My foray into kavalactone extraction

[Palmetto]

I bought some Isa with the express purpose of making a high DHM / high flavokawain extract. Flavokawains, DHM, DHK, and Yangonin have all been proven to produce a number of anticancer effects, including: cancer cell apoptosis, inhibition of metastasis, and other cancer fighting abilities. I have a relative who has taken kava to fight her disease. She had stomach problems from drinking kavas (probably exacerbated by chemotherapy), so I mentioned extracting the active ingredients to eliminate the fibers and sediment that cause most of the stomach issues.

Since I have little scientific equipment at home, I decided to do a basic alcohol extraction. I bought 2 liters of 151 proof everclear and added a couple choline pills to the mix. I put about a half lb of medium grind Isa into a container with most of the alcohol. I shook, mashed, and strained for several rounds at room temperature. Occasionally I would take a volume of the strained mixture and put it into the freezer (set at extra cold temp unknown). After a few hours, a sludge precipatated on the bottom, and the supernatant was a dark orange colored liquid, which didn't freeze due to the high alcoholic content. The supernatant was then reused to resoak the remaining grind again. After several rounds of this, I had a predominantly sludge, slightly alcoholic paste that filled 2 extra large baby food jars. I still have the orangy supernatant which I will dry this week in my brand new vacuum dessicator. I suspect this supernatant is flavokawain enriched, but I have no proof as yet.

But this led me to think that, if you took a noble kava and performed an alcohol extraction, you could still remove much of the flavokawains by precipitating the kavalactones and decanting the supernatant off.

So I mailed the baby food jars to the person and described my methods, in case she wanted to perform the extraction herself. She tried a teaspoon mixed with spicy food. Immediately she texted me that she couldn't feel her tongue at all from the teaspoon she took a minute before.

 

[HeadHodge]

I bought some Isa with the express purpose of making a high DHM / high flavokawain extract. Flavokawains, DHM, DHK, and Yangonin have all been proven to produce a number of anticancer effects, including: cancer cell apoptosis, inhibition of metastasis, and other cancer fighting abilities. I have a relative who has taken kava to fight her disease. She had stomach problems from drinking kavas (probably exacerbated by chemotherapy), so I mentioned extracting the active ingredients to eliminate the fibers and sediment that cause most of the stomach issues.

Since I have little scientific equipment at home, I decided to do a basic alcohol extraction. I bought 2 liters of 151 proof everclear and added a couple choline pills to the mix. I put about a half lb of medium grind Isa into a container with most of the alcohol. I shook, mashed, and strained for several rounds at room temperature. Occasionally I would take a volume of the strained mixture and put it into the freezer (set at extra cold temp unknown). After a few hours, a sludge precipatated on the bottom, and the supernatant was a dark orange colored liquid, which didn't freeze due to the high alcoholic content. The supernatant was then reused to resoak the remaining grind again. After several rounds of this, I had a predominantly sludge, slightly alcoholic paste that filled 2 extra large baby food jars. I still have the orangy supernatant which I will dry this week in my brand new vacuum dessicator. I suspect this supernatant is flavokawain enriched, but I have no proof as yet.

But this led me to think that, if you took a noble kava and performed an alcohol extraction, you could still remove much of the flavokawains by precipitating the kavalactones and decanting the supernatant off.

So I mailed the baby food jars to the person and described my methods, in case she wanted to perform the extraction herself. She tried a teaspoon mixed with spicy food. Immediately she texted me that she couldn't feel her tongue at all from the teaspoon she took a minute before.

Other than not understanding some of your terminology, I'm glad you reported your experiment for us. I don't see anything wrong with what you have done except that I've read but don't know for a fact that alcohol extraction will not only extract the desired lactones but possibly other unwanted stuff because of its efficiency and nondiscrimination. The problem is there so much hype out there and so little facts its hard to tell if your procedure is perfectly fine or if it's a concoction made in hell.

 

[HeadHodge]

@Palmetto if you continue with your alcohol extraction, I think there are at least more than a few of us interested in determining the best process for doing it. i.e. a while back I saw an interesting prep where they used the everclear with dry ice to extract. For a non chemist this is pretty interesting stuff because its like writing software, you don't need a major investment in equipment to create something that is possibly extraordinaire.

If you decide to end your experiments, I'll pm you my address to send your left over everclear to.

 

[Palmetto]

@HeadHodge I want the "undesirable stuff" in there because it helps fight cancer. Whilst I was doing the experiments, I remembered something Chris Allen said about refrigerating water prep kava to precipitate the kavalactones. Turns out, keeping alcohol prep in the freezer for a few hours seems to do the same thing. I strongly suspect that most of the flavokawains remain in the liquid (supernatant) and not in the jelly like sludge (precipitate) at the bottom. That could potentially be a way to turn a no longer noble extract back into a noble one, if you weren't aiming predominantly for the antitumor effect.

