice
    • Erlund I, Meririnne E, Alfthan G, Aro A,. Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice. J Nutr 2001; 131: 235-241. (Pubitemid 32115362)
    • (2001) Journal of Nutrition , vol.131 , Issue.2 , pp. 235-241
    • Erlund, I.1    Meririnne, E.2    Alfthan, G.3    Aro, A.4
  • 27
    • 0037871830 scopus 로고    scopus 로고
    • Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: Comparison with grapefruit juice
    • DOI 10.1016/S0009-9236(03)00051-1
    • Bailey DG, Dresser GK, Bend JR,. Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice. Clin Pharmacol Ther 2003; 73: 529-537. (Pubitemid 37249123)
    • (2003) Clinical Pharmacology and Therapeutics , vol.73 , Issue.6 , pp. 529-537
    • Bailey, D.G.1    Dresser, G.K.2    Bend, J.R.3
  • 30
    • 0141790334 scopus 로고    scopus 로고
    • Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation
    • DOI 10.1002/chir.10262
    • Caccamese S, Manna L, Scivoli G,. Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation. Chirality 2003; 15: 661-667. (Pubitemid 37158930)
    • (2003) Chirality , vol.15 , Issue.8 , pp. 661-667
    • Caccamese, S.1    Manna, L.2    Scivoli, G.3
  • 31
    • 34249915577 scopus 로고    scopus 로고
    • Racemization at C-2 of naringin in sour oranges with increasing maturity determined by chiral high-performance liquid chromatography
    • DOI 10.1021/jf063355w
    • Caccamese S, Bianca S, Santo D,. Racemization at C-2 of naringin in sour oranges with increasing maturity determined by chiral high-performance liquid chromatography. J Agric Food Chem 2007; 55: 3816-3822. (Pubitemid 46867384)
    • (2007) Journal of Agricultural and Food Chemistry , vol.55 , Issue.10 , pp. 3816-3822
    • Caccamese, S.1    Bianca, S.2    Santo, D.3
  • 32
    • 74049114147 scopus 로고    scopus 로고
    • Racemization at C-2 of naringin in pummelo (Citrus grandis) with increasing maturity determined by chiral high-performance liquid chromatography
    • Caccamese S, Chillemi R,. Racemization at C-2 of naringin in pummelo (Citrus grandis) with increasing maturity determined by chiral high-performance liquid chromatography. J Chromatogr A 2010; 1217: 1089-1093.
    • (2010) J Chromatogr A , vol.1217 , pp. 1089-1093
    • Caccamese, S.1    Chillemi, R.2
  • 33
    • 0031966729 scopus 로고    scopus 로고
    • Drug interactions with grapefruit juice: Extent, probable mechanism and clinical relevance
    • DOI 10.2165/00002018-199818040-00002
    • Fuhr U,. Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance. Drug Saf 1998; 18: 251-272. (Pubitemid 28177290)
    • (1998) Drug Safety , vol.18 , Issue.4 , pp. 251-272
    • Fuhr, U.1


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