253435-07-3

Upstream product

• 1246746-89-3 1-(β-D-glucopyranosyloxy)-5-{(2R,3R)-6-(β-glucopyranosyloxy)-2-(4-hydroxyphenyl)-4-[(E)-4-hydroxystyryl]-2,3-dihydrobenzofuran-3-yl}benzene-3-ol 
• 62250-12-8 (-)-ε-viniferin 
• 1207104-86-6 (E)-5-[2-(3,5-dibromo-4-hydroxyphenyl)vinyl]benzene-1,3-diol 
• 412004-56-9 4-bromo-1-(cyclopropylmethoxy)benzene 
• 540-38-5 p-Iodophenol 
• 106-41-2 4-bromo-phenol 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 
• 855400-66-7 3-bromo-5-methoxyphenol 
• 33527-94-5 4-acetoxyiodobenzene 

Downstream Products

• 872357-75-0 (+)-cis-ε-viniferin 
• 223558-50-7 trans-ε-viniferin pentaacetate 
• 165883-77-2 (-)-vitisin B 
• 165883-77-2 (+)-vitisin C 
• 1527502-97-1 C₂₁H₁₆O₂ 
• 1527502-99-3 C₂₈H₂₂O 
• 1527503-02-1 C₃₃H₁₇F₁₅O₁₆S₅ 

Relevant academic research and scientific papers

Identification of isomers of resveratrol dimer and their analogues from wine grapes by HPLC/MSn and HPLC/DAD-UV

A facile method based on HPLC/(-)ESI-MSn is established for the analysis of seven isomers of resveratrol dimers and three of their analogues in Xinjiang wine grapes. The structures of these compounds are positively or tentatively determined. Among them, three are tentatively identified as new compounds. MSn experiments on the [M-H]- ions provide abundant structural information, especially regarding the relative abundance of the key product ions, m/z 333 and 369 (385 in compound 3), which can be utilised to distinguish whether or not the compound identified contains the scaffold of the isomer of a resveratrol dimer. The relative abundance of key product ions remains unchanged as collision energy varies from 0.60 to 0.95 V. All the trans-, and cis-isomers could be identified by HPLC/DAD-UV spectra. The UV spectra of compounds 2 and 9 tentatively show cis and trans- configurations, respectively.

Regioselective biomimetic oxidation of halogenated resveratrol for the synthesis of (±)-ε-viniferin and its analogues

FeCl3·6H2O-promoted biomimetic oxidations of 3,5-dihalogeno-resveratrol in different acetone systems produced several coupling intermediates bearing distinct dimeric skeletons with moderate yields. The subsequent deprotection reactio

Investigation of monomeric and oligomeric wine stilbenoids in red wines by ultra-high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry

RATIONALE Stilbenoids are secondary plant metabolites responsible for the protection of multiple plant species including grape vine from bacterial and fungal infection. Red wine has been shown to be a major source of these compounds in the human diet, where they display an array of health benefits. Providing a more complete profile of the stilbenoids present in red wine, this study detects 41 stilbenoid compounds, 23 of which have never before been detected in red wine. METHODS Red wine extracts were scanned using an ultra-high-performance liquid chromatograph coupled to a hybrid quadrupole time-of-flight mass analyzer. Multiple targeted MS/MS precursor ion scan experiments were performed using electrospray ionization operated in negative mode. Precursor ion masses were scanned for the monomeric and oligomeric stilbenoids, as well as modifications such as O-glycosylation, methoxylation and oxidation products of these compounds. Accurate mass precursor and characteristic product ions afforded partial structural elucidation and assignment of these compounds. RESULTS A total of 41 (both known and novel) stilbenoids were detected in extracted red wine. In addition to the well-known monomeric stilbenes, several resveratrol-resveratrol homodimers (m/z 453.1344), resveratrol-piceatannol heterodimers (m/z 469.1293) and piceatannol-piceatannol homodimers (m/z 485.1236) were detected. Modified dimers of resveratrol including O-glycosylated (m/z 615.1872), methoxylated (m/z 485.1606) and oxidized (m/z 471.1449) dimers were also detected. Multiple trimers of resveratrol (m/z 679.1978) were detected for the first time in red wine, as well as some known and some novel stilbenoid tetramers (m/z 905.2604). CONCLUSIONS In summary, 41 stilbenoids were detected in red wine, 23 for the first time. Both monomeric and oligomeric stilbenoids were partially identified and assigned by their accurate mass precursor ions and characteristic stilbenoid fragmentation patterns. Knowledge gained from these experiments contributes to a more complete understanding of the origin of the beneficial properties of red wine. Copyright

Oxidative cross-coupling approach to the biomimetic synthesis of the heterodimers of resveratrol and isorhapontigenin

The regioselective oxidative cross-coupling reactions of two different stilbene precursors catalyzed by FeCl3 or horseradish peroxidase-H2O2 in acetone solvent produced three dihydrobenzofuran-type heterodimers. The reductive debrominations of these cross-coupled dimers synthesized two heterodimers of resveratrol and isorhapontigenin, an analogue of (±)-scirpusin A and (±)-gnetuhainin Q.

Viniferin derivatives, preparation method thereof and composition for preventing or treating infection caused by pneumococcal biofilm comprising the same as an active ingredient

The present invention relates to a viniferin derivative compound represented by chemical formula 1 to chemical formula 4; a method for producing the same; a composition for preventing or treating an infection caused by a pneumococcal biofilm, wherein the composition comprises the viniferin derivative compound as an active ingredient; an antibacterial composition for Streptococcus pneumoniae; and a coating composition for inhibiting pneumococcal biofilm formation. The pharmaceutical composition, the antibacterial composition, and the coating composition of the present invention have excellent antibacterial effects.

Applications of Amurensin H derivatives in treating and prevention liver related diseases

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.

Plant-derived purification, chemical synthesis, and in vitro/in vivo evaluation of a resveratrol dimer, viniferin, as an HCV Replication inhibitor

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.

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological activity and molecular modelling evidence for cooperativity between viniferin enantiomers

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.

A focused multiple reaction monitoring (MRM) quantitative method for bioactive grapevine stilbenes by ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ)

Grapevine stilbenes are a family of polyphenols which derive from trans-resveratrol having antifungal and antimicrobial properties, thus being considered as phytoalexins. In addition to their diverse bioactive properties in animal models, they highlight a strong potential in human health maintenance and promotion. Due to this relevance, highly-specific qualitative and quantitative methods of analysis are necessary to accurately analyze stilbenes in different matrices derived from grapevine. Here, we developed a rapid, sensitive, and specific analysis method using ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ) in MRM mode to detect and quantify five grapevine stilbenes, trans-resveratrol, trans-piceid, trans-piceatannol, trans-pterostilbene, and trans-?-viniferin, whose interest in relation to human health is continuously growing. The method was optimized to minimize in-source fragmentation of piceid and to avoid co-elution of cis-piceid and trans-resveratrol, as both are detected with resveratrol transitions. The applicability of the developed method of stilbene analysis was tested successfully in different complex matrices including cellular extracts of Vitis vinifera cell cultures, reaction media of biotransformation assays, and red wine.

Biomimetic synthesis of resveratrol trimers catalyzed by horseradish peroxidase

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.