Piperine

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Not to be confused with piperidine.
Piperine
Piperin.svg
Piperine crystals.jpg
Names
IUPAC name
1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
Other names
5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine
Piperoylpiperidine
Bioperine
Identifiers
94-62-2 YesY
ChEBI CHEBI:28821 N
ChEMBL ChEMBL43185 N
ChemSpider 553590 N
2489
Jmol 3D model Interactive image
PubChem 638024
UNII U71XL721QK N
  • InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+ N
    Key: MXXWOMGUGJBKIW-YPCIICBESA-N N
  • InChI=1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
    Key: MXXWOMGUGJBKIW-YPCIICBEBY
  • O=C(N1CCCCC1)\C=C\C=C\c2ccc3OCOc3c2
Properties
C17H19NO3
Molar mass 285.34 g·mol−1
Density 1.193 g/cm3
Melting point 130 °C (266 °F; 403 K)
Boiling point decomposes
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references
Piperine
Hottest-chili-rating.gif
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 (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.

Preparation

Piperine is commercially available. If desired, it may be extracted from black pepper using dichloromethane.[2] Aqueous hydrotopes can 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

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 the presence of a little hydrochloric acid gives a characteristic periodide, B2•HI•I2, crystallising in steel-blue needles, mp. 145 °C.

History

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] Flückiger and Hanbury found piperine in Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper".[7] West African pepper also contains piperine.[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

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 (which is a 20-fold increase, as 100% is just normal absorption),[18] most likely due to inhibition of glucuronidation by the enzyme UDP-glucuronosyltransferase in the liver and small intestine.[19] Chemopreventive efficacy of curcumin and piperine has been shown during 7,12-dimethylbenz[a]anthracene-induced hamster buccal pouch carcinogenesis.[20]

Piperine may enhance the pharmacokinetic parameters of resveratrol via inhibiting glucuronidation, thereby slowing its metabolism.[21]

In February 2008, researchers discovered that piperine can stimulate pigmentation in the skin, together with the exposure to UVB light.[22][23]

Piperine has shown "anti-depression like activity" and cognitive-enhancing effects in rats.[24]

Piperine has shown anti-inflammatory and anti-arthritic effects in human interleukin-1beta-stimulated fibroblast-like synoviocytes and in rat arthritis models.[25]

Piperine also possesses anti-angiogenic activities.[26]

See also

References

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  1. ↑ Merck Index, 11th Edition, 7442
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Majeed, M. Use of piperine as a bioavailability enhancer. US Patent 5744161, October 26, 1999.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ 16.0 16.1 Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Manoharan S, Balakrishnan S, Menon V, et al. Singapore Med J. 2009 Feb;50(2):139-46.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  25. ↑ Bang JS, Oh DH, Choi HM, et al. Anti-inflammatory and antiarthritic effects of piperine in human interleukin 1β-stimulated fibroblast-like synoviocytes and in rat arthritis models, Arthritis Research & Therapy 2009 Mar 30;11(2):R49.
  26. ↑ Doucette CD, Hilchie AL, Liwski R, Hoskin DW. J Nutr Biochem 2013;24:231-239.
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