메뉴 건너뛰기




Volumn 25, Issue 11, 2011, Pages 1671-1677

Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives

Author keywords

carboline alkaloids; CYP2D6; CYP3A4; Harmine derivatives; Inhibition; Peganum harmala

Indexed keywords

BETA CARBOLINE DERIVATIVE; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; HARMALINE; HARMALOL; HARMAN; HARMINE; HARMOL;

EID: 80054956542     PISSN: 0951418X     EISSN: 10991573     Source Type: Journal    
DOI: 10.1002/ptr.3458     Document Type: Article
Times cited : (47)

References (32)
  • 1
    • 0028964602 scopus 로고
    • Association between the oxidative polymorphism and the early onset of Parkinson's disease
    • Agúndez JA, Jiménez-Jiménez FJ, Luengo A et al. 1995. Association between the oxidative polymorphism and the early onset of Parkinson's disease. Clin Pharmacol Ther 57: 291-298.
    • (1995) Clin Pharmacol Ther , vol.57 , pp. 291-298
    • Agúndez, J.A.1    Jiménez-Jiménez, F.J.2    Luengo, A.3
  • 2
    • 38849151152 scopus 로고    scopus 로고
    • Peganum harmala can minimize Escherichia coli infection in poultry, but long-term feeding may induce side effects
    • DOI 10.3382/ps.2007-00341
    • Arshad N, Neubauer C, Hasnain S, Hess M. 2008. Peganumharmala can minimize Escherichia coli infection in poultry, but long-term feeding may induce side effects. Poult Sci 87: 240-249. (Pubitemid 351198488)
    • (2008) Poultry Science , vol.87 , Issue.2 , pp. 240-249
    • Arshad, N.1    Neubauer, C.2    Hasnain, S.3    Hess, M.4
  • 3
    • 51649084496 scopus 로고    scopus 로고
    • Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities
    • Astulla A, Zaima K, Matsuno Y et al. 2008. Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities. Nat Med 62: 470-472.
    • (2008) Nat Med , vol.62 , pp. 470-472
    • Astulla, A.1    Zaima, K.2    Matsuno, Y.3
  • 4
    • 0030047286 scopus 로고    scopus 로고
    • The effect of tobacco on lung cancer risk depends on CYP2D6 activity
    • Bouchardy C, Benhamou S, Dayer P. 1996. The effect of tobacco on lung cancer risk depends on CYP2D6 activity. Cancer Res 56: 251-253. (Pubitemid 26026349)
    • (1996) Cancer Research , vol.56 , Issue.2 , pp. 251-253
    • Bouchardy, C.1    Benhamou, S.2    Dayer, P.3
  • 7
    • 77956494409 scopus 로고
    • Chemical and pharmacology studies on the plants of Peganum
    • Fan ZR, Yao XS. 1992. Chemical and pharmacology studies on the plants of Peganum. J Shenyang Pharm Univ 9: 144-151.
    • (1992) J Shenyang Pharm Univ , vol.9 , pp. 144-151
    • Fan, Z.R.1    Yao, X.S.2
  • 8
    • 37349127848 scopus 로고    scopus 로고
    • Evaluation of the analgesic effect of alkaloid extract of Peganum harmala L.: Possible mechanisms involved
    • DOI 10.1016/j.jep.2007.10.014, PII S0378874107005466
    • Farouk L, Laroubi A, Aboufatima R, Benharref A, Chait A. 2008. Evaluation of the analgesic effect of alkaloid extract of Peganum harmala L possible mechanisms involved. J Ethnopharmacol 115: 449-454. (Pubitemid 350299085)
    • (2007) Journal of Ethnopharmacology , vol.115 , Issue.3 , pp. 449-454
    • Farouk, L.1    Laroubi, A.2    Aboufatima, R.3    Benharref, A.4    Chait, A.5
  • 9
    • 70349100119 scopus 로고    scopus 로고
    • In vitro inhibition of multiple cytochrome P450 isoforms by xanthone derivatives from mangosteen extract
    • Foti RS, Pearson JT, Rock DA, Wahlstrom JL, Wienkers LC. 2009. In vitro inhibition of multiple cytochrome P450 isoforms by xanthone derivatives from mangosteen extract. Drug Metab Dispos 37:1848-1855.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1848-1855
    • Foti, R.S.1    Pearson, J.T.2    Rock, D.A.3    Wahlstrom, J.L.4    Wienkers, L.C.5
