- Complete assignment of the1H and13C NMR spectra of resveratrol derivatives
-
Contract/grant sponsor: Korea Ministry of Marine Affairs and Fishery The complete 1H and 13C chemical shift assignments of six derivatives of resveratrol [(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol] that possess leukotriene D
- Koh, Dongsoo,Park, Kwan Ha,Jung, Jihyun,Yang, Heejung,Hun Mok,Lim, Yoongho
-
-
Read Online
- η6-arene-tricarbonylchromium complexes in the syntheses of trans-resveratrol and pinostilbene
-
New syntheses of trans-resveratrol (trans-3,5,4′-trihydroxystilbene) and pinostilbene (trans-3,4′-dihydroxy-5-methoxystilbene) via nucleophilic demethylation of trimethoxystilbene were performed, whereby trans-3,5,4′-trimethoxystilbene was obtained through facilitated benzylic deprotonation of an η6-benzene-Cr(CO)3 derivative and subsequent coupling with para-anisaldehyde in an aldol-type or Wittig-Horner reaction.
- Polunin, Konstantin E.,Polunina, Irina A.,Schmalz, Hans-Guenther
-
-
Read Online
- Heterogeneous heck coupling in multivariate metal-organic frameworks for enhanced selectivity
-
Abstract Highly selective heterogeneous Heck coupling has been demonstrated inside a series of metal-organic frameworks (MOFs). These MOFs, Zn4O(BDC-NH2)n(BDC)(3 - n) (n = 3, 2.4, 1.8, 1.2, 0.9, 0.75, 0.6, 0.3,
- Brown, Jonathan W.,Jarenwattananon, Nanette N.,Otto, Trenton,Wang, James L.,Gl?ggler, Stefan,Bouchard, Louis-S.
-
-
Read Online
- Anti-allergic action of resveratrol and related hydroxystilbenes
-
Resveratrol (1) and nine related hydroxystilbene compounds (2-9) isolated from plants were evaluated for the anti-allergic activities in vitro. Resveratrol (1) and rhapontigenin (5) demonstrated significant inhibitions upon the release of β-hexosaminidase
- Cheong, Ho,Ryu, Shi-Yong,Kim, Kyeong-Man
-
-
Read Online
- Novel resveratrol-based flavonol derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo
-
In order to discover novel anti-inflammatory agents, total thirty-seven new resveratrol-based flavonol derivatives were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition effect of LPS-induced NO production in RAW 264.7 macrophages. Their toxicity was also assessed in vitro. Structure-activity relationships (SARs)have been concluded, and finally 2-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)-3-hydroxy-4H-chromen-4-one was found to be the most active scaffold with low toxicity. This compound could significantly decrease productions of NO, IL-6 and TNF-α with IC50 values of 1.35, 1.12 and 1.92 μM, respectively in RAW 264.7 macrophages. Preliminary mechanism studies indicated that it could inhibit the expression of TLR4 protein, resulting in activation of the NF-?B cell signaling pathway. The in vivo anti-inflammatory activity of this compound could reduce pulmonary inflammation by mouse model of LPS-induced acute lung injury (ALI). We believe these findings would further support studies of rational design of more efficient acute lung injury regulatory inhibitors.
- Chen, Liu Zeng,Yao, Li,Jiao, Ming Ming,Shi, Jing Bo,Tan, Yue,Ruan, Ban Feng,Liu, Xin Hua
-
-
Read Online
- A new synthesis of resveratrol
-
Resveratrol was synthesized in a 4-step synthesis using a simple Sonogashira type reaction with 93% yield using commercially available 3,5-dimethoxy-1-ethynyl-benzene and 4-iodoanisole, followed by reduction, isomerization, and deprotection and with an overall yield of 63%.
