Resveratrol and its oligomers: modulation of sphingolipid metabolism and signaling in disease

Lim, Keng Gat; Gray, Alexander I.; Anthony, Nahoum G.; Mackay, Simon P.; Pyne, Susan; Pyne, Nigel J.

doi:10.1007/s00204-014-1386-4

Cited by 18 publications

(12 citation statements)

References 203 publications

(237 reference statements)

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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: 92%

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: 92%

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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“…Our results suggested that the EC 50 of three cis isomers were significantly higher than their corresponding trans isomer, which agreed with our current knowledge that the trans isomer of natural compounds is a more active form than cis because of its lower steric hindrance [22]. The activity of oligostilbenes to promote chondrocyte proliferation often increased with the degree of polymerization, which was consistent with their structure-antioxidant activity [23,24]. Additionally, both of cis-suffruticosol D and cis-gnetin H are trimers that differ only in their three-dimensional structures but had significant differences in their efficacies, which indicated that the effect of three-dimensional structure is also worth paying attention.…”

Section: Discussionsupporting

confidence: 91%

Protective effects of ten oligostilbenes from Paeonia suffruticosa seeds on interleukin-1β-induced rabbit osteoarthritis chondrocytes

Cen

Liu

et al. 2019

BMC Chemistry

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Background: Paeonia suffruticosa is an important traditional Chinese herb used to treat osteoarthritis (OA) and oligostilbenes are the main active ingredient of the seeds of P. suffruticosa. The monomer trans-resveratrol of this species was demonstrated to have chondroprotective effects as a lead compound for the treatment of osteoarthritis, but it has not been applied due to its low efficacy. Methods: Oligostilbenes were isolated by chromatography and were identified by NMR and HPLC. A rabbit osteoarthritis chondrocyte model was induced by interleukin-1β and was treated with individual drugs to systematically evaluate their effects. Cell Counting Kit 8 was used to test their effects on cell viability, calculate EC 50 and plot a doseresponse curve.Their effects on apoptosis were analyzed by Annexin V and PI staining, and the expression of chondrocyte-specific genes COL2A1, MMP13 and SOX9 was evaluated by real-time PCR. Results: Paeonia suffruticosa seed extract could promote the cell viability of rabbit OA chondrocytes at low concentration and then ten oligostilbenes were isolated from it. Trans-oligostilbenes were better than their cis-forms, trimers and dimers were better than monomers for promoting the cell viability of rabbit osteoarthritis chondrocytes. None of the oligostilbenes was more effective than seed extract at the appropriate concentration; 1 μM oligostilbenes all showed various anti-apoptotic effects. Trans-gnetin H showed the best effect on proliferation and inhibition of MMP13 expression on OA chondrocytes, while trans-viniferin was most effective in promoting the expression of COL2A1 and SOX9. Conclusions: Ten oligostilbenes from P. suffruticosa seed all have certain protective effects on OA chondrocytes at low concentration. The trans-viniferin and some trimers have the potential to be further developed for the treatment of osteoarthritis because they were more effective than resveratrol and diacerein. The synergistic effect that may exist between oligostilbenes also warrants further research.

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“…In addition some evidences demonstrate that resveratrol modulates sphingolipid metabolism by forming higher order oligomers that exhibit better selectivity and potency in modulating sphingolipid metabolism. 38 It has been determined, that resveratrol has very low bioavailability and is rapidly metabolized to yield plasma and tissue levels that are several-fold lower than those typically used in experiments with cultured cells. On Fig.…”

Section: In Foodsmentioning

confidence: 99%

Untitled

2015

IJPSR

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ABSTRACT:Resveratrol, an antioxidant found in red wine and certain foods, has been touted as a natural way to slow aging and fight cancer, obesity, heart disease, and diabetes. It also could be accounted as an agent, which has effects to reduced risk of inflammation and blood clotting. In addition there are some studies showing that resveratrol may actually reduce the positive effect of exercise on the heart in older men, but it's important to know that its effects only last a short time after drinking red wine. As promising as it sounds, it is not yet established how resveratrol affects humans, since most studies have been conducted on animals and microbes. Because the information on resveratrol, presented in literature, pointing its health and adverse effects is full with contradictions, especially with respect to the human response, we tried to present the available information with minimal commentary, remaining as neutral as possible and allowing the reader to draw its own conclusion on recommendation of the wide increase usage of resveratrol and a prematurity of such a decision.

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Resveratrol and its oligomers: modulation of sphingolipid metabolism and signaling in disease

Cited by 18 publications

References 203 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

Protective effects of ten oligostilbenes from Paeonia suffruticosa seeds on interleukin-1β-induced rabbit osteoarthritis chondrocytes

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