- cis- and trans-resveratrol are glucuronidated in rat brain, olfactory mucosa and cultured astrocytes
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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
- Sabolovic, Nicole,Heurtaux, Tony,Humbert, Anne-Claude,Krisa, Stephanie,Magdalou, Jacques
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- Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)- resveratrol
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Resveratrol, natural compound found in grapes and wine, has been reported to have a variety of health benefit properties. Based on the structural similarity to the synthetic estrogen diethylstilbestrol, we investigated estrogenic/antiestrogenic effects on
- Basly, Jean-Philippe,Marre-Fournier, Francoise,Bail, Jean-Christophe Le,Habrioux, Gerard,Chulia, Albert Jose
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- Ethylchloroformate derivatization for GC-MS analysis of resveratrol isomers in red wine
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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
- Boffi, Alberto,Bonamore, Alessandra,Di Fabio, Elisa,Incocciati, Alessio,Macone, Alberto,Palombarini, Federica
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- Isolation and identification of 2,4,6-trihydroxyphenanthrene as a byproduct of trans-resveratrol photochemical isomerization and electrocyclization
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UV irradiation of trans-resveratrol leads to its photochemical isomerization and electrocyclization, giving rise to different byproducts. Preliminary attempts to purify and characterize these products were in the majority of cases unsuccessful. In the present work, the resveratrol photoreaction products were analyzed by HPLC, and one of these compounds, 2,4,6-trihydroxyphenanthrene (THP), was purified and unambiguously identified. The structure of THP was unequivocally characterized for the first time by combined GC-MS, ESI-MS/MS, NMR, and FT-IR analyses.
- Francioso, Antonio,Boffi, Alberto,Villani, Claudio,Manzi, Lucio,D'Erme, Maria,Macone, Alberto,Mosca, Luciana
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- On the Chemistry of the Resveratrol Diastereomers
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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,
- Deak, Martin,Falk, Heinz
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- Isolation, Characterization, and Evolution in Red Wine Vinification of Resveratrol Monomers
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Isolation from red wine and characterization of trans- and cis-resveratrol, trans-resveratrol β-D-glucopyranoside, and cis-resveratrol β-D-glucopyranoside are described.Extraction from grape skin and chemical changes of the four compounds during a convent
- Mattivi, Fulvio,Reniero, Fabiano,Korhammer, Siegfried
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- Photo-induced chemical reaction of trans-resveratrol
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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
- Zhao, Yue,Shi, Meng,Ye, Jian-Hui,Zheng, Xin-Qiang,Lu, Jian-Liang,Liang, Yue-Rong
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- Activation energy of light induced isomerization of resveratrol
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Isomerization of trans-stilbenes is known to be induced by light. The two isomers have distinct absorption, fluorescence excitation and emission spectra. Resveratrol, 3,4′,5-trihydroxystilbene, is a member of the stilbene family. The interest of the scien
- Figueiras, Teresa Sofia,Neves-Petersen, Maria Teresa,Petersen, Steffen B.
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- Energy efficient, facile and cost effective methodology for formation of an inclusion complex of resveratrol with hp-β-CD
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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.
- Kaur, Khushwinder,Uppal, Shivani,Kaur, Ravneet,Agarwal, Jyoti,Mehta, Surinder Kumar
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- Contribution of malolactic fermentation by Oenococcus oeni and Lactobacillus plantarum to the changes in the nonanthocyanin polyphenolic composition of red wine
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The changes in the nonanthocyanin phenolic composition during red wine malolactic fermentation carried out spontaneously and by four different starter cultures of the species Oenococcus oeni and Lactobacillus plantarum were examined to determine whether d
- Hernandez,Estrella,Perez-Gordo,Alegria,Tenorio,Ruiz-Larrrea,Moreno-Arribas
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- UV light stability of α-cyclodextrin/resveratrol host-guest complexes and isomer stability at varying pH
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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.
- Allan, Kerrilee E.,Lenehan, Claire E.,Ellis, Amanda V.
