676596-85-3Relevant articles and documents
Silyl resveratrol derivatives as potential therapeutic agents for neurodegenerative and neurological diseases
Belmonte-Reche, Efres,Pe?alver, Pablo,Caro-Moreno, Marta,Mateos-Martín, María Luisa,Adán, Norma,Delgado, Mario,González-Rey, Elena,Morales, Juan Carlos
, (2021)
Natural phenolic compounds found in food have demonstrated interesting preventive and therapeutic effects on a large variety of pathologies. Indeed, some of them, such as resveratrol (RES), have been examined in clinical trials. Nevertheless, their success has been scarce mainly due to their low bioavailability. In this study, we found serendipitously that O-silyl RES derivatives exerted a better neuroprotective activity than resveratrol itself and decided to explore them as potential drugs for neurodegenerative and neurological diseases. We have also designed and prepared a series of O-silyl RES prodrugs to improve their bioavailability. We found that di-triethylsilyl and di-triisopropylsilyl RES derivatives were better in vitro neuroprotective and anti-inflammatory agents than RES. Among these derivatives and their corresponding acyl-, glycosyl- and carbamoyl-prodrugs, 3,5-triethylsilyl-4’-(6″-octanoylglucopyranosyl) resveratrol 26 showed the best profile on toxicity and neuroprotective activity in zebra fish embryo. Compound 26 was also capable of reducing the loss of motor coordination in a 3-nitropropionic acid mice model of Huntington's disease, in a similar way to RES. However, 26 diminished pro-inflammatory cytokine IL-6 to a higher extent than RES and improved the latency to fall in the rotarod test by 10% with respect to RES. Finally, we investigated 26 and RES as potential treatments on an experimental autoimmune encephalomyelitis (EAE) multiple sclerosis mice model. We observed that, in a therapeutic regimen, 26 significantly diminished the progression of EAE severity and reduced the percentage of animals with moderate to severe clinical score, whereas RES showed no improvement.
Cytotoxic, Antiangiogenic and Antitelomerase Activity of Glucosyl- and Acyl- Resveratrol Prodrugs and Resveratrol Sulfate Metabolites
Falomir, Eva,Lucas, Ricardo,Pe?alver, Pablo,Martí-Centelles, Rosa,Dupont, Alexia,Zafra-Gómez, Alberto,Carda, Miguel,Morales, Juan C.
, p. 1343 - 1348 (2016/08/28)
Resveratrol (RES) is a natural polyphenol with relevant and varied biological activity. However, its low bioavailability and rapid metabolism to its glucuronate and sulfate conjugates has opened a debate on the mechanisms underlying its bioactivity. RES prodrugs are being developed to overcome these problems. We have synthesized a series of RES prodrugs and RES sulfate metabolites (RES-S) and evaluated their biological activities. RES glucosylated prodrugs (RES-Glc) were more cytotoxic in HT-29 and MCF-7 cells than RES itself whereas RES-S showed similar or higher cytotoxicity than RES. VEGF production was decreased by RES-Glc, and RES-disulfate (RES-diS) diminished it even more than RES. Finally, RES-Glc and RES-diS inhibited hTERT gene expression to a higher extent than RES. In conclusion, resveratrol prodrugs are promising candidates as anticancer drugs. In addition, RES-S showed distinct biological activity, thus indicating they are not simply RES reservoirs.
Biomimic transformation of resveratrol
Takaya, Yoshiaki,Terashima, Kenji,Ito, Junko,He, Yue-Hua,Tateoka, Maki,Yamaguchi, Naho,Niwa, Masatake
, p. 10285 - 10290 (2007/10/03)
Resveratrol was treated with several kinds of peroxidases and inorganic reagents so as to prepare ε-viniferin. Among several inorganic reagents, which were investigated in this study, thallium(III) nitrate in methanol gave (±)-ε-viniferin in the yield of 68%. On the other hand, peroxidases did not lead to ε-viniferin, but some stilbenedimers such as pallidol, resveratrol trans-dehydrodimer, and leachianol F were obtained.
