59985-52-3

Upstream product

• 143631-95-2 acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester 
• 133-89-1 UDP-glucose 
• 117-39-5 quercetol 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 
• 1313191-78-4 2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3,5-bisbenzyloxy-7-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 
• 1313191-77-3 2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3-benzyloxy-5-hydroxyl-7-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 
• 357194-11-7 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-[tetra-O-acetyl-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 339276-12-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 1064-06-8 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 
• 357194-04-8 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one 

Downstream Products

• 50-99-7 D-glucose 
• 117-39-5 quercetol 
• 492-61-5 β-D-glucose 
• 2280-44-6 D-Glucose 

Relevant academic research and scientific papers

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.

Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-β-d-glucuronide and quercetin 3′-O-β-d-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-β-d-glucosides and four O-β-d-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-β-d-glucuronide.

Cloning and functional characterisation of two regioselective flavonoid glucosyltransferases from Beta vulgaris

Two full-length cDNAs encoding flavonoid-specific glucosyltransferases, UGT73A4 and UGT71F1, were isolated from a cDNA library of Beta vulgaris (Amaranthaceae) cell suspension cultures. They displayed high identity to position-specific betanidin and flavonoid glucosyltransferases from Dorotheanthus bellidiformis (Aizoaceae) and to enzymes with similar substrate specificities from various plant families. The open reading frame of the sequences encode proteins of 476 (UGT73A4) and 492 (UGT71F1) amino acids with calculated molecular masses of 54.07 kDa and 54.39 kDa, and isoelectric points of 5.8 and 5.6, respectively. Both enzymes were functionally expressed in Escherichia coli as His- and GST-tagged proteins, respectively. They exhibited a broad substrate specificity, but a distinct regioselectivity, glucosylating a variety of flavonols, flavones, flavanones, and coumarins. UGT73A4 showed a preference for the 4′- and 7-OH position in the flavonoids, whereas UGT71F1 preferentially glucosylated the 3- or the 7-OH position. Glucosylation of betanidin, the aglycone of the major betacyanin, betanin, in B. vulgaris was also observed to a low extent by both enzymes. Several O-glycosylated vitexin derivatives isolated from leaves of young B. vulgaris plants and rutin obtained from B. vulgaris tissue culture are discussed as potential endogenous products of UGT73A4 and UGT71F1. The results are analyzed with regard to evolution and specificity of plant natural product glucosyltransferases.

Characterization of flavonoid 7-O-glucosyltransferase from Arabidopsis thaliana

Most flavonoids found in plants exist as glycosides, and glycosylation status has a wide range of effects on flavonoid solubility, stability, and bioavailability. Glycosylation of flavonoids is mediated by Family 1 glycosyltransferases (UGTs), which use UDP-sugars, such as UDP-glucose, as the glycosyl donor. AtGT-2, a UGT from Arabidopsis thaliana, was cloned and expressed in Escherichia coli as a gluthatione S-transferase fusion protein. Several compounds, including flavonoids, were tested as potential substrates. HPLC analysis of the reaction products indicated that AtGT-2 transfers a glucose molecule into several different kinds of flavonoids, eriodictyol being the most effective substrate, followed by luteolin, kaempferol, and quercetin. Based on comparison of HPLC retention times with authentic flavonoid 7-O-glucosides and nuclear magnetic resonance spectroscopy, the glycosylation position in the reacted flavonoids was determined to be the C-7 hydroxyl group. These results indicate that AtGT-2 encodes a flavonoid 7-O-glucosyltransferase.

Flavonoids from Cephalaria gigantea flowers

Luteolin, quercetin, cinaroside, quercimeritrin, and the new flavonol bioside gigantoside A were isolated from Cephalaria gigantea (Ledeb.) Bobr. (Dipsacaceae) flowers. Spectral properties and chemical transformations established that gigantoside A had the structure quercetin-7-O-[α-L- arabinopyranosyl(1→6)]-β-D-glucopyranoside.

Facile synthesis of flavonoid 7-O-glycosides

Highly regioselective removal of the 7-O-acyl groups of the peracylated flavones, isoflavones, and flavonols (PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF 3·Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.

Quercetin (=2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one) Glycosides and Sulfates: Chemical Synthesis, Complexation, and Antioxidant Properties

Glycosides, acylated glycosides, and sulfates of Quercetin (=3,3',4',5,7-pentahydroxyflavone; 1), which is, together with its derivatives, among the most common polyophenols found in plants and in the human diet, were prepared and quantitatively investiga