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Synthesis and evaluation of resveratrol derivatives as fetal hemoglobin inducers
Resveratrol (RVT) derivatives (10a-i) were designed, synthesized, and evaluated for their potential as gamma-globin inducers in treating Sickle Cell Disease (SCD) symptoms. All compounds were able to release NO at different levels ranging from 0 to 26.3percent, while RVT did not demonstrate this effect. In vivo, the antinociceptive effect was characterized using an acetic acid-induced abdominal contortion model. All compounds exhibited different levels of protection, ranging from 5.9 to 37.3percent; the compound 10a was the most potent among the series. At concentrations between 3.13 and 12.5 μM, the derivative 10a resulted in a reduction of 41.1–64.3percent in the TNF-α levels in the supernatants of macrophages that were previously LPS-stimulated. This inhibitory effect was higher than that of RVT used as the control. In addition, the compound 10a and RVT induced double the production of the gamma-globin chains (γG + γA), compared to the vehicle, using CD34+ cells. Compound 10a also did not induce membrane perturbation and it was not mutagenic in the in vivo assay. Thus, compound 10a emerged as a new prototype of the gamma-globin-inducer group with additional analgesic and anti-inflammatory activities and proving to be a useful alternative to treat SCD symptoms.
Andersen, Olaf Sparre,Barbieri, Karina Pereira,Bosquesi, Priscila Longhin,Carlos, Iracilda Zepone,Chelucci, Rafael Consolin,Costa, Fernando Ferreira,Dos Santos, Jean Leandro,Fernandes, Guilherme Felipe dos Santos,Lanaro, Carolina,Melchior, Aylime Castanho Bolognesi,Pavan, Aline Renata,Rusinova, Radda,de Souza, Cristiane Maria
(2020/05/25)

Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors
Stilbenes with well-known antioxidant and antiradical properties are beneficial in different pathologies including cardiovascular diseases. The present research was performed to investigate the potential protective effect of resveratrol (1) and piceatannol (2), against hypoxia-induced oxidative stress in the H9c2 cardiomyoblast cell line, and the underlying mechanisms. Compounds 1 and 2 significantly inhibited the release of peroxynitrite and thiobarbituric acid levels at na no- or submicromolar concentrations, and this effect was more evident in piceatannol-treated cells, that significantly increased MnSOD protein level in a concentration dependent manner. Furthermore, since piceatannol, which is far less abundant in natural sources, displayed a higher bioactivity than the parent compound, we hereby report on a very fast synthesis and detailed structure-based design of a focused stilbene library. Finally, taking into account that hypoxia-induced ROS accumulation also increases expression and activity of 5-lipoxygenase (5-LOX) with production of leukotrienes, we have disclosed structural key factors crucial for 5-LOX activity. Among the synthesized analogues (3–7), compound 7 was the most effective in improving cardiomyocytes viability and in 5-LOX inhibition. In conclusion, modeling and experimental studies provided the basis for further optimization of stilbene analogues as multi-target inhibitors of the inflammatory and oxidative pathway.
Boccellino, Mariarosaria,Donniacuo, Maria,Bruno, Ferdinando,Rinaldi, Barbara,Quagliuolo, Lucio,Ambruosi, Marika,Pace, Simona,De Rosa, Mario,Olga?, Abdurrahman,Banoglu, Erden,Alessio, Nicola,Massa, Antonio,Kahn, Haroon,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna
p. 637 - 647
(2019/07/31)

Preparation method of resveratrol compound
The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.
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Paragraph 0082-0084

(2019/07/16)

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes
A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.
Girase, Tejpalsingh Ramsingh,Kapdi, Anant R.
supporting information
p. 2611 - 2619
(2019/07/05)

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage
C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.
Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai
supporting information
p. 8389 - 8394
(2019/10/16)

Synthesis method of pterostilbene
The invention provides a synthesis method of pterostilbene. The synthesis method takes 4-hydroxybenzaldehyde as a raw material and comprises the following steps: carrying out acetylation reaction to generate 4-acetoxybenzaldehyde; then carrying out wittig reaction to generate 4-acetoxystyrene; carrying out hydrolysis reaction on 4-acetoxystyrene to generate 4-hydroxystyrene; carrying out Heck reaction on 4-hydroxystyrene to obtain a target product pterostilbene. The method provided by the invention has the advantages of easiness for obtaining the raw materials, high product selectivity, relatively high yield, moderate reaction conditions and simplicity in operation.
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(2018/09/21)

