482-35-9

Usage

Uses

Used in Pharmaceutical Industry:
ISOQUERCITRIN is used as a standard for identifying chromatographic peaks during flavonoid identification by Orbitrap UHPLC-MS/MS analysis. This application is crucial for the accurate identification and quantification of flavonoids in pharmaceutical research and development.
Used in Nutritional Supplements:
ISOQUERCITRIN is used as a dietary flavonoid supplement to check its binding capacity with human small ubiquitin-related modifier 1 (SUMO1) protein using surface plasmon resonance (SPR). This helps in understanding the interaction between ISOQUERCITRIN and human proteins, which can be beneficial for developing nutritional supplements with potential health benefits.
Used in Microbiology Research:
ISOQUERCITRIN is used as an inhibitor for Escherichia coli adenosine triphosphate (ATP) synthase. This application aids in studying the effects of ISOQUERCITRIN on bacterial energy production and understanding its potential as an antimicrobial agent.
Used in Neurodegenerative Disease Research:
ISOQUERCITRIN is used as an anti-aggregation agent to test its activity against β-amyloid, green fluorescent protein (GFP), and chymotrypsinogen proteins. This application is significant for understanding the potential of ISOQUERCITRIN in preventing protein aggregation associated with neurodegenerative diseases such as Alzheimer's and Parkinson's.
General Information:
ISOQUERCITRIN is produced and qualified by HWI pharma services GmbH. The exact content can be determined by quantitative NMR, and the information can be found on the certificate provided by the company.

Biochem/physiol Actions

Quercetin 3-β-D-glucoside possesses strong antioxidant and anti-inflammatory activities. Being a potent oxygen-radical scavenger, it is a neuroprotective agent that improves Alzheimer′s disease (AD) condition in mice models. It has shown antiproliferative activity against colon, lung, and hepatocellular cell lines and MCF-7 human breast cancer cells in combination with apple extracts.

InChI:InChI=1/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2/t12-,16-,17-,19-,21+/m1/s1

Upstream product

• 133-89-1 UDP-glucose 
• 117-39-5 quercetol 
• 153-18-4 rutin 
• 53171-28-1 quercetin-3-O-(6-O-galloyl)-β-D-glucopyranoside 
• 477244-20-5 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-β-D-glucopyranosyloxy-5,7-bisbenzyloxy-4H-chromen-4-one 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 7431-83-6 5,7,3',4'-tetrahydroxyflavonol-3-O-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside 
• 39028-59-6 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol 
• 108-93-0 cyclohexanol 
• 83144-69-8 3,,4,,5,7-tetrahydroxyflavonol 3-O-β-D-glucopyranosyl (2->1) O-β-D-xylopyranoside 
• 120221-14-9 (2-chloro-4-nitrophenyl)-β-D-glucopyranoside 
• 1332833-27-8 5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one 
• 1332833-26-7 C₅₇H₅₂O₁₆ 
• 116973-12-7 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 

Downstream Products

• 18705-98-1 3',4',5,7-tetra-O-acetylquercetin 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside) 
• 153874-66-9 6''-O-<2-(methoxycarbonyl)acetyl>isoquercitrin 
• 117-39-5 quercetol 
• 2280-44-6 D-Glucose 
• 492-61-5 β-D-glucose 
• 96862-01-0 quercetin 3-O-(6′′-O-malonyl)-β-glucopyranoside 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 54542-51-7 quercetin 3-O-(6''-O-acetyl)-β-D-glucopyranoside 
• 743434-65-3 ((2R,3R,4S,5R,6S)-4-acetoxy-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate 
• 959833-95-5 isoquercitrin 2'',3'',6''-triacetate 
• 50-99-7 D-glucose 
• 1237534-64-3 ((2R,3S,4S,5R,6S)-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl hexanoate 
• 1237535-18-0 ((2R,3S,4S,5R,6S)-6-{(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (Z)-octadec-9-enoate 
• 1237534-66-5 ((2R,3S,4S,5R,6S)-6-{(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl octanoate 

Relevant academic research and scientific papers

Isolation and characterization of a glycosyltransferase with specific catalytic activity towards flavonoids from Tripterygium wilfordii

Flavonoids are important secondary metabolites that exist in many medicinal plants. Flavonoid glycosyltransferases can transfer sugar moieties to their parent rings, producing various flavonoid glycosides with significant pharmacological activities. Here, we report the molecular cloning of the O-glycosyltransferase TwUGT2 from Tripterygium wilfordii and its catalytic activity was explored by heterologous expression in E. coli. The results showed that TwUGT2 has specific glycosyltransferase activity towards C-3 and 7 hydroxyl groups of flavonoids, thereby converting quercetin and pinocembrin into isoquercitrin and pinocembrin 7-O-beta-D-glucoside, respectively. The identification of TwUGT2 will provide a useful molecular tool for synthetic biology and contribute to drug discovery. (Figure presented.).

