Resveratrol and trans-resveratrol: What is the difference?
You have probably heard that a molecule found in grapes and red wine called resveratrol can promote
health and longevity. You may have even tried to purchase resveratrol in order to start enjoying the
health benefits of this compound. In your research you may have come across the term “trans-
resveratrol.” Is trans-resveratrol different from resveratrol? Do they do the same thing? Which one is
going to help me?
Put on your lab coat
In order to understand the difference between trans-resveratrol and resveratrol it is necessary to
understand a bit about chemistry—organic chemistry to be precise. Every molecule in existence can be
described in several ways and can be called different things. For example water is also known as H2O or
even dihydrogen monoxide. The alcohol that we consume can be called ethanol, ethyl alcohol, C2H6O
and so on. As you might imagine, as molecules get larger, the names tend to get longer. Therefore
scientists devised a way to name every molecule, discovered or undiscovered, based on the chemical
structure. This universally accepted system is called the IUPAC (International Union of Pure and Apllied
Chemistry) naming system and the system is important when it comes to resveratrol.
What does this have to do with resveratrol?
One of the naming conventions of the IUPAC system is the “cis/trans” system. This naming system
describes a difference between molecules that have the same molecular formula, but the molecules are
shaped differently. When two important pieces of the molecule face each other, the molecule is said to
H3C H3C CH3 be “cis” and when they face away from each other, they are
CH3 “trans.” This naming convention is important for a molecule like
trans cis
resveratrol, also known as 3,4’,5-trihydroxystilbene, because it has
a couple of important pieces. When the important pieces of
resveratrol face each other, it is in its cis configuration and when they face apart, it is in its trans
configuration. HO OH OH
Both forms of
the molecule, cis
HO
and trans, occur
OH
naturally certain
foods that we HO
eat, like peanuts 3, 4’, 5-trihydroxy-trans-stilbene 3, 4’, 5-trihydroxy-cis-stilbene
and grapes. In
some wines, the concentration of the trans form of resveratrol is greater than the cis form. In other
wines, the opposite is true. Foods that contain resveratrol likely contain a blend of the two forms.
So which one is good for you, cis or trans?
Almost all of the studies that have examined the health benefits of resveratrol have studied the trans
form of the molecule. Likewise, most resveratrol supplements that are available for human consumption
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are of the trans variety, primarily because the trans form is easier to make. In fact, if the supplement
does not make a distinction between the cis and trans form of resveratrol, it is probably the trans form
(though if this point is important to you, you may want to check before purchasing). Unfortunately we
simply do not know if the cis form has the same health benefits as the trans. In the few studies that have
been done on the cis form, it seems to behave in a manner similar to the trans form. For example, in
laboratory studies the cis form of resveratrol was able to act as an anti-inflammatory.
Which form of resveratrol should I buy?
At this point it is not clear which form of resveratrol is better for your health or even if one form is
superior to the other. If you are considering taking resveratrol supplements, it is by far more important
to make sure you are actually getting high-quality resveratrol regardless of whether it is cis or trans. If
you are forced to choose, most scientists have used trans-resveratrol in their studies, so this would be
the form of choice.
References
Burns J, Gardner PT, O'Neil J, et al. (2000) Relationship among antioxidant activity, vasodilation capacity, and phenolic content
of red wines. J Agric Food Chem. 48(2) 220-30.
Leiro J, Alvarez E, Arranz JA, et al. Effects of cis-resveratrol on inflammatory murine macrophages: antioxidant activity and
down-regulation of inflammatory genes. J Leukoc Biol. (2004) 75(6) 1156-65.
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