  • 10
    • 0035930413 scopus 로고    scopus 로고
    • Toxicokinetics of tremorogenic natural products, harmane and harmine, in male sprague-dawley rats
    • DOI 10.1080/152873901753246241
    • Guan Y, Louis ED, Zheng W. 2001. Toxicokinetics of tremorogenic natural products, harmane and harmine, in male Sprague-Dawley rats. J Toxicol Environ Health A 64:645-660. (Pubitemid 33132019)
    • (2001) Journal of Toxicology and Environmental Health - Part A , vol.64 , Issue.8 , pp. 645-660
    • Guan, Y.1    Louis, E.D.2    Zheng, W.3
  • 11
    • 0032924934 scopus 로고    scopus 로고
    • Cytochrome P-450 3A4: Regulation and role in drug metabolism
    • DOI 10.1146/annurev.pharmtox.39.1.1
    • Guengerich FP. 1999. Cytochrome P-450 3A4: Regulation and role in drug metabolism. Annu Rev Pharmacol Toxicol 39: 1-17. (Pubitemid 29222549)
    • (1999) Annual Review of Pharmacology and Toxicology , vol.39 , pp. 1-17
    • Guengerich, F.P.1
  • 12
    • 57449102342 scopus 로고    scopus 로고
    • Oxidative metabolism of the bioactive and naturally occurring β-carboline alkaloids, norharman and harman, by human cytochrome P450 enzymes
    • Herraiz T, Guillén H, Arán VJ. 2008. Oxidative metabolism of the bioactive and naturally occurring β-carboline alkaloids, norharman and harman, by human cytochrome P450 enzymes. Chem Res Toxicol 21: 2172-2180.
    • (2008) Chem Res Toxicol , vol.21 , pp. 2172-2180
    • Herraiz, T.1    Guillén, H.2    Arán, V.J.3
  • 13
    • 21844447128 scopus 로고    scopus 로고
    • Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent
    • DOI 10.1016/j.phytochem.2005.04.035, PII S0031942205002104
    • Jahaniani F, Ebrahimi SA, Rahbar-Roshandel N, Mahmoudian M. 2005. Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent. Phytochemistry 66: 1581-1592. (Pubitemid 40950551)
    • (2005) Phytochemistry , vol.66 , Issue.13 , pp. 1581-1592
    • Jahaniani, F.1    Ebrahimi, S.A.2    Rahbar-Roshandel, N.3    Mahmoudian, M.4
  • 14
    • 0029917318 scopus 로고    scopus 로고
    • Quantification of dextromethorphan and metabolites: A dual phenotypic marker for cytochrome P450 3A4/5 and 2D6 activity
    • DOI 10.1016/0378-4347(95)00431-9
    • Jones DR, Gorski JC, Hamman MA, Hall SD. 1996. Quantification of dextromethorphan and metabolites: a dual phenotypic marker for cytochrome P450 3A4/5 and 2D6 activity. J Chromatogr B Biomed Appl 678: 105-111. (Pubitemid 26114746)
    • (1996) Journal of Chromatography B: Biomedical Applications , vol.678 , Issue.1 , pp. 105-111
    • Jones, D.R.1    Gorski, J.C.2    Hamman, M.A.3    Hall, S.D.4
  • 15
    • 0031003993 scopus 로고    scopus 로고
    • Inhibition of monoamine oxidase A by beta-Carboline derivatives
    • DOI 10.1006/abbi.1996.9771
    • Kim H, Sablin SO, Ramsay RR. 1997. Inhibition of monoamine oxidase A by beta-carboline derivatives. Arch Biochem Biophys 337: 137-142. (Pubitemid 27198065)
    • (1997) Archives of Biochemistry and Biophysics , vol.337 , Issue.1 , pp. 137-142
    • Hoon, K.1    Sablin, S.O.2    Ramsay, R.R.3
  • 16
    • 0034668719 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships in a series of endogenous and synthetic steroids exhibiting induction of CYP3A activity and hepatomegaly associated with increased DNA synthesis
    • DOI 10.1016/S0960-0760(00)00121-7, PII S0960076000001217
    • Lewis DF, Ioannides C, Parke DV, Schulte-Hermann R. 2000. Quantitative structure-activity relationships in a series of endogenous and synthetic steroids exhibiting induction of CYP3A activity and hepatomegaly associated with increased DNA synthesis. J Steroid Biochem Mol Biol 74: 179-185. (Pubitemid 32121653)
