50450-48-1

Upstream product

• 105304-51-6 resveratrol-4′-O-β-D-(2′′-O-galloyl)glucopyranoside 
• 38968-01-3 (E)-1-(3,5-diacetoxy)-2-(4'-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)ethene 
• 5328-37-0 L-arabinose 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 669763-44-4 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 133-89-1 UDP-glucose 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 155222-48-3 5-vinyl-1,3-phenylene diacetate 
• 540-38-5 p-Iodophenol 
• 827348-00-5 (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-hydroxyphenyl)ethene 
• 892402-78-7 (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene 

Downstream Products

• 1367297-96-8 trans-3,5-bis(triphenylmethyloxy)stilbene-4'-O-β-D-glucopyranoside 
• 1367297-97-9 C₇₇H₆₄O₈ 
• 50450-35-6 trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside 

Relevant academic research and scientific papers

Switching glycosyltransferase UGTBL1 regioselectivity toward polydatin synthesis using a semi-rational design

The 62nd residue of glycosyltransferase UGTBL1 was identified as a "hotspot" for glycosylation at 3-OH of resveratrol. Via semi-rational design including structure-guided alanine scanning and saturation mutations, the mutation I62G significantl

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.

Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation

The phytochemical resveratrol (trans-3,5,4′-trihydroxystilbene) has drawn great interest as health-promoting food ingredient and potential therapeutic agent. However, resveratrol shows vanishingly low water solubility; this limits its uptake and complicates the development of effective therapeutic forms. Glycosylation should be useful to enhance resveratrol solubility, with the caveat that unselective attachment of sugars could destroy the molecule's antioxidant activity. UGT71A15 (a uridine 5′-diphosphate α-D-glucose-dependent glucosyltransferase from apple) was used to synthesize resveratrol 3,5-β-D-diglucoside; this was about 1700-fold more water-soluble than the unglucosylated molecule (～0.18 mM), yet retained most of the antioxidant activity. Resveratrol 3-β-D-glucoside, which is the naturally abundant form of resveratrol, was a practical substrate for perfect site-selective conversion into the target diglucoside in quantitative yield (gL-1 concentration).

Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius

The catalytic promiscuity of a new glycosyltransferase (UGT73AE1) from Carthamus tinctorius was explored. UGT73AE1 showed the capability to glucosylate a total of 19 structurally diverse types of acceptors and to generate O-, S-, and N-glycosides, making it the first reported trifunctional plant glycosyltransferase. The catalytic reversibility and regioselectivity were observed and modeled in a one-pot reaction transferring a glucose moiety from icariin to emodin. These findings demonstrate the potential versatility of UGT73AE1 in the glycosylation of bioactive natural products.

Assessing the regioselectivity of oleD-catalyzed glycosylation with a diverse set of acceptors

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavonesnY (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2- methoxyestradiol)- were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.

Glycosylation of trans-resveratrol by plant-cultured cells

Plant-cultured cells of Catharanthus roseus converted trans-resveratrol into its 3-O-β-D-glucopyranoside, 40-O-β-D-glucopyranoside, 3-O-(6-O-β-D-xylopyranosyl)-β-Dglucopyranoside, and 3-O-(6-O-α-L-arabinopyranosyl)-β- D-glucopyranoside. The 3-O-(6-O-β-D-x

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.

Substrate specificities of family 1 UGTs gained by domain swapping

Family 1 glycosyltransferases are a group of enzymes known to embrace a large range of different substrates. This study devises a method to enhance the range of substrates even further by combining domains from different glycosyltransferases to gain impro

Regioselective glucosylation of aromatic compounds: Screening of a recombinant glycosyltransferase library to identify biocatalysts

(Chemical Equation Presented) A novel whole-cell screen for the identification of new glucosyltransferase (GT) biocatalysts within a recombinant enzyme library was developed. Following biotransformation, levels of D-glucose were used as a measure of biocatalysis. Twenty five enzymes that transfer D-glucose to trans-resveratrol were identified that have the regioselectivity shown in the picture.

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.