50450-35-6

Usage

Uses

Used in Pharmaceutical Industry:
Trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside is used as a medicinal compound for its antioxidant, anti-inflammatory, and anti-cancer effects. It has been studied for its ability to inhibit the growth of cancer cells and reduce inflammation in various disease conditions.
Used in Cardiovascular Disease Prevention and Treatment:
Trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside is used as a potential agent for preventing and treating cardiovascular diseases due to its medicinal properties.
Used in Neurodegenerative Disorder Prevention and Treatment:
Trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside is used as a potential agent for preventing and treating neurodegenerative disorders, given its potential medicinal properties.

Upstream product

• 38963-95-0 trans-resveratroloside 
• 74-88-4 methyl iodide 
• 58762-96-2 3,4'-dihydroxy-5-methoxy-trans-stilbene 4'-O-β-D-glucopyranoside 
• 537-42-8 3,5-dimethoxy-4'-hydroxy-trans-stilbene 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 1367298-00-7 trans-2,6-dichloro-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside 
• 1367298-01-8 trans-2,6-dichloro-3,5-dimethoxystilbene-4'-O-β-D-glucuronide 

Relevant academic research and scientific papers

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.

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

The stilbene compound resveratrol was glycosylated to give its 4′-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4′-O-β-D-glucoside, and converted pinostilbene to its 4′-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.

Reaction of several resveratrol glycoside derivatives with hypochlorites in various media

The reactions of pterostilbenoside (trans-3,5-dimethoxystilben-4′-O- β-D-glucoside) and Ar-O-Tr derivatives of resveratroloside (3,5-dihydroxystilben-4′-O-β-D-glucoside) and pinostilbenoside (3-methoxy-5-hydroxystilben-4′-O-β-D-glucoside) with NaOCl and t-BuOCl in the presence of the stable nitroxyl radical TEMPO were studied in various media. It was found that the principal product of pterostilbenoside transformation was its 2,6-dichloroderivative, a part of which was oxidized to form 2,6-dichloropterostilbene glucuronide. Trityl ethers of resveratroloside and pinostilbenoside reacted with the hypochlorites to form mixtures of products.

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.