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Black pepper (Piper nigrum)


Black pepper (Piper nigrum) Image
Synonyms / Common Names / Related Terms

Bisalkaloids, black pepper oil, Brazilian black pepper, dipiperamide D, dipiperamide E, green pepper, pink pepper, Piperaceae (family), piperine, piptigrine, red pepper, white pepper, wisanine.

Note: Black pepper, white pepper, green pepper, pink pepper, and red pepper are all differently preserved berries or seeds of the Piper nigrum plant.

http://www.sigmaaldrich.com/life-science/nutrition-research/learning-center/plant-profiler/piper-nigrum.html


Mechanism of Action

Pharmacology:

  • Constituents: Black pepper has been found to contain piperine1, alkamides9, piptigrine7, wisanine7, dipiperamide D10, and dipiperamide E10.
  • Acetylcholinesterase inhibitory activity: In an in vitro study, an extract of Piper nigrum L. seeds showed 50-65% inhibitory activity on acetylcholinesterase.2
  • Antibacterial effects: In an in vitro study using 12 different genera of bacterial populations isolated from the oral cavity of 200 individuals, an aqueous decoction of black pepper (Piper nigrum L.) exhibited 75% antibacterial activity as compared to aqueous decoction of bay leaf (53.4%) and aqueous decoction of aniseed (18.1%), at the concentration of 10mL/disc.4
  • Anti-inflammatory effects: Based on animal study, a polyherbal formulation (Aller-7/NR-A2) containing extracts from seven medicinal plants including Phyllanthus emblica, Terminalia chebula, Terminalia bellerica, Albizia lebbeck, Piper nigrum, Zingiber officinale, and Piper longum demonstrated 31.3% inhibition against carrageenan-induced acute inflammation in Wistar Albino rats, while ibuprofen (50 mg/kg orally) exerted 68.1% inhibition.3 Aller-7 also exhibited a dose-dependent (150-350mg/kg) anti-inflammatory effect against Freund's adjuvant-induced arthritis in Wistar Albino rats; an approximately 63% inhibitory effect was observed at a dose of 350mg/kg.
  • Antilarval activity: Piptigrine, isolated from the dried ground seeds of Piper nigrum Linn., exhibited toxicity of 15.0ppm against fourth instar larvae of Aedes aegypti Liston.7
  • Antioxidant effects: Based on animal study, a polyherbal formulation (Aller-7/NR-A2) containing extracts from seven medicinal plants including Phyllanthus emblica, Terminalia chebula, Terminalia bellerica, Albizia lebbeck, Piper nigrum, Zingiber officinale, and Piper longum exhibited concentration-dependent scavenging activities toward biochemically generated hydroxyl radicals (IC50 741.73mcg/mL); superoxide anion (IC50 24.65mcg/mL by phenazine methosulfate-nicotinamide adenine dinucleotide [PMS-NADH] assay and IC50 4.27mcg/mL by riboflavin/nitroblue tetrazolium [NBT] light assay), nitric oxide (IC50 16.34mcg/mL); 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical (IC50 5.62mcg/mL); and 2,2-azinobis-ethyl-benzothiozoline-sulphonic acid diammonium salt (ABTS) radical (IC50 7.35mcg/mL).5 Aller-7 inhibited free radical-induced hemolysis in the concentration range of 20-80mcg/mL. Aller-7 also significantly inhibited nitric oxide release from lipopolysaccharide-stimulated murine macrophages.
  • Cytochrome P (CYP) 450 effects: In in vitro studies, constituents isolated from Piper nigrum, including piperine and dipiperamides D and E, potently inhibited some CYP450 metabolic pathways, including CYP2D69 and CYP3A48 ,10.
  • Gastrointestinal effects: In a clinical study of intestinal peristalsis in 16 healthy volunteers, consumption of 1.5g of black pepper in capsules increased the orocecal transit time from 90 ± 51 minutes to 122 ± 88 minutes (p=0.09).11 In an in vitro study, piperine inhibited digoxin and cyclosporine A transport in Caco-2 cells with IC50 values of 15.5 and 74.1mcM, respectively.8 The bactericidal and anti-adhesive properties of black pepper have also been investigated against Helicobacter pylori, however, aqueous extracts did not show bactericidal effect on any of the isolates.6
  • Neural effects: In an in vitro study using whole-cell patch-clamp electrophysiology, piperine, a pungent alkaloid found in black pepper, had similar agonist effects on the human vanilloid receptor TRPV1 as capsaicin.1 However, piperine could induce greater receptor desensitization and exhibit a greater efficacy than capsaicin.