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- Development and validation of an analytical method for the determination of trans - And cis -resveratrol in wine: Analysis of its contents in 186 Portuguese red wines
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A simple procedure based on solid-phase extraction and high performance liquid chromatography coupled to diode array detector has been developed and validated for the qualitative and quantitative analysis of cis- and trans-resveratrol in wines.The method
- Paulo, Luisa,Domingues, Fernanda,Queiroz, Joao Antonio,Gallardo, Eugenia
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- Photostability and skin penetration of different E-resveratrol-loaded supramolecular structures
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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
- Detoni, Cassia Britto,Souto, Gabriele Dadalt,Da Silva, Ana Luiza Maurer,Pohlmann, Adriana Raffin,Guterres, Silvia Stanisuaski
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- Resveratrol: Isomeric molar absorptivities and stability
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Resveratrol has attracted interest as a wine constituent that may reduce heart disease. Published data on the molar absorptivity and chemical stability of cis- and trans-resveratrol have varied greatly. Accurate values for UV absorbance for trans-resverat
- Trela, Brent C.,Waterhouse, Andrew L.
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- Processable cyanate ester resin from Cis resveratrol
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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
- Cambrea, Lee R.,Davis, Matthew C.,Garrison, Michael D.,Groshens, Thomas J.,Lyon, Richard E.,Safronava, Natallia
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- Determination of resveratrol in grains, hulls and leaves of common and tartary buckwheat by HPLC with electrochemical detection at carbon paste electrode
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A reverse-phase high-performance liquid chromatographic method for the determination of trans-resveratrol with spectrophotometric detection (306 nm) and amperometric detection at carbon paste electrode (E = + 1,2 V) was developed and tested on real sample
- Němcová, Lenka,Zima, Ji?í,Barek, Ji?í,Janovská, Dagmar
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- Stability and solubility of trans-resveratrol are strongly influenced by pH and temperature
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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
- Zupan?i?, ?pela,Lavri?, Zoran,Kristl, Julijana
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- Novel resveratrol as well as derivative synthesis method and application thereof
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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.
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Paragraph 0065; 0072-0073
(2019/08/02)
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- Synthesis and switching properties of new derivatives of azoresveratrol
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The synthesis and response upon light irradiation of azoresveratrol and six derivatives are reported. While UV irradiation of para-hydroxy trans compounds leads to thermally unstable cis isomers, the para-methoxy and the para-phosphoric ester substituents
- Berthet, Jér?me,Agouridas, Laurence,Chen, Siyao,Allouchi, Hassan,Melnyk, Patricia,Champagne, Beno?t,Delbaere, Stéphanie
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- Synthesis method of resveratrol
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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.
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Paragraph 0053; 0069; 0070; 0071
(2018/07/30)
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- Synthesis method of resveratrol
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The invention provides a synthesis method of resveratrol, and belongs to the technical field of natural product synthesis. The synthesis method comprises the following steps: with 3,5-dimethoxy benzoic acid as a raw material, generating 3,5-dimethoxy benzoyl chloride (12) through an acylating chlorination reaction; generating 3,5-dimethoxy benzamide (13) through an amidation reaction of the (12);generating 3,5-dimethoxyaniline (14) through a Hofmann degradation reaction of the (13); generating 3,5-dimethoxy iodobenzene (15) through a Sandmeyer reaction on the (14); generating 3,5,4'-trimethoxy diphenylethene (31) through a reaction between the (15) and p-methoxystyrene (23), and performing demethylation of the (31) to finally obtain resveratrol (1), wherein total yield is 23.3%. Accordingto the method, the adopted reagent is cheap and easily available, aftertreatment is simple, and two expensive intermediates for Heck reaction are synthesized by adopting cheap raw materials. A new synthesis method is provided for synthesizing resveratrol.
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Paragraph 0047; 0048
(2018/05/03)
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- Preparation method of resveratrol
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The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.
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Paragraph 0044-0048; 0049-0051; 0053-0055
(2018/11/03)
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- 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)
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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.
- Hurtado-Gaitán, Elías,Sellés-Marchart, Susana,Martínez-Márquez, Ascensión,Samper-Herrero, Antonio,Bru-Martínez, Roque
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- Preparation method for health product resveratrol
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The invention provides a preparation method for a health product resveratrol. According to the invention, 1, a deprotection method used in the invention is green, environment-friendly and pollution-free, the preparation method is almost free of production of waste gas, waste water and industrial residues, and the product 1,4-pentadiene has economic value; 2, a catalyst used in the invention has good cycle repeatability and can be cyclically used 50 times or more; 3, the preparation method is simple in operation requirements, mild in reaction conditions, good in specificity, simple in post-treatment and purification of the product, and suitable for industrial production; and 4, the resveratrol prepared by using the method is free of impurity and has high purity.
