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Pterostilbene and cyclodextrin study


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#1 malbecman

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Posted 26 May 2009 - 04:02 PM


for those of you interested in the whole solubility and relative stoichiometry issue.....

It also references two other papers a little more specific to resveratrol.

J Agric Food Chem. 2009 May 21.
Physicochemical Study of the Complexation of Pterostilbene by Natural and Modified Cyclodextrins.
López-Nicolás JM, Rodríguez-Bonilla P, Méndez-Cazorla L, García-Carmona F.
Department of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia, Campus de Espinardo, Murcia 30071, Spain.

In this paper, the interaction between pterostilbene and cyclodextrins (CDs) is described for the first time using steady-state fluorescence. It was seen that pterostilbene forms a 1:1 complex with all of the natural (alpha-, beta-, and gamma-CDs) and modified (HP-beta-CD, methyl-beta-CD, and ethyl-beta-CD) CDs tested. Among natural CDs, the interaction of pterostilbene with beta-CD was the most efficient. However, all of the modified CDs showed higher complexation constants (K(F)) than beta-CD. The highest K(F) was found for HP-beta-CD (17520 +/- 981 M(-1)), in which its value showed a strong dependence upon pH in the region where the pterostilbene begins the deprotonation of its hydroxyl group. Moreover, the values of K(F) decreased as the system temperature increased. To obtain information on the mechanism of pterostilbene affinity for CD, the thermodynamic parameters of the complexation (DeltaH degrees , DeltaS degrees , and DeltaG degrees ) were studied. Finally, a comparison of the K(F) values obtained for three types of stilbenes revealed that both the stoichiometry and the K(F) values of the complex are dependent upon the structure of the guest molecule. While the trans-resveratrol-HP-beta-CD and pterostilbene-HP-beta-CD complexes showed a 1:1 stoichiometry with a higher K(F) value for the trans-resveratrol-HP-beta-CD complexes, trans-stilbene showed a 1:2 stoichiometry.

PMID: 19459636

#2 Anthony_Loera

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Posted 26 May 2009 - 04:50 PM

Hi malbecman,

thanks for that. The problem is that beta-cyclodextrine is limited by the FDA to a very small amount, and can't really be used in the amounts needed to provide a supplement. I have a sample made for us using resveratrol and beta-cyclodextrin that dissolves into water in a completely clear fashion.

Problem is, I can't sell it to anyone or provide it as a supplement, as we would need much more than 2% per the current GRAS notice.
Here, have a look: http://www.cfsan.fda...b/opa-g074.html

Now if you are talking about developing a drug... well that is certainly possible.

A

Edited by Anthony_Loera, 26 May 2009 - 04:54 PM.


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#3 malbecman

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Posted 26 May 2009 - 11:55 PM

Well, they do also state on that web site that the "acceptable daily intake (ADI) of 0-5 mg/kg body weight/day for beta-cyclodextrin, equivalent to 300 mg per person per day (mg/p/day) for a 60 kg person". So one could, on their own, theoretically, that is, mix 300mgs of t-resveratrol and 300 mgs of beta-cyclodextrin in a 1:1 stoichoimetry and probably make a nice soluble mixture. In theory, of course.....



Hi malbecman,

thanks for that. The problem is that beta-cyclodextrine is limited by the FDA to a very small amount, and can't really be used in the amounts needed to provide a supplement. I have a sample made for us using resveratrol and beta-cyclodextrin that dissolves into water in a completely clear fashion.

Problem is, I can't sell it to anyone or provide it as a supplement, as we would need much more than 2% per the current GRAS notice.
Here, have a look: http://www.cfsan.fda...b/opa-g074.html

Now if you are talking about developing a drug... well that is certainly possible.

A



#4 Anthony_Loera

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Posted 27 May 2009 - 03:47 PM

In theory, but in practice you can only produce a 10% - 14% which provides beta-cyclodextrin way over what is necessary.

A

Edited by Anthony_Loera, 27 May 2009 - 03:48 PM.


#5 motorcitykid

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Posted 08 April 2016 - 03:53 PM

Cyclodextrin in the news:

http://arstechnica.c...und-by-parents/



#6 maxwatt

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Posted 29 April 2016 - 06:44 PM

http://stm.sciencema...t/8/333/333ra50

 

The paper is at the link above, albeit behind a paywall.

 

Seem in mice fed high-cholesterol diets, cyclodextrin cleared away plaques and helped prevent more plaques from forming, .... The chemical also activated cholesterol metabolism that boosted clearance of the waxy substance from arteries, plus dampened inflammation responses that spur atherosclerosis.

 

Not clear from the abstract whether it was administered by injection, or as part of the diet.



#7 david ellis

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Posted 29 April 2016 - 07:06 PM

http://stm.sciencema...t/8/333/333ra50

 

The paper is at the link above, albeit behind a paywall.

 

Seem in mice fed high-cholesterol diets, cyclodextrin cleared away plaques and helped prevent more plaques from forming, .... The chemical also activated cholesterol metabolism that boosted clearance of the waxy substance from arteries, plus dampened inflammation responses that spur atherosclerosis.

 

Not clear from the abstract whether it was administered by injection, or as part of the diet.

 

https://www.scienced...60419083902.htm

 

 


Edited by david ellis, 29 April 2016 - 07:24 PM.


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#8 hav

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Posted 05 May 2017 - 07:30 PM

FWIW, I've been having good success with cyclodextrin for about a year and a half now. Studies suggest it increases the bioavailability of fat soluble nutrients by as much as about 4x or 5x. Which is consistent with what I observe experimenting with dosages of things I can perceive like CBD for pain relief. I grind it 1:1 for about 5 minutes. Probably not as good as mincronizing them together but it does seem to work.  With Resveratrol, however, it takes up half the space in the capsule, so probably reduces the maximum increase in potency to 2x per capsule. I think it works better with things like Cycloastrenol normally administered at smaller dosages ranging from 10mg to 40mg, displacing fillers rather than the active ingredient.

 

Here's an interesting analysis comparing different complexing methods with silymarin: https://www.ncbi.nlm...pubmed/21897659

 

And here's another one for tadalafil: http://www.sciencedi...939641108002269

 

Only down side I see is that it might also increase the bioavalability of fat soluble heavy metals and other toxins. So you might want to go with the purest suppliers.

 

Howard


Edited by hav, 05 May 2017 - 07:31 PM.

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