Trans Resveratrol Half-Life

So Trans-Resveratrol degrades over time to Cis-Resveratrol in the presence of: UV Light, O2, and heat.

So, does anyone know the half-life of the trans form of resveratrol in normal atmosphere at room temperature when protected from UV light? I can't find anything on it via google...

This will have a bearing on how important inert heavy gas and refrigeration is in the storage and packaging of t-Resv. I am also wondering how long my 300g of Product will last...

IIRC, earlier proprietary study results, and some peer reviewed testing results, indicated very long 1/2 life and very slow degradation of trans-resveratrol kept in refrigerator or freezer (like over 2 years without significant degradation...)

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Trans-res is quite stable actually.

Journal of Medicinal Food
Resveratrol and Its Glycon Piceid Are Stable Polyphenols

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To cite this paper:
Jiri Prokop, Petr Abrman, Allen L. Seligson, Milos Sovak. Journal of Medicinal Food. 2006, 9(1): 11-14. doi:10.1089/jmf.2006.9.11.

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Jiri Prokop
1Interpharma Praha, a.s., Prague, Czech Republic.
Petr Abrman
1Interpharma Praha, a.s., Prague, Czech Republic.
Allen L. Seligson
Biophysica Research, San Diego, La Jolla, California.
Milos Sovak
Biophysica Research and University of California, San Diego, La Jolla, California.
Plant extracts containing phytopolyphenols, including resveratrol, are extensively used as nutraceutical supplements. Recent reports allege their lack of stability at ambient conditions. We have studied the stability of resveratrol and its glycon piceid in a mixture with a whole grape extract for 2 years (long-term stability) under Good Manufacturing Practice pharmaceutical protocols (at 60% humidity and 25?C). The neat compounds were followed for 4 years under conditions of "accelerated stability," at 75% humidity and 40?C, all in the presence of ambient air. Chromatographic analysis did not detect any instability, thus disproving the claims to the opposite. No storage precautions are necessary for these nutritional supplements.






Stability of resveratrol over time and in the various stages of grape transformation.Bertelli AA, Gozzini A, Stradi R, Stella S, Bertelli A.
Institute of Human Anatomy, University of Milan, Italy.

Research has been carried out with the purpose of verifying whether the resveratrol content in the skins or pomace of grapes stored for a long period of time without any particular protection with regard to temperature and humidity, could lead to a reduction of the content of this product detected at the beginning of the processing of grapes in vinification procedures. The dosages carried out both on the grape skin and on the pomace taken after fermentation and stored for a certain period of time, as well as on the products derived from alcoholic distillation, did not show the expected alterations in resveratrol content, considering their storage in bad environmental conditions for a long period of time. The results obtained confirm that resveratrol, unlike anthocyanins and other polyphenols, is stable and stores well over time.

Nice. Thanks dannov. The papers don't specifically mention that trans-resveratrol is stable. Perhaps they were testing for degrading of resveratrol into other organic compounds and not the degrading of trans form into cis form, so I am unclear on that point. It is certainly encouraging though, David Sinclair certain makes the trans form out to be much more fragile.

This is true. For what it's worth, I keep my kilo in the basement (they're in 10 separate bags so only one is opened). All the bags are stored in a box so no light gets to it, and it's fairly cool down there.

Trans-resveratrol does not convert to cis-resveratrol, except under ultraviolet light, or where the pH is around 11. Acid solutions tend to convert cis-resveratrol to trans resveratrol, and visible light does the same. This is from the Brent Trela paper that has been cited in these forums several times.

(fixed typo)

Edited by maxwatt, 14 September 2007 - 01:40 AM.

Thanks a bunch, Sinclair certainly makes it sound more fragile, as does the wiki page (I might go and edit it).

dannov, thanks for the Prokop paper. That is quite good to see. Some of the early claims regarding resveratrol instability may have come from solution studies. Compounds in solution are almost always less stable than the solid form, frequently a lot less. I read a study somewhere (sorry for the lack of ref) looking at resveratrol in solution (EtOH, I believe) and even there it was pretty stable at 4 degrees C. This business of isomerizing to the cis form always seemed a little strange to me, as the trans form is more stable.

I think the idea (apparently mythological) of resveratrol instability has been advanced as a marketing tool by some. I suspect at the time they thought they were doing the right thing, or at least "being on the safe side". I wonder what they might say in light of the latest analytical results? Something tells me this will be a hard meme to kill.

No problem Niner, and I do agree with the marketing tool aspect.

Trans-resveratrol does not convert to cis-resveratrol, except under ultraviolet light, or where the pH is around 11.  Acid solutions tend to convert cis-resveratrol to trans resveratrol, and visible light does the same.  This is from the Brent Trela paper that has been cited in these forums several times.

