|Jmol-3D images||Image 1|
|Molar mass||285.34 g mol−1|
|Melting point||130 °C (266 °F; 403 K)|
|MSDS||MSDS for piperine|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pepper and long pepper. It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water (1 g/25 L (18 °C)), and is highly soluble in alcohol (1 g/15 mL), ether (1 g/36 mL) and chloroform (1 g/1.7 mL). The solution in alcohol has a pepper-like taste.
Piperine is commercially available. If desired, it may be extracted from black pepper using dichloromethane. Aqueous hydrotopes can also be used in the extraction to result in high yield and selectivity. The amount of piperine varies from 1-2% in long pepper, to 5-10% in commercial white and black peppers. Further, it may be prepared by treating the solvent-free residue from an alcoholic extract of black pepper, with a solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine) and solution of the washed, insoluble residue in warm alcohol, from which the alkaloid crystallises on cooling.
Piperine yields salts only with strong acids. The platinichloride B4•H2PtCl6 forms orange-red needles. ("B" denotes one mole of the alkaloid base in this and the following formulae.) Iodine in potassium iodide added to an alcoholic solution of the base in presence of a little hydrochloric acid gives a characteristic periodide, B2•HI•I2, crystallising in steel-blue needles, mp. 145 °C.
Piperine was discovered in 1819 by Hans Christian Ørsted, who isolated it from the fruits of Piper nigrum, the source plant of both the black and white pepper grains. Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl),[vague] two species called "long pepper" also were found to contain it by Flückiger and Hanbury. West African pepper also contains it.
Anderson first hydrolysed piperine by alkalis into a base and an acid, which were later named piperidine and piperic acid respectively. The alkaloid was first synthesised by the action of piperoyl chloride on piperidine.
The full mechanism of piperine's bioavailability enhancing abilities is unknown. But it has been found to inhibit human CYP3A4 and P-glycoprotein, enzymes important for the metabolism and transport of xenobiotics and metabolites. In animal studies, piperine also inhibited other CYP 450 enzymes important for drug metabolism. By inhibiting certain enzyme metabolism, piperine may alter the effectiveness of certain medications by increasing the bioavailability of various compounds. Notably, piperine may enhance bioavailability of curcumin by 2000% in humans (which is a 20 fold increase as 100% is just normal absorption), most likely due to inhibition of glucuronidation by the enzyme UDP-glucuronosyltransferase in the liver and small intestine. Chemopreventive efficacy of curcumin and piperine has been shown during 7,12-dimethylbenz[a]anthracene-induced hamster buccal pouch carcinogenesis.
Piperine has shown 'anti-depression like activity', and cognitive enhancing effects in rats.
Piperine has shown anti-inflammatory and anti-arthritic effects in human interleukin-1beta-stimulated fibroblast-like synoviocytes and in rat arthritis models.
Piperine also possesses anti-angiogenic activities.
- Piperidine, a cyclic six-membered amine that results from hydrolysis of piperine
- Capsaicin, the active piquant chemical in chili peppers
- Allyl isothiocyanate, the active piquant chemical in mustard, radishes, horseradish, and wasabi
- Allicin, the active piquant flavor chemical in raw garlic and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)
- Merck Index, 11th Edition, 7442
- Epstein, William W.; Netz, David F.; Seidel, Jimmy L. (1993). "Isolation of piperine from black pepper". J. Chem. Ed. 70 (7): 598. doi:10.1021/ed070p598.
- Gaikar. Process for extraction of piperine from piper species. US 6365601, April 2, 2002.
- Ikan, Raphael (1991). Natural Products: A Laboratory Guide 2nd Ed.. San Diego: Academic Press, Inc. pp. 223–224. ISBN 0123705517.
- Oersted, "Über das Piperin, ein neues Pflanzenalkaloid" [On piperine, a new plant alkaloid], (Schweigger's) Journal für Chemie und Physik, vol. 29, no. 1, pages 80-82 (1820).
