108957-75-1Relevant academic research and scientific papers
Near infrared dyes by combination of squaraine and ferrocene chromophores
Meier, Herbert,Petermann, Ralf
, p. 5475 - 5478 (2000)
Squaraines represent a class of compounds which attracts a lot of attention in materials science. A synthetic sequence for the preparation of the symmetrical squaraines 12a,b, which contain ferrocene units as electron donors, is described. The compounds exhibit, in dichloromethane or chloroform, two intense absorption bands. One of them is located at 641/650 nm - a normal region for squaraines; however, the other band is strongly shifted to long wavelengths and has its maximum at 921/961 nm. Alkyl sidechains enhance the solubility of 12a,b, which represent a new type of NIR dyes. (C) 2000 Elsevier Science Ltd.
Antioxidant properties of trans-epsilon-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media.
Privat, Christelle,Telo, Joao Paulo,Bernardes-Genisson, Vania,Vieira, Abel,Souchard, Jean-Pierre,Nepveu, Francoise
, p. 1213 - 1217 (2002)
trans-Epsilon-viniferin, the dimer of resveratrol, extracted from Vitis vinifera, has been evaluated for its antioxidant capacity. Its properties have been compared to those of resveratrol and synthetic stilbenic derivatives (4-hydroxystilbene, 4,4'-dihydroxystilbene, 3,5-dihydroxystilbene, and trimethylresveratrol), in regard to their liposolubility using two media with different polarity. The bleaching of beta-carotene by lipoperoxyl (LOO.) radicals in an oil/water (O/W) emulsion and the scavenging of superoxide anions (O(-)(2) in dimethyl sulfoxide (DMSO) using 5,5-dimethyl-1-pyrroline-N-oxide as a spin trap were followed using UV-visible and electron paramagnetic resonance, respectively. Epsilon-viniferin exhibits the best antioxidant capacity in the DMSO/O(-)(2) polar system (IC(50) = 0.14 mM) while 4,4'-dihydroxystilbene presents the highest antioxidant capacity in the O/W/LOO. system (inhibition of beta-carotene bleaching, 82%). Partition coefficients and kinetics of partition between 1-octanol and water were measured to discuss the antioxidant efficiency of the compounds in relation with their chemical structure.
Parallel in vitro and in silico investigations into anti-inflammatory effects of non-prenylated stilbenoids
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)
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.
Synthesis and evaluation of 18F-labeled styryltriazole and resveratrol derivatives for β-amyloid plaque imaging
Lee, Iljung,Choe, Yearn Seong,Choi, Joon Young,Lee, Kyung-Han,Kim, Byung-Tae
, p. 883 - 892 (2012)
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.
Dimerization of resveratrol trimethyl ether by phosphotungstic acid, structure confirmation of resformicol A and B
Davis, Matthew C.,Groshens, Thomas J.
, p. 3521 - 3523 (2012)
Dimerization of the trimethyl ether of resveratrol catalyzed by phosphotungstic acid gave two tetralins and a naphthalene derivative. The structure of the tetralins was obtained by X-ray crystallography and confirms the reported stereochemical configuration of resformicol A and B.
Practical preparation of resveratrol 3-O-β-D-glucuronide
Jungong, Christian S.,Novikov, Alexei V.
, p. 3589 - 3597,9 (2012)
A practical synthesis of resveratrol 3-Oβl-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.
Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase
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)
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.
Comparative inhibitory activity of the stilbenes resveratrol and oxyresveratrol on African swine fever virus replication
Galindo,Hernaez,Berna,Fenoll,Cenis,Escribano,Alonso
, p. 57 - 63 (2011)
Stilbenols are polyphenolic phytoalexins produced by plants in response to biotic or abiotic stress. These compounds have received much attention because of their significant biological effects. One of these is their antiviral action, which has previously been documented for two members of this class, namely resveratrol and oxyresveratrol. Here we tested the antiviral effect of these two compounds on African swine fever virus, the only member of the newly created family Asfarviridae and a serious limitation to porcine production worldwide. Our results show a potent, dose-dependent antiviral effect of resveratrol and oxyresveratrol in vitro. Interestingly, this antiviral activity was found for these synthetic compounds and also for oxyresveratrol extracted from new natural sources (mulberry twigs). The antiviral effect of these two drugs was demonstrated at concentrations that do not induce cytotoxicity in cultured cells. Moreover, these antivirals achieved a 98-100% reduction in viral titers. Both compounds allowed early protein synthesis but inhibited viral DNA replication, late viral protein synthesis and viral factory formation.
Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition
Cardullo, Nunzio,Spatafora, Carmela,Musso, Nicolò,Barresi, Vincenza,Condorelli, Daniele,Tringali, Corrado
, p. 2675 - 2683 (2015)
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.
A convenient synthesis of 14C-labelled resveratrol
Zeng, Dongli,Mi, Qixi,Sun, Hongfang,Wang, Haifang
, p. 167 - 174 (2004)
Resveratrol (trans-3,4′,5-trihydroxystilbene) is a naturally occurring phytoalexin and polyphenol existing in grapes and various plants. It shows remarkable beneficial bioactivities in the prevention of cancer, inflammation and platelet aggregation, etc. This paper reports the synthesis of [β-14C]-trans-resveratrol using 14C-formic acid (exchanged with sodium 14C-formate) and 3,5-dihydroxybenzoic acid as the starting materials. [14C-formyl]-4-methoxybenzaldehyde and diethyl 3,5-dimethoxy benzylphosphonate reacted following the Wittig-Horner reaction to give trans-3,4′,5-[β-14C]-trimethoxystilbene. The final product was obtained through the demethylation of trans-3,4′ ,5-[β-14C]-trimethoxystilbene and identified by TLC and UV spectroscopy. Adoption of the whole procedure provided 14C-resveratrol with a specific radioactivity of 40.8 μCi/mmol, chemical yield of 15.3% and radiochemical yield of 12.5%. Copyright