BTW, the only everclear I have left is loaded with flavokawains. Do you really still want it? My NC house where I performed the experiments reeks of alcohol now, like the day after a college party.

 

[Palmetto]

I also believe that choline is a poor choice for an emulsifier of kavalactones. Polysorbate 80 (Tween 80) is probably a better choice. I plan to test that out soon. I might get around to posting pictures soon too.

 

[verticity]

That's interesting. That should work, but I would expect that the precipitate would be enhanced in FKs, and the supernatant will be depleted, not the other way around. 151 proof alcohol still is 25% water. FKs are less polar than KLs, so they will precipitate out first when you chill it. In my experience with acetone, you can actually get them to precipitate out at room temperature if you add about 50% water. Of course, the kavalactones are not very water soluble either, so if you freeze a 25% water solution, there will probably be a lot of KLs in the precipitate as well, but a lot will probably stay in the liquid also. The cold precipitation method is mentioned in this patent:
https://patents.google.com/patent/US5296224

A couple suggestions to improve the yield:
- as a first step you could sonicate the kava in the alcohol, or alternately heat (under reflux if you have a reflux tube)
- If you want to maximize FKs, try 190 proof everclear instead of 151 to minimize water
- or try extracting using d-limonene, which I expect would be a good solvent for FKs, and is food safe as well

(Note to anyone else reading this: the latter two suggestions are intended to maximize flavokavain content, which is normally exactly the opposite of what you want in a kava extract...)

 

[verticity]

I also believe that choline is a poor choice for an emulsifier of kavalactones. Polysorbate 80 (Tween 80) is probably a better choice. I plan to test that out soon. I might get around to posting pictures soon too.

If you're using a solvent like alcohol I don't think you really need an emulsifier. KLs and FKs are already very soluble in ethanol.

 

[Palmetto]

@verticity Emulsifiers can help with breaking up cells or releasing things from cleaved cells, even in ethanol. At least they do with animal cells. I am planning on getting a cheapo water bath sonicator soon. That might be best for releasing components, but worsen the filtration process. I'm trying to keep this low cost and easy for other to copy.

I hadn't checked the partition coefficients (or other polarity indices) of FKs vs. KLs. You may be right about the supernatant having less FKs, but there was also a nonpolar film on top that was very thin. Perhaps the FKs partitioned out in that way, due to lower density? I'm just rambling late at night now.

These experiments were kind of spur of the moment. I did get an offer to pay for half the lab equipment I ordered to study it, but I only ordered a vacuum dessicator. I need that for some unrelated experiments anyway.

So what do you think about polarity sponges to pull components out of solution based on their partitioning? I was envisioning having a nonpolar food item in water that would yank KLs out of solution, allowing for more KLs to partition into the solution and permit hydration. Casein or fruit maybe?

And the tween 80 is for water based preps, moreso than alcohol extracts.

 

[verticity]

@verticity Emulsifiers can help with breaking up cells or releasing things from cleaved cells, even in ethanol. At least they do with animal cells. I am planning on getting a cheapo water bath sonicator soon. That might be best for releasing components, but worsen the filtration process. I'm trying to keep this low cost and easy for other to copy.

I hadn't checked the partition coefficients (or other polarity indices) of FKs vs. KLs. You may be right about the supernatant having less FKs, but there was also a nonpolar film on top that was very thin. Perhaps the FKs partitioned out in that way, due to lower density? I'm just rambling late at night now.

These experiments were kind of spur of the moment. I did get an offer to pay for half the lab equipment I ordered to study it, but I only ordered a vacuum dessicator. I need that for some unrelated experiments anyway.

So what do you think about polarity sponges to pull components out of solution based on their partitioning? I was envisioning having a nonpolar food item in water that would yank KLs out of solution, allowing for more KLs to partition into the solution and permit hydration. Casein or fruit maybe?

And the tween 80 is for water based preps, moreso than alcohol extracts.

Interesting. I did not know emulsifiers would do anything in ethanol. I think casein is basically an emulsifier? so if you are talking about using it in water in a conventional prep it might help...in alcohol it might just be denatured because it is a protein, but maybe could still act as an emulsifier in the denatured state, so I don't know. I guess in general I have seen things like standard HPLC methods, which use either sonication or reflux in methanol and claim to be highly efficient at extracting practically all the KLs/FKs. Ethanol is probably similar, so I don't know how much an emulsifier could improve on that. But I guess if you don't have a sonicator and don't want to use heat, an emulsifier could be an alternative.

