Piperine Impairs Cytochrome P4501A1 Activity by Direct Interaction with the Enzyme and Not by Down Regulation of CYP1A1 Gene Expression in the Rat Hepatoma 5L Cell Line

Reen, Rashmeet K.; Roesch, Siegfried F.; Kiefer, Franz; Wiebel, Friedrich J.; Singh, Jaswant

doi:10.1006/bbrc.1996.0100

Cited by 48 publications

(30 citation statements)

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“…It was found that despite its ability to activate moderately CYP1A1 gene transcription, the alkaloid regulate CYP1A1 gene expression posttranslationally where it inhibits its catalytic activity by binding with the enzyme without destroying the AHH. 7 However, it is not known that which CYP form (s) is involved in the metabolism of piperine.…”

Section: Discussionmentioning

confidence: 99%

“…19 Though piperine also induced the CYP1A1 activity by transcription activation, the overall inhibition of benzo(a)pyrene metabolism and AHH activity appeared to be the consequence of direct interaction of piperine with CYP1A1 gene product. 7 Thus apparent shortcomings, if any, in piperine molecule could perhaps be overcome by introducing various structural modi®cations in the molecule.…”

Section: Introductionmentioning

confidence: 99%

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Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

Koul

Taneja

et al. 2000

Bioorganic & Medicinal Chemistry

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AbstractÐInhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)-dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modi®cations in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC-and PB-treated rat liver in vitro. Modi®ca-tions were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure± activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modi®cation in either of the three components of piperine. Saturation of the side chain resulted in signi®cantly enhanced inhibition of CYP while modi®cations in the phenyl and basic moieties in few analogues oered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. #

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

Koul

Taneja

et al. 2000

Bioorganic & Medicinal Chemistry

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“…Piperine (1-piperol piperidine) is an amide found in Piper species that non-specifically increases the bioavailability of several drugs and nutritional supplements, involving different P-450 cytochrome types (2,11) and plays a chemoprotector role against the procarcinogenic toxicity of benzo(a)pyrene, heavy metals and aflatoxins (9,12,13).…”

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confidence: 99%

Oral administration of piperine for the control of aflatoxin intoxication in rats

Gagini¹,

Silva²,

Castro³

et al. 2010

Braz. J. Microbiol.

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Aflatoxins are mycotoxins that have important toxic effects on human and animal health, even if consumed at low doses. The oral administration of piperine (1.12 mg/kg) during 23 days in rats seemingly interfered with the toxicity of aflatoxins, decreasing hepatic injuries and the leukocyte depletion in experimentally intoxicated animals.Key words: aflatoxins, piperine, experimental intoxication, rats. Piperine (1-piperol piperidine) is an amide found in Piper species that non-specifically increases the bioavailability of several drugs and nutritional supplements, involving different P-450 cytochrome types (2, 11) and plays a chemoprotector role against the procarcinogenic toxicity of benzo(a)pyrene, heavy metals and aflatoxins (9, 12, 13).Considering that piperine can be a powerful chemopreventive agent against the activation of procarcinogens in vitro, such as aflatoxins, this research was carried out in vivo in order to evaluate whether piperine, orally supplied to rats, is able to decrease the toxic effect of aflatoxins on white blood cells and the liver.

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“…The property of enhancing the bioavailability of drugs is partly due to the increased blood supply to the intrinsic vessels as a result of local vasodilation. In case of enzymatic activity, Glucoronyl transferase inhibits the endogenous UDP glucoronic acid content and by decreasing transferase activity [119]. One more mechanism of action of piperine was also explains by IIIM, Jammu, which states that Piperine act as a cell membrane modulator and thus helps in transportation of the drugs molecules across the barriers.…”

Section: Different Effect Of Piperine Referencesmentioning

confidence: 99%

“…[190,191] Piperine shows antidiarrhoel activity [76,192] The study carried out by Reen's observes and concludes that methylenedioxyphenyl ring founds to be responsible in inhibiting the drug metabolizing enzymes [119]. Another study by Atal in 1985 concludes that we can enhance the invivo drug bioavailability by inhibiting the hepatic and non hepatic drug metabolizing enzymes [59].…”

Section: Different Effect Of Piperine Referencesmentioning

confidence: 99%

Piperine and Its Various Physicochemical and Biological Aspects: A Review

Chopra¹,

Dhingra²,

Kapoor³

et al. 2016

CHEM

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Abstract:Piper nigrum L. is examined as the king of species worldwide by virtue of its principle piperine. In Ayurveda, since from the ancient times, it is known as "Yogvahi". It is one of the important alkaloids of Pepper fruits (Family Piperaceae) and has been found to have numerous medicinal properties such as antioxidant, antiplatelet, anti-inflammatory, antihypertensive, hepatoprotective, antithyroid, antitumor, antiasthmatic activity and also have significant role as fertility enhancer. The present review discusses the biosynthetic pathway, extraction process, chemistry and various analytical methods of piperine. It also describes the structural modification of piperine and its various effects on biological system. The utility of piperine as a bioenhancer for certain antibacterialantibiotics and a potent inhibitor of drug metabolism are also discussed. Thus, review provides knowledgeable erudition on the piperine which paves way for further work.

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Piperine Impairs Cytochrome P4501A1 Activity by Direct Interaction with the Enzyme and Not by Down Regulation of CYP1A1 Gene Expression in the Rat Hepatoma 5L Cell Line

Cited by 48 publications

References 0 publications

Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

Oral administration of piperine for the control of aflatoxin intoxication in rats

Piperine and Its Various Physicochemical and Biological Aspects: A Review

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