    • (2000) Journal of Steroid Biochemistry and Molecular Biology , vol.74 , Issue.4 , pp. 179-185
    • Lewis, D.F.V.1    Ioannides, C.2    Parke, D.V.3    Schulte-Hermann, R.4
  • 17
    • 33644553478 scopus 로고    scopus 로고
    • 1 on human cytochrome P450 enzymes
    • DOI 10.1055/s-2005-873197
    • Liu Y, Ma H, Zhang JW, Deng MC, Yang L. 2006. Influence of ginsenoside Rh1 and F1 on human cytochrome P450 enzymes. Planta Med 72: 126-131. (Pubitemid 43293866)
    • (2006) Planta Medica , vol.72 , Issue.2 , pp. 126-131
    • Liu, Y.1    Ma, H.2    Zhang, J.-W.3    Deng, M.-C.4    Yang, L.5
  • 19
    • 0032847733 scopus 로고    scopus 로고
    • Antibacterial activity of Peganum harmala
    • DOI 10.1016/S0367-326X(99)00065-9, PII S0367326X99000659
    • Prashanth D, John S. 1999. Antibacterial activity of Peganum harmala. Fitoterapia 70: 438-439. (Pubitemid 29422648)
    • (1999) Fitoterapia , vol.70 , Issue.4 , pp. 438-439
    • Prashanth, D.1    John, S.2
  • 20
    • 46449109055 scopus 로고    scopus 로고
    • Inhibitory effects of seven components of danshen extract on catalytic activity of cytochrome P450 enzyme in human liver microsomes
    • DOI 10.1124/dmd.108.021030
    • Qiu F, Zhang R, Sun J et al. 2008. Inhibitory effects of seven components of danshen extract on catalytic activity of cytochrome P450 enzyme in human liver microsomes. Drug Metab Dispos 36: 1308-1314. (Pubitemid 351929315)
    • (2008) Drug Metabolism and Disposition , vol.36 , Issue.7 , pp. 1308-1314
    • Qiu, F.1    Zhang, R.2    Sun, J.3    Jiye, A.4    Hao, H.5    Peng, Y.6    Ai, H.7    Wang, G.8
  • 21
    • 0038613425 scopus 로고    scopus 로고
    • Human pharmacology of ayahuasca: Subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics
    • DOI 10.1124/jpet.103.049882
    • Riba J, Valle M, Urbano G, Yritia M, Morte A, Barbanoj MJ. 2003. Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics. J Pharmacol Exp Ther 306: 73-83. (Pubitemid 36734359)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.306 , Issue.1 , pp. 73-83
    • Riba, J.1    Valle, M.2    Urbano, G.3    Yritia, M.4    Morte, A.5    Barbanoj, M.J.6
  • 22
    • 0042698684 scopus 로고    scopus 로고
    • Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism
    • DOI 10.1016/S0091-3057(03)00129-1
    • Schwarz MJ, Houghton PJ, Rose S, Jenner P, Lees AD. 2003. Activities of extract and constituents of Banisteriopsis caapi relevant to Parkinsonism. Pharmacol Biochem Behav 75: 627-633. (Pubitemid 36936896)
    • (2003) Pharmacology Biochemistry and Behavior , vol.75 , Issue.3 , pp. 627-633
    • Schwarz, M.J.1    Houghton, P.J.2    Rose, S.3    Jenner, P.4    Lees, A.D.5
  • 23
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. 1994. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270: 414-423. (Pubitemid 24229655)
    • (1994) Journal of Pharmacology and Experimental Therapeutics , vol.270 , Issue.1 , pp. 414-423
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 24
    • 0026459382 scopus 로고
    • Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes
    • Smith DA, Jones BC. 1992. Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes. Biochem Pharmacol 44: 2089-2098.
    • (1992) Biochem Pharmacol , vol.44 , pp. 2089-2098
    • Smith, D.A.1    Jones, B.C.2
  • 25
    • 33846852196 scopus 로고    scopus 로고
    • Ethnopharmacological survey of plants used in the traditional treatment of hypertension and diabetes in south-eastern Morocco (Errachidia province)
    • DOI 10.1016/j.jep.2006.09.011, PII S0378874106004600
