Chemists figure out how to synthesize compounds from resveratrol

Jun 23, 2011 by Bob Yirka report
Skeletal formula of trans-resveratrol. Image: Wikipedia

(PhysOrg.com) -- Researchers working at Columbia University in New York have succeeded in synthesizing several compounds from the stilbenoid, resveratrol, a chemical commonly found in the skin of grapes that has been shown to have a wide variety of medicinal benefits.

The team, led by Scott Snyder, devised a technique to get around the problem of individual plants making such minute quantities of the that it has been virtually impossible until now to isolate and then put them to good use; they built that are similar to the normally produced by grapes, but different enough to allow the syntheses of differing chemicals contained within them.

The of resveratrol are wide and varied; some have suggested that it’s responsible for the relatively low levels of coronary disease in France, due to the resveratrol in red wine that is consumed widely in the country, this despite the fact that the French diet is known for inclusion of lots of fatty foods. Also, a recent study by a University of Florida team of researchers found evidence that resveratrol might make getting older a less traumatic experience.

Thus, the search to find ways to extract the chemical from grapes, or other resveratrol producing plants, so as to put it in a pill that people could take, has been underway for several years. Until now though, the going has been extremely slow due to the stubborn insistence on making just enough of the stuff to ward of diseases such as fungus.

Now however, Snyder and his colleagues Andreas Gollner and Maria Chiriac, have figured out a way to use a reagent (a chemical or substance added to something to produce a specific reaction) called bromodiethylsulfide bromopentachloroantimonate to cause a resveratrol dimer (a chemical structure consisting of two sub-units) to accept additional monomers (a molecule that binds to other molecules to form a polymer) to in effect, grow more resveratrol from its basic unit, allowing for the production of virtually any amount of the precious .

Having in pill form would offer the benefits of drinking red wine to consumers without the drawbacks, such as the ill effects of alcohol and the breakdown of tooth enamel that occurs with all citric based drinks that lead to dental problems.

Explore further: Active, biodegradable packaging for oily products

More information: Regioselective reactions for programmable resveratrol oligomer synthesis, Nature 474, 461–466 (23 June 2011) doi:10.1038/nature10197

Abstract
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the ‘French paradox’—the observation that French people have a relatively low incidence of coronary heart disease, even though their diet is high in saturated fats—the oligomers of resveratrol have been largely ignored despite their high biological activity. Challenges in achieving their isolation in sufficient quantity from natural sources, coupled with an inability to prepare them easily synthetically, are seen as the main obstacles. Here we report a programmable, controlled and potentially scalable synthesis of the resveratrol family via a three-stage design. The synthetic approach requires strategy- and reagent-guided chemical functionalizations to differentiate two distinct cores possessing multiple sites with the same or similar reactivity, ultimately leading to five higher-order natural products. This work demonstrates that challenging, positionally selective functionalizations of complex materials are possible where biosynthetic studies have indicated otherwise, it provides materials and tools with which to unlock the full biochemical potential of this family of natural products, and it affords an intellectual framework within which other oligomeric families could potentially be accessed.

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User comments : 9

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CapitalismPrevails
2 / 5 (3) Jun 23, 2011
I thought resveratrol was already in condensed pill form.
El_Nose
not rated yet Jun 23, 2011
you are correct Capital it is in pill form -- but very expensive -- 400$ for a 30 day supply
Telekinetic
2.3 / 5 (3) Jun 23, 2011
It doesn't cost that much at all. Anyway, it turns out that pterostilbenes from blueberries may be more effective. Look at Life Extension's website. I wouldn't take a synthetic pill when a natural source is available.
Azpod
4 / 5 (1) Jun 24, 2011
You can get resveratrol much more cheaply in pill form, but nearly everything you find in your heath food store is derived from Japanese knotweed extract, which contains resveratrol but in amounts that vary greatly from batch to batch.
jamesinraro
not rated yet Jun 24, 2011
The resveratrol used in virtually all human clinical trials and the one that the NIH has certified as an IND is biotivia transmax. Their pteromax supplement is by an order of magnitude the most potent pterostilbene supplement. They are also consumer lab approved unlike most of the other brands. Life extension's resveratrol failed the first consumer lab trial with only 26% of the resveratrol it claimed to have. Best to do some research before buying these more costly supplements.
Telekinetic
1 / 5 (2) Jun 24, 2011
"Consumerlabs is a "for-profit" company, which are not legally required to be accurate. It is headed by a former FDA employee. I personally don't trust their findings, and never consider their logo on products to be a sign of quality, just like I don't consider an "FDA Approved" stamp on over the counter substances to be a sign of quality, in fact, the total opposite. So, I just buy LEF stuff - just trying to improve myself; to each his own."
The above was from a poster on another site regarding LEF's failed product. I agree that LEF's products are more expensive, so I buy selectively. I don't begrudge them the cost because their research is cutting edge and I support them by being a member and get discounts that way. I am not a shill for them, but they introduced compounds like co-enzyme Q10 to the mainstream, and have a phone service to speak to M.D.'s.
I also applaud their continuing battle with the corrupt toady to the pharmaceutical mafia, the FDA.
jamesinraro
not rated yet Jun 24, 2011
Consumer Lab may be for profit but even non-profit testing organisations must earn income to pay their expenses. In reality there is very little distinction between for profit and non profit. The point is that they do a good job on testing of products and are very transparent as to the test methods and even the independent labs they use to validate their testing. If a product fails their test there is a good reason why and Consumer Lab explains the reason for the deficiency.
Comparing Consumer Lab and FDA approved is a bit absurd. There is no association or relationship between the two and the analogy makes very little sense.
Telekinetic
1 / 5 (1) Jun 24, 2011
"However, in addition to getting money from the 'consumers', Consumer Labs also gets money from the supplement companies themselves. Companies voluntarily pay them thousands of dollars for favorable product analysis and reviews. Recommendations from Consumer Labs have expiry dates, so manufacturers must pay again every 12 months, if they wish to continue using the certified 'C.L. seal'."
http://healthwyze...abs.html
Justsayin
1 / 5 (1) Jun 28, 2011
It is in pill form at lef.org

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