Quantitative structure–antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4′-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: Trans-piceid, cis-piceid, trans-astringin and trans-resveratrol-4′-O-β-D-glucopyranoside

Mikulski, Damian; Molski, Marcin

doi:10.1016/j.ejmech.2010.02.016

Cited by 96 publications

(57 citation statements)

References 28 publications

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“…Oligomers with more repeating resveratrol units were more active than smaller oligomers, as evidenced by the order of their potency: Trimers (cis-and trans-gnetin H, suffruticosol A-C, cis-and trans-suffruticosol D), followed by dimers (cis-and trans-ε-viniferin) and, lastly, the resveratrol monomer. This observation is consistent with previous findings of the structure-antioxidant activity of resveratrol oligomers (30,31). Secondly, the double bond in the stilbenic skeleton and its trans-isomerism were important to the antitumor activity of oligostilbenes.…”

Section: Discussionsupporting

confidence: 82%

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

Gao

2017

Oncol Lett

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Abstract. Paeonia suffruticosa from the section Moutan of the genus Paeonia is an important Chinese medicinal herb. In our previous study, 10 oligostilbenes from the seeds of P. suffruticosa, including trans-resveratrol and its dimers and trimers, were isolated and identified. In the present study, the anti-proliferative effects of these 10 oligostilbenes were systemically evaluated in a panel of human lung, breast and bone cancer cell lines, and their apoptotic effects were analyzed using a high-content multiplex apoptosis assay and a fluorescent caspase-3/7 assay. Furthermore, their anti-metastasis effects were examined in an invasive breast cancer cell line. Among the ten compounds, two resveratrol dimers, trans-and cis-gnetin H, showed the most potent anti-proliferative and anti-metastasis effects. All trans-oligostilbenes were more effective than their cis-forms, and trimers of resveratrol were more effective than dimers and the resveratrol isomer. The structure-activity relationships revealed that the polymerization degree, the double bond in the stilbene skeleton, and the steric arrangement and conformation of oligostilbenes obviously affected their antitumor potential. The results from this study provide valuable information for future semi-synthesis of resveratrol derivatives to develop novel cancer chemopreventive agents.

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Section: Discussionsupporting

confidence: 82%

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

Gao

2017

Oncol Lett

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“…Therefore, a comparative transcriptome analysis of transgenic MYB15 and GFP:GUS grapevine hairy roots could lead to the identification of genes involved in stilbene modification and transport. The analysis of these unknown enzymes would expand our knowledge of the stilbene biosynthetic pathway in plants and would be valuable tools for the pharmacological industry exploring modified resveratrol derivatives and their beneficial effect on human health (Mikulski and Molski, 2010;Agarwal and Baur, 2011;Kapetanovic et al, 2011). Quantitative variation of polyphenol levels, including anthocyanins and stilbenes, has been detected for different grapevine cultivars and susceptibility to fungal diseases has been correlated to the content and composition of the stilbene derivatives (Pezet et al, 2004).…”

Section: Ectopic Expression Of Myb15 In Grapevine Hairy Roots Resultsmentioning

confidence: 99%

The R2R3-MYB Transcription Factors MYB14 and MYB15 Regulate Stilbene Biosynthesis in Vitis vinifera

et al. 2013

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Plant stilbenes are phytoalexins that accumulate in a small number of plant species, including grapevine (Vitis vinifera), in response to biotic and abiotic stresses and have been implicated in many beneficial effects on human health. In particular, resveratrol, the basic unit of all other complex stilbenes, has received widespread attention because of its cardio-protective, anticarcinogenic, and antioxidant properties. Although stilbene synthases (STSs), the key enzymes responsible for resveratrol biosynthesis, have been isolated and characterized from several plant species, the transcriptional regulation underlying stilbene biosynthesis is unknown. Here, we report the identification and functional characterization of two R2R3-MYB-type transcription factors (TFs) from grapevine, which regulate the stilbene biosynthetic pathway. These TFs, designated MYB14 and MYB15, strongly coexpress with STS genes, both in leaf tissues under biotic and abiotic stress and in the skin and seed of healthy developing berries during maturation. In transient gene reporter assays, MYB14 and MYB15 were demonstrated to specifically activate the promoters of STS genes, and the ectopic expression of MYB15 in grapevine hairy roots resulted in increased STS expression and in the accumulation of glycosylated stilbenes in planta. These results demonstrate the involvement of MYB14 and MYB15 in the transcriptional regulation of stilbene biosynthesis in grapevine.

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“…PD is more resistant to enzymatic oxidation than resveratrol owing to the change of molecule structure (Fabris et al, 2008). In fact, the antioxidative activity of trans-polydatin is stronger than cis-PD and trans-resveratrol (Mikulski & Molski, 2010).…”

Section: Anti-oxidative Activitymentioning

confidence: 97%

“…There are four main derivatives of PD in nature, including trans-polydatin, trans-resveratrol, cis-polydatin and cis-resveratrol. The bioactivity of trans-isomers is higher than that of cis-isomers (Mikulski & Molski, 2010).…”

Section: Introductionmentioning

confidence: 97%

Polydatin: A review of pharmacology and pharmacokinetics

Peng

Zhang

2013

Pharmaceutical Biology

211

162

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Context: Polydatin, also named piceid (3,4 0 ,5-trihydroxystilbene-3-b-D-glucoside, PD), is a monocrystalline compound isolated from Polygonum cuspidatum Sieb. et Zucc. (Polygonaceae), but is also detected in grape, peanut, hop cones, red wines, hop pellets, cocoa-containing products, chocolate products and many daily diets. There are numerous investigations reported of PD in the past 22 years, but they are usually scattered across various publications, which may block further research and clinical use of PD. Objective: The article summarizes and evaluates the published scientific information of PD pharmacological effects and pharmacokinetics since 1990. Materials and methods: The information from 98 cases included in this review was compiled using major databases such as MEDLINE, Elsevier, Springer, PubMed, Scholar and CNKI. Results: Numerous pharmacological investigations of PD mainly focus on cardiovascular effects, neuroprotection, anti-inflammatory and immunoregulatory effects, anti-oxidation, anti-tumor, liver and lung protection, etc. Conclusion: A great number of pharmacological and pharmacokinetic investigations in the past 22 years have demonstrated that PD has favorable therapeutic properties, indicating its potential as an effective material. However, further research is needed to explore its molecular mechanisms of action and definitive target proteins.

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Quantitative structure–antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4′-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: Trans-piceid, cis-piceid, trans-astringin and trans-resveratrol-4′-O-β-D-glucopyranoside

Cited by 96 publications

References 28 publications

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

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

The R2R3-MYB Transcription Factors MYB14 and MYB15 Regulate Stilbene Biosynthesis in Vitis vinifera

Polydatin: A review of pharmacology and pharmacokinetics

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