    • Tahraoui A, El-Hilaly J, Israili ZH, Lyoussi B. 2007. Ethnopharmacological survey of plants used in the traditional treatment of hypertension and diabetes in south-eastern Morocco (Errachidia province). J Ethnopharmacol 110: 105-117. (Pubitemid 46217839)
    • (2007) Journal of Ethnopharmacology , vol.110 , Issue.1 , pp. 105-117
    • Tahraoui, A.1    El-Hilaly, J.2    Israili, Z.H.3    Lyoussi, B.4
  • 26
    • 59449097654 scopus 로고    scopus 로고
    • Inhibition of cytochrome P450 enzymes by rhein in rat liver microsomes
    • Tang JC, Yang H, Song XY et al. 2009. Inhibition of cytochrome P450 enzymes by rhein in rat liver microsomes. Phytother Res 23: 159-164.
    • (2009) Phytother Res , vol.23 , pp. 159-164
    • Tang, J.C.1    Yang, H.2    Song, X.Y.3
  • 27
    • 2442690439 scopus 로고    scopus 로고
    • Validated assays for human cytochrome P450 activities
    • DOI 10.1124/dmd.32.6.647
    • Walsky RL, Obach RS. 2004. Validated assays for human cytochrome P450 activities. Drug Metab Dispos 32: 647-660. (Pubitemid 38668158)
    • (2004) Drug Metabolism and Disposition , vol.32 , Issue.6 , pp. 647-660
    • Walsky, R.L.1    Obach, R.S.2
  • 28
    • 0036297455 scopus 로고    scopus 로고
    • Analysis of harmine and harmaline of Peganum harmala in different parts of different localities
    • Wang CH, Liu J, Zheng LM. 2002. Analysis of harmine and harmaline of Peganum harmala in different parts of different localities. Chin Pharm J 37: 212-215.
    • (2002) Chin Pharm J , vol.37 , pp. 212-215
    • Wang, C.H.1    Liu, J.2    Zheng, L.M.3
  • 29
    • 67651171204 scopus 로고    scopus 로고
    • Effects of CYP2D6 status on harmaline metabolism, pharmacokinetics and pharmacodynamics, and a pharmacogenetics-based pharmacokinetic model
    • Wu C, Jiang XL, Shen HW, Yu AM. 2009. Effects of CYP2D6 status on harmaline metabolism, pharmacokinetics and pharmacodynamics, and a pharmacogenetics-based pharmacokinetic model. Biochem Pharmacol 78: 617-624.
    • (2009) Biochem Pharmacol , vol.78 , pp. 617-624
    • Wu, C.1    Jiang, X.L.2    Shen, H.W.3    Yu, A.M.4
  • 30
    • 0037381219 scopus 로고    scopus 로고
    • Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic α-carboline alkaloids harmaline and harmine
    • DOI 10.1124/jpet.102.047050
    • Yu AM, Idle JR, Krausz KW, Küpfer A, Gonzalez FJ. 2003. Contribution of individual cytochrome P450 isozymes to the o-demethylation of the psychotropic α-carboline alkaloids harmaline and harmine. J Pharmacol Exp Ther 305: 315-322. (Pubitemid 36373866)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.305 , Issue.1 , pp. 315-322
    • Yu, A.-M.1    Idle, J.R.2    Krausz, K.W.3    Kupfer, A.4    Gonzalez, F.J.5
  • 31
    • 70349554496 scopus 로고    scopus 로고
    • Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigelastrum Bunge by an in vitro TLC bioautographic assay
    • Zheng XY, Zhang ZJ, Chou GX et al. 2009. Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigelastrum Bunge by an in vitro TLC bioautographic assay. Arch Pharm Res 32: 1245-1251.
    • (2009) Arch Pharm Res , vol.32 , pp. 1245-1251
    • Zheng, X.Y.1    Zhang, Z.J.2    Chou, G.X.3
  • 32
    • 25144524302 scopus 로고    scopus 로고
    • Prediction of herb-drug metabolic interactions: A simulation study
    • DOI 10.1002/ptr.1559
    • Zhou S, Huang M, Xu A, Yang H, Duan W, Paxton JW. 2005. Prediction of herb-drug metabolic interactions: a simulation study. Phytother Res 19: 464-471. (Pubitemid 41345519)
    • (2005) Phytotherapy Research , vol.19 , Issue.6 , pp. 464-471
    • Zhou, S.1    Huang, M.2    Xu, A.3    Yang, H.4    Duan, W.5    Paxton, J.W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.