Piperine

Quality 0.50 · 1 view · Updated 2 months ago

Alkaloid responsible for the pungency of black pepper

title: "Piperine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["1-piperidinyl-compounds", "benzodioxoles", "carboxamides", "cyp1a2-inhibitors", "cyp3a4-inhibitors", "enones", "monoamine-oxidase-inhibitors", "piperidine-alkaloids", "polyenes", "pungent-flavors", "reversible-inhibitors-of-mao-a", "substances-discovered-in-the-19th-century"] description: "Alkaloid responsible for the pungency of black pepper" topic_path: "general/1-piperidinyl-compounds" source: "https://en.wikipedia.org/wiki/Piperine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Alkaloid responsible for the pungency of black pepper ::

::data[format=table title="Infobox pepper"]

FieldValue
scoville150,000
::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 414843869 | ImageFile1 = piperin.svg | ImageClass1 = skin-invert-image | ImageFile2 = Piperine_crystals.jpg | ImageName = Octane-3D-balls.png | PIN = (2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one | OtherNames = (2E,4E)-5-(Benzo[d] [1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one Piperoylpiperidine Bioperine | Section1 = {{Chembox Identifiers | IUPHAR_ligand = 2489 | CASNo = 94–62–2 | CASNo_Ref = | ChEBI_Ref = | ChEBI = 28821 | ChEMBL_Ref = | ChEMBL = 43185 | ChemSpiderID_Ref = | ChemSpiderID = 553590 | DrugBank = DB12582 | EC_number = 202–348–0 | Gmelin = 341351 | KEGG = C03882 | PubChem = 638024 | UNII_Ref = | UNII = U71XL721QK | SMILES = O=C(N1CCCCC1)\C=C\C=C\c2ccc3OCOc3c2 | 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+ | InChIKey = MXXWOMGUGJBKIW-YPCIICBEBY | StdInChI_Ref = | StdInChI = 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+ | StdInChIKey_Ref = | StdInChIKey = MXXWOMGUGJBKIW-YPCIICBESA-N | Section2 = {{Chembox Properties | C=17|H=19|N=1|O=3 | Density = 1.193 g/cm3 | MeltingPtC = 130 | BoilingPt = Decomposes | pKa = | Solubility = 40mg/l | Solvent1 = ethanol | Solubility1 = soluble | Solvent2 = chloroform | Solubility2 = 1g/1.7ml | Section3 = {{Chembox Hazards | GHS_ref=https://pubchem.ncbi.nlm.nih.gov/compound/638024#section=Safety-and-Hazards | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = | ExternalSDS = MSDS for piperine }} | scoville = 150,000 Piperine, possibly along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper via activation of TRPV1. It has been used in some forms of traditional medicine.{{cite journal |title=Black pepper and its pungent principle-piperine: A review of diverse physiological effects |author=Srinivasan, K.|doi=10.1080/10408390601062054|journal=Critical Reviews in Food Science and Nutrition|volume=47|year=2007|issue=8|pages=735–748|pmid=17987447|s2cid=42908718}}

Preparation

Extraction

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

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).

Chemical synthesis

Piperine has been synthesized by the reaction of piperonoyl chloride with piperidine.

Biosynthesis

The biosynthesis of piperine is only partially known.

  • 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 ) besides piperine found in black pepper. Both enzymes are BAHD acyltransferases.

Reactions

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.

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

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

History

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. Piperine was also found in Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper".

Uses

Piperine is widely used in the supplements industry for its effect on enhancing absorption and bioavailability of other compounds such as curcumin, 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, UDP-glucose 6-dehydrogenase, and glucuronosyltransferase. The last two activities (inhibition of glucuronidation) are most relevant for curcumin.

References

References

  1. Mangathayaru, K.. (2013). "Pharmacognosy: An Indian perspective". Pearson Education India.
  2. {{Merck11th
  3. (20 August 2019). "A distinct structural mechanism underlies TRPV1 activation by piperine.". Biochemical and Biophysical Research Communications.
  4. (1993). "Isolation of Piperine from Black Pepper". [[J. Chem. Educ.]].
  5. (2 June 2009). "One Step Purification of Piperine Directly from Piper nigrum L. by High Performance Centrifugal Partition Chromatography". Separation Science and Technology.
  6. "Pepper".
  7. Henry, Thomas Anderson. (1949). "The Plant Alkaloids". The Blakiston Company.
  8. Ikan, Raphael. (1991). "Natural Products: A Laboratory Guide". Academic Press.
  9. (8 April 2021). "Identification and characterization of piperine synthase from black pepper, Piper nigrum L.". Communications Biology.
  10. (9 December 2023). "Characterization and Isolation of Piperamides from Piper nigrum Cultivated in Costa Rica". Horticulturae.
  11. (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..
  12. (1972). "Constituents of peppers. I Qualitative Analysis of Piperine Isomers". Chromatografia.
  13. Ørsted, Hans Christian. (1820). "Über das Piperin, ein neues Pflanzenalkaloid". Schweiggers Journal für Chemie und Physik.
  14. (1879). "Pharmacographia : a History of the Principal Drugs of Vegetable Origin, Met with in Great Britain and British India". Macmillan.
  15. (2017). "Curcumin: A Review of Its Effects on Human Health". Foods.
  16. (2016). "Piperine and Its Various Physicochemical and Biological Aspects: A Review". Open Chemistry Journal.
  17. (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.
  18. (1 December 2007). "Bioavailability of Curcumin: Problems and Promises". Molecular Pharmaceutics.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

1-piperidinyl-compoundsbenzodioxolescarboxamidescyp1a2-inhibitorscyp3a4-inhibitorsenonesmonoamine-oxidase-inhibitorspiperidine-alkaloidspolyenespungent-flavorsreversible-inhibitors-of-mao-asubstances-discovered-in-the-19th-century