- Lara-Ochoa, Francisco,Sandoval-Minero, Leticia C.,Espinosa-Pérez, Georgina
-
-
Read Online
- Resveratrol and trimethylated resveratrol protect from acute liver damage induced by CCI4 in the rat
-
The importance of hydroxyl groups in the antioxidant and hepatoprotective properties of resveratrol was investigated. To achieve this, resveratrol or its trimethylated analog were administered (10 mg kg-1, p.o.) to male Wistar rats and liver damage was induced by acute administration of CCl 4 (4 g kg-1, p.o.); appropriate controls were performed. The animals were killed 24 h after CCl4 intoxication. The amount of reduced glutathione (GSH) in the liver was not modified by any treatment; interestingly, the GSH/GSSG (oxidized glutathione) ratio decreased in the groups receiving CCl4 and resveratrol associated with an increase in GSSG. In blood GSH and the GSH/GSSG ratio were decreased by CCl4; both effects were completely prevented by any of the compounds tested. Lipid peroxidation and the activity of γ-glutamyl transpeptidase were increased significantly after CCl4. Resveratrol partially prevented these increases and surprisingly, trimethylated resveratrol completely prevented the increase of these markers. Both compounds partially but significantly prevented the increase in the activity of alanine aminotransferase; this result agrees with observations in the histological analysis. Both tested compounds administered alone produced no effect. The results of the present study suggest that OH groups are important for the antioxidant and hepatoprotective properties of the molecule of resveratrol; nevertheless, these effects can be improved by replacing hydrogen by a methyl in these groups. The differences in the antioxidant and hepatoprotective effects of these compounds could be due to the possibility that the trimethylated resveratrol acts like a prodrug, prolonging, probably, the half-life of the original compound. Copyright
- Rivera, Horacio,Shibayama, Mineko,Tsutsumi, Victor,Perez-Alvarez, Victor,Muriel, Pablo
-
-
Read Online
- Application of chromium-arene complexes in the organic synthesis. Efficient synthesis of stilbene phytoalexins
-
Planar chiral η6-arene-Cr(CO)3 complexes represent highly valuable building blocks for the diastereo- and enantioselective synthesis. Their employment as synthons offer new and unique opportunities for the stereoselective multistep synthesis of complex natural products. The strategy of novel efficient synthesis of stilbene phytoalexins was based on arene chromium chemistry and the chemical and stereochemical effects of the metal unit on the reactivity of complexed arene ligand and stereochemical features of such compounds. Two variants for the construction of the trans-stilbene and diarylethanol framework via facilitated benzylic deprotonation of an η6benzene-Cr(CO)3 complex and subsequent coupling with para-anisaldehyde in an aldol-type or a Wittig-Horner reaction were suggested.
- Polunin,Schmalz
-
-
Read Online
- An expedient synthesis of resveratrol through a highly recoverable palladium catalyst
-
A straightforward two-step synthesis of resveratrol is described, with total isolated yields in the range of 75–80%. The key synthetic step, a Heck–Mizoroki C[sbnd]C cross-coupling reaction, is efficiently promoted by a heterogeneous catalyst consisting of palladium nanoparticles supported on synthetic clay. This solid catalyst is quite handy and displays high stability and robustness under reaction conditions. The catalyst can be easily recovered and reused at least 10 times, which improves the overall catalytic efficiency of the system. Moreover, the use of solvents is limited, and the reaction procedure allows a facile separation and purification of the desired product, free from the concomitant ionic by-product and from palladium contamination.
- Martínez, Alejandro V.,García, José I.,Mayoral, José A.
-
-
Read Online
- PACHARIN: A NEW DIBENZO(2,3-6,7)OXEPIN DERIVATIVE FROM BAUHINIA RACEMOSA LAMK
-
The isolation of resveratrol and a new dibenzoxepin derivative, pacharin, from the heartwood of Bauhinia racemosa Lamk is reported.The structure of pacharin has been established as 1,7-dihydroxy-3-methoxy-2-methyl-dibenzo(2,3-6,7)oxepin (Va) by a study of its chemical and spectroscopic properties, including X-ray analysis.
- Anjaneyulu, A. S. R.,Raghava Reddy, A. V.,Reddy, D. S. K.,Ward, R. S.,Adhikesavalu, D.,Cameron, T. Stanley
-
-
Read Online
- Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis
-
The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.
- Babu, Reshma,Balaraman, Ekambaram,Midya, Siba P.,Subaramanian, Murugan,Yadav, Vinita
-
p. 7552 - 7562
(2021/06/28)
-
- Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
-
A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
- Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua
-
supporting information
p. 5317 - 5322
(2021/06/28)
-
- Non-Chelate-Assisted Palladium-Catalyzed Aerobic Oxidative Heck Reaction of Fluorobenzenes and Other Arenes: When Does the C?H Activation Need Help?