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- Method for preparing resvertrol (by machine translation)
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The invention discloses method for preparing resvertrol, in order to 3,5-dimethoxy-methanol as the raw material, through chloropivaloyl, to obtain 3,5-dimethoxy oxygen radical chlorine animal pen, through the 3,5-dimethylbenzaldehyde by oxygen radical chlorine animal pen 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works. This invention, through the triphosgene 3,5-dimethoxy-methanol chloropivaloyl, instead of ethanol using sodium hydride and sodium, synthetic 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works, preparation method has high yield, low cost. (by machine translation)
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Paragraph 0029; 0030; 0031; 0032; 0033
(2016/10/31)
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- Recent advances of resveratrol in nanostructured based delivery systems and in the management of HIV/AIDS
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Resveratrol, a natural polyphenolic compound present in trees, in peanuts, in grapevines and exhibited multiple pharmacological activities. Extensive research in last two decades suggested that resveratrol possesses anti-inflammatory, anti-cancer, anti-viral, anti-amyloid, anti-arthritic and antioxidant properties. Some clinical reports have proposed that resveratrol might be a potential candidate for the prevention and/or treatment of HIV/AIDS and synergistically enhances the anti-HIV-1 activity. Resveratrol is not toxic to cells, and by itself reduces viral replication by 20% to 30%. With almost 12% of the world population suffering from HIV/AIDS including its resurgence in the developed world, better management of this global threat is highly desired. Further, various studies demonstrated several issues associated with resveratrol which account for its poor systemic bioavailability (almost zero) due to rapid and extensive first pass metabolism and existence of enterohepatic recirculation. In order to improve bioavailability and cellular uptake of resveratrol, various strategies have been adopted to date which includes resveratrol prodrug and the development of nanostructured delivery systems. Besides, nanostructured delivery systems are also known to inhibit the P-glycoprotein (P-gp) efflux, reduced metabolism by gut cytochrome P-450 enzymes, and circumnavigate the hepatic first-pass effect, facilitating absorption of drugs via intestinal lymphatic pathways. This review paper provides an updated bird's-eye view account on the publications and patents study on the recent novel approaches to deliver resveratrol in order to enhance oral bioavailability, overcome first pass metabolism and trounce enterohepatic recirculation to make resveratrol a therapeutically potent drug. Providing a relatively pithy overview, this paper thus presents recent advances of resveratrol for the treatment and prevention of HIV/AIDS.
- Singh, Gurinder,Pai, Roopa S.
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p. 178 - 188
(2015/01/08)
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- Modulation of photochemical damage in normal and malignant cells by naturally occurring compounds
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Certain phytochemicals, such as the stilbene, resveratrol (RES, found in red grapes and berries), and the triterpenoid, ursolic acid (UA, found in waxy berries and herbs such as rosemary and oregano), have antioxidant, anti-inflammatory and antiproliferative effects. Two human-derived cell lines, hTERT-RPE with a nonmalignant phenotype derived from retinal pigment epithelium, and ATCC CRL-11147 derived from a malignant skin melanoma, were used as in vitro models of photooxidative stress produced by exposure to the broadband output of a 150 W Hg vapor arc lamp at an irradiance of 19-26 mW cm -2. In untreated cells, UV-VIS broadband light exposure produced a loss of proliferative ability, an activation of NF-κB and an increase in protein carbonyl adducts at 24 h postexposure. Pretreatment of the cells with RES or UA at 1-2 μmsignificantly reduced the amount of phosphorylated NF-κB at 24 h postexposure. RES pretreatment reduced the burden of light-induced protein carbonyl adducts by up to 25% in exposed cells. UA treatment markedly increased the sensitivity of melanoma cells to UV radiation, while conferring some photoprotection to RPE cells. These observations indicate that phytochemicals modulate the cellular response to photochemical stress by interacting with specific cell-signaling pathways. There is heightened interest in naturally occurring compounds as potential therapeutic agents. One such compound is ursolic acid (UA), a triterpenoid found in common foods such as cranberries, apples, as well as rosemary and other herbs. When skin melanoma (SM) cells are treated with UA, they become more susceptible to UV and visible light exposure, in contrast to normal phenotype retinal pigment epithelial (RPE) cells, whose sensitivity to light damage is unchanged by UA treatment. The figure shows the appearance of SM and RPE cells 24 h following light exposure with or without UA pretreatment. 2012 Wiley Periodicals, Inc. Photochemistry and Photobiology
- Lee, Yuan-Hao,Kumar, Neeru C.,Glickman, Randolph D.