Pharmacodynamics/Kinetics:

  • Pharmacokinetics: In an animal study, piperine from black pepper was shown to enhance the bioavailability of EGCG, a polyphenol constituent from green tea (Camellia sinensis).12 Intragastric coadministration of 163.8mcM/kg EGCG and 70.2mcM/kg piperine to male CF-1 mice increased the plasma Cmax and area under the curve (AUC) by 1.3-fold compared to mice treated with EGCG only. The authors report that piperine appeared to increase EGCG bioavailability by inhibiting glucuronidation and gastrointestinal transit. Piperine (100mmM/L) inhibited EGCG glucuronidation in mouse small intestine (by 40%), but not in hepatic microsomes. Piperine (20mcM/L) also inhibited production of EGCG-3"-glucuronide in human HT-29 colon adenocarcinoma cells. Small intestinal EGCG levels in CF-1 mice following treatment with EGCG alone had a Cmax = 37.50 ± 22.50nM/g at 60 min that then decreased to 5.14 ± 1.65nM/g at 90 min; however, cotreatment with piperine resulted in a Cmax = 31.60 ± 15.08nM/g at 90 min, and levels were maintained above 20nM/g until 180 min. This resulted in a significant increase in the small intestine EGCG AUC (4,621.80 ± 1,958.72 vs. 1,686.50 ± 757.07 (nM/g·min)). EGCG appearance in the colon and the feces of piperine-cotreated mice was slower than in mice treated with EGCG alone.
  • Pharmacodynamics: Based on animal study, a polyherbal formulation (Aller-7/NR-A2) containing extracts from seven medicinal plants including Phyllanthus emblica, Terminalia chebula, Terminalia bellerica, Albizia lebbeck, Piper nigrum, Zingiber officinale, and Piper longum exhibited concentration-dependent scavenging activities toward biochemically generated hydroxyl radicals (IC50 741.73mcg/mL); superoxide anion (IC50 24.65mcg/mL by phenazine methosulfate-nicotinamide adenine dinucleotide [PMS-NADH] assay and IC50 4.27mcg/mL by riboflavin/nitroblue tetrazolium [NBT] light assay), nitric oxide (IC50 16.34mcg/mL); 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical (IC50 5.62mcg/mL); and 2,2-azinobis-ethyl-benzothiozoline-sulphonic acid diammonium salt (ABTS) radical (IC50 7.35mcg/mL).5
  • In an in vitro study, piperine inhibited digoxin and cyclosporine A transport in Caco-2 cells with IC50 values of 15.5 and 74.1mcM, respectively.8

References

  1. McNamara, F. N., Randall, A., and Gunthorpe, M. J. Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1). Br J Pharmacol 2005;144(6):781-790. 15685214
  2. Ingkaninan, K., Temkitthawon, P., Chuenchom, K., Yuyaem, T., and Thongnoi, W. Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies. J Ethnopharmacol 2003;89(2-3):261-264. 14611889
  3. Pratibha, N., Saxena, V. S., Amit, A., D'Souza, P., Bagchi, M., and Bagchi, D. Anti-inflammatory activities of Aller-7, a novel polyherbal formulation for allergic rhinitis. Int J Tissue React<.em> 2004;26(1-2):43-51. 15573692
  4. Chaudhry, N. M. and Tariq, P. Bactericidal activity of black pepper, bay leaf, aniseed and coriander against oral isolates. Pak J Pharm Sci 2006;19(3):214-218. 16935829
  5. D'Souza, P., Amit, A., Saxena, V. S., Bagchi, D., Bagchi, M., and Stohs, S. J. Antioxidant properties of Aller-7, a novel polyherbal formulation for allergic rhinitis. Drugs Exp Clin Res 2004;30(3):99-109. 15366786
  6. O'Mahony, R., Al Khtheeri, H., Weerasekera, D., Fernando, N., Vaira, D., Holton, J., and Basset, C. Bactericidal and anti-adhesive properties of culinary and medicinal plants against Helicobacter pylori. World J Gastroenterol 12-21-2005;11(47):7499-7507. 16437723
  7. Siddiqui, B. S., Gulzar, T., Begum, S., and Afshan, F. Piptigrine, a new insecticidal amide from Piper nigrum Linn. Nat Prod Res 2004;18(5):473-477. 15248617
  8. Bhardwaj, R. K., Glaeser, H., Becquemont, L., Klotz, U., Gupta, S. K., and Fromm, M. F. Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. J Pharmacol Exp Ther 2002;302(2):645-650. 12130727
  9. Subehan, Usia, T., Kadota, S., and Tezuka, Y. Mechanism-based inhibition of human liver microsomal cytochrome P450 2D6 (CYP2D6) by alkamides of Piper nigrum. Planta Med 2006;72(6):527-532. 16808005
  10. Tsukamoto, S., Tomise, K., Miyakawa, K., Cha, B. C., Abe, T., Hamada, T., Hirota, H., and Ohta, T. CYP3A4 inhibitory activity of new bisalkaloids, dipiperamides D and E, and cognates from white pepper. Bioorg Med Chem 2002;10(9):2981-2985. 12110320
  11. Vazquez-Olivencia, W., Shah, P., and Pitchumoni, C. S. The effect of red and black pepper on orocecal transit time. J Am Coll Nutr 1992;11(2):228-231. 1578101
  12. Lambert, J. D., Hong, J., Kim, D. H., Mishin, V. M., and Yang, C. S. Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. J Nutr 2004;134(8):1948-1952. 15284381


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