Glucose tolerance-improving activity of helichrysoside in mice and its structural requirements for promoting glucose and lipid metabolism

An acylated flavonol glycoside, helichrysoside, at a dose of 10 mg/kg/day per os for 14 days, improved the glucose tolerance in mice without affecting the food intake, visceral fat weight, liver weight, and other plasma parameters. In this study, using hepatoblastoma-derived HepG2 cells, helichrysoside, trans-tiliroside, and kaempferol 3-O-β-D-glucopyranoside enhanced glucose consumption from the medium, but their aglycones and p-coumaric acid did not show this activity. In addition, several acylated flavonol glycosides were synthesized to clarify the structural requirements for lipid metabolism using HepG2 cells. The results showed that helichrysoside and related analogs significantly inhibited triglyceride (TG) accumulation in these cells. The inhibition by helichrysoside was more potent than that by other acylated flavonol glycosides, related flavonol glycosides, and organic acids. As for the TG metabolism-promoting activity in high glucose-pretreated HepG2 cells, helichrysoside, related analogs, and their aglycones were found to significantly reduce the TG contents in HepG2 cells. However, the desacyl flavonol glycosides and organic acids derived from the acyl groups did not exhibit an inhibitory impact on the TG contents in HepG2 cells. These results suggest that the existence of the acyl moiety at the 6'' position in the D-glucopyranosyl part is essential for glucose and lipid metabolism-promoting activities.

Enzymatic synthesis of novel quercetin sialyllactoside derivatives

Quercetin and its derivatives are important flavonols that show diverse biological activity, such as antioxidant, anticarcinogenic, anti-inflammatory, and antiviral activities. Adding different substituents to quercetin may change the biochemical activity

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Highly Promiscuous Flavonoid 3- O-Glycosyltransferase from Scutellaria baicalensis

A highly regio-specific and donor-promiscuous 3-O-glycosyltransferase, Sb3GT1 (UGT78B4), was discovered from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could be a promising catalyst to increase structural diversity of flavonoid 3-O-glycosides.

On the Catalytic Activity of a GT1 Family Glycosyltransferase from Streptomyces venezuelae ISP5230

GT1 family glycosyltansferase, Sv0189, from Streptomyces venezuelae ISP5230 (ATCC 10721) was characterized. The recombinantly produced protein Sv0189 possessed UDP-glycosyltransferase activity. Screening, using an assay employing unnatural nitrophenyl glycosides as activated donors, resulted in the discovery of a broad substrate scope with respect to both acceptor molecules and donor sugars. In addition to polyphenols, including anthraquinones, simple aromatics containing primary or secondary alcohols, a variety of complex natural products and synthetic drugs were glucosylated or xylosylated by Sv0189. Regioselectivity was established through the isolation and characterization of glucosylated products. Sv0189 and homologous proteins are widely distributed among Streptomyces species, and their apparent substrate promiscuity reveals potential for their development as biocatalysts for glycodiversification.

Isoquercetin and derivative and application and preparation methods thereof

The invention provides an isoquercetin and derivative. The structural formula of the isoquercetin and derivative is shown as the formula I, wherein n=1-9, and R is selected from Glu, Rha, Gal, Xyl orAll. The isoquercetin and derivative solves the problem of poor solubility of rutin and quercetin as well as in vivo digestion and absorption of rutin, improves the bioavailability of isoquercetin andpolysaccharide isoquercetin and achieves significant therapeutic effects on prevention and treatment of osteoporosis and hyperlipidemia.

An alkali tolerant α-L-rhamnosidase from Fusarium moniliforme MTCC-2088 used in de-rhamnosylation of natural glycosides

Analkali tolerant α-L-rhamnosidase has been purified to homogeneity from the culture filtrate of a new fungal strain, Fusarium moniliforme MTCC-2088, using concentration by ultrafiltration and cation exchange chromatography on CM cellulose column. The molecular mass of the purified enzyme has been found to be 36.0 kDa using SDS-PAGE analysis. The Km value using p-nitrophenyl-α-L-rhamnopyranoside as the variable substrate in 0.2 M sodium phosphate buffer pH10.5 at50 °C was 0.50 mM. The catalytic rate constant was15.6 s?1giving the values of kcat/Km is 3.12 × 104M?1 s?1. The pH and temperature optima of the enzyme were 10.5 and 50 °C, respectively. The purified enzyme had better stability at 10 °C in basic pH medium. The enzyme derhamnosylated natural glycosides like naringin to prunin, rutin to isoquercitrin and hesperidin to hesperetin glucoside. The purified α-L-rhamnosidase has potential for enhancement of wine aroma.

Efficient Synthesis of Crocins from Crocetin by a Microbial Glycosyltransferase from Bacillus subtilis 168

Crocins are the most important active ingredient found in Crocus sativus, a well-known "plant gold". The glycosyltransferase-catalyzed glycosylation of crocetin is the last step of biosynthesizing crocins and contributes to their structural diversity. Crocin biosynthesis is now hampered by the lack of efficient glycosyltransferases with activity toward crocetin. In this study, two microbial glycosyltransferases (Bs-GT and Bc-GTA) were successfully mined based on the comprehensive analysis of the PSPG motif and the N-terminal motif of the target plant-derived UGT75L6 and Cs-GT2. Bs-GT from Bacillus subtilis 168, an enzyme with a higher activity of glycosylation toward crocetin than that of Bc-GTA, was characterized. The efficient synthesis of crocins from crocetin catalyzed by microbial GT (Bs-GT) was first reported with a high molecular conversion rate of 81.9%, resulting in the production of 476.8 mg/L of crocins. The glycosylation of crocetin on its carboxyl groups by Bs-GT specifically produced crocin-5 and crocin-3, the important rare crocins.