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p. 1385 - 1395
(2013/01/15)
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- Photochemical generation of a new, highly fluorescent compound from non-fluorescent resveratrol
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UV irradiation of trans-resveratrol leads to its photochemical transformation to a new, highly fluorescent compound, whose chemical structure was unambiguously identified. The new compound has large values of fluorescence quantum yield, Stokes' shift, and two-photon absorption cross section, which make it suitable for bio-imaging, multi-color labeling, and two-photon microscopy. The Royal Society of Chemistry 2012.
- Yang, Ilseung,Kim, Eunha,Kang, Junhee,Han, Hyouksoo,Sul, Soohwan,Park, Seung Bum,Kim, Seong Keun
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p. 3839 - 3841
(2012/05/20)
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- A joint experimental and theoretical investigation on the oxidative coupling of resveratrol induced by copper and iron ions
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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.
- Tamboli, Vajir F.,Re, Nazzareno,Coletti, Cecilia,Defant, Andrea,Mancini, Ines,Tosi, Paolo
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p. 55 - 63
(2012/08/28)
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- Theoretical and experimental exploration of the photochemistry of resveratrol: Beyond the simple double bond isomerization
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The photochemical isomerization of resveratrol has been the subject of recent studies in which contradictory results were reported. The photoproduct mixture of this reaction needs to be considered more complex than the coexistence of cis and trans isomers
- Rodríguez, Roi álvarez,Lahoz, Inmaculada R.,Faza, Olalla Nieto,Cid, María Magdalena,Lopez, Carlos Silva
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p. 9175 - 9182
(2013/01/15)
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- Process for the preparation of resveratrol
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Process for the preparation of resveratrol by reacting a solution of acetylated 1-(3.5-dihydroxyphenyl)-bromoethane in DMA or NMP containing alkaline or alkaline earth carbonate or phosphate with a solution of acetylated p-bromophenol in the same solvent containing alkaline or alkaline earth carbonate or phosphate and a catalytic amount of palladium oximate under heating, addition of water and optionally isolating the resveratrol and purifying it.
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(2012/07/03)
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- MOLECULARLY IMPRINTED POLYMERS
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The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
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- Structural determinants of resveratrol for cell proliferation inhibition potency: Experimental and docking studies of new analogs
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Resveratrol is the subject of intense research because of the abundance of this compound in the human diet and as one of the most valuable natural chemopreventive agents. Further advances require new resveratrol analogs be used to identify the structural determinants of resveratrol for the inhibition potency of cell proliferation by comparing experimental and docking studies. Therefore, we synthesized new trans/(E)- and cis/(Z)-resveratrol - analogs not reported to date - by modifying the hydroxylation pattern of resveratrol and a double bond geometry. We included them in a larger panel of 14 molecules, including (Z)-3,5,4′-trimethoxystilbene, the most powerful molecule that is used as reference. Using a docking model complementary to experimental studies on the proliferation inhibition of the human colorectal tumor SW480 cell line, we show that methylation is the determinant substitution in inhibition efficacy, but only in molecules bearing a Z configuration. Most of the synthetic methylated derivatives (E or Z) stop mitosis at the M phase and lead to polyploid cells, while (E)-resveratrol inhibits cells at the S phase. Docking studies show that almost all of the docked structures of (Z)-polymethoxy isomers, but not most of the (E)-polymethoxy isomers substantially overlap the docked structure of combretastatin A-4, taken as reference ligand at the colchicine-tubulin binding site.
