Inhibition of CYP1 by berberine, palmatine, and jatrorrhizine: Selectivity, kinetic characterization, and molecular modeling

Lo, Sheng Nan; Yw, Chang; Tsai, Keng‐Chang; Chang, Chia Yu; Wu, Tian Shung; Ueng, Yune-Fang

doi:10.1016/j.taap.2013.07.005

Cited by 44 publications

(32 citation statements)

References 40 publications

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“…But Cyp1A1 is inducible by various herbal substances, e.g. by the flavonoids quercetin and kaempferol (Ciolino et al, 1999), catechins like epigallocatechin-3-gallate (Palermo et al, 2005) or alkaloids like berberine (Vrzal et al, 2005;Zhou et al, 2011;Chatuphonprasert et al, 2011;Salminen et al, 2011;Lo et al, 2013). Cyp3A4 has a share of 30% of the relative abundance of cytochromes in the liver and plays a dominant role in drug metabolism (Rendic and Di Carlo, 1997).…”

Section: Discussionmentioning

confidence: 99%

Combining metabolomic analysis and microarray gene expression analysis in the characterization of the medicinal plant Chelidonium majus L

Orland¹,

Knapp²,

König³

et al. 2014

Phytomedicine

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Section: Discussionmentioning

confidence: 99%

Combining metabolomic analysis and microarray gene expression analysis in the characterization of the medicinal plant Chelidonium majus L

Orland¹,

Knapp²,

König³

et al. 2014

Phytomedicine

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“…Inhibited the activity of CYP1A1, CYP1A2, CYP1B1, CYP2D6, CYP2C9, CYP3A4 CYP3A11 and CYP2D22 enzymes [133][134][135] .…”

Section: Berberinementioning

confidence: 99%

Chelidonium majus L. (Greater celandine) – A Review on its Phytochemical and Therapeutic Perspectives

Maji¹,

Banerji²

2015

Int. J. Herb. Med.

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Chelidonium majus L. (Papaveraceae) is a medicinal herb used in various traditional systems of medicine to treat ulcer, cancer, oral infection, liver disorders, chronic bronchitis, asthma, etc. Different parts of this plant contain numerous therapeutically important alkaloidal constituents such as chelidonine, chelerythrine, sanguinarine, berberine and so on. The plant and its active compounds exhibit a wide range of pharmacological activities. The plants has long history of therapeutic use in medicines without any toxic effect. Today it is one of the important components of some pharmaceutical preparations. Consumption of C. majus preparations possesses toxic effects on the liver although the effect becomes controversial with its hepatoprotective effect. Numerous active constituents of C. majus interact with various drug metabolizing enzymes that mimic possible interactions of this herb with the conventional drugs. This review provides detailed phytochemical, pharmacological and toxicological information of C. majus along with mechanisms of action of its various active compounds on different aspects of pharmacology. This review also highlights plausible drug interaction of its various active compounds and the future prospect of this herb.

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“…The expression constructs of CYP1A1*1, CYP1A2*1, and CYP1B1*3 with N-terminal modification were generously provided by F. Peter Guengerich (Nashville, TN) (Shimada et al, 1998b). The construct for expressing CYP1B1.1 (Leu432) was prepared as described before (Lo et al, 2013). Bicistronic human constructs consisting of the coding sequence of P450 followed by that of NADPH-P450 reductase were transformed to Escherichia coli DH5a by electroporation (Gene Pulser II; Bio-Rad, Hercules, CA).…”

Section: Methodsmentioning

confidence: 99%

“…The construct of CYP1B1*4 was prepared by introducing the 4390A.G substitution to CYP1B1*1 using the primer-directed enzymatic amplification method, according to the manufacturer's instructions for the QuickChange Lightning site-directed mutagenesis kit (Stratagene, an Agilent Technologies Company, La Jolla, CA). The oligonucleotide primer sets used for mutagenesis were described in a previous report (Lo et al, 2013). P450 expression and membrane preparation were performed following the methods of Shimada et al (1998a) and Parikh et al (1997), respectively.…”

Section: Methodsmentioning

confidence: 99%

“…CYP1B1 was considered to be involved in angiotensin II-induced hypertension (Jennings et al, 2010). Using 7-ethoxyresorufin as a substrate, our previous report demonstrates that berberine potently inhibits CYP1B1, and CYP1A2 shows resistance to berberinemediated inhibition (Lo et al, 2013). To elucidate the influence of metabolism on the berberine-mediated inhibition of human CYP1s, berberine oxidation and the CYP1 inhibition by oxidation metabolites were determined in recombinant enzyme systems.…”

Section: Introductionmentioning

confidence: 99%

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The Effect of Oxidation on Berberine-Mediated CYP1 Inhibition: Oxidation Behavior and Metabolite-Mediated Inhibition

Shen

Chang

et al. 2015

Drug Metab Dispos

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The protoberberine alkaloid berberine carries methylenedioxy moiety and exerts a variety of pharmacological effects, such as anti-inflammation and lipid-lowering effects. Berberine causes potent CYP1B1 inhibition, whereas CYP1A2 shows resistance to the inhibition. To reveal the influence of oxidative metabolism on CYP1 inhibition by berberine, berberine oxidation and the metabolite-mediated inhibition were determined. After NADPH-fortified preincubation of berberine with P450, the inhibition of CYP1A1 and CYP1B1 variants (CYP1B1.1, CYP1B1.3, and CYP1B1.4) by berberine was not enhanced, and CYP1A2 remained resistant. Demethyleneberberine was identified as the most abundant metabolite of CYP1A1- and CYP1B1-catalyzed oxidations, and thalifendine was generated at a relatively low rate. CYP1A1-catalyzed berberine oxidation had the highest maximal velocity (V max) and exhibited positive cooperativity, suggesting the assistance of substrate binding when the first substrate was present. In contrast, the demethylenation by CYP1B1 showed the property of substrate inhibition. CYP1B1-catalyzed berberine oxidation had low K m values, but it had V max values less than 8% of those of CYP1A1. The dissociation constants generated from the binding spectrum and fluorescence quenching suggested that the low K m values of CYP1B1-catalyzed oxidation might include more than the rate constants describing berberine binding. The natural protoberberine/berberine fmetabolites with methylenedioxy ring-opening (palmatine, jatrorrhizine, and demethyleneberberine) and the demethylation (thalifendine and berberrubine) caused weak CYP1 inhibition. These results demonstrated that berberine was not efficiently oxidized by CYP1B1, and metabolism-dependent irreversible inactivation was minimal. Metabolites of berberine caused a relatively weak inhibition of CYP1.

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Inhibition of CYP1 by berberine, palmatine, and jatrorrhizine: Selectivity, kinetic characterization, and molecular modeling

Cited by 44 publications

References 40 publications

Combining metabolomic analysis and microarray gene expression analysis in the characterization of the medicinal plant Chelidonium majus L

Combining metabolomic analysis and microarray gene expression analysis in the characterization of the medicinal plant Chelidonium majus L

Chelidonium majus L. (Greater celandine) – A Review on its Phytochemical and Therapeutic Perspectives

The Effect of Oxidation on Berberine-Mediated CYP1 Inhibition: Oxidation Behavior and Metabolite-Mediated Inhibition

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