61434-67-1Relevant articles and documents
cis- and trans-resveratrol are glucuronidated in rat brain, olfactory mucosa and cultured astrocytes
Sabolovic, Nicole,Heurtaux, Tony,Humbert, Anne-Claude,Krisa, Stephanie,Magdalou, Jacques
, p. 185 - 192 (2007)
Background/Aims: Glucuronidation of cis- and trans-resveratrol (3,5,4′-trihydroxy-trans-stilbene), which is a naturally occurring phytoalexin known to exert a number of beneficial health effects, was investigated in rat brain, cultured astrocytes and olfactory mucosa. Methods: The isomers were incubated with tissue homogenates, microsomes, or rat liver recombinant UDP-glucuronosyltransferases in the presence of UDP-glucuronic acid. The glucuronides were separated by HPLC and quantitated. Astrocytes were exposed to lipopolysaccharide to promote inflammatory conditions. Results: All tissues were able to form resveratrol glucuronides although at a lower extent, when compared to the liver. The reaction was stereo- and regioselective. In brain tissue, trans-resveratrol 3-O-glucuronide was mainly formed, whereas the cis-isomer was glucuronidated at a lower rate on that position. No 4′-O-glucuronide was detected in brain. In olfactory mucosa homogenates, the cis 3-O-glucuronide was mainly formed, whereas the trans-isomer was glucuronidated only on the 3-position. In astrocytes, 3-O-glucuronides of the cis- and trans-resveratrol were only detected. The rat recombinant UGT1A6 and UGT2B1 isoforms were able to glucuronidate cis- and trans-resveratrol. Finally, in inflammatory conditions, trans-resveratrol glucuronidation was enhanced in astrocytes. Conclusion: Brain tissues are effective in the glucuronidation of resveratrol isomers. This metabolism pathway is likely to modulate the concentration of these biologically active substances. Copyright
Ethylchloroformate derivatization for GC-MS analysis of resveratrol isomers in red wine
Boffi, Alberto,Bonamore, Alessandra,Di Fabio, Elisa,Incocciati, Alessio,Macone, Alberto,Palombarini, Federica
, (2020)
Resveratrol (3,5,40-trihydroxystilbene) is a natural compound that can be found in high concentrations in red wine and in many typical foods found in human diet. Over the past decades, resveratrol has been widely investigated for its potential
On the Chemistry of the Resveratrol Diastereomers
Deak, Martin,Falk, Heinz
, p. 883 - 888 (2003)
The (E)- and (Z)-diastereomers of resveratrol were investigated with respect to their photochemical and thermal diastereomerization reactions. The free enthalpy difference between the two diastereomers was estimated to be in the order of common stilbenes,
Photo-induced chemical reaction of trans-resveratrol
Zhao, Yue,Shi, Meng,Ye, Jian-Hui,Zheng, Xin-Qiang,Lu, Jian-Liang,Liang, Yue-Rong
, p. 137 - 143 (2014)
Photo-induced chemical reaction of trans-resveratrol has been studied. UV B, liquid state and sufficient exposure time are essential conditions to the photochemical change of trans-resveratrol. Three principal compounds, cis-resveratrol, 2,4,6-phenanthren
Energy efficient, facile and cost effective methodology for formation of an inclusion complex of resveratrol with hp-β-CD
Kaur, Khushwinder,Uppal, Shivani,Kaur, Ravneet,Agarwal, Jyoti,Mehta, Surinder Kumar
, p. 8855 - 8865 (2015)
A distinctive, effortless, proficient and innovative process for preparation of an inclusion complex (IC) of resveratrol (Res) with hp-β-CD was developed. The methodology overcame the hindrance of low solubility of Res which is a potential anticancer agent and makes its use more practical. The strategy involved the utilization of a microwave meant for conventional use and the process of sonication in the laboratory. It considerably saved time and labour besides cutting down on energy consumption. The prepared inclusion complexes were characterised by FTIR, UV-visible absorption spectroscopy, NMR, TGA, DSC, XRD and CHNS analysis. Phase solubility studies along with Gaussian studies proved the formation of a 1:1 complex whose physical nature and stability were studied using XRD and UV-visible absorption spectroscopy, respectively. This effortless and economical process could pave the way for the formation of inclusion complexes of other nutraceuticals and pharmaceuticals.