- Mazué, Frédéric,Colin, Didier,Gobbo, Jessica,Wegner, Maria,Rescifina, Antonio,Spatafora, Carmela,Fasseur, Dominique,Delmas, Dominique,Meunier, Philippe,Tringali, Corrado,Latruffe, Norbert
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experimental part
p. 2972 - 2980
(2010/08/22)
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- Isomeric effect on H/D exchange of resveratrol studied by NMR spectroscopy
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Resveratrol (3,5,4′-trihydroxylstilbene), a phytoalexin in response to injury or fungal attack, is found in grapes and other food products. It has been well documented that the compound has beneficial effects as hypolipidemic, anticancer, antiviral, neuro
- Jiang, Haipeng,Fang, Hanjun,Jiang, Ling,Zheng, Limin,Wang, Nian,Zheng, Anmin,Deng, Feng,Liu, Maili
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experimental part
p. 2281 - 2286
(2011/10/12)
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- Screening non-colored phenolics in red wines using liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry libraries
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Liquid chromatography/ultraviolet (LC/UV) and mass spectrometry/mass spectrometry (MS/MS) libraries containing 39 phenolic compounds were established by coupling a LC and an ion trap MS with an electrospray ionization (ESI) source, operated in negative io
- Sun, Jianping,Liang, Feng,Bin, Yan,Li, Ping,Duan, Changqing
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p. 679 - 693
(2008/02/01)
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- A SINGLE STEP MICROWAVE INDUCED PROCESS FOR THE PREPARATION OF SUBSTITUTED STILBENES AND ITS ANALOGS
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The present invention relates to a single step, microwave induced process for the preparation of substituted stilbenes and its analogs. Particularly, provides a method for the preparation of commercially important 2- or 4-hydroxy substituted stilbenes in one pot utilizing cheaper substrates in the form of 2- or 4-hydroxy substituted arylaldehyde and/or phenylacetic acids as well as regents in the form of base such as collidine, triethylamine, pyridine, piperidine, sodium acetate, ammonium acetate, imidazole, methyl imidazoles and the like and/or acid such as formic acid, acetic acid, propionic acid and the like for a reaction time varying from lmin-16 hrs depending upon microwave or conventional heating, without using decarboxylating agents with yield varying from 37-66 % depending upon the base and/or acid, solvent and substrate used. It is important to mention that the presence of hydroxy substitution at 2- or 4- position of arylaldehyde and/or aryl acetic acid is essential requirements towards formation of stilbenes in one step.
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(2008/06/13)
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- Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and mammalian cells
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Resveratrol is a naturally occurring defense compound produced by a limited number of plants in response to stresses. Besides cardiovascular benefits, this health-promoting compound has been reported to extend life spans in yeasts, flies, worms, and fish. To biosynthesize resveratrol de novo, tyrosine ammonia lyase (TAL), 4-coumarate CoA-ligase (4CL), and stilbene synthase (STS) were isolated from Rhodobacter sphaeroides, Arabidopsis thaliana, and Vitis vinifera, respectively. Yeast cells expressing 4CL and STS produce resveratrol when fed with 4-coumaric acid, the substrate of 4CL. When a translational fusion protein joining 4CL and STS was used, yeast cells produced 15-fold more resveratrol than the cotransformed cells, suggesting that physical localization of 4CL and STS facilitate resveratrol production. When the resveratrol pathway was introduced into human HEK293 cells, de novo biosynthesis was detected, leading to intracellular accumulation of resveratrol. We successfully engineered an entire plant natural product pathway into a mammalian host. Copyright
- Zhang, Yansheng,Li, Song-Zhe,Li, Jia,Pan, Xiangqing,Cahoon, Rebecca E.,Jaworski, Jan G.,Wang, Xuemin,Jez, Joseph M.,Chen, Feng,Yu, Oliver
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p. 13030 - 13031
(2008/02/05)
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- Hop as an interesting source of resveratrol for brewers: Optimization of the extraction and quantitative study by liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry
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Nowadays, hop is used almost exclusively by brewers for bitterness and flavor. Although hop polyphenols have been widely studied in the past decade for their antioxidant activity in the boiling kettle, very little is known about their real impact on healt
- Callemien, Delphine,Jerkovic, Vesna,Rozenberg, Raoul,Collin, Sonia
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p. 424 - 429
(2007/10/03)
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- PROCESS FOR THE PREPARATION OF STILBENE DERIVATIVES
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A novel process for the preparation of resveratrol and piceatannol and esters thereof involving a Heck type reaction is disclosed. Also disclosed are novel intermediates in that process.
