Piperine

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Not to be confused with piperidine.
Piperine
Piperin.svg
Piperine crystals.jpg
Identifiers
CAS number 94-62-2 YesY
PubChem 638024
ChemSpider 553590 N
UNII U71XL721QK N
ChEBI CHEBI:28821 N
ChEMBL CHEMBL43185 N
Jmol-3D images Image 1
Properties
Molecular formula C17H19NO3
Molar mass 285.34 g mol−1
Density 1.193 g/cm3
Melting point 130 °C (266 °F; 403 K)
Boiling point decomposes
Hazards
MSDS MSDS for piperine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
Piperine
Heat (SR: 100,000)

Piperine, along with its isomer chavicine, is the alkaloid[1] 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 (1g/25L (18°C)), and is highly soluble in alcohol (1g/15mL), ether (1g/36mL) and chloroform (1g/1.7mL). The solution in alcohol has a pepper-like taste.

Preparation[edit]

Piperine is commercially available only in limited quantities for research purposes. If desired, it may be extracted from black pepper using dichloromethane.[2] Aqueous hydrotopes can also be used in the extraction to result in high yield and selectivity.[3] The amount of piperine varies from 1-2% in long pepper, to 5-10% in commercial white and black peppers.[4] 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.[5]

Reactions[edit]

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.

History[edit]

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.[6] 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.[7] West African pepper also contains it.[8]

Anderson[9] first hydrolysed piperine by alkalis into a base and an acid, which were later named[10] piperidine and piperic acid respectively. The alkaloid was first synthesised[11] by the action of piperoyl chloride on piperidine.

Biological activity[edit]

The pungency of capsaicin and piperine is caused by activation of the heat and acidity sensing TRPV ion channel TRPV1 on nociceptors (pain sensing nerve cells).[12]

The full mechanism of piperine's bioavailability enhancing abilities is unknown.[13] But it has been found to inhibit human CYP3A4 and P-glycoprotein, enzymes important for the metabolism and transport of xenobiotics and metabolites.[14][15] In animal studies, piperine also inhibited other CYP 450 enzymes important for drug metabolism.[16][17] By inhibiting certain enzyme metabolism, piperine may alter the effectiveness of certain medications by increasing the bioavailability of various compounds.[16] Notably, piperine may enhance bioavailability of curcumin by 2000% in humans.[18] Chemopreventive efficacy of curcumin and piperine has been shown during 7,12-dimethylbenz[a]anthracene-induced hamster buccal pouch carcinogenesis.[19]

Piperine may enhance the pharmacokinetic parameters of resveratrol via inhibiting glucuronidation, thereby slowing its metabolism.[20]

In February 2008, researchers discovered that piperine can stimulate pigmentation in the skin, together with the exposure to UVB light.[21][22]

Piperine has shown 'anti-depression like activity', and cognitive enhancing effects in rats.[23]

Piperine has shown anti-inflammatory and anti-arthritic effects in human interleukin-1beta-stimulated fibroblast-like synoviocytes and in rat arthritis models.[24]

Piperine also possesses anti-angiogenic activities.[25]

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 7442
  2. ^ 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. 
  3. ^ Gaikar. Process for extraction of piperine from piper species. US 6365601, April 2, 2002.
  4. ^ http://www.tis-gdv.de/tis_e/ware/gewuerze/pfeffer/pfeffer.htm#selbsterhitzung
  5. ^ Ikan, Raphael (1991). Natural Products: A Laboratory Guide 2nd Ed.. San Diego: Academic Press, Inc. p. 223-224. ISBN 0123705517. 
  6. ^ 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).
  7. ^ Pharmacographia (London: Macmillan & Co., 1879), p. 584.
  8. ^ Stenhouse in Pharm. J., 1855, 14, 363.
  9. ^ Annalen, 1850, 75, 82; 84, 345, cf. Wertheim and Rochleder, ibid., 1845, 54, 255.
  10. ^ Babo & Keller, Journ. pr. chem., 1857, 72, 53.
  11. ^ Rugheimer, Ber., 1882, 15, 1390.
  12. ^ 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. 
  13. ^ Majeed, M. Use of piperine as a bioavailability enhancer. US Patent 5744161, October 26, 1999.
  14. ^ 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. 
  15. ^ 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.  edit
  16. ^ a b 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. 
  17. ^ 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. 
  18. ^ 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. 
  19. ^ Manoharan S, Balakrishnan S, Menon V, et al. Singapore Med J. 2009 Feb;50(2):139-46.
  20. ^ 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.  edit
  21. ^ 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. 
  22. ^ "Pepper 'to treat pigment disease'". BBC News. 2008-02-14. 
  23. ^ 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. 
  24. ^ Bang JS, Oh DH, Choi HM, et al. Arthritis Res Ther. 2009 Mar 30;11(2):R49.
  25. ^ Doucette CD, Hilchie AL, Liwski R, Hoskin DW. J Nutr Biochem 2013;24:231-239.