Talk:Piperine

Piperine?
Stop reverting moron. That website you link doesn't even mention piperine retard. —Preceding unsigned comment added by 65.96.69.94 (talk) 21:23, 10 July 2009 (UTC)

I,m deleting the line saying piperine increases the bio availability of curcumin because it links to a website that doesn't even say anything about it. Also websites are not proof of anything. Sounds like some marketing crap. —Preceding unsigned comment added by 24.62.15.201 (talk) 17:02, 10 July 2009 (UTC)

Piperine ABSOLUTELY increases the bioavailability of curcumin. Here is a link to an abstract on pubmed.gov (a US gov't website) that shows the increase in bioavailability of curcumin is 2,000%:

http://www.ncbi.nlm.nih.gov/pubmed/9619120


 * Correct link, but the abstract states that the improved bioavailability of curcumin was 154%, not 2000%.David notMD (talk) 19:07, 9 August 2016 (UTC)

"Piperine (C17H19NO3) is the alkaloid responsible for the taste and smell of black pepper." - I'm almost definite that this isn't quite true. Piperine is relatively non-flammable so it's pretty widely accepted that it's not the cause of pepper's aroma. Furthermore, saying that's it's the source of pepper's taste isn't quite right either: piperine has extremely low solubility in water and therefore cannot penetrate the saliva in the mouth easily. Because of this, piperine isn't the cause of the initial taste of pepper but it is the source of the sharp after-taste. —The preceding unsigned comment was added by 82.41.255.235 (talk • contribs).


 * Piperine *is* a major, if not the major constituent of black pepper's taste. The smell is mostly the result of one of piperine's diastereomers, chavacine. This means it is of the same molecular weight as piperine and as you say, 'non-volatile'. Regardless to such classification, it smells.
 * Superkuh 07:10, 30 July 2009 (UTC)


 * Piperine is relatively non-flammable...


 * Umm, only "flammable" things have odor? Perhaps you meant "volatile"?


 * Atlant 16:31, 29 September 2006 (UTC)


 * Oops, yeah - piperine is non-volatile, hence no odour. Sorry about that! —The preceding unsigned comment was added by 82.41.255.235 (talk • contribs).

Alkaloid?
According to the article on alkaloids (and my own knowledge), an alkaloid has to be a base. This definitely does not correspond with the structure of piperine, which is an amide and hence a very weak base. However, I'm no expert in natural products and piperine is listed as the only amide member of the pyridine family of alkaloids in the alkaloid classification... But is it really an alkaloid? -- docking man  talk 04:06, 5 January 2007 (UTC)


 * Yes, there are non-basic alkaloids, and piperine is one, along with colchicine and a variety of others. Definitions such as the one on the page alkaloid are ex-post-facto attempts to rationalize terminology that was already in use; they are attempts to describe existing terminology rather than to redefine it. Googling "non-basic alkaloids" will reveal much more. Merenta 19:59, 21 September 2007 (UTC)

A better def of alkaloid is simply nitrogen containing organic compound. Obviously there are issues with such a loose definition, but classically thats all it means. — Preceding unsigned comment added by 74.243.253.245 (talk) 00:36, 18 March 2012 (UTC)

CYP2D6 Inducer?
Interestingly, the article discusses the inhibition of drug metabolism via CYP3A4 while the article on CYP2D6 lists piperidines as an inducer of CYP2D6, thereby increasing metabolism. Does anyone know if piperine induces CYP2D6? This is something of great interest to me. If anyone has more info please let me know. --Jmcclare (talk) 00:57, 4 April 2008 (UTC)

Piperine analogs: S. Mishra et. al. have synthesized various conjugates of curcumin. And it was found that curcumin bioconjugates containing glycine, alanine, and/or piperic acid were found to show improved antimicrobial properties over curcumin, suggesting increased cellular uptake or reduced metabolism of these bioconjugates resulting in increased concentration inside the infected cells.

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pKa of 1.98?
Piperine has no acidic hydrogens, so the assertion in the chemical properties box that it has a pKa of 1.98 is dubious. Either that's the pKa of the protonated form, or it's of piperic acid, what remains of piperine after hydrolytic removal of piperidine.
 * I agree that data cannot be correct, so I have removed it. If anyone can check the reference  to find out what the cited value of 1.98 is actually referring to, that would be helpful.  -- Ed (Edgar181) 23:05, 26 June 2009 (UTC)

Insecticide
Other than an episode of Doctor Who, is there anything anywhere about the actual insecticidal properties of piperine? 203.211.77.193 (talk) 11:53, 6 August 2009 (UTC)
 * Could not find any lit on actual use as an insecticide, so deleted.David notMD (talk) 01:33, 27 June 2017 (UTC)

What is bioperine?
Came here looking for info on bioperine but it is not mentioned other than a redirect? 79.79.251.109 (talk) 09:09, 7 August 2012 (UTC)
 * As far as I can tell, it is just a brand name for a pepper extract that contains piperine. -- Ed (Edgar181) 12:16, 7 August 2012 (UTC)
 * Confirming BioPerine is a branded piperine product.David notMD (talk) 19:05, 9 August 2016 (UTC)

Solubility
I miss sources for the solubilty numbers. Horst Emscher (talk) 08:37, 18 April 2013 (UTC)

Adverse effects
This Wikipedia now looks like an advertisement. Which is Completely OK, except please include negative effects also. For example, piperine and other bioenhancers => Leaky Gut => problems?? ee1518 (talk) 10:33, 20 March 2015 (UTC)

Chem Abstracts report
Data: 3598 references to piperine, 3024 since 2001, of which 140 are classified as reviews. Conclusions, with about 5 publications appearing weekly, let's mainly focus on general sources.--Smokefoot (talk) 14:38, 16 April 2021 (UTC)

Alkaloid or not... Revisited
It seems a few edits have been made to this article recently to remove the mention of piperine being an alkaloid.

The IUPAC Gold Book states alkaloids are ''basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom (but not excluding those of animal origin). Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. By extension, certain neutral compounds biogenetically related to basic alkaloids are included.''

While piperine may not be considered a basic nitrogen compound because it is an amide, piperine is referred to as an alkaloid widely in the literature along with numerous other amide compounds (e.g. colchicine, capsaicin). As Merenta mentioned in the first discussion about this topic nearly 14 years ago, a google search for "nonbasic alkaloids" or "amide alkaloids" will reveal many examples.

See:
 * Dostál, Jirí. "Two faces of alkaloids." Journal of Chemical Education 77.8 (2000): 993.
 * Gorgani, Leila, et al. "Piperine—the bioactive compound of black pepper: from isolation to medicinal formulations." Comprehensive Reviews in Food Science and Food Safety 16.1 (2017): 124-140.
 * Hesse, Manfred. Alkaloids: Nature's curse or blessing?. John Wiley & Sons, 2002.

Natural products are out of my realm of expertise, so perhaps I'm incorrect. Can anybody make a case for why piperine should not be referred to as an alkaloid in this article? Does it even matter?

Davination (talk) 00:41, 27 August 2021 (UTC)

Preparation
Re: "by using organic solvents like dichloromethane", is DCM as something highly toxic and damaging to humans and the environment, really the best example to use? Higher yield volumes are reported from both ethanol and isopropanol, so it's unnecessary to guide people down the path of DCM. Especially when U.S. EPA and most others are trying to phase its use out where possible. 120.17.36.136 (talk) 11:41, 10 April 2024 (UTC)
 * Editors are supposed to report facts and information. --Smokefoot (talk) 13:34, 10 April 2024 (UTC)