- Pharmacographia (London: Macmillan & Co., 1879), p. 584.
- Stenhouse in Pharm. J., 1855, 14, 363.
- Annalen, 1850, 75, 82; 84, 345, cf. Wertheim and Rochleder, ibid., 1845, 54, 255.
- Babo & Keller, Journ. pr. chem., 1857, 72, 53.
- Rugheimer, Ber., 1882, 15, 1390.
- McNamara FN, Randall A, Gunthorpe MJ (March 2005). "Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1)". Br. J. Pharmacol. 144 (6): 781–90. doi:10.1038/sj.bjp.0706040. PMC 1576058. PMID 15685214.
- Majeed, M. Use of piperine as a bioavailability enhancer. US Patent 5744161, October 26, 1999.
- Bhardwaj RK, Glaeser H, Becquemont L, Klotz U, Gupta SK, Fromm MF (August 2002). "Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4". J. Pharmacol. Exp. Ther. 302 (2): 645–50. doi:10.1124/jpet.102.034728. PMID 12130727.
- Srinivasan, K (2007). "Black pepper and its pungent principle-piperine: A review of diverse physiological effects". Critical Reviews in Food Science and Nutrition 47 (8): 735–48. doi:10.1080/10408390601062054. PMID 17987447.
- Atal CK, Dubey RK, Singh J (January 1985). "Biochemical basis of enhanced drug bioavailability by piperine: evidence that piperine is a potent inhibitor of drug metabolism". J. Pharmacol. Exp. Ther. 232 (1): 258–62. PMID 3917507.
- Reen RK, Jamwal DS, Taneja SC, et al. (July 1993). "Impairment of UDP-glucose dehydrogenase and glucuronidation activities in liver and small intestine of rat and guinea pig in vitro by piperine". Biochem. Pharmacol. 46 (2): 229–38. doi:10.1016/0006-2952(93)90408-O. PMID 8347144.
- Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS (May 1998). "Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers". Planta Med. 64 (4): 353–6. doi:10.1055/s-2006-957450. PMID 9619120.
- Singh J, Dubey RK, Ata CK l (1986). "Piperine-mediated inhibition of glucuronidation activity in isolated epithelial cells of the guinea-pig small intestine: evidence that piperine lowers the endogeneous UDP-glucuronic acid content". Pharamcol. Exp. Ther. 236: 488–493.
- Manoharan S, Balakrishnan S, Menon V, et al. Singapore Med J. 2009 Feb;50(2):139-46.
- Johnson, J. J.; Nihal, M; Siddiqui, I. A.; Scarlett, C. O.; Bailey, H. H.; Mukhtar, H; Ahmad, N (2011). "Enhancing the bioavailability of resveratrol by combining it with piperine". Molecular Nutrition & Food Research 55 (8): 1169–76. doi:10.1002/mnfr.201100117. PMC 3295233. PMID 21714124.
- Faas, L.; Venkatasamy, R.; Hider, R. C.; Young, A. R.; Soumyanath, A. (2008). "In vivo evaluation of piperine and synthetic analogues as potential treatments for vitiligo using a sparsely pigmented mouse model". British Journal of Dermatology 158 (5): 941–50. doi:10.1111/j.1365-2133.2008.08464.x. PMID 18284389.
- "Pepper 'to treat pigment disease'". BBC News. 2008-02-14.
- Wattanathorna, Jintanaporn; Pennapa Chonpathompikunlertb; Supaporn Muchimapuraa; Aroonsri Pripremc; Orathai Tankamnerdthai (September 2008). "Piperine, the potential functional food for mood and cognitive disorders". Food and Chemical Toxicology 46 (9): 3106–3110. doi:10.1016/j.fct.2008.06.014. PMID 18639606.
- Bang JS, Oh DH, Choi HM, et al. Arthritis Res Ther. 2009 Mar 30;11(2):R49.
- Doucette CD, Hilchie AL, Liwski R, Hoskin DW. J Nutr Biochem 2013;24:231-239.