-
The pyridone fragment in the ligand [2, 2’-bipyridin]-6(1H)-one (bipy-6-OH) enables the oxidative Heck reaction of simple arenes with oxygen as the sole oxidant and no redox mediator. Arenes with either electron-donating or electron-withdrawing groups can be functionalized in this way. Experimental data on the reaction with toluene as the model arene shows that the C?H activation step is turnover limiting and that the ligand structure is crucial to facilitate the reaction, which supports the involvement of the pyridone fragment in the C?H activation step. In the case of fluoroarenes, the alkenylation of mono and 1,2-difluoro benzenes requires the presence of bipy-6-OH. In contrast, this ligand is detrimental for the alkenylation of 1,3-difluoro, tri, tetra and pentafluoro benzenes which can be carried out using just [Pd(OAc)2]. This correlates with the acidity of the fluoroarenes, the most acidic undergoing easier C?H activation so other steps of the reaction such as the coordination-insertion of the olefin become kinetically important for polyfluorinated arenes. The use of just a catalytic amount of sodium molybdate as a base proved to be optimal in all these reactions. (Figure presented.).
- Albéniz, Ana C.,Villalba, Francisco
-
supporting information
p. 4795 - 4804
(2021/09/06)
-
- METHODS OF ARENE ALKENYLATION
-
The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).
- -
-
Page/Page column 18; 66-68
(2021/11/26)
-
- A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation
-
Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.
- Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.
-
p. 1597 - 1603
(2020/02/05)
-
- Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
-
Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25–50 μM typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 μM enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated β galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 μM many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 μM, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
- Birar, Vishal C.,Faragher, Richard G. A.,Ostler, Elizabeth L.,Sheerin, Angela N.
-
p. 817 - 826
(2020/08/17)
-
- Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo
-
Phthalide is a promising chemical scaffold and has been proved to show potent anti-inflammatory efficacy. In this study, three series, total of 31 novel phthalide derivatives were designed and synthesized, their anti-inflammatory activities were screened
- Chen, Liu Zeng,Wu, Jing,Li, Kang,Wu, Qian Qian,Chen, Rui,Liu, Xin Hua,Ruan, Ban Feng
-
-
- Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation
-
Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.
- Jia, Xiaofan,Frye, Lucas I.,Zhu, Weihao,Gu, Shunyan,Gunnoe, T. Brent
-
supporting information
p. 10534 - 10543
(2020/06/08)
-
- Antiproliferative activity of stilbene derivatives and other constituents from the stem bark of Morus nigra L
-
The antiproliferative activities of 2′,3,4′,5,5′-pentahydroxy-cis-stilbene 1, resveratrol 2, oxyresveratrol 3, norartocarpetin 4, kuwanon C 5, morusin 6, cudraflavone A7, kuwanon G 8, albafuran C 9, mulberrofuran G 10, 3-acetyl-O-α-amyrin 11, 3-acetyl-O-β
- Abdel Bar, Fatma M.,Abbas, Ghada M.,Gohar, Ahmed A.,Lahloub, Mohamed-Farid I.
-
p. 3506 - 3513
(2019/03/11)
-
- Parallel in vitro and in silico investigations into anti-inflammatory effects of non-prenylated stilbenoids
-
Stilbenoids represent a large group of bioactive compounds, which occur in food and medicinal plants. Twenty-five stilbenoids were screened in vitro for their ability to inhibit COX-1, COX-2 and 5-LOX. Piceatannol and pinostilbene showed activity comparable to the zileuton and ibuprofen, respectively. The anti-inflammatory potential of stilbenoids was further evaluated using THP-1 human monocytic leukemia cell line. Tests of the cytotoxicity on the THP-1 and HCT116 cell lines showed very low toxic effects. The tested stilbenoids were evaluated for their ability to attenuate the LPS-stimulated activation of NF-κB/AP-1. Most of the tested substances reduced the activity of NF-κB/AP-1 and later attenuated the expression of TNF-α. The effects of selected stilbenoids were further investigated on inflammatory signaling pathways. Non-prenylated stilbenoids regulated attenuation of NF-?B/AP-1 activity upstream by inhibiting the phosphorylation of MAPKs. A docking study used to in silico analyze the tested compounds confirmed their interaction with NF-?B, COX-2 and 5-LOX.
