Piperine
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
Identifiers
CAS number	94-62-2
PubChem	638024
ChemSpider	553590
UNII	U71XL721QK
ChEMBL	CHEMBL43185
Jmol-3D images
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)

Piperine 

Heat	(SCOVALE SCALE: 100,000)

Preparation

Piperine is commercially available. If desired, it may be extracted from black pepper using dichloromethane.[5] Aqueous hydrotopes can also be used in the extraction to result in high yield and selectivity.[6] The amount of piperine varies from 1-2% in long pepper, to 5-10% in commercial white and black peppers.[7] 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.[8]

Biological activity

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.[9] 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.[10] West African pepper also contains it.[11]

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]

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

Recently the journal Molecular Nutrition Food Research published evidence that piperine can enhance the pharmacokinetic parameters of resveratrol via inhibiting its glucuronidation, thereby slowing its elimination. In February 2008, researchers discovered that piperine can stimulate pigmentation in the skin, together with the exposure to UVB light.[19][20] Piperine has shown 'anti-depression like activity', and cognitive enhancing effects in rats.[21 Piperine has shown anti-inflammatory and anti-arthritic effects in human interleukin-1beta-stimulated fibroblast-like synoviocytes and in rat arthritis models.[22]

References