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Page/Page column 12
(2010/02/11)
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- Low-valent titanium mediated synthesis of hydroxystilbenoids: Some new observations
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A series of phenolic stilbenoids possessing different numbers and positions of hydroxylation, partial methoxyl substituents and nature of olefinic moieties has been synthesized by McMurry coupling. It is found that the McMurry coupling of the phenolic aldehydes furnishes the dihydrostilbenes via an in situ hydrogenation, while the phenolic ketones give the stilbenes. Interestingly, the study also reveals that the low-valent titanium reagent (TiCl 3-Zn-THF) could selectively depyranylate phenolic -OTHP function without affecting alcoholic -OTHP group.
- Shadakshari,Rele,Nayak,Chattopadhyay
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p. 1934 - 1938
(2007/10/03)
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- A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids
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A re-investigation of resveratrol synthesis by Perkins reaction allowed to improve this method and to determine the configuration of the intermediates. The results were applied to the synthesis of several aryl cinnamic acids for biological evaluation.
- Solladié, Guy,Pasturel-Jacopé, Yacine,Maignan, Jean
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p. 3315 - 3321
(2007/10/03)
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- Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents
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Resveratrol 1 (3,4′,5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3′-trihydroxy-4′methoxy-transstilbene) and its 3′-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G0-G1 peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.
- Roberti, Marinella,Pizzirani, Daniela,Simoni, Daniele,Rondanin, Riccardo,Baruchello, Riccardo,Bonora, Caterina,Buscemi, Filippo,Grimaudo, Stefania,Tolomeo, Manlio
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p. 3546 - 3554
(2007/10/03)
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- Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate
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As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI50 = 0.01-0.001 μg/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.
- Pettit, George R.,Grealish, Matthew P.,Jung, M. Katherine,Hamel, Ernest,Pettit, Robin K.,Chapuis, J.-Charles,Schmidt, Jean M.
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p. 2534 - 2542
(2007/10/03)
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- Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests
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Vitis vinifera cell suspensions were used to isolate and characterize the flavonoids (anthocyanins, catechins) and non-flavonoids (stilbenes) found in red wine. Furthermore, we showed that astringin is produced although this stilbene has not previously been reported to be a constituent of V. vinifera or wine. The ability of these compounds to act as radical scavengers was investigated using 1,1-diphenyl-2-picryl-hydrazyl (DPPH), a stable free radical. Antioxidant activities were assessed by their capacity to prevent Fe2+-induced lipid peroxidation in microsomes and their action on Cu2+-induced lipid peroxidation in low-density lipoproteins. The results showed that astringin has an important antioxidant effect similar to that of trans-resveratrol, and a higher radical scavenger activity than the latter. Astringinin appeared to be more active. These data indicate that phenolic compounds (stilbenes, catechins, anthocyanins) exhibit interesting properties which may account in part for the so-called 'French paradox,' i.e. that moderate drinking of red wine over a long period of time can protect against coronary heart disease.
- Fauconneau, Bernard,Waffo-Teguo, Pierre,Huguet, Francois,Barrier, Laurence,Decendit, Alain,Merillon, Jean-Michel
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p. 2103 - 2110
(2007/10/03)
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- Inhibition of both peroxidase and laccase by desferal (desferrioxamine mesylate)
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The effect of desferal (desferrioxamine mesylate), a transition metal chelator with a stability constant for iron of 1031, on the catalytic activity of the hemoprotein peroxidase, and on the catalytic activities of the cuproproteins, laccase and catechol oxidase, was studied. The results showed that desferal is an inhibitor of peroxidase and laccase activities but not of catechol oxidase activity, the inhibitory properties being strongly dependent on the phenolic substrate used to measure enzymatic activities. Thus, the inhibitory effect of desferal was not dependent on the nature of the prosthetic group. However, its use as an inhibitor of phenol-oxidizing enzymes, such as peroxidase and laccase, is promising since desferal seems to deactivate phenoxy radicals formed by the action of these enzymes. A mechanism to explain the inhibitory effect of desferal on these phenol-oxidizing enzymes, based on the reaction of desferal with phenoxy radicals, is proposed.
- De Pinto,Ros Barcelo
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p. 283 - 286
(2007/10/03)
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