Piperine
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| Names | |
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| Preferred IUPAC name
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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| Other names
(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Piperoylpiperidine Bioperine |
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| Identifiers | |
94-62-2  |
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| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:28821  |
| ChEMBL | ChEMBL43185 |
| ChemSpider | 553590 |
| ECHA InfoCard | 100.002.135 |
| 2489 | |
| PubChem | 638024 |
| UNII | U71XL721QK |
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| 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 |
| 40mg/L | |
| Solubility in alcohol | 1g/15ml |
| Solubility in ether | 1g/36ml |
| Solubility in chloroform | 1g/1.7ml |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
| Piperine | |
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| 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.
Preparation[edit]
Piperine is extracted from black pepper using dichloromethane.[2] Aqueous hydrotropes 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[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 the 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] 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.
Preliminary research[edit]
A component of pungency by piperine results from activation of the heat- and acidity-sensing TRPV ion channels, TRPV1 and TRPA1, on nociceptors, the pain-sensing nerve cells.[12]
Piperine is being studied for its potential to affect bioavailability of other compounds in food. One example investigated is the potential for piperine to enhance the bioavailability of curcumin.[13] In laboratory studies, it inhibits human CYP3A4 and P-glycoprotein[14] which are enzymes involved in the metabolism and transport of xenobiotics and metabolites.[14][15] Other research indicates it inhibits the degradation of ABCA1, a key transporter protein involved in cholesterol efflux.[16] In animal studies, piperine inhibited CYP450 enzymes involved in drug metabolism.[17]
See also[edit]
- 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)
- Ilepcimide
- Piperlongumine
References[edit]
- ^ Merck Index, 11th Edition, 7442
- ^ Epstein WW, Netz DF, Seidel JL (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.
- ^ http://www.tis-gdv.de/tis_e/ware/gewuerze/pfeffer/pfeffer.htm#selbsterhitzung
- ^ Ikan R (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)". British Journal of Pharmacology. 144 (6): 781–90. doi:10.1038/sj.bjp.0706040. PMC 1576058
. PMID 15685214. - ^ 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 Medica. 64 (4): 353–6. doi:10.1055/s-2006-957450. PMID 9619120.
- ^ a b 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". The Journal of Pharmacology and Experimental Therapeutics. 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.
- ^ Wang, L; Palme, V; Rotter, S; Schilcher, N; Cukaj, M; Wang, D; Ladurner, A; Heiss, E. H.; Stangl, H; Dirsch, V. M.; Atanasov, A. G. (2016). "Piperine inhibits ABCA1 degradation and promotes cholesterol efflux from THP-1-derived macrophages". Molecular Nutrition & Food Research: 1500960. doi:10.1002/mnfr.201500960. PMID 27862930.
- ^ 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". The Journal of Pharmacology and Experimental Therapeutics. 232 (1): 258–62. PMID 3917507.