- Leláková, Veronika,?mejkal, Karel,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Václavík, Ji?í,Bobá?, Pavel,Pí?ová, Hana,Temml, Veronika,Steinacher, Theresa,Schuster, Daniela,Granica, Sebastian,Hanáková, Zuzana,Ho?ek, Jan
-
p. 431 - 440
(2019/02/19)
-
- Preparation method of resveratrol
-
The invention belongs to the technical field of preparation of medicine key intermediates, and particularly relates to a preparation method of resveratrol. The synthesis and preparation method of theresveratrol comprises the following steps: a, taking 3, 5-dimethoxybenzyl alcohol and phosphorus tribromide as raw materials, and synthesizing 3, 5-dimethoxybenzyl bromide (a compound A); b, taking the compound A, triethyl phosphite and tetrabutylammonium bromide as raw materials, and synthesizing to obtain 3, 5-dimethoxy benzyl diethyl phosphate (a compound B); c, taking the compound B, dimethyldiamide, sodium hydride and anisaldehyde as raw materials, and carrying out a reaction to synthesize to obtain (E) 3, 4 ', 5-trimethoxystilbene (compound C); and d, using the compound C and pyridine hydrochloride as raw materials, carrying out a reaction to synthesize 3, 4, 5-trihydroxy-1, 2-stilbene, namely the resveratrol. The method has the characteristics of cheap and easily available raw materials, mild reaction conditions, simple operation, high yield and low cost, and is beneficial to industrial production.
- -
-
Paragraph 0031; 0033
(2019/12/29)
-
- 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)
-
- Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase
-
Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-κB (NF-κB) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.
- Ho?ek, Jan,Leláková, Veronika,Bobál, Pavel,Pí?ová, Hana,Gazdová, Markéta,Malaník, Milan,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Temml, Veronika,Schuster, Daniela,Prachyawarakorn, Vilailak,Pailee, Phanruethai,Ren, Gang,Zpurny, Filip,Oravec, Michal,?mejkal, Karel
-
p. 1839 - 1848
(2019/08/20)
-
- Novel resveratrol as well as derivative synthesis method and application thereof
-
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.
- -
-
Paragraph 0065; 0070-0071
(2019/08/02)
-
- Resveratrol-phthalide heterozygosis compounds and preparing method and application thereof
-
The invention discloses resveratrol-phthalide heterozygosis compounds and a preparing method and application thereof. The structural general formula of the resveratrol-phthalide heterozygosis compounds is shown in the description, wherein R is selected fr
- -
-
Paragraph 0034-0036
(2019/10/01)
-
- 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%.
- -
-
Paragraph 0067; 0068; 0070; 0071; 0074; 0075
(2019/07/16)
-
- Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2
-
A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.
- Landge, Vinod G.,Yadav, Vinita,Subaramanian, Murugan,Dangarh, Pragya,Balaraman, Ekambaram
-
supporting information
p. 6130 - 6133
(2019/06/03)
-
- Resveratrol nitroethylene compound as well as preparation method and application thereof (by machine translation)
-
The invention discloses a resveratrol nitroethylene compound as well as a preparation method and application, and relates to the technical field of drug design and synthesis, and has the following general formula: The resveratrol nitroethylene compound, p
- -
-
Paragraph 0024; 0027
(2019/08/06)
-
- Cobalt catalyzed stereodivergent semi-hydrogenation of alkynes using H2O as the hydrogen source
-
Cobalt-catalyzed stereodivergent semi-hydrogenation of internal alkynes to alkenes is developed. The reaction proceeded through transfer hydrogenation under mild conditions using a base metal CoI2 as the catalyst, and H2O/MeOH as the hydrogen source with Zn as the reductant. The E/Z-selectivity of the product could be switched by changing the solvent and by inclusion/exclusion of a bidentate phosphine ligand (dppe). This method provides a simple and cost effective pathway for the synthesis of 1,2-dideuterioalkenes.
