62218-08-0Relevant articles and documents
Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological activity and molecular modelling evidence for cooperativity between viniferin enantiomers
Mattio, Luce M.,Marengo, Mauro,Parravicini, Chiara,Eberini, Ivano,Dallavalle, Sabrina,Bonomi, Francesco,Iametti, Stefania,Pinto, Andrea
supporting information, (2019/09/09)
To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.
Plant-derived purification, chemical synthesis, and in vitro/in vivo evaluation of a resveratrol dimer, viniferin, as an HCV Replication inhibitor
Lee, Sungjin,Mailar, Karabasappa,Il Kim, Mi,Park, Minkyung,Kim, Jiseon,Min, Dal-Hee,Heo, Tae-Hwe,Bae, Soo Kyung,Choi, Wonjun,Lee, Choongho
, (2019/11/11)
Oligostilbenoid compounds, a group of resveratrol multimers, display several anti-microbial activities through the neutralization of cytotoxic oxidants, and by inhibiting essential host and viral enzymes. In our previous study, we identified a series of oligostilbenoid compounds as potent hepatitis C virus (HCV) replication inhibitors. In particular, vitisin B, a resveratrol tetramer, exhibited the most dramatic anti-HCV activity (EC50 = 6 nM and CC50 > 10 μ M) via the disruption of the viral helicase NS3 (IC50 = 3 nM). However, its further development as an HCV drug candidate was halted due to its intrinsic drawbacks, such as poor stability, low water solubility, and restricted in vivo absorption. In order to overcome these limitations, we focused on (+)-"-viniferin, a resveratrol dimer, as an alternative. We prepared three different versions of (+)-"-viniferin, including one which was extracted from the grapevine root (EVF) and two which were chemically synthesized with either penta-acetylation (SVF-5Ac) or no acetylation (SVF) using a newly established synthesis method. We confirmed their anti-HCV replication activities and minimal cytotoxicity by using genotype 1b and 2a HCV replicon cells. Their anti-HCV replication action also translated into a significant reduction of viral protein expression. Anti-HCV NS3 helicase activity by EVF was also verified in vitro. Finally, we demonstrated that SVF has improved pharmacokinetic properties over vitisin B. Overall, the favorable antiviral and pharmacokinetic properties of these three versions of viniferin warrant their further study as members of a promising new class of anti-HCV therapeutics.
Applications of Amurensin H derivatives in treating and prevention liver related diseases
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Paragraph 0116-0121, (2019/11/20)
The invention discloses applications of Amurensin H derivatives shown as a formula (I) and (II) and pharmaceutically acceptable salt thereof in the preparation of drugs for treating and/or preventingliver related diseases, and also discloses the preparation method of a compound, and applications of the pharmaceutical composition of the compound in the preparation of the drugs for treating and/orpreventing the liver related diseases.
Biomimetic synthesis of resveratrol trimers catalyzed by horseradish peroxidase
Zhang, Jian-Qiao,Li, Gan-Peng,Kang, Yu-Long,Teng, Bin-Hao,Yao, Chun-Suo
supporting information, (2017/06/08)
Biotransformation of trans-resveratrol and synthetic (±)-viniferin in aqueous acetone using horseradish peroxidase and hydrogen peroxide as oxidants resulted in the isolation of two new resveratrol trimers (3 and 4), one new resveratrol derivative (5) with a dihydrobenzofuran skeleton, together with two known stilbene trimers (6 and 7), and six known stilbene dimers (8-13). Their structures and relative configurations were identified through spectral analysis and possible formation mechanisms were also discussed. Among these oligomers, trimers 6 and 7 were obtained for the first time through direct transformation from resveratrol. Results indicated that this reaction is suitable for the preparation of resveratrol oligomers with a complex structure.
A joint experimental and theoretical investigation on the oxidative coupling of resveratrol induced by copper and iron ions
Tamboli, Vajir F.,Re, Nazzareno,Coletti, Cecilia,Defant, Andrea,Mancini, Ines,Tosi, Paolo
body text, p. 55 - 63 (2012/08/28)
Currently, a mounting interest exists on the biological activity of polyphenolic compounds, which have been suggested to exert positive effects on the human health. In this paper we report the first electrospray ionization mass spectrometry (ESI-MS) study on the gas-phase production of isomeric δ-viniferin and ε-viniferin dimers in racemic form, starting from acetonitrile/water solutions containing resveratrol and CuSO4 or FeCl3, respectively. Interestingly, the formation of racemic δ-viniferin dehydrodimer is observed in ESI-MS experiments carried out on resveratrol-copper mixtures, while the analogous resveratrol-iron reaction affords the racemic ε-viniferin dehydrodimer. The use of gas-phase techniques and of ab initio calculations, at BHandHLYP/LACV3P + +** level of theory, allowed us to elucidate some important aspects of these reaction mechanisms. In particular, a different stability for the resveratrol radicals involved in the oxidative coupling has been obtained in the presence of copper ion, favoring the formation of δ-viniferin, as proposed for the in vivo mechanism where copper is able to switch the resveratrol from an antioxidant to a prooxidant agent. Finally, the structure-reactivity relationship has been investigated for synthetic analogues of resveratrol, showing the crucial role of the OH group in para position.
Resveratrol oligomers from Vatica albiramis
Abe, Naohito,Ito, Tetsuro,Ohguchi, Kenji,Nasu, Minori,Masuda, Yuichi,Oyama, Masayoshi,Nozawa, Yoshinori,Ito, Masafumi,Iinuma, Munekazu
experimental part, p. 1499 - 1506 (2010/12/24)
Five new stilbenoids, vatalbinosides A-E (1-5), and 13 known compounds (6-18) were isolated from the stem of Vatica albiramis. The effects of these new compounds on interleukin-1β-induced production of matrix metalloproteinase-1 (MMP-1) in human dermal fibroblasts were examined. Three resveratrol tetramers, (-)-hopeaphenol (6), vaticanol C (13), and stenophyllol C (14), were identified as strong inhibitors of MMP-1 production.
