Dihydro-resveratrol—A potent dietary polyphenol

Gakh, Andrei A.; Anisimova, Natalia; Kiselevsky, M. V.; Садовников, С. В.; Stankov, Ivan N.; Yudin, M. V.; Rufanov, Konstantin A.; Krasavin, Mikhail; Соснов, А. В.

doi:10.1016/j.bmcl.2010.08.002

Cited by 25 publications

(31 citation statements)

References 23 publications

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“…The effect was not observed in cell lines without estrogen receptors, and the proliferative effect could be reversed by the action of estrogen antagonists, such as the known breast cancer drug Tamoxifen. This is consistent with the assumption that dihydro - R is a potent phytoestrogen, even though the conformationally flexible chemical structure of dihydro - R makes it a very unlikely analog of 17β-estradiol and other synthetic nonsteroidal estrogens such as diethylstilbestrol (DES) [6]. …”

Section: Introductionsupporting

confidence: 82%

“…Trans - R is a known inhibitor of human prostate cancer cell growth at concentrations of 1 × 10 -6 to 1 × 10 -4 M (e.g., GI(50) = 2.41 × 10 -5 M, DU-145 [8]) depending on the prostate cancer cell line and experimental conditions [9]. The biphasic action of the third form of R , dihydro - R , in comparison with the better studied trans - R requires further evaluation, especially in relation to estrogen receptors [6] present in both the PC-3 and the DU-145 prostate cancer cell lines [10-14]. …”

Section: Resultsmentioning

confidence: 99%

“…In our experiments dihydro - R demonstrated strong proliferative properties in hormone-dependent cell lines (such as MCF-7) at picomolar (10 -12 M) concentrations [6]. The effect was not observed in cell lines without estrogen receptors, and the proliferative effect could be reversed by the action of estrogen antagonists, such as the known breast cancer drug Tamoxifen.…”

Section: Introductionmentioning

confidence: 91%

“…The predominant trans - R comes along with a lesser-known companion, cis -resveratrol ( cis - R ), and they are almost always present in red wine together (Figure 1). We recently discovered [6] that the GC-MS peak of cis - R was usually accompanied by a close peak of another polyphenol having molecular weight 2 Da higher than cis - R . Independent synthesis confirmed that this peak is the peak of the third form of R , dihydro -resveratrol ( dihydro - R ).…”

Section: Introductionmentioning

confidence: 99%

“…Independent synthesis confirmed that this peak is the peak of the third form of R , dihydro -resveratrol ( dihydro - R ). Dihydro - R is a well-known metabolite of trans - R [7], but it had not been identified in red wines before the study [6]. …”

Section: Introductionmentioning

confidence: 99%

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

Anisimova

Kiselevsky

Соснов

et al. 2011

Chemistry Central Journal

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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.

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Section: Introductionsupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Anisimova

Kiselevsky

Соснов

et al. 2011

Chemistry Central Journal

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Influence of Glucuronidation and Reduction Modifications of Resveratrol on its Biological Activities

Ding

Yan

et al. 2013

ChemBioChem

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Resveratrol (3,5,4'-trihydroxystilbene, RES), a star among dietary polyphenols, shows a wide range of biological activities, but it is rapidly and extensively metabolized into its glucuronide and sulfate conjugates as well as to the corresponding reduced products. This begs the question of whether the metabolites of RES contribute to its in vivo biological activity. To explore this possibility, we synthesized its glucuronidation (3-GR and 4'-GR) and reduction (DHR) metabolites, and evaluated the effect of these structure modifications on biological activities, including binding ability with human serum albumin (HSA), antioxidant activity in homogeneous solutions and heterogeneous media, anti-inflammatory activity, and cytotoxicity against various cancer cell lines. We found that 1) 4'-GR, DHR and RES show nearly equal binding to HSA, mainly through hydrogen bonding, whereas 3-GR adopts a quite different orientation mode upon binding, thereby resulting in reduced ability; 2) 3-GR shows comparable (even equal) ability to RES in FRAP- and AAPH-induced DNA strand breakage assays; DHR, 3-GR, and 4'-GR exhibit anti-hemolysis activity comparable to that of RES; additionally, 3-GR and DHR retain some degree activity of the parent molecule in DPPH.-scavenging and cupric ion-initiated oxidation of LDL assays, respectively; 3) compared to RES, 4'-GR displays equipotent ability in the inhibition of COX-2, and DHR presents comparable activity in inhibiting NO production and growth of SMMC-7721 cells. Relative to RES, its glucuronidation and reduction metabolites showed equal, comparable, or some degree of activity in the above assays, depending on the specific compound and test model, which probably supports their roles in contributing to the in vivo biological activities of the parent molecule.

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Nickel‐Catalysed Cross‐Electrophile Coupling of Benzyl Bromides and Sulfonium Salts towards the Synthesis of Dihydrostilbenes

Río-Rodríguez

Blanco

Collado

et al. 2022

Chemistry A European J

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A nickel-catalysed reductive cross-coupling reaction between benzyl sulfonium salts and benzyl bromides is reported. Simple, stable and readily available sulfonium salts have shown their ability as leaving groups in cross-electrophile coupling, allowing the formation of challenging sp 3 -sp 3 carbon-carbon bonds, towards the synthesis of interesting dihydrostilbene derivatives. In addition, benzyl tosyl derivatives have been demonstrated to be suitable substrates for reductive cross-coupling by in-situ formation of the corresponding sulfonium salt.

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Dihydro-resveratrol—A potent dietary polyphenol

Cited by 25 publications

References 23 publications

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

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

Influence of Glucuronidation and Reduction Modifications of Resveratrol on its Biological Activities

Nickel‐Catalysed Cross‐Electrophile Coupling of Benzyl Bromides and Sulfonium Salts towards the Synthesis of Dihydrostilbenes

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