- Li, Kangkui,Khan, Ruhima,Zhang, Xuexin,Gao, Yang,Zhou, Yongyun,Tan, Heng,Chen, Jingchao,Fan, Baomin
-
supporting information
p. 5663 - 5666
(2019/05/21)
-
- Xanthate-mediated synthesis of (E)-alkenes by semi-hydrogenation of alkynes using water as the hydrogen donor
-
Semi-hydrogenation of alkynes is one of the most widely used methods for obtaining alkenes in laboratory preparation and in industry. Transition metal catalysts have been extensively studied for this transformation, but the tolerance of functional groups, such as pyridine,-OH,-NH2,-Bpin, and halides, and the toxicity of the trace amount of transition metal catalysts are still highly challenging. In this study, we report a general and robust strategy to achieve the semi-hydrogenation of alkynes using inexpensive and commercially available xanthate as the mediator. Mechanism studies support a non-radical process and H2O acts as the hydrogen donor.
- Luo, Xianglin,Chen, Xiuwen,Chen, Lu,Zhang, Kun,Li, Yibiao
-
supporting information
p. 2170 - 2173
(2019/02/24)
-
- O -Iodoxybenzoic acid mediated generation of aryl free radicals: Synthesis of stilbenes through C-C cross-coupling with β-nitrostyrenes
-
The generation of an aryl free radicals in the presence of nitrostyrenes through a combination of aryl hydrazines and o-iodoxybenzoic acid led to the synthesis of stilbenes by forming a new carbon-carbon bond after subsequent elimination of a nitrosyl radical. The symmetrical and unsymmetrical stilbenes with excellent E-selectivity were synthesized in good yields, with advantages of broad substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,3-dimethoxy-5-(4-methoxystyryl)benzene.
- Wagh, Ganesh,Autade, Snehalata,Patil, Pravin C.,Akamanchi, Krishnacharya G.
-
p. 3301 - 3309
(2018/03/06)
-
- Direct Wittig Olefination of Alcohols
-
A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination products. By the strategy of simultaneously in situ generation of ylides and aldehydes, for the first time, alcohols are directly transferred to olefins with no need of prepreparation of either aldehydes or ylides. Thus, the di/monocontrollable olefination of diols is accomplished. This synthetically practical method has been applied in the gram-scale synthesis of pharmaceuticals, such as DMU-212 and resveratrol from alcohols.
- Li, Qiang-Qiang,Shah, Zaher,Qu, Jian-Ping,Kang, Yan-Biao
-
p. 296 - 302
(2018/02/19)
-
- Preparation method of resveratrol
-
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.
- -
-
Paragraph 0035-0040
(2018/11/03)
-
- Synthesis method of resveratrol
-
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.
- -
-
-
- Synthesis method of resveratrol
-
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.
- -
-
-
- One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes
-
The phospha-Peterson reaction between a lithiated secondary phosphane, MesP(Li)TMS, and an aldehyde affords Mes-phosphaalkenes which, upon methanol addition and P-oxidation, react with a second carbonyl compound site specifically to produce unsymmetric alkenes. The E/Z selectivity of the one-pot cross coupling is largely determined by the electronic nature of the aryl substituent of the first aldehyde, with electron-donating groups giving rise to increased amounts of Z-alkenes.
- Arkhypchuk, Anna I.,D'Imperio, Nicolas,Ott, Sascha
-
supporting information
p. 5086 - 5089
(2018/09/13)
-
- Alkylated resveratrol prodrugs and metabolites as potential therapeutics for neurodegenerative diseases
-
Resveratrol is a naturally occurring stilbene which has shown promising results as treatment for several neurodegenerative diseases. However, its application is limited due to its low efficacy and bioavailability. Here, we have designed and synthesized alkylated resveratrol prodrugs combining structural modification to improve antioxidant and anti-inflammatory properties and the preparation of prodrugs to extend drug bioavailability. For comparison we also studied resveratrol prodrugs and alkylated resveratrol derivatives. Methylated and butylated resveratrol derivatives showed the best in vitro neuroprotective and anti-inflammatory activity. The glucosyl- and glucosyl-acyl- prodrugs of these derivatives showed lower toxicity on zebra fish embryo. When neuroprotection was examined on pentylenetetrazole challenged zebra fish, they were capable of reverting neuronal damage but to a lower extent than resveratrol. Nevertheless, 3-O-(6′-O-octanoyl)-β-D-glucopyranoside resveratrol (compound 8) recovered AChE activity over 100% whereas resveratrol only up to 92%. In a 3-nitropropionic acid mice model of Huntington's disease, resveratrol derivative 8 delayed the onset and reduced the severity of HD-like symptoms, by improving locomotor activity and protecting against weight loss. Its effects involved an equal antioxidant but better anti-inflammatory profile than resveratrol as shown by SOD2 expression in brain tissue and circulating levels of IL-6 (11 vs 18 pg/mL), respectively. Finally, the octanoyl chain in compound 8 could be playing a role in inflammation and neuronal development indicating it could be acting as a double-drug, instead of as a prodrug.