Chemo-enzymatic synthesis of (: E)-2,3-diaryl-5-styryl- trans -2,3-dihydrobenzofuran-based scaffolds and their in vitro and in silico evaluation as a novel sub-family of potential allosteric modulators of the 90 kDa heat shock protein (Hsp90)
Herein we propose a facile, versatile and selective chemo-enzymatic synthesis of substituted (E)-2,3-diaryl-5-styryl-trans-2,3-dihydrobenzofurans based on the exploitation of the laccase-mediated oxidative (homo)coupling of (E)-4-styrylphenols. Thanks to this novel synthetic strategy, a library of benzofuran-based potential allosteric activators of the Heat shock protein 90 (Hsp90) was easily prepared. Moreover, considering their structural analogies to previously reported allosteric modulators, the sixteen new compounds synthesized in this work were tested in vitro for their potential stimulatory action on the ATPase activity of the molecular chaperone Hsp90. Combining experimental and computational results, we propose a mechanism of action for these compounds, and expand the structure-activity relationship (SAR) information available for benzofuran-based Hsp90 activators.
Bassanini, Ivan,D'Annessa, Ilda,Costa, Massimo,Monti, Daniela,Colombo, Giorgio,Riva, Sergio
p. 3741 - 3753
(2018/05/31)

Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two-step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model-aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene. (Figure presented.).
Barlow, Helen,Buser, Jonas Y.,Glauninger, Hendrik,Luciani, Carla V.,Martinelli, Joseph R.,Oram, Niall,Thompson-Van Hook, Nichole,Richardson, Jeffery
p. 2678 - 2690
(2018/06/04)

Light-catalyzed synthesis method of trans-stilbene compound
The invention relates to a light-catalyzed synthesis method of a trans-stilbene compound. Substituted iodobenzene and a substituted styrene compound perform light-catalyzed reaction in a DMF solution in the presence of a catalytic system, the reaction process is monitored by TLC, reaction liquid is subjected to separation and purification to obtain the substituted stilbene compound after the reaction is completed. By the adoption of the technology, a common dye serves as a visible-light-induced photocatalyst for catalyzed synthesis of the trans-stilbene compound according to the novel method, and the method has the advantages that reaction conditions are mild, the photocatalyst is cheap and easy to obtain, the selectivity is good, the yield is high and the like and is suitable for industrial production and application.
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(2017/08/28)

An effective Pd nanocatalyst in aqueous media: Stilbene synthesis by Mizoroki-Heck coupling reaction under microwave irradiation
Aqueous Mizoroki-Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h-1). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple product work-up make this protocol a great option for stilbene syntheses by Mizoroki-Heck reaction.
García, Carolina S.,Uberman, Paula M.,Martín, Sandra E.
p. 1717 - 1727
(2017/09/27)

Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
Reduction of hippocampal neurogenesis caused by aging and neurological disorders would impair neural circuits and result in memory loss. A new lead compound (N-trans-3′,4'-methylenedioxystilben-4-yl acetamide 27) has been discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the benzene ring. Immunohistochemical staining and biochemical analysis indicate, in contrast to previously reported neuroprotective chemicals, N-stilbenyl carboxamides have extra capacity for neuroproliferation-type neurogenesis, thereby providing a foundation for improving the plasticity of the adult mammalian brain.
Liang, Jian-Hua,Yang, Liang,Wu, Si,Liu, Si-Si,Cushman, Mark,Tian, Jing,Li, Nuo-Min,Yang, Qing-Hu,Zhang, He-Ao,Qiu, Yun-Jie,Xiang, Lin,Ma, Cong-Xuan,Li, Xue-Meng,Qing, Hong
p. 382 - 392
(2017/05/19)

Method for synthesizing artificially all-trans-resveratrol and derivative thereof
The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.
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Paragraph 0031; 0032

(2017/08/31)

Synthesis and biological evaluation of novel resveratrol-oxadiazole hybrid heterocycles as potential antiproliferative agents
A novel class of resveratrol-oxadiazole hybrid compounds was synthesized to screen for their in vitro antiproliferative activity against three human cancer cell lines. All the compounds showed superior antiproliferative activity than the reference compound resveratrol. The most promising active compounds in this series were 1g, 2g, 1c, 2c, 2i and 1a (GI50 0.1 μM), endowed with excellent antiproliferative activity. Thus, we believe that resveratrol-oxadiazole hybrid compounds may possibly be used as a good leads for the development of new antiproliferative agents. Structures of newly synthesized compounds were confirmed by NMR and IR spectral data.
Murty,Penthala, Raju,Polepalli, Sowjanya,Jain
p. 627 - 643
(2016/03/08)

