88885-07-8

Upstream product

• 2280-44-6 D-Glucose 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 50-99-7 D-glucose 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 169566-46-5 1-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethanone 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1309438-45-6 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone 
• 133-89-1 UDP-glucose 

Downstream Products

• 88885-08-9 2,4,6-triacetoxy-3-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)acetophenone 
• 1266170-01-7 C₃₅H₃₆O₉ 
• 1248653-90-8 C₁₉H₂₆O₁₃ 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 160913-21-3 3',5'-di-C-β-D-glucosyl-2',4',6'-trihydroxyacetophenone 

Relevant academic research and scientific papers

Probing the catalytic promiscuity of a regio- and stereospecific C-glycosyltransferase from Mangifera indica

The catalytic promiscuity of the novel benzophenone C-glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio- and stereospecific C-glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP-glucose, and also formed O- and N-glycosides. Moreover, MiCGT was able to generate C-xylosides with UDP-xylose. The OGT-reversibility of MiCGT was also exploited to generate C-glucosides with simple sugar donor. Three aryl-C-glycosides exhibited potent SGLT2 inhibitory activities with IC50 values of 2.6×, 7.6×, and 7.6×10-7-M, respectively. These findings demonstrate for the first time the significant potential of an enzymatic approach to diversification through C-glycosidation of bioactive natural and unnatural products in drug discovery. C-glycodiversification: MiCGT, as the first benzophenone C-glycosyltransferase (CGT) from Mangifera indica, showed robust regio- and stereospecific C-glycosylation activity for 35 structurally diverse acceptors with UDP-glucose or xylose. The aryl-C-glycoside 1 exhibited potent antidiabetic activity toward SGLT2.

Tannins and related compounds. CXXIII. Chromone, acetophenone and phenylpropanoid glycosides and their galloyl and/or hexahydroxydiphenoyl esters from the leaves of Syzygium aromaticum Merr. et Perry

From the dried leaves of Syzygium aromaticum MERR. et PERRY (Myrtaceae), eleven new compounds, i.e., eugenol 4-O-β-D-(6'-O-galloyl)glucopyranoside (17), 2-methyl-5,7-dihydroxychromone 8-C-β-D-glucopyranoside (18) and its 6'-O-gallate (19), 2,4,6-trihydrox

Scandium cation-exchanged montmorillonite catalyzed direct C-glycosylation of a 1,3-diketone, dimedone, with unprotected sugars in aqueous solution

The condensation of dimedone with unprotected sugars in aqueous solution in the presence of a catalytic amount of Sc3+-montmorillonite (Sc3+-mont) gave 9-hydroxyalkyl-3,3,6,6,-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dio

Conversion of β-D-C-glucopyranosyl phloroacetophenone to a spiroketal compound

Treatment of β-D-C-glucopyranosyl phloroacetophenone in water in the presence of a catalytic amount of p-TsOH afforded a spiroketal product. This is the first demonstration of ring conversion in aryl C-glycoside. The structure of the product was determine

Synthesis and evaluation of a new water-soluble fluorescent red dye, xanthene bis-C-glycoside

Condensation of 2 eq. of C-β-D-glucosylphloroacetophenone with glyoxylic acid in an aqueous solution of Na2CO3, followed by air oxidation in MeOH in the presence of 11 eq. of pyridine to afford a 36percent yield of a bright red dye, xanthene bis-C-glycoside. This dye is 10 times more fluorescent (Φf [EtOH]581 nm = 3.9 × 10?2) and 7.5 times more water-soluble (57 mg/mL H2O) than the natural red pigment, carthamin. Detailed NMR analysis of its methyl analogs was used to confirm the structure of the dye as methyl 4,5-diacetyl-1,3,8-trihydroxy-3-oxo-3H-2,7-di-C-β-D-glucopyranosylxanthene-9-carboxylate from among three possible ring-closure isomers. Xanthene is safe and shows high light-resistance; therefore, xanthene bis-C-glycoside could be used as a food colorant or an in vivo probe.

Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease

Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.

Functional Characterization and Structural Basis of an Efficient Di-C-glycosyltransferase from Glycyrrhiza glabra

A highly efficient di-C-glycosyltransferase GgCGT was discovered from the medicinal plant Glycyrrhiza glabra. GgCGT catalyzes a two-step di-C-glycosylation of flopropione-containing substrates with conversion rates of >98%. To elucidate the catalytic mech

Synthesis and antihyperglycemic activity of phenolic C-glycosides

Various phenolic C-glycosides were evaluated for their in vitro and in vivo antihyperglycemic activity employing glucose uptake by rat muscle cell lines (L-6) and low dosed-streptozotocin-induced diabetic rats, respectively. Some of phenolic C-glycosides were isolated from Pterocarpus marsupium and Ulmus wallichiana and other were synthesized by unprotected sugar and phloroacetophenone using Sc(OTf)3 in aqueous ethanol. Eight among tested compounds showed significant lowering of blood glucose level on low dosed-streptozotocin-induced diabetic rats. The compound 24 lowered the blood glucose levels by 34.9% and 33.6% during 0-5 h and 0-24 h, respectively, at the dose of 25 mg/kg body weight which is comparable to standard antidiabetic drug metformin.

Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-β-d-(glucopyranosyl- xylopyranosyl)-4′,5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected d-glucose and d-xylose in aqueous solution as the key reactions

Vicenin-3 was synthesized from naringenin via a short five-step reaction, which included two regioselective direct C-glycosylations with d-glucose and d-xylose (yields: 22% and 30%, respectively) as the key reactions for a total yield of 4.4%. Vicenin-1 was also synthesized from phloroacetophenone via a 10-step reaction, including the same glycosylation described above, for a total yield of 2.7% with a vicenin-3 yield of 1.7%.

Environmentally friendly C-glycosylation of phloroacetophenone with unprotected d-glucose using scandium(III) trifluoromethanesulfonate in aqueous media: Key compounds for the syntheses of mono- and di-C-glucosylflavonoids

The direct C-glycosylation of phloroacetophenone with an unprotected d-glucose in aqueous media using scandium(III) trifluoromethanesulfonate (Sc(OTf)3) as the catalyst, gave mono- and bis-C-β-glycosylic compounds in highest total yield of 81%.