- Pe?alver, Pablo,Belmonte-Reche, Efres,Adán, Norma,Caro, Marta,Mateos-Martín, María Luisa,Delgado, Mario,González-Rey, Elena,Morales, Juan Carlos
-
p. 123 - 138
(2018/02/10)
-
- Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction
-
Abstract: Five different Ru metal precursors were reduced in imidazolium based ionic liquids under hydrogen atmosphere (4?bar) at 50 °C to obtain well-dispersed and stable Ru nanoparticles. Transmission electron microscopy (TEM) analysis confirmed size of well dispersed ionic liquid mediated Ru particles (Ru NPs) of 5?nm (±0.5) in diameter. These ruthenium nanoparticles (in ionic liquids) were used for Wittig type olefination reaction under mild reaction environment (70 °C and 1?h). The corresponding stilbenes were obtained in good yield with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212. Graphical Abstract: [Figure not available: see fulltext.]
- Srivastava, Vivek
-
p. 693 - 703
(2017/03/08)
-
- Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
-
The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn
- Moodie, Lindon W. K.,Trepos, Rozenn,Cervin, Gunnar,Brathen, Kari Anne,Lindgard, Bente,Reiersen, Rigmor,Cahill, Patrick,Pavia, Henrik,Hellio, Claire,Svenson, Johan
-
supporting information
p. 2001 - 2011
(2017/08/04)
-
- Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System
-
The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.
- El-Deeb, Ibrahim Yussif,Funakoshi, Tatsuya,Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
-
p. 2630 - 2640
(2017/03/14)
-
- Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
-
A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.
- Nakao, Syuhei,Mabuchi, Miyuki,Wang, Shenglan,Kogure, Yoko,Shimizu, Tadashi,Noguchi, Koichi,Tanaka, Akito,Dai, Yi
-
supporting information
p. 3167 - 3172
(2017/06/13)
-
- Development of resveratrol-curcumin hybrids as potential therapeutic agents for inflammatory lung diseases
-
Acute lung injury (ALI) is a major cause of acute respiratory failure in critically-ill patients. Resveratrol and curcumin are proven to have potent anti-inflammatory efficacy, but their clinical application is limited by their metabolic instability. Here, a series of resveratrol and the Mono-carbonyl analogs of curcumin (MCAs) hybrids were designed and synthesized by efficient aldol construction strategy, and then screened for anti-inflammatory activities in vitro and in vivo. The results showed that the majority of analogs effectively inhibited the LPS-induced production of IL-6 and TNF-α. Five analogs, a9, a18, a19, a20 and a24 exhibited excellent anti-inflammatory activity in a dose-dependent manner along with low toxicity in vitro. Structure activity relationship study revealed that the electron-withdrawing groups at meta-position and methoxyl group ([sbnd]OCH3) at the para position of the phenyl ring were important for anti-inflammatory activities. The most promising compound a18 decreased LPS induced TNF-α, IL-6, IL-12, and IL-33 mRNA expression. Additionally, a18 significantly protected against LPS-induced acute lung injury in the in vivo mouse model. The research of resveratrol and MCAs hybrids could bring insight into the treatment of inflammatory diseases and compound a18 may serve as a lead compound for the development of anti-ALI agents.
