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Piperine

From Wikipedia, the free encyclopedia
Not to be confused with piperidine.
Piperine
Names
Preferred IUPAC name
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Other names
(2E,4E)-5-(Benzo[d] [1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Piperoylpiperidine
Bioperine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.135 Edit this at Wikidata
UNII
  • 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 285.343 g·mol−1
Density 1.193 g/cm3
Melting point 130 °C (266 °F; 403 K)
Boiling point Decomposes
40 mg/l
Solubility in ethanol soluble
Solubility in chloroform 1 g/1.7 ml
Hazards
Safety data sheet (SDS) MSDS for piperine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Piperine
Scoville scale150,000[1] SHU

Piperine, possibly along with its isomer chavicine,[2] is the compound[3] responsible for the pungency of black pepper and long pepper via activation of TRPV1.[4] It has been used in some forms of traditional medicine.[5]

Preparation

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Extraction

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Due to its poor solubility in water, piperine is typically extracted from black pepper by using organic solvents like dichloromethane[6] or ethanol.[7] The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers.[8][9]

Piperine can also be prepared by treating the solvent-free residue from a concentrated alcoholic extract of black pepper with a solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine).[9] The solution is decanted from the insoluble residue and left to stand overnight in alcohol. During this period, the alkaloid slowly crystallizes from the solution.[10]

Chemical synthesis

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Piperine has been synthesized by the action of piperonoyl chloride on piperidine.[9]

Biosynthesis

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The biosynthesis of piperine is only partially known.[11]

  • The last step is catalyzed by piperine synthase (piperoyl-CoA:piperidine piperoyl transferase). As suggested by its systematic name, it converts piperoyl-CoA and piperidine into piperine.
  • Piperoyl-CoA is made by piperoyl-CoA ligase from piperic acid, which is in turn made from feruperic acid by CYP719A37.
  • Feruperic acid is presumably made from ferulic acid. Piperine is presumably made from lysine.

In addition to piperine synthase PipBAHD2, there is an orthologous enzyme with broader substract specificity in Piper nigrum with gene symbol PipBAHD1, called a "piperamide synthase". This other enzyme is responsible for the many piperamide compounds (see [12]) besides piperine found in black pepper. Both enzymes are BAHD acyltransferases.[11]

Reactions

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Piperine forms 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 formula). 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, crystallizing in steel-blue needles with melting point 145 °C.[9]

Piperine can be hydrolyzed by an alkali into piperidine and piperic acid.[9]

In light, especially ultraviolet light, piperine is changed into its isomers chavicine, isochavicine and isopiperine, which are tasteless.[13][2]

History

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Piperine was discovered in 1819 by Hans Christian Ørsted, who isolated it from the fruits of Piper nigrum, the source plant of both black and white pepper.[14] Piperine was also found in Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper".[15]

Uses

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Piperine is widely used in the supplements industry for its effect on enhancing absorption and bioavailability of other compounds such as curcumin,[16] resveratrol, ashwaganda, amino acids, vitamins and several minerals including selenium. It has been reported to inhibit several enzymes that participate in xenobiotic metabolism, including CYP3A4, P-gp,[17] UDP-glucose 6-dehydrogenase, and glucuronosyltransferase.[18] The last two activities (inhibition of glucuronidation) are most relevant for curcumin.[19]

