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. 2011 Dec 20:5:88.
doi: 10.1186/1752-153X-5-88.

Trans-, cis-, and dihydro-resveratrol: a comparative study

Natalia Yu Anisimova  1 , Mikhail V Kiselevsky, Andrey V Sosnov, Sergey V Sadovnikov, Ivan N Stankov, Andrei A Gakh
Affiliations

Trans-, cis-, and dihydro-resveratrol: a comparative study

Natalia Yu Anisimova et al. Chem Cent J. .

Abstract

Background: Recent studies showed that moderate consumption of red or white wines increased the chances of breast cancer, while similar consumption of red wines, rich in trans-resveratrol (trans-R), decreased the rate of prostate cancer. This prompted us to explore the role of various forms of R in cancer proliferation.

Results: Trans-R was found to be the most potent antiproliferative agent. Cis-R demonstrated somewhat less potency compared to trans-R. Unlike cis-R and trans-R, dihydro-R exhibits moderate proliferative effect on androgen-independent prostate cancer cell lines PC-3 and DU-145 at picomolar concentrations. At higher concentrations, dihydro-R caused proliferation inhibition, similar to cis-R and trans-R. The proliferative effect of dihydro-R at low concentrations can be reversed by trans-R which acts as a partial antagonist in the presence of dihydro-R. Mixtures of dihydro-R and trans-R demonstrated complex non-monotonic cross-modulation activity patterns.

Conclusions: Dihydro-R exhibits proliferative effects in androgen-independent prostate cancer cells at picomolar and nanomolar concentrations. While the exact mechanism of these effects requires further evaluation, our preliminary results point to hormone receptor modulation activity. We also observed strong cross modulation between trans-R and dihydro-R at sub-picomolar concentrations. The role of dihydro-R in cancer proliferation related to moderate consumption of red wine remains an open question because dihydro-R has a very complex activity pattern in the presence of trans-R.

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Figures

Figure 1
Figure 1
Structures of trans-resveratrol (trans-R), cis-resveratrol (cis-R), and dihydro-resveratrol (dihydro-R) isomers.
Figure 2
Figure 2
Biological activity of dihydro-R, trans-R and cis-R in the PC-3 cell line.
Figure 3
Figure 3
Biological activity of dihydro-R and trans-R in the DU-145 cell line.
Figure 4
Figure 4
Biological activity of dihydro-R in PC-3, DU-145, and MCF-7 cell lines.
Figure 5
Figure 5
Structures of genistein and E2.
Figure 6
Figure 6
Biological activity of dihydro-R and trans-R mixtures (1/1; 10/1; 1/10) in PC-3 cells.
Figure 7
Figure 7
Biological activity of trans-R and dihydro-R mixtures (1/1; 1/10; 10/1) in MCF-7 cells line.
See this image and copyright information in PMC

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