Question for you kava chemists. ..

[Ricardo Piquant]

Turmeric is often bundled with black pepper extract (piperine) to increase the bioavailibility of the beneficial turmeric compounds (curcumins). For some reason, this combination unlocks turmeric, whereas without it, it simply passes through your system mostly unabsorbed.

Does kava, being a close relative of the pepper plant, contain any piperine or piperine-like compounds that would also increase the bioavailibility of curcumins?

 

[Shiny]

I too, have been exploring the hepatoprotective and antioxidant effects of piperine found in the black pepper plant. I add black pepper to most of my meals in order to increase the bioavailability of not just curcumins in turmeric, but also resveratrol (found in the skin of grapes, blueberries, raspberries, mulberries.) and other polyphenols.

 

[Shiny]

Did a little research online. Found that kava contains a compound called Methysticin, which is similar to Piperine, but not the same. So I suspect that no, kava does not contain Piperine but yes, it does contain a Piperine-like substance, but not sure if it has the same qualities.

Source: https://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1973-01-01_2_page008.html

 

[Alia]

Turmeric is often bundled with black pepper extract (piperine) to increase the bioavailibility of the beneficial turmeric compounds (curcumins). For some reason, this combination unlocks turmeric, whereas without it, it simply passes through your system mostly unabsorbed.

Does kava, being a close relative of the pepper plant, contain any piperine or piperine-like compounds that would also increase the bioavailibility of curcumins?

After reading @Shiny and your Posts I checked and found that piperine is an alkaloid and there is a compound found in the stems and leaves of Kava (not roots) called- pipermethystine which is also an alkaloid. Not sure if they are related in any way. If you can link to on-line version of Chapter 3 (Active Ingredients in 'Awa) in Hawaiian 'Awa Views of an Etnobotanical Treasure you can read and maybe do some cross-reference. Best never to consume the stems or leaves of kava.

 

[verticity]

After reading @Shiny and your Posts I checked and found that piperine is an alkaloid and there is a compound found in the stems and leaves of Kava (not roots) called- pipermethystine which is also an alkaloid. Not sure if they are related in any way. If you can link to on-line version of Chapter 3 (Active Ingredients in 'Awa) in Hawaiian 'Awa Views of an Etnobotanical Treasure you can read and maybe do some cross-reference. Best never to consume the stems or leaves of kava.

The category of alkaloids is very broad and contains many chemicals, and the only thing they really have in common is that they contain nitrogen, and tend to be basic. Pipermethystine is toxic and pretty different from piperine.

The structure of methysticin does have some similarities to piperine, like Shulgin notes in that article, although methysticin is not an alkaloid (there are no alkaloids in kava roots). Basically half of the molecules are similar to each other, but the other half is completely different. However, it actually is possible that kavalactones could have a similar potentiating effect to piperine, not necessarily because the molecules are partly similar, but because they are metabolized similarly. According to wikipedia:

"Piperine is being studied for its potential to affect bioavailability of other compounds in dietary supplements. One example investigated is the potential for piperine to enhance the bioavailability of curcumin. In laboratory studies, it inhibits human CYP3A4 and P-glycoprotein which are enzymes involved in the metabolism and transport of xenobiotics and metabolites. Other research indicates it inhibits the degradation of ABCA1, a key transporter protein involved in cholesterol efflux. In animal studies, piperine inhibited CYP450 enzymes involved in drug metabolism."
https://en.wikipedia.org/wiki/Piperine
​

It is known that kavalactones are metabolized by CYP450 enzymes, including CYP3A4.

And interestingly, there is also evidence that kava inhibits P-glycoprotein:
Drug Metabolism and Disposition November 2005, 33 (11) 1580-1583
P-glycoprotein is involved in removing "foreign substances" including drugs and other chemicals from human cells. If is inhibited, the substances stay in the cells longer, so are more effective.

So the answer to the question seems to be: it is actually plausible.

 

[Alia]

The category of alkaloids is very broad and contains many chemicals, and the only thing they really have in common is that they contain nitrogen, and tend to be basic. Pipermethystine is toxic and pretty different from piperine.

The structure of methysticin does have some similarities to piperine, like Shulgin notes in that article, although methysticin is not an alkaloid (there are no alkaloids in kava roots). Basically half of the molecules are similar to each other, but the other half is completely different. However, it actually is possible that kavalactones could have a similar potentiating effect to piperine, not necessarily because the molecules are partly similar, but because they are metabolized similarly. According to wikipedia:

"Piperine is being studied for its potential to affect bioavailability of other compounds in dietary supplements. One example investigated is the potential for piperine to enhance the bioavailability of curcumin. In laboratory studies, it inhibits human CYP3A4 and P-glycoprotein which are enzymes involved in the metabolism and transport of xenobiotics and metabolites. Other research indicates it inhibits the degradation of ABCA1, a key transporter protein involved in cholesterol efflux. In animal studies, piperine inhibited CYP450 enzymes involved in drug metabolism."
https://en.wikipedia.org/wiki/Piperine
​

It is known that kavalactones are metabolized by CYP450 enzymes, including CYP3A4.

And interestingly, there is also evidence that kava inhibits P-glycoprotein:
Drug Metabolism and Disposition November 2005, 33 (11) 1580-1583
P-glycoprotein is involved in removing "foreign substances" including drugs and other chemicals from human cells. If is inhibited, the substances stay in the cells longer, so are more effective.

So the answer to the question seems to be: it is actually plausible.

Great explanation, thanks for making it understandable.