Anything you throw in to a water prep could actually act as an emulsifier if it is in the form of fine particles: it could form a Pickering emulsion. I suspect this might be happening with the fine root particles in kava beverage with nothing extra added.

 

[Krunkie McKrunkface]

I hate to say this but what we know of kava and cancer is that grog can prevent cancer and shrink tumors for some people. We don't know what it is in grog that has this effect, so we have no way of knowing what if anything could be extracted from grog to reproduce this effect. Also, AFAIK, this effect is noted mostly in Fijian kavas. It could be the effect is unrelated to kavalactones but comes from something else in the grog. Or, it could be that is only bio-available in grog and cannot be extracted or that the active ingredient involved requires other ingredients in the grog to be effective.

Also, we don't know how this effect works, whether it can be elicited by simply drinking some grog or if it requires drinking grog regularly over decades throughout one's life while living in a grog-drinking culture, i.e. eating that culture's foods and living that culture's lifestyles.

I sure wish there was more medical research on this subject.

 

[sɥɐʞɐs]

That's some interesting guinea pigging. It's like hearing preliminary reports that aids patients have significantly lower cancer growth rates and then hopping a plane to west hollywood and raw doggin' some booty holes in hopes of catching that sweet cure.

It reminds me of those people who try to take their cancer treatment into their own hands, cuz they heard about some herbal cure from mexico and they end up dying of organ failure from the herb.

I'm sorry, I'm probably sounding negative, I do hope that someday constituents within the kava plant are definitely proven to be safe and effective cancer treatment, but it seems pretty sketchy to be whipping up some residential kitchen extract of FK-B and blindly administering it to a patient who's body is already weakened by chemotherapy. I admire the sentiment though, taking matters in your own hands in attempt to save someone's life. I'll just be hoping it doesn't accomplish the opposite. Best of luck to ya.

If you master the art of DHM extraction, let me know, I wouldn't mind a salt shaker full of it...to sprinkle on all these weak kavas out there.

 

[kastom_lif]

If you master the art of DHM extraction, let me know, I wouldn't mind a salt shaker full of it...to sprinkle on all these weak kavas out there.

Totally. Sign me up for more yangonin, too.

 

[Palmetto]

@verticity if the partitioning of some compound has more affinity to a moiety on the surfactant than it does for solvent, then the surfactant can help in any solvent. But you are right in thinking that due to the diminished polarity of ethanol that surfactants have less efficacy in general than in aqueous solutions. I've even toyed with the idea of poloxamers to make use of the temperature dependency of partitioning and detergency. Many years ago, I worked with several poloxamers and membranes to develop drug delivery vehicles. Many years ago. My chemistry is a bit rustier now.

 

[Palmetto]

@Krunkie McKrunkface multiple studies have pointed to the direct antitumor effects of several isolated kava components: DHM, DHK, yangonin, methysticin, FKA, FKB, FKC. There are probably some unknown components as well. But those compounds are already proven to have some positive effect in cells and mice.

Also I believe I read in an article that Tongan cancer rates are lower than Fijian cancer rates. That might suggest that Tongan kava is more effective, or that Tongans just drink more than Fijians (or more effectively), which is not what I read. So that leads me to believe that Tongan kava is better than Fijian for antitumor properties.

 

[verticity]

I hate to say this but what we know of kava and cancer is that grog can prevent cancer and shrink tumors for some people. We don't know what it is in grog that has this effect, so we have no way of knowing what if anything could be extracted from grog to reproduce this effect. Also, AFAIK, this effect is noted mostly in Fijian kavas. It could be the effect is unrelated to kavalactones but comes from something else in the grog. Or, it could be that is only bio-available in grog and cannot be extracted or that the active ingredient involved requires other ingredients in the grog to be effective.

Also, we don't know how this effect works, whether it can be elicited by simply drinking some grog or if it requires drinking grog regularly over decades throughout one's life while living in a grog-drinking culture, i.e. eating that culture's foods and living that culture's lifestyles.

I sure wish there was more medical research on this subject.

That's some interesting guinea pigging. It's like hearing preliminary reports that aids patients have significantly lower cancer growth rates and then hopping a plane to west hollywood and raw doggin' some booty holes in hopes of catching that sweet cure.

It reminds me of those people who try to take their cancer treatment into their own hands, cuz they heard about some herbal cure from mexico and they end up dying of organ failure from the herb.