- Pan, Jialing,Xu, Tingting,Xu, Fengli,Zhang, Yali,Liu, Zhiguo,Chen, Wenbo,Fu, Weitao,Dai, Yuanrong,Zhao, Yunjie,Feng, Jianpeng,Liang, Guang
-
p. 478 - 491
(2016/10/04)
-
- Green hydroselenation of aryl alkynes: Divinyl selenides as a precursor of resveratrol
-
A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60°C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.
- Perin, Gelson,Barcellos, Angelita M.,Luz, Eduardo Q.,Borges, Elton L.,Jacob, Raquel G.,Lenard?o, Eder J.,Sancineto, Luca,Santi, Claudio
-
-
- Synthesis of trans-resveratrol using modified Julia olefination route
-
Bioactive hydroxystilbinoid-trans-resveratrol [(E)-3,5,4′ trihydroxy stilbene, 1] has been synthesized by modified Julia olefination method. The reaction between corresponding carbanion of benzothiazol-2-yl sulfone derivative and p-anisaldehyde dimethyl acetal with sodium hydride as a base, affords mainly cis-3,5,4′ trimethoxystilbene 10b with minor quantity of trans-isomev. Both the isomers have been separated in pure form and confirmed by their NMR spectral data. Demethylation of cis-3,5,4′ trimethoxystilbene either with AlCVpyridine or AlCl3/triethylamine results in the formation of trans-resveratrol.
- Shenvi, Suvarna,Shivanna, Shivaprakash,Reddy, G. Chandrasekara
-
p. 1035 - 1038
(2017/11/10)
-
- Nickel-catalyzed synthesis of (E)-olefins from benzylic alcohol derivatives and arylacetonitriles via C-O activation
-
An efficient Ni-catalyzed synthesis of (E)-olefins using the readily available benzylic alcohol derivatives and arylacetonitriles is described. This transformation should proceed via a tandem process involving nickel-catalyzed cross coupling via C-O activation and subsequent stereoselective E2 elimination.
- Xiao, Jing,Yang, Jia,Chen, Tieqiao,Han, Li-Biao
-
p. 2157 - 2160
(2016/02/05)
-
- Method for preparing resvertrol (by machine translation)
-
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)
- -
-
Paragraph 0027; 0028; 0033
(2016/10/31)
-
- TRPA1 channels as targets for resveratrol and related stilbenoids
-
A series of twenty resveratrol analogues was synthesized and tested on TRPA1 and TRPV1 channels. None was able to significantly modulate TRPV1 channels. Conversely, most of them exhibited remarkably higher TRPA1 modulating activity than resveratrol. Optimal potency was observed with ortho monoxygenated stilbenes 6 and 17.
- Nalli, Marianna,Ortar, Giorgio,Moriello, Aniello Schiano,Morera, Enrico,Di Marzo, Vincenzo,De Petrocellis, Luciano
-
p. 899 - 902
(2016/05/24)
-
- Convenient One-Step Synthesis of Benzo[c]phenanthridines by Three-Component Reactions of Isochromenylium Tetrafluoroborates and Stilbenes in Acetonitrile
-
A new type of three-component reaction of air-stable isochromenylium tetrafluoroborates with electron-rich stilbenes in acetonitrile has been developed under catalyst-free conditions in this work. This cascade multibond-formation reaction is initiated by an intermolecular oxa [4 + 2]-cycloaddition, relayed with a nucleophilic addition of acetonitrile, and terminated by an intramolecular Friedel-Crafts reaction, affording the corresponding benzo[c]phenanthridine analogues in one step.
- Chen, Gang-Gang,Wei, Jun-Qiang,Yang, Xiaoliang,Yao, Zhu-Jun
-
supporting information
p. 1502 - 1505
(2016/05/02)
-
- Design and synthesis of resveratrol-salicylate hybrid derivatives as CYP1A1 inhibitors
-
Resveratrol and aspirin are known to exert potential chemopreventive effects through modulation of numerous targets. Considering that the CYP450 system is responsible for the activation of environmental procarcinogens, the aim of this study was to design a new class of hybrid resveratrol-aspirin derivatives possessing the stilbene and the salicylate scaffolds. Using HepG2 cells, we evaluated (a) the inhibition of TCDD-mediated induction of CYP1A1 exerted by resveratrol-aspirin derivatives using the EROD assay, and (b) CYP1A1 mRNA in vitro. We observed significant inhibition (84%) of CYP1A1 activity and a substantial decrease in CYP1A1 mRNA with compound 3, compared to control. Resveratrol did not exert inhibition under the same experimental conditions. This inhibitory profile was supported by docking studies using the crystal structure of human CYP1A1. The potential effect exerted by compound 3 (the most active), provide preliminary evidence supporting the design of hybrid molecules combining the chemical features of resveratrol and aspirin.
