18259-15-9

Usage

Uses

Used in Health and Wellness Industry:
Pterostilbene is used as a dietary supplement for its potential health benefits, including anti-inflammatory, anti-cancer, and anti-aging properties. It helps protect cells from damage caused by free radicals and oxidative stress, promoting overall health and well-being.
Used in Cognitive Function Improvement:
Pterostilbene is used as a cognitive enhancer for its potential to improve cognitive function, particularly in aging populations. Its antioxidant properties may help protect the brain from oxidative stress and support healthy cognitive function.
Used in Cardiovascular Health:
Pterostilbene is used as a cardiovascular health supplement for its potential to improve heart health. Its antioxidant and anti-inflammatory properties may help reduce the risk of heart disease and support healthy blood circulation.
Used in Diabetes Management:
Pterostilbene is used as a diabetes management aid for its potential to help regulate blood sugar levels and improve insulin sensitivity. Its antioxidant properties may also help protect against the oxidative stress associated with diabetes.
Used in Anti-Aging Applications:
Pterostilbene is used as an anti-aging agent for its potential to slow down the aging process and promote healthy aging. Its antioxidant and anti-inflammatory properties may help protect against age-related diseases and support overall health and longevity.

InChI:InChI=1/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+

Upstream product

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 77-78-1 dimethyl sulfate 
• 848487-76-3 (E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 353227-95-9 α-[(3,5-dimethoxyphenyl)methylene]-4-hydroxy-(αZ)-benzeneacetic acid 
• 18259-14-8 (E)-1-(4'-acetoxyphenyl)-2-(3,5-dimethoxyphenyl)ethene 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 54900-97-9 3,5-dimethoxybenzyltriphenylphosphonium chloride 

Downstream Products

• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 1028098-06-7 (E)-dibenzyl 4-(3,5-dimethoxystyryl)phenyl phosphate 
• 116518-94-6 3,5-di-O-methyldihydroresveratrol 
• 1032508-01-2 (E)-O-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate 
• 42438-89-1 pinostilbene 
• 60640-98-4 2,4-Dimethoxy-6-hydroxy-phenanthren 
• 441351-32-2 (Z)-4-hydroxy-3',5'-dimethoxystilbene 
• 1304126-72-4 pterostilbene-glutaric acid cocrystal 
• 1032508-02-3 (E)-S-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate 
• 1032508-00-1 trans-3',5'-dimethoxy-4-mercaptostilbene 
• 1511857-25-2 (E)-4-(3,5-dimethoxystyryl)phenyl 2-acetoxybenzoate 
• 1094101-40-2 4-(3,5-dimethoxystyryl)phenyl-2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl propanoate 

Relevant academic research and scientific papers

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.

Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol

Pterostilbene, a natural methoxylated analogue of resveratrol, was evaluated for antioxidative potential. The peroxyl-radical scavenging activity of pterostilbene was the same as that of resveratrol, having total reactive antioxidant potentials of 237 ± 58 and 253 ± 53 μM, respectively. Both compounds were found to be more effective than Trolox as free radical scavengers. Using a plant system, pterostilbene also was shown to be as effective as resveratrol in inhibiting electrolyte leakage caused by herbicide-induced oxidative damage, and both compounds had the same activity as α-tocopherol. Pterostilbene showed moderate inhibition (IC50 = 19.8 μM) of cyclooxygenase (COX)-1, and was weakly active (IC50 = 83.9 μM) against COX-2, whereas resveratrol strongly inhibited both isoforms of the enzyme with IC50 values of approximately 1 μM. Using a mouse mammary organ culture model, carcinogen-induced preneoplastic lesions were, similarly to resveratrol, significantly inhibited by pterostilbene (ED50 = 4.8 μM), suggesting antioxidant activity plays an important role in this process.

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.

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.

Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.

Phytochemical studies on the stem bark of Guibourtia tessmanii yielded a dihydrochalcone glucoside, 2',4-dihydroxy-4'-methoxy-6'-O-beta-glucopyranoside dihydrochalcone and a new stilbene glycoside, 3,5-dimethoxy-4'-O-(beta-rhamnopyranosyl-(1-->6)-beta- glucopyranoside) stilbene besides the known pterostilbene. Their structures were established on the basis of one and two dimensional NMR spectroscopic techniques, FABMS and chemical evidence.

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.

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.

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.

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%.

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.