See also

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References

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  1. ^ Mangathayaru, K. (2013). Pharmacognosy: An Indian perspective. Pearson Education India. p. 274. ISBN 9789332520264.
  2. ^ a b De Cleyn, R; Verzele, M (1972). "Constituents of peppers. I Qualitative Analysis of Piperine Isomers" (PDF). Chromatografia. 5: 346–350. doi:10.1007/BF02315254. S2CID 56022338. Retrieved 26 September 2023.
  3. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. p. 7442. ISBN 091191028X.
  4. ^ Dong, Y; Yin, Y; Vu, S; Yang, F; Yarov-Yarovoy, V; Tian, Y; Zheng, J (20 August 2019). "A distinct structural mechanism underlies TRPV1 activation by piperine". Biochemical and Biophysical Research Communications. 516 (2): 365–372. doi:10.1016/j.bbrc.2019.06.039. PMC 6626684. PMID 31213294.
  5. ^ 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): 735–748. doi:10.1080/10408390601062054. PMID 17987447. S2CID 42908718.
  6. ^ Epstein, William W.; Netz, David F.; Seidel, Jimmy L. (1993). "Isolation of Piperine from Black Pepper". J. Chem. Educ. 70 (7): 598. Bibcode:1993JChEd..70..598E. doi:10.1021/ed070p598.
  7. ^ Chen∗, Zhe; Wu∗, Jian Bing; Zhang, Jie; Li, Xiao Juan; Shen, Min He (2 June 2009). "One Step Purification of Piperine Directly from Piper nigrum L. by High Performance Centrifugal Partition Chromatography". Separation Science and Technology. 44 (8): 1884–1893. doi:10.1080/01496390902775877.
  8. ^ "Pepper". Tis-gdv.de. Retrieved 2 September 2017.
  9. ^ a b c d e Henry, Thomas Anderson (1949). "Piperine". The Plant Alkaloids (4th ed.). The Blakiston Company. pp. 35–37.
  10. ^ Ikan, Raphael (1991). Natural Products: A Laboratory Guide (2nd ed.). San Diego, CA: Academic Press. pp. 223–224. ISBN 0123705517.
  11. ^ a b Schnabel, Arianne; Athmer, Benedikt; Manke, Kerstin; Schumacher, Frank; Cotinguiba, Fernando; Vogt, Thomas (8 April 2021). "Identification and characterization of piperine synthase from black pepper, Piper nigrum L." Communications Biology. 4 (1): 445. doi:10.1038/s42003-021-01967-9. PMC 8032705. PMID 33833371.
  12. ^ Vargas-Huertas, Luis Felipe; Alvarado-Corella, Luis Diego; Sánchez-Kopper, Andrés; Araya-Sibaja, Andrea Mariela; Navarro-Hoyos, Mirtha (9 December 2023). "Characterization and Isolation of Piperamides from Piper nigrum Cultivated in Costa Rica". Horticulturae. 9 (12): 1323. doi:10.3390/horticulturae9121323.
  13. ^ Kozukue, Nobuyuki; Park, Mal-Sun; others, and 5 (2007). "Kinetics of Light-Induced Cis−Trans Isomerization of Four Piperines and Their Levels in Ground Black Peppers as Determined by HPLC and LC/MS". J. Agric. Food Chem. 55 (17): 7131–7139. Bibcode:2007JAFC...55.7131K. doi:10.1021/jf070831p. PMID 17661483. Retrieved 26 September 2023.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  14. ^ Ørsted, Hans Christian (1820). "Über das Piperin, ein neues Pflanzenalkaloid" [On piperine, a new plant alkaloid]. Schweiggers Journal für Chemie und Physik (in German). 29 (1): 80–82.
  15. ^ Friedrich A. Fluckiger; Daniel Hanbury (1879). Pharmacographia : a History of the Principal Drugs of Vegetable Origin, Met with in Great Britain and British India. London: Macmillan. p. 584. ASIN B00432KEP2.
  16. ^ Hewlings, Susan; Kalman, Douglas (2017). "Curcumin: A Review of Its' Effects on Human Health". Foods. 6 (10): 92. doi:10.3390/foods6100092. PMC 5664031. PMID 29065496.
  17. ^ Chopra, Bhawna; Dhingra, Ashwani (2016). "Piperine and Its Various Physicochemical and Biological Aspects: A Review". Open Chemistry Journal. 3: 75–96. doi:10.2174/1874842201603010075. Retrieved 7 May 2025.
  18. ^ Reen, RK; Jamwal, DS; Taneja, SC; Koul, JL; Dubey, RK; Wiebel, FJ; Singh, J (20 July 1993). "Impairment of UDP-glucose dehydrogenase and glucuronidation activities in liver and small intestine of rat and guinea pig in vitro by piperine". Biochemical Pharmacology. 46 (2): 229–38. doi:10.1016/0006-2952(93)90408-o. PMID 8347144.
  19. ^ Anand, Preetha; Kunnumakkara, Ajaikumar B.; Newman, Robert A.; Aggarwal, Bharat B. (1 December 2007). "Bioavailability of Curcumin: Problems and Promises". Molecular Pharmaceutics. 4 (6): 807–818. doi:10.1021/mp700113r. PMID 17999464.
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