Anxiolytic Effect of Pterostilbene
We report for the first time that pterostilbene, a natural analog of resveratrol, shows anxiolytic-like action by downregulating phosphorylated levels of ERKs in the hippocampus of mice. Mice administered pterostilbene (1-10 mg/kg BW) by oral gavage were subjected to the Elevated-plus maze (EPM) test. Pterostilbene manifested anxiolytic activity at 1 and 2 mg/kg doses, demonstrated by an increase in percent permanence time and number of entries in open arms, critical determinants correlated with anxiety. This anxiolytic activity of pterostilbene was comparable to that of diazepam at 1 and 2 mg/kg in the EPM. The percent traveled distance and the percent permanence time in the enclosed arms were decreased with the 1 and 2 mg/kg doses. The 5 and 10 mg/kg doses did not show any anxiolytic effect. Locomotor activity was unaffected in all doses. Western blot analysis corroborated the observed behaviors in the EPM, revealing a decrease in both ERK1 and ERK2 phosphorylation in hippocampal homogenates from mice treated with 1 and 2 mg/kg doses; the 5 and 10 mg/kg doses showed no significant effect on the phosphorylation of ERKs. Pterostilbene was detected in serum and brain tissue following a single oral administration, demonstrating that the compound can cross the blood-brain barrier to reach the brain regions, including hippocampus, and thereby exert its anxiolytic effect. Resveratrol, the parent molecule of pterostilbene, did not have any anxiolytic effect.
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Paragraph 0052

(2016/04/20)

Antifungal activity of resveratrol derivatives against Candida Species
trans-Resveratrol (1a) is a phytoalexin produced by plants in response to infections by pathogens. Its potential activity against clinically relevant opportunistic fungal pathogens has previously been poorly investigated. Evaluated herein are the candidacidal activities of oligomers (2a, 3-5) of 1a purified from Vitis vinifera grape canes and several analogues (1b-1j) of 1a obtained through semisynthesis using methylation and acetylation. Moreover, trans-ε-viniferin (2a), a dimer of 1a, was also subjected to methylation (2b) and acetylation (2c) under nonselective conditions. Neither the natural oligomers of 1a (2a, 3-5) nor the derivatives of 2a were active against Candida albicans SC5314. However, the dimethoxy resveratrol derivatives 1d and 1e exhibited antifungal activity against C. albicans with minimum inhibitory concentration (MIC) values of 29-37 μg/mL and against 11 other Candida species. Compound 1e inhibited the yeast-to-hyphae morphogenetic transition of C. albicans at 14 μg/mL.
Houillé, Benjamin,Papon, Nicolas,Boudesocque, Leslie,Bourdeaud, Eric,Besseau, Sébastien,Courdavault, Vincent,Enguehard-Gueiffier, Cécile,Delanoue, Guillaume,Guérin, Laurence,Bouchara, Jean-Philippe,Clastre, Marc,Giglioli-Guivarc'H, Nathalie,Guillard, Jér?me,Lanoue, Arnaud
p. 1658 - 1662
(2014/08/18)

CuI/1,10-phen/PEG promoted decarboxylation of 2,3-diarylacrylic acids: Synthesis of stilbenes under neutral and microwave conditions with an in situ generated recyclable catalyst
A series of trans- or cis-stilbenes have been synthesized in good to excellent yields via a functional group-dependent decarboxylation process from the corresponding 2,3-diaryl acrylic acids in a neutral CuI/1,10-phen/PEG-400 system under microwave conditions. The in situ generation of the recyclable catalytic complex, the use of environmentally benign solvent PEG-400, the operational simplicity, the short reaction times, as well as the functional group-dependent chemo- and stereo-selectivity have made the decarboxylation process a highly efficient and applicable protocol.
Zou, Yong,Huang, Qi,Huang, Tong-Kun,Ni, Qing-Chun,Zhang, En-Sheng,Xu, Tian-Long,Yuan, Mu,Li, Jun
p. 6967 - 6974
(2013/10/08)