- Aldawsari, Fahad S.,Elshenawy, Osama H.,El Gendy, Mohamed A. M.,Aguayo-Ortiz, Rodrigo,Baksh, Shairaz,El-Kadi, Ayman O. S.,Velázquez-Martínez, Carlos A.
-
p. 884 - 895
(2015/11/09)
-
- Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition
-
A small library of polymethoxystilbene glycosides (20-25) related to the natural polyphenol resveratrol have been synthesized and subjected, together with their aglycones 17-19, to an antiproliferative activity bioassay toward Caco-2 and SH-SY5Y cancer cells. Six of the compounds exhibit antiproliferative activity against at least one cell line. In particular, compounds 17 and 18 proved highly active on at least one of the two cell cultures. Compound 18 showed a GI50 value of 3 ΜM against Caco-2 cells, a value comparable to that of the anticancer drug 5-fluorouracil. The closely related compound 19 proved inactive, and its conjugates 22 and 25 showed weak cell growth inhibition. The results indicate that minimal differences in the structure of both polymethoxystilbenes and their glycosides can substantially affect the antiproliferative activity. The possible hydrolytic release of the aglycones 17-19 by β-glucosidase or β-galactosidase was also evaluated. Compounds 20-25 were also tested as potential β-glucosidase, β-galactosidase, and α-glucosidase inhibitors. A promising inhibitory activity toward α-glucosidase was observed for 21 (IC50 = 78 ΜM) and 25 (IC50 = 70 ΜM), which might be indicative of their potential as lead compounds for development of antidiabetic or antiobesity agents.
- Cardullo, Nunzio,Spatafora, Carmela,Musso, Nicolò,Barresi, Vincenza,Condorelli, Daniele,Tringali, Corrado
-
p. 2675 - 2683
(2015/12/09)
-
- Synthesis and evaluation of a series of resveratrol analogues as potent anti-cancer agents that target tubulin
-
A series of novel diarylacrylonitrile and trans-stilbene analogues of resveratrol has been synthesized and evaluated for their anticancer activities against a panel of 60 human cancer cell lines. The diarylacrylonitrile analogues 3b and 4a exhibited the m
- Madadi, Nikhil R.,Zong, Hongliang,Ketkar, Amit,Zheng, Chen,Penthala, Narsimha R.,Janganati, Venumadhav,Bommagani, Shobanbabu,Eoff, Robert L.,Guzman, Monica L.,Crooks, Peter A.
-
p. 788 - 794
(2015/05/27)
-
- THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS
-
The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.
- -
-
Page/Page column 36; 48-49; 53
(2015/06/18)
-
- Selective deoxygenation of hydroxybenzaldehydes
-
A method for selective deoxygenation of hydroxybenzaldehydes including, condensing syringaldehyde (3,5-dimethoxy-4-hydroxybenzaldehyde) and a functionalized phenylacetic acid with at least one first base and at least one anhydride to produce an arylcinnamic acid, decarboxylating of said arylcinnamic acid with at least one decarboxylation catalyst at temperatures ranging from about 30° C. to 200° C. or thermally at temperatures ranging from about 100° C. to 350° C. to produce a first stilbene, hydrodeoxygenating the stilbene by conversion to a sulfonate in the presence of at least one second base in water or at least one organic solvent to yield a sulfonate reducing the sulfonate(s) with a reductive elimination catalyst to produce a second stilbene, and reacting the second stilbene with a hydrolyzing agent to generate a polyphenol.
- -
-
-
- Synthesis and bioactivity of resveratrol analogues
-
It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.
- Ao, Junli,Chen, Yuanmou,Xu, Xiaoling,Zhang, Xu,Yu, Yue,Yu, Peng,Hua, Erbing
-
p. 2092 - 2098
(2014/06/09)
-