(fixed typo)

I agree, recently we tested a sample (3 month old sample) that we had left in a closed bottle (without encapsulation, just the powder in an average bottle that we use at RevGenetics for our capsules). The sample was left in a room with a single window that allows ambient sunlight from the outside to enter the room at various times throughout the day. The window itself has UV sheeting to block UV light from entering. The room temperature remained at about 72 degrees, and sometimes spiked at 78 degrees on a very hot and sunny day, but generally remaind between 72 and 76 degrees.

It was really exciting to see the results of the test:

After 3 months in this spectacularly normal environment (except for the uv sheeting on the windows) our 50% powder we use for the R500 and R300 capsules still tested at 50% trans-resveratrol.



The test was using our current lab, AACL of Illinois.

thanks
Anthony Loera

Very nice Anthony, further evidence.

Wonderful to have this cleared up. I'll go ahead and edit the wiki page.

You know, I was looking through the Longevinex site, and found this blurb:

Three different production lots of Longevinex® capsules maintained high amounts of trans resveratrols (93-98% of labeled dosage) over a 2-year shelf life period (+- 4-5% for variance in raw materials). On average, there was only 4% undesirable conversion to cis resveratrol in Longevinex® capsules versus 26% in 5 competing brands of resveratrol supplements. Trans resveratrol, considered the more biologically active molecule, is the form of resveratrol known to activate the Sirtuin 1 DNA-repair gene.

now that I have my marketing antenna up, I read it and realized that Longevinex states that many competitor products change 26% (from Cis to Res) in their 2 year study, otherwise they would have mentioned that competitors changed within months as it would have been a much better for their marketing.

2 years!

That is very slow, and that is from the Longevinex website. It goes to show that the half-life of trans-resveratrol sitting on your shelf is quite long according to Longevinex.

Can someone explain the significance or lack of taking trans-piceid aka "Trans Resveratrol Glucoside)? This company imports/manufactures the 98% Trans Resveratrol and its Glucoside "Resveratrol-Glycon HP" which they claim is more water soluble than plain Trans Res. http://www.resveratr....com/index.html

They sell it through: http://www.nutriguar...3&products_id=2

200mg/60 caps for $25.95

How useful is this for health benefits of Trans Res? Is there anyone who sells a 98% pure Trans Resveratrol in a smaller dose than 500mg? I'd like to start off with a smaller dosage and then work up.

I've just done some research and seems to confirm what the above company has stated: "Resveratrol in its natural form is predominantly found coupled to a sugar (i.e., "glycon"), which makes the poorly soluble parent compound, trans-resveratrol, more water soluble. Also, the glycon is highly orally bioavailable and its stability is much greater compared to resveratrol without the sugar moiety (see reference Prokop et al.)."

ALL NATURAL SOURCES OF TRANS-RESVERATROL contain TRANS-PICEID as the active form of Trans-Res. So wouldn't it make sense to ingest it in that form?

I've just done some research and seems to confirm what the above company has stated: "Resveratrol in its natural form is predominantly found coupled to a sugar (i.e., "glycon"), which makes the poorly soluble parent compound, trans-resveratrol, more water soluble. Also, the glycon is highly orally bioavailable and its stability is much greater compared to resveratrol without the sugar moiety (see reference Prokop et al.)."

ALL NATURAL SOURCES OF TRANS-RESVERATROL contain TRANS-PICEID as the active form of Trans-Res. So wouldn't it make sense to ingest it in that form?

The information is not correct, trans-resveratrol occurs naturally in a number of sources. Furthermore the research has been done with the trans-resveratrol form; SirT1 activation is not known to occur from the piceid, and probably does not occur.

Maxwatt, please explain why in the following chart, only trans-piceid is specified to be found occuring naturally in the listed foods and plants, and not its aglycone trans-resveratrol. http://www.nature.co...nrd2060_T1.html

I believe most studies so far did not use trans-piceid to achieve positive results.

If folks want to take trans-piceid instead of trans-resveratrol, then that is up to them, but you have to ask yourself what studies have used trans-piceid and which have used trans-resveratrol.

Just weigh the facts, and see which is more suitable for you.



A

We need to clear this up because the above table was taken from:

TABLE 1 | Dietary sources of resveratrol
From the following article:

Therapeutic potential of resveratrol: the in vivo evidence

Joseph A. Baur & David A. Sinclair

Nature Reviews Drug Discovery 5, 493-506 (June 2006)

Isn't Sinclair the pioneer behind the resveratrol studies? Trans-pIceid is in fact Trans-Resveratrol only with a Glucoside attached. It may be in fact more bioavailable than its aglycon form.

Thats great, I have that study as well.

there is this neat little graphic that has the trans-resveratrol structures along with 5 others:

Here they are:

Trans-resveratrol
cis-resveratrol
Resveratrol-3-0-B-D-glucoside (this one is the piceid one I believe)
Resveratrol-3-sulphate
Resveratrol-3-0-glucuronide
Dihydroresveratrol

(I might have fat-fingered something, so excuse me...)

Now, do all these activate the SIRT1 gene?

Quick answer... No.