UV light stability of α-cyclodextrin/resveratrol host-guest complexes and isomer stability at varying pH
Allan, Kerrilee E.,Lenehan, Claire E.,Ellis, Amanda V.
, p. 921 - 926 (2009)
trans-Resveratrol is an antioxidant that readily isomerizes to the cis isomer under UV irradiation. Here we report on the UV-Visible analysis of the stability of both trans- and cis-resveratrol isomers in the presence of UV light over a pH range of 2.0-9.
Photostability and skin penetration of different E-resveratrol-loaded supramolecular structures
Detoni, Cassia Britto,Souto, Gabriele Dadalt,Da Silva, Ana Luiza Maurer,Pohlmann, Adriana Raffin,Guterres, Silvia Stanisuaski
, p. 913 - 921 (2012)
It is desirable and challenging to prevent E-resveratrol (E-RSV) from photoisomerizing to its Z-configuration to preserve its biological and pharmacological activities. The aim of this research was to evaluate the photostability of E-RSV-loaded supramolec
Processable cyanate ester resin from Cis resveratrol
Cambrea, Lee R.,Davis, Matthew C.,Garrison, Michael D.,Groshens, Thomas J.,Lyon, Richard E.,Safronava, Natallia
, p. 971 - 980 (2017)
Trans resveratrol isomerizes to cis resveratrol (cRes) with ultra-violet light and undergoes cyanation to the new compound cRes tricyanate (2). Monomer 2 polymerizes to a polycyanurate that is remarkably stable to heat with a glass transition temperature
Stability and solubility of trans-resveratrol are strongly influenced by pH and temperature
Zupan?i?, ?pela,Lavri?, Zoran,Kristl, Julijana
, p. 196 - 204 (2015)
Recently trans-resveratrol (trans-RSV) has received great attention due to its prophylactic and therapeutic properties. Its limited bioavailability provides compelling evidence of the need for more suitable formulations in order to attain better clinical
Novel resveratrol as well as derivative synthesis method and application thereof
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Paragraph 0065; 0072-0073, (2019/08/02)
The invention belongs to the technical field of organic synthesis and discloses novel resveratrol as well as a derivative synthesis method and application thereof. A target product resveratrol is obtained by taking 3,5-disubstituted aniline I as a raw material through the steps of carrying out diazotization reduction to generate 3,5-disubstituted arylhydrazine II, carrying out acetylation to obtain acyl arylhydrazine III, carrying out Heck coupling under the common catalysis of transition metal palladium and copper to obtain a resveratrol derivative and finally carrying out deprotection. The invention provides an efficient synthesis method of the resveratrol. The acyl arylhydrazine is used as a novel arylation reagent and the resveratrol is stereoselectively synthesized under the catalysisof a transition metal catalyst. The method provided by the invention has the advantages of easiness for obtaining the raw material, simplicity in operation and high stereoselectivity and the invention can provides an efficient method for synthesizing the resveratrol and related derivatives.
Synthesis method of resveratrol
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Paragraph 0053; 0069; 0070; 0071, (2018/07/30)
The invention discloses a synthesis method of resveratrol. The synthesis method comprises the steps of a preparation technology of 3,5-dibromo-4-aminotoluene, a preparation technology of 3, 5-dibromotoluene, a preparation technology of (E)-1,3-dibromo-5-(4-methoxy-styrene)benzene, a preparation technology of (E)-1,3-dimethoxy-5-(4-methoxy-styrene)benzene and a preparation technology of resveratrol. The synthesis method has the advantages of being low in raw material price, less in step, high in yield and suitable for scale production.