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Piperine

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Piperine
Names
IUPAC name 1-piperidine
Other names 5-(3,4-methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine
piperoylpiperidine
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.002.135 Edit this at Wikidata
CompTox Dashboard (EPA)
SMILES
  • O=C(/C=C/C=C/C2=CC=C
    (OCO3)C3=C2)N1CCCCC1
Properties
Chemical formula C17H19NO3
Molar mass 285.343 g·mol
Density 1.193 g/cm
Melting point 130 °C (266 °F; 403 K)
Boiling point decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
For the organic compound used in drug production, see: Piperidine

Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine (an isomer of piperine). It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water and more so in alcohol, ether or chloroform: the solution in alcohol has a pepper-like taste. It 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. Anderson first hydrolysed piperine by alkalis into a base and an acid, which were later named piperidine and piperic acid respectively. The alkaloid was synthesised by the action of piperoyl chloride on piperidine.

Preparation

Piperine is commercially available. If desired, it may be extracted from black pepper using dichloromethane. The amount of piperine varies from 1-2% in long pepper, to 5-9% in the white and the black peppers of commerce. Further, it may be prepared by treating the solvent-free residue from an alcoholic extract of black pepper, with a solution of sodium 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.

Biological activity

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

Piperine has also 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 enzymes important in drug metabolism. By inhibiting drug metabolism, piperine may increase the bioavailability of various compounds and alter the effectiveness of some medications. Notably, piperine may enhance bioavailability of curcumin by 2000% in humans.

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

Piperine was discovered by Hans Christian Ørsted in 1819, he 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), two species called "long pepper" also found containing it by Flückiger and Hanbury. West African Pepper also contains it.

See also

References

  1. Merck Index, 11th Edition, 7442
  2. Annalen, 1850, 75, 82; 84, 345, cf. Wertheim and Rochleder, ibid., 1845, 54, 255.
  3. Babo & Keller, Journ. pr. chem., 1857, 72, 53.
  4. Rugheimer, Ber., 1882, 15, 1390.
  5. Epstein, William W.; Netz, David F.; Seidel, Jimmy L. (1993). "Isolation of piperine from black pepper". J. Chem. Ed. 70: 598. doi:10.1021/ed070p598.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. http://www.tis-gdv.de/tis_e/ware/gewuerze/pfeffer/pfeffer.htm#selbsterhitzung
  7. McNamara FN, Randall A, Gunthorpe MJ (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. Bhardwaj RK, Glaeser H, Becquemont L, Klotz U, Gupta SK, Fromm MF (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  9. ^ Atal CK, Dubey RK, Singh J (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  10. Reen RK, Jamwal DS, Taneja SC; et al. (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. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  11. Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  12. 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. doi:10.1111/j.1365-2133.2008.08464.x. PMID 18284389.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  13. "Pepper 'to treat pigment disease'". BBC News. 2008-02-14.
  14. Oersted, "Über das Piperin, ein neues Pflanzenalkaloid" , (Schweigger's) Journal für Chemie und Physik, vol. 29, no. 1, pages 80-82 (1820). Available on-line (in German): http://books.google.com/books?id=k-M4AAAAMAAJ&pg=PA80&lpg=PA81&ots=BOH_h5pA3s&ie=ISO-8859-1&output=html .
  15. Pharmacographia (London: Macmillan & Co., 1879), p. 584.
  16. Stenhouse in Pharm. J., 1855, 14, 363.
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