Piperine

Piperine is a piperidine alkaloid from the group of acid amide alkaloids with the molecular formula: C17H19NO3. Piperine is the most important ingredient of black pepper (Piper nigrum), one of the most commonly used spices, and gives it its pungency. Piperine is found in all types of pepper. Its concentration is particularly high in black pepper, at around 4.6 to 9.7 percent. Piperine is also found in white pepper, long pepper and 0.4% in cubeb pepper. However, the pungency of piperine is nowhere near as pronounced as that of capsaicin, which is found in chilies. The pungency of piperine is linked to the trans-trans position of the two double bonds (see figure). Under the influence of light, isomers of piperine are formed whose pungency is lost.

Piperine, like all pungent substances, stimulates metabolism and gastrointestinal secretion and has antimicrobial activity (Derosa G et al. 2016). Furthermore, piperine possesses immunomodulatory, antioxidant, anti-asthmatic, anticarcinogenic and antiphlogistic activities (Manayi A et al. 2018, Meghwal M et al. 2013). Piperine is used as a dietary supplement. A postive effect in oral lichen planus has been reported (Yang JY et al. 2019).

Starting point of the plant biosynthesis of piperine is L-lysine, which is metabolized after binding to pyridoxal phosphate. Synthetically, piperine can be produced from piperidine and piperic acid.

In 1979 piperine was described as the first bioenhancer. There is evidence that piperine increases the bioavailability of turmeric and ibuprofen (increased absorption in the gastrointestinal tract - Berginc K et al. 2012). Therefore, piperine is a popular additive in food supplements.

1. Berginc K et al (2012) Physiological barriers to the oral delivery of curcumin. Pharmacy 67:518-524.
2. Derosa G et al (2016) Piperine and Its Role in Chronic Diseases. Adv Exp Med Biol 928:173-184.
3. Manayi A et al. (2018) Piperine as a Potential Anti-cancer Agent: A Review on Preclinical Studies. Curr Med Chem 25:4918-4928.
4. Meghwal M et al (2013) Piper nigrum and piperine: an update. Phytother Res. 27:1121-130.
5. Yang JY et al. (2019) Black pepper and its bioactive constituent piperine: promising therapeutic strategies for oral lichen planus. Inflammopharmacology 27:5-13.