A

Maxwatt, please explain why in the following chart, only trans-piceid is specified to be found occuring naturally in the listed foods and plants, and not its aglycone trans-resveratrol. http://www.nature.co...nrd2060_T1.html

That’s not my interpretation of this chart. It shows the concentration of trans-resveratrol (second column from left), and in the comments it shows compounds present in addition to trans-resveratrol.

Source.......................trans-Resveratrol concentration..................comments


Red wines..................0.1–14.3 mg l-1..........................................cis-Resveratrol, trans-piceid and cis-piceid also present, typically at slightly lower concentrations.

Longevinex is citing a study from Journal of Pharmaceutics (August 2007) that claims that resveratrol rapidly "degrades" under lab temperature and lighting conditions. I don't know what they mean by "degrades" but here is the study. Costs $30 to see the full text.

Abstract
The photosensitive resveratrol was successfully encapsulated in yeast cells for the first time, as characterized by FT-IR spectra, fluorescence and confocal micrographs of the yeast cells, resveratrol and microcapsules. The release characteristic of the obtained yeast-encapsulated resveratrol in simulated gastric fluid was evaluated, and its storage stability as a powder was investigated at 25 °C/75% relative humidity (RH), 25 °C/90% RH and 60 °C under the laboratory fluorescent lighting conditions (ca. 300 lx) or in the dark. Also, the scavenging capacity of yeast-encapsulated resveratrol on DPPH radical was compared with that of non-encapsulated resveratrol. It could be demonstrated clearly that no chemical changes occurred during the encapsulation. Besides, the DPPH radical-scavenging activity increased after the encapsulation. In addition, the yeast-encapsulated resveratrol exhibited good stability, and its bioavailability was enhanced as a result of increased solubility of resveratrol and sustained releasing.

http://www.sciencedi...0ce941ac8d49f16

Here is a chart that Sardi took from the study (I assume). It's at the bottom of this link. I can't copy it.
http://www.longevinex.com/

I don't trust Sardi but I'm willing to hear all sides.

Longevinex is citing a study from Journal of Pharmaceutics (August 2007) that claims that resveratrol rapidly "degrades" under lab temperature and lighting conditions. I don't know what they mean by "degrades" but here is the study. Costs $30 to see the full text.

Abstract
The photosensitive resveratrol was successfully encapsulated in yeast cells for the first time, as characterized by FT-IR spectra, fluorescence and confocal micrographs of the yeast cells, resveratrol and microcapsules. The release characteristic of the obtained yeast-encapsulated resveratrol in simulated gastric fluid was evaluated, and its storage stability as a powder was investigated at 25 °C/75% relative humidity (RH), 25 °C/90% RH and 60 °C under the laboratory fluorescent lighting conditions (ca. 300 lx) or in the dark. Also, the scavenging capacity of yeast-encapsulated resveratrol on DPPH radical was compared with that of non-encapsulated resveratrol. It could be demonstrated clearly that no chemical changes occurred during the encapsulation. Besides, the DPPH radical-scavenging activity increased after the encapsulation. In addition, the yeast-encapsulated resveratrol exhibited good stability, and its bioavailability was enhanced as a result of increased solubility of resveratrol and sustained releasing.

http://www.sciencedi...0ce941ac8d49f16

Here is a chart that Sardi took from the study (I assume). It's at the bottom of this link. I can't copy it.
http://www.longevinex.com/

I don't trust Sardi but I'm willing to hear all sides.

The claims are dubious. We know that resveratrol is stable unless it is in solution. with high pH, and only converts to Cis-resveratrol under ultraviolet light*; anything Sardi says is, in my experience, more self-serving than accrate.

* Drugs Exp Clin Res. 1998;24(4):207-11.Links
Stability of resveratrol over time and in the various stages of grape transformation.Bertelli AA, Gozzini A, Stradi R, Stella S, Bertelli A.
PMID: 10051967

J. Agric. Food Chem. 1996, 44, 1253-1257
Resveratrol: Isomeric Molar Absorptivities and Stability
Brent C. Trela and Andrew L. Waterhouse

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under lab temperature and lighting conditions.

The lighting conditions can do it.
I believe that If you don't have the right lighting in your cGMP facility, you maybe allowing t-res to 'degrade' as many fluorescent lights can radiate enough UV to make a difference. If you have windows in your facility, and allow unfiltered sunlight in... you are also asking for trouble.

Of course, we don't have these issues.
[thumb]

Remember a cGMP facility certifies the facility, not the end products. GMP regulations address issues including recordkeeping, personnel qualifications, sanitation, cleanliness, equipment verification, process validation, and complaint handling... issues regarding improper lighting for a particular supplement are not addressed, as long a facility has some paper verification that a safe and verified supplement entered the facility, it meets cGMP guidelines.

Most 3rd party cGMP facilities that do private labeling will not change lighting conditions, even if you ask them to.

A

Edited by Anthony_Loera, 06 November 2007 - 03:46 PM.