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

Abstract

BackgroundRecent 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.ResultsTrans-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.ConclusionsDihydro-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.

Anti‑proliferative and anti‑metastasis effects of ten oligostilbenes from the seeds of Paeonia suffruticosa on human cancer cells

“…Approximately 80% of trans-resveratrol was converted to cis-resveratrol upon UV light exposure for 1 h (32), and ~86% of trans-gnetin H was converted to cis-gnetin H upon UV light exposure for 6 h (18). It is well known that cis-and trans-isomers of naturally occurring compounds can differ in their bioactivities, and that trans-isomers are believed to be the more abundant and active form (33)(34)(35). In the present study, the three cis-isomers of oligostilbenes, in which the double bond is reduced, were significantly less effective than their trans-isomers.…”

Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

“…Besides a number of biological activities of resveratrol and its derivatives beneficial to health (12)(13)(14), recent evidence has also demonstrated an important role of resveratrol in the activation of SIRT1, a protein that has been shown to lengthen the life spans of yeast, worms, flies, fish, and mice (31,66,67). Upregulation of SIRT1 has also been shown to reduce cellular oxidative stress in the diabetic milieu (68).…”

“…Other postmodified resveratrol derivatives with potent biological activities, such as antioxidant, cardioprotective, neuroprotective, anticancer, antiestrogenic, and antiaging properties, have also been identified in different plant sources, including pterostilbene, trans-polydatin (trans-piceid), piceatannol (synonym astringinin), and astringin ( Fig. 1) (12)(13)(14).…”

Proanthocyanidin: Chemistry and Biology: From Phenolic Compounds to Proanthocyanidins

“…It contains five (R) groups, 3(OH) and 2(H). 63 The isomers of RESV could be prepared from t-RESV; cis-RESV could be obtained from t-RESV by photoisomerization; and the dihydro-RESV could be synthesized from t-RESV by catalytic hydrogenation. 63 The isomers of RESV could be prepared from t-RESV; cis-RESV could be obtained from t-RESV by photoisomerization; and the dihydro-RESV could be synthesized from t-RESV by catalytic hydrogenation.…”