A scalable process for the synthesis of (E)-pterostilbene involving aqueous Wittig olefination chemistry
A synthetic approach toward the pharmacologically active (E)-stilbene pterostilbene is described using a Wittig reaction conducted under mildly basic, aqueous conditions. A surprising, non-intuitive difference in (E)/(Z) stereoselectivity was observed comparing the two possible isomeric Wittig routes, allowing for the development of a highly efficient process to access the title stilbene derivative through a one-pot olefination deprotection sequence.
McNulty, James,McLeod, David
p. 6303 - 6306
(2013/11/06)

Synthesis of pterostilbene by julia olefination
A simple, E-stereoselective route for the synthesis of the biologically active compounds trans-pterostilbene and tetramethoxy stilbene from the readily available starting materials 3,5-dimethoxy benzyl alcohol and 4-hydroxy benzaldehyde was developed using Julia olefination as a key reaction. Taylor & Francis Group, LLC.
Peddikotla, Prabhakar,Chittiboyina, Amar G.,Khan, Ikhlas A.
p. 3217 - 3223
(2014/01/06)

Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
p. 3674 - 3691
(2013/06/27)

Anti-Obesity Properties of Pterostilbene
We have determined that pterostilbene demonstrates anti-obesity properties. Rats were fed a commercial obesogenic diet supplemented or not with pterostilbene: PT15 (low dose: 15 mg/kg body weight/d) or PT30 (high dose: 30 mg/kg body weight/d) for 6 weeks. Pterostilbene significantly reduced total adipose tissue mass (15.1% in the PT15 group; 22.9% in the PT30 group) without changes in food intake. The activities of lipogenic enzymes were reduced in white adipose tissue and liver. Activities of enzymes involved in liver fatty acid oxidation were significantly increased in the PT30 group. Low dose pterostilbene can reduce body fat by reducing lipogenesis in adipose tissue. At the high dose, two mechanisms contribute to reduction in body fat: (1) decrease in adipose tissue and liver lipogenesis, and (2) an increase in liver fatty acid oxidation.
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Paragraph 0050

(2013/11/19)

Tandem heck/decarboxylation/heck strategy: Protecting-group-free synthesis of symmetric and unsymmetric hydroxylated stilbenoids
Ride the (micro)wave: The title strategy has been developed for the synthesis of various symmetric or unsymmetric hydroxylated stilbenoids utilizing 4-halophenols and acrylic acid as coupling partners (see scheme; DMA=N,N-dimethylacetamide, MW=microwave). Protecting groups are not necessary and a single palladium catalyst is used. Copyright
Shard, Amit,Sharma, Naina,Bharti, Richa,Dadhwal, Sumit,Kumar, Rajesh,Sinha, Arun K.
p. 12250 - 12253
(2013/02/22)

Hydroxyl substitutional effect on selective synthesis of CIS, trans stilbenes and 3-arylcoumarins through perkin condensation
The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%). Copyright Taylor & Francis Group, LLC.
Xiao, Chun-Fen,Zou, Yong,Du, Jian-Li,Sun, Hong-Yi,Liu, Xian-Ke
experimental part
p. 1243 - 1258
(2012/04/04)

Synthesis and evaluation of 18F-labeled styryltriazole and resveratrol derivatives for β-amyloid plaque imaging
In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for β-amyloid (Aβ) plaque imaging. On the basis of their binding affinities to Aβ(1-42) aggregates, the styryltriazole (1, Ki = 12.8 nM) and one resveratrol derivative (5, Ki = 0.49 nM) were labeled with 18F. In normal mice, tissue distribution of [18F]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [18F]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [ 18F]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [18F]1 is a desirable PET radioligand for Aβ plaque imaging.
Lee, Iljung,Choe, Yearn Seong,Choi, Joon Young,Lee, Kyung-Han,Kim, Byung-Tae
p. 883 - 892
(2012/04/04)

Synthesis and biological evaluation of novel (E) stilbene-based antitumor agents
Several new (E) stilbenes were synthesized by a combination of a Wittig olefination followed by Mizoroki-Heck coupling reactions. These compounds were screened for antitumor activity in a panel of 8 human cancer cell lines by a colorimetric SRB assay. Several of these compounds exhibit strong cytotoxicity. The most active compound of this series showed an average IC50 value of 0.03 μmol; it acts by apoptosis as shown by a dye-exclusion test, an extra acridine orange/ethidium bromide staining and DNA-laddering experiments.
Csuk, Rene,Albert, Sabrina,Siewert, Bianka,Schwarz, Stefan
experimental part
p. 669 - 678
(2012/09/07)

Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.
Chalal, Malik,Vervandier-Fasseur, Dominique,Meunier, Philippe,Cattey, Hélène,Hierso, Jean-Cyrille
p. 3899 - 3907
(2012/07/14)

Extraordinary radical scavengers: 4-mercaptostilbenes
In the past decade, there was a great deal of interest and excitement in developing more active antioxidants and cancer chemoprevention agents than resveratrol, a naturally occurring stilbene. In this work, eight resveratrol-directed 4-mercaptostilbenes were constructed based on the inspiration that thiophenol should be a stronger radical scavenger than phenol, and their reaction rates with galvinoxyl (GO.) and 2,2-diphenyl-1-picrylhydrazyl (DPPH.) radicals in methanol and ethyl acetate were measured by using stopped-flow UV/Vis spectroscopy at 25 °C. Kinetic analysis demonstrates that 4-mercaptostilbenes are extraordinary radical scavengers, and the substitution of the 4-SH group for the 4-OH group in the stilbene scaffold is an important strategy to improve the radical-scavenging activity of resveratrol. Surprisingly, in methanol, some of the 4-mercaptostilbenes are 104-times more active than resveratrol, dozens of times to hundreds of times more effective than known antioxidants (α-tocopherol, ascorbic acid, quercetin, and trolox). The detailed radical-scavenging mechanisms were discussed based on acidified-kinetic analysis. Addition of acetic acid remarkably reduced the GO. and DPPH. radical-scavenging rates of the 4-mercaptostilbenes in methanol, a solvent that supports ionization, suggesting that the reactions proceed mainly through a sequential proton loss electron transfer mechanism. In contrast, an interesting acid-promoted kinetics was observed for the reactions of the 4-mercaptostilbenes with DPPH. in ethyl acetate, a solvent that weakly supports ionization. The increased ratio in rates is closely correlated with the electron-rich environment in the molecules, suggesting that the acceleration could benefit from the contribution of the electron transfer from the 4-mercaptostilbenes and DPPH.. However, the addition of acetic acid had no influence on the GO.-scavenging rates of the 4-mercaptostilbenes in ethyl acetate, due to the occurrence of the direct hydrogen atom transfer. Our results show that the radical-scavenging activity and mechanisms of 4-mercaptostilbenes depends significantly on the molecular structure and acidity, the nature of the attacking radical, and the ionizing capacity of the solvent. Copyright
Cao, Xiao-Yan,Yang, Jie,Dai, Fang,Ding, De-Jun,Kang, Yan-Fei,Wang, Fu,Li, Xiu-Zhuang,Liu, Guo-Yun,Yu, Sha-Sha,Jin, Xiao-Ling,Zhou, Bo
p. 5898 - 5905
(2012/06/30)

Synthesis and antimicrobial activity of (E) stilbene derivatives
Plants use multiple defence mechanisms comprising both constitutive and inducible barriers to prevent entering of phytopathogenic micro-organisms. In many plant species one of the most efficient responses to combat attacking microbes is the rapid synthesis of antimicrobial low molecular weight phytoalexins, for example, resveratrol, 3,5,4′-trihydroxystilbene (1). Resveratrol and its natural derivatives, however, display only moderate antimicrobial effects. Nevertheless, resveratrol may be a useful lead structure for the chemical synthesis of antimicrobials. In this study, several series of stilbenes have been synthesized, starting from the aldehydes using Wittig reactions to access the corresponding styrenes that were subjected to Mizoroki-Heck reactions to yield the stilbenes in good yields. The stilbenes were tested in an agar diffusion assay against several bacteria and fungi. For some of these compounds the inhibiting zones for bacteria and fungi were comparable with those of the antibiotics tetracycline, streptomycin, ampicillin, or kanamycin, directed against prokaryotes, and nourseothricin or hygromycin controlling fungi, respectively.
Albert, Sabrina,Horbach, Ralf,Deising, Holger B.,Siewert, Bianka,Csuk, René
p. 5155 - 5166
(2011/10/04)

Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes
Resveratrol is a polyphenol isolated from many natural sources including grapes, mulberries, eucalyptus, spruce, lilies, and peanuts. The hydroxyl groups in polyphenols can be substituted with various functional groups, allowing production of multiple derivatives. NMR spectroscopy is used to identify new derivatives. Since the complete NMR data of the known derivatives can be useful for identification of the newly isolated derivatives, here, we report the synthesis of 14 methoxylated stilbenes and four 1,2-diphenylethanes and their NMR data.
Jo, Geunhyeong,Hyun, Jiye,Hwang, Doseok,Lee, Young Han,Koh, Dongsoo,Lim, Yoongho
scheme or table
p. 374 - 377
(2011/12/04)

2-pyridyl sulfoxide: A versatile and removable directing group for the PdII-catalyzed direct C-H olefination of arenes
Removable and versatile: The 2-pyridylsulfinyl group has proved to be an efficient directing group in the PdII-catalyzed aryl ortho C-H olefination. This catalyst system enables the sequential double olefination to give asymmetrically di-ortho-functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3-disubstituted arenes, or transformed into a thiol group.
Garcia-Rubia, Alfonso,Fernandez-Ibanez, M. Ungeles,Gomez Arrayas, Ramon,Carretero, Juan Carlos
p. 3567 - 3570
(2011/05/12)

Determination and imaging of metabolites from Vitis vinifera leaves by laser desorption/ionisation time-of-flight mass spectrometry
Analysis of grapevine phytoalexins at the surface of Vitis vinifera leaves has been achieved by laser desorption/ionisation time-of-flight mass spectrometry (LDI-ToFMS) without matrix deposition. This simple and rapid sampling method was successfully applied to map small organic compounds at the surface of grapevine leaves. It was also demonstrated that the laser wavelength is a highly critical parameter. Both 266 and 337nm laser wavelengths were used but the 266nm wavelength gave increased spatial resolution and better sensitivity for the detection of the targeted metabolites (resveratrol and linked stilbene compounds). Mass spectrometry imaging of grapevine Cabernet Sauvignon leaves revealed specific locations with respect to Plasmopara viticola pathogen infection or light illumination.
Hamm, Gregory,Carre, Vincent,Poutaraud, Anne,Maunit, Benoit,Frache, Gilles,Merdinoglu, Didier,Muller, Jean-Francois
scheme or table
p. 335 - 342
(2011/10/12)

Syntheses of resveratrol and its hydroxylated derivatives as radical scavenger and tyrosinase inhibitor
Eight hydroxylated stilbene derivatives including resveratrol, desoxyrhapontigenin and piceatannol as potential radical scavenger and tyrosinase inhibitor are synthesized using optimized Wittig-Horner reaction for excellent trans-selectivity in good yields. Antioxidant activity was tested against ABTS radical and tyrosinase inhibitory activity was performed with L-tyrosine as the substrate based on previous procedure with some modification. In general, catecholic stilbenes showed stronger activity against ABTS radical and resorcinolic moiety showed stronger tyrosinase inhibitory activity. Synthetic piceatannol which containing both catecholic and resorcinolic moieties showed the strongest activity in both as ABTS radical scavenger and tyrosinase inhibitor with IC50 values of 4.1 and 8.6 μM, respectively.
Lee, Hyun Suck,Lee, Byung Won,Kim, Mi Ran,Jun, Jong-Gab
experimental part
p. 971 - 975
(2010/10/21)

Modified approach for preparing (E)-Stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed as E-isomers only (using Wittig-Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-a were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.
Smidrkal, Jan,Harmatha, Juraj,BudiSinsky, Milo,Vokae, Karel,ZIDEKc, Zdenik,Kmoniekova, Eva,Merkl, Roman,Filip, Vladimir
experimental part
p. 175 - 186
(2010/07/10)

A KEY INTERMEDIATE FOR THE PREPARATION OF STILBENES
The present invention provides a scalable process for the preparation of Stilbenes by (i) condensing 3,5-dialkylbenzyl phosphonates with 4'-O-tetrahydropyranyl benzaldehyde to get 3,5-alkyl-4'-O-tetrahydropyranyl Stilbene (ii) deprotecting the obtained 3,5-Dialkyl- 4'-O-tetrahydropyranylstilbene yields Stilbenes. The present invention also provides a novel intermediate 3,5-Dialkyl-4'-O-tetrahydropyranylstilbene, which is a key intermediate for the synthesis of Stilbenes such as Pterostilbene and Resveratrol.
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(2010/04/03)

Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer
A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 μM) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 μM. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC 50 1.7 μM and 0.27 μM, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer.
Sun, Bin,Hoshino, Juma,Jermihov, Katie,Marler, Laura,Pezzuto, John M.,Mesecar, Andrew D.,Cushman, Mark
experimental part
p. 5352 - 5366
(2010/09/05)

Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent
An emulsion cosmetic composition comprising at least one resveratrol derivative, an aqueous phase, and an oil phase having at and at least one oil phase structuring agent, and a method for preparing emulsions capable of delivering active resveratrol to the skin.
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(2009/07/02)

Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Silicone Surfactant
An emulsion cosmetic composition comprising at least one resveratrol derivative, an aqueous phase, and an oil phase, having at least one silicone surfactant, and a method for preparing emulsions capable of delivering active resveratrol to the skin.
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(2009/07/02)

Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
An aqueous based cosmetic composition comprising at least one resveratrol derivative and a water phase containing at least one aqueous phase structuring agent; or an emulsion composition comprising at least one water phase, at least one oil phase containing at least one nonvolatile silicone, and at least one resveratrol derivative.
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(2009/07/02)

Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
An emulsion cosmetic composition comprising at least one resveratrol derivative, a water phase, and an oil phase containing at least one linear or branched volatile or near volatile silicone and a method for delivering active resveratrol to the skin.
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(2009/07/02)

Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
An anhydrous color cosmetic composition comprising at least one resveratrol derivative and particulates; and an anhydrous emulsion skin care composition.
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(2009/07/02)

Heck arylation of styrenes with arenediazonium salts: short, efficient, and stereoselective synthesis of resveratrol, DMU-212, and analogues
Short, efficient, and stereoselective synthesis of the trans-stilbenes resveratrol, DMU-212, and analogues of both compounds are described. The synthesis of these important anti-cancer agents feature the palladium catalyzed Heck-Matsuda arylation of styre
Moro, Angélica Venturini,Cardoso, Flávio Sega P.,Correia, Carlos Roque D.
p. 5668 - 5671
(2008/12/22)

PREVENTION AND TREATMENT OF COLON CANCER
Stilbene compounds for the prevention and treatment of colon cancer or colon inflammation and methods of using same are provided.
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(2008/12/06)

An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction
A mild and convenient one-pot two-step synthesis of hydroxystilbenes with trans selectivity has been developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence of piperidine-methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation-decarboxylation leading to the unusual formation of hydroxystilbenes in lieu of α-phenylcinnamic acid reveals an interesting facet to the classical Perkin reaction. The developed protocol provides a green alternative to the prevalent methods employing a toxic decarboxylating agent in the form of quinoline/Cu salt, and the requirement for harsh protection-deprotection steps for the synthesis of hydroxylated stilbenes.
Sinha, Arun K.,Kumar, Vinod,Sharma, Abhishek,Sharma, Anuj,Kumar, Rakesh
p. 11070 - 11077
(2008/02/12)

Laccase-catalyzed dimerization of hydroxystilbenes
A series of hydroxystilbenes, analogues of the bioactive phytoalexin resveratrol, were synthesized and submitted to the catalytic action of a laccase from Trametes pubescens in a biphasic system made of ethyl acetate and acetate buffer. Oxidation took place at the 4′-hydroxy (4-hydroxy) position of the hydroxystilbenic moieties, followed by radical-radical coupling dimerization reactions. Most of the products were isolated in good yields and fully characterized. Depending on the substrates, three different dimeric products could be identified, the main products usually being 4-O-α-β-5 (dihydrofuran-like) dimers.
Ponzoni, Chiara,Beneventi, Elisa,Cramarossa, Maria Rita,Raimondi, Stefano,Trevisi, Giulia,Pagnoni, Ugo Maria,Riva, Sergio,Forti, Luca
p. 1497 - 1506
(2008/09/17)

Process for the synthesis of biologically active oxygenated compounds by dealkylation of the corresponding alkylethers
Alkoxy aromatic compounds are conveniently dealkylated to the corresponding phenolic compounds by treatment with aluminum chloride/N,N-dimethyl aniline complex. Aromatic poly O-demethylation is a unique feature of this invention. This process is applicable to the manufacture of polyphenols such as Resveratrol, Oxyresveratrol, Gnetol.
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(2008/06/13)

Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: a clean synthesis of hydroxylated (E)-stilbenes
A metal-free protocol for decarboxylation of substituted α-phenylcinnamic acid derivatives in aqueous media is developed, wherein a remarkable synergism between methylimidazole and aq NaHCO3 in polyethylene glycol under microwave furnished the corresponding para/ortho hydroxylated (E)-stilbenes in a mild and efficient manner. The critical role of water in facilitating the decarboxylation imparts an interesting facet to the synthetic utility of water mediated organic transformations. The developed protocol provides a clean alternative to the hitherto indispensable multistep approaches involving toxic quinoline and a copper salt combination as the common decarboxylating agent.
Kumar, Vinod,Sharma, Abhishek,Sharma, Anuj,Sinha, Arun K.
p. 7640 - 7646
(2008/02/09)

Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers
New carbon-11 and fluorine-18 labeled stilbene derivatives, cis-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]8a), cis-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]8b), trans-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]10a), trans-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]10b), cis-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]12a), and trans-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]13a), were designed and synthesized as potential PET probes for aryl hydrocarbon receptor (AhR) in cancers.
Gao, Mingzhang,Wang, Min,Miller, Kathy D.,Sledge, George W.,Hutchins, Gary D.,Zheng, Qi-Huang
p. 5767 - 5772
(2007/10/03)

Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes
The parallel solution-phase synthesis of a series of 30 monohydroxylated (E)-stilbene analogues is described. In vitro screening revealed low micromolar activity (GI50) against the MDA MB 468 breast cancer cell line. Activity in MDA MB 468 cells correlated with the ability to induce apoptosis following drug treatment by the most potent agents in the series, e.g., 5dy and 5jy, an observation further reinforced by Annexin V-FITC analysis and fluorescence microscopy.
Lion, Cedric J.,Matthews, Charles S.,Stevens, Malcolm F. G.,Westwell, Andrew D.
p. 1292 - 1295
(2007/10/03)

Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor α-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters
Resveratrol, a stilbenoid antioxidant found in grapes, wine, peanuts and other berries, has been reported to have hypolipidemic properties. We investigated whether resveratrol and its three analogues (pterostilbene, piceatannol, and resveratrol trimethyl ether) would activate the peroxisome proliferator-activated receptor α (PPARα) isoform. This nuclear receptor is proposed to mediate the activity of lipid-lowering drugs such as the fibrates. The four stilbenes were evaluated at 1, 10, 100, and 300 μM along with ciprofibrate (positive control), for the activation of endogenous PPARα in H4IIEC3 cells. Cells were transfected with a peroxisome proliferator response element-AB (rat fatty acyl CoA β-oxidase response element)-luciferase gene reporter construct. Pterostilbene demonstrated the highest induction of PPARα showing 8- and 14-fold increases in luciferase activity at 100 and 300 μM, respectively, relative to the control. The maximal luciferase activity responses to pterostilbene were higher than those obtained with the hypolipidemic drug, ciprofibrate (33910 and 19460 relative luciferase units, respectively), at 100 μM. Hypercholesterolemic hamsters fed with pterostilbene at 25 ppm of the diet showed 29% lower plasma low density lipoprotein (LDL) cholesterol, 7% higher plasma high density lipoprotein (HDL) cholesterol, and 14% lower plasma glucose as compared to the control group. The LDL/HDL ratio was also statistically significantly lower for pterostilbene, as compared to results for the control animals, at this diet concentration. Results from in vitro studies showed that pterostilbene acts as a PPARα agonist and may be a more effective PPARα agonist and hypolipidemic agent than resveratrol. In vivo studies demonstrate that pterostilbene possesses lipid and glucose lowering effects.
Rimando, Agnes M.,Nagmani, Rangaswamy,Feller, Dennis R.,Yokoyama, Wallace
p. 3403 - 3407
(2007/10/03)

Resveratrol Derivatives and Their Role as Potassium Channels Modulators
A series of stilbenoid analogues of resveratrol (trans-3,4′ ,5-trihydroxystilbene) with a stilbenic or a bibenzylic skeleton have been prepared by partial synthesis from resveratrol and dihydroresveratrol. The synthesized compounds have been evaluated for their ability to modulate voltage-gated channels.
Orsini,Verotta,Lecchi,Restano,Curia,Redaelli,Wanke
p. 421 - 426
(2007/10/03)

Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents
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
p. 3546 - 3554
(2007/10/03)