I'm sorry I'm probably sounding negative, I do hope that someday constituents within the kava plant are definitely proven to be safe and effective cancer treatment, but it seems pretty sketchy to be whipping up some residential kitchen extract of FK-B and blindly administering it to a patient who's body is already weakened by chemotherapy. I admire the sentiment though, taking matters in your own hands in attempt to save someone's life. I'll just be hoping it doesn't accomplish the opposite. Best of luck to ya.

If you master the art of DHM extraction, let me know, I wouldn't mind a salt shaker full of it...to sprinkle on all these weak kavas out there.

You are both right that this is very far from a proven treatment.

The type of extract suggested in this post has potential risks and potential benefits.

On the risk side:

- There is a risk of side effects such as nausea, as well of a risk of interactions with other medications/chemotherapy agents the patient might be taking. It sounds like this has already happened in this case, so I would hope this person is being open with their doctor about what they are trying.

- Since FKB is known to be toxic in vitro (but not proven to be harmful to people in traditional kava), there is some risk associated with intentionally consuming a high-FKB extract. Exactly how high this risk might be is unknown.

On the potential benefit side

- Epidemiological studies, studies with mice (unclear if the mice adopted an island lifestyle), and in vitro studies suggest the possiblity of some benefit (but no evidence for a full cure). There is specific in vitro [EDIT: in mice] evidence for FKB and especially DHM. So I would have to say the potential benefits are a long shot but non-zero.

In our society, we have generally concluded that patients with diseases such as incurable cancer should be allowed very wide leeway to try experimental treatments that in normal circumstances are considered too experimental or too risky. People in that situation can make that risk-benefit calculation for themselves. In this case it seems like the potential benefits are not very likely, and the potential risks are real but are less certain than the risks from intentionally contracting AIDS... which isn't saying much, I know..

 

[Krunkie McKrunkface]

You are both right that this is very far from a proven treatment.

The type of extract suggested in this post has potential risks and potential benefits.

On the risk side:

- There is a risk of side effects such as nausea, as well of a risk of interactions with other medications/chemotherapy agents the patient might be taking. It sounds like this has already happened in this case, so I would hope this person is being open with their doctor about what they are trying.

- Since FKB is known to be toxic in vitro (but not proven to be harmful to people in traditional kava), there is some risk associated with intentionally consuming a high-FKB extract. Exactly how high this risk might be is unknown.

On the potential benefit side

- Epidemiological studies, studies with mice (unclear if the mice adopted an island lifestyle), and in vitro studies suggest the possiblity of some benefit (but no evidence for a full cure). There is specific in vitro evidence for FKB and especially DHM. So I would have to say the potential benefits are a long shot but non-zero.

In our society, we have generally concluded that patients with diseases such as incurable cancer should be allowed very wide leeway to try experimental treatments that in normal circumstances are considered too experimental or too risky. People in that situation can make that risk-benefit calculation for themselves. In this case it seems like the potential benefits are not very likely, and the potential risks are real but are less certain than the risks from intentionally contracting AIDS... which isn't saying much, I know..

Only thing I really know is we don't really know. We see Polynesians with lower cancer rates, they move to Australia and stop drinking kava and their cancer rates rapidly go up to normal cancer rates and their low cancer rates are gone (and we don't kow if they get those low cancer rates back if they return home). We also know that in looking at populations where the men enjoy low cancer rates and the women do not the only major difference we find is the men drink kava and for women it's taboo. (kind of a shame, that). There may be indications that kava drinkers have lower lung cancer rates than other populations even when they smoke, so there might be some protective factor going on there. Maybe.

So it looks very likely that some kavas can effect lower cancer rates in the population (in the aggregate, we don't know how this might work with individuals) within the cultures in which it is traditionally consumed. We don't really know what we can extrapolate from that. If anything cried out for "further research" this seems a prime candidate to me.

The real problem with this is that the major data element here concerns prostate cancer and in our society we simply don't give a shit if men die of prostate cancer, especially if they are old. Truth be told our society is more in favour of old men dying of prostate cancer than against it so don't hold your breath on this one. Nothing's going to happen for a long time, and you can take that to the bank. Would t'were otherwise, but our world is as we made it.

 

[Intrepidus_dux]

Where is everyone pulling these studies from? Pubmed or somewhere else?

 

[kasa_balavu]

or somewhere else?

... and does the sun shine there?

I kid i kid..

 

[Intrepidus_dux]

... and does the sun shine there?

Yas! Are there rainbows and such?

 

[verticity]

Where is everyone pulling these studies from? Pubmed or somewhere else?

There is an in depth discussion of this stuff with a bunch of references in this thread:
http://kavaforums.com/forum/threads...-cancer-incidence-and-kava-consumption.12740/