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Upstream product

• 827348-00-5 (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-hydroxyphenyl)ethene 
• 339276-12-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 151767-11-2 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 

Downstream Products

• 38963-95-0 trans-resveratroloside 

Relevant academic research and scientific papers

Preventive oral treatment with resveratrol pro-prodrugs drastically reduce colon inflammation in rodents

There is no pharmaceutical or definitive surgical cure for inflammatory bowel diseases (IBDs). The naturally occurring polyphenol resveratrol exerts anti-inflammatory properties. However, its rapid metabolism diminishes its effectiveness in the colon. The design of prodrugs to targeting active molecules to the colon provides an opportunity for therapy of IBDs. Herein we explore the efficacy of different resveratrol prodrugs and pro-prodrugs to ameliorate colon inflammation in the murine dextran sulfate sodium (DSS) model. Mice fed with a very low dose (equivalent to 10 mg for a 70 kg-person) of either resveratrol-3-O-(6′-O-butanoyl)-β-d-glucopyranoside (6) or resveratrol-3-O-(6′-O-octanoyl)-β-d-glucopyranoside (7) did not develop colitis symptoms and improved 6-fold the disease activity index (DAI) compared to resveratrol. Our results indicate that these pro-prodrugs exerted a dual effect: (1) they prevented the rapid metabolism of resveratrol and delivered higher quantities of resveratrol to the colon and (2) they reduced mucosal barrier imbalance and prevented diarrhea, which consequently facilitated the action of the delivered resveratrol in the colon mucosa.

Synthesis of mono- and di-O-β-D-glucopyranoside conjugates of (E)-resveratrol

Starting from the commercially available natural product (E)-resveratrol (1), the four selectively tert-butyldimethylsilyl (TBS) protected (E)-resveratrols 6-9 were prepared by one reaction. Using 6-9 as glucosyl acceptors and trifluoroacetimidate 11 as glucosyl donor, three bioactive natural glucopyranoside conjugates of (E)-resveratrol 2-4 and one novel compound (5) were efficiently prepared in two steps. Georg Thieme Verlag Stuttgart.