92631-83-9

Upstream product

• 519-34-6 maclurin 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 133-89-1 UDP-glucose 
• 92631-84-0 maclurin 3-C-(2''-O-galloyl-6''-O-p-hydroxybenzoyl)-β-D-glucoside 
• 92631-85-1 maclurin 3-C-(2''-O-p-hydroxybenzoyl-6''-O-galloyl)-β-D-glucoside 
• 92665-82-2 maclurin 3-C-(6''-O-p-hydroxybenzoyl)-β-D-glucoside 

Downstream Products

• 4773-96-0 mangiferin 
• 24699-16-9 4-β-D-glucopyranosyl-1,3-6,7-tetrahydroxy-9H-xanthen-9-one 

Relevant academic research and scientific papers

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

Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica

A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5′-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides. One enzyme, one product: A novel C-glycosyltransferase from Mangifera indica is reported, which is a promiscuous catalyst that synthesizes bioactive C-glucosides from natural and unnatural acylphloroglucinol 2-O-gulcosides in one-pot reactions. High yields of C-glucosides were achieved even with a catalytic amount of uridine 5′-diphosphate. This study demonstrates for the first time the significant potential of a single-enzyme approach for the C-glycodiversification.

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. XXI. Isolation and Characterization of Galloyl and p-Hydroxybenzoyl Esters of Benzophenone and Xanthone C-glucosides from Mangifera indica L.

Six new galloyl and p-hydroxybenzoyl esters (2-7) of benzophenone C-glucosides have been isolated, together with a new benzophenone C-glucoside (1), from the leaves of Mangifera indica L. (Anacardiaceae).On the basis of chemical and spectroscopic evidence, the structures of these compounds have been established as maclurin 3-C-β-D-glucoside (1), maclurin 3-C-(6''-O-p-hydroxybenzoyl)-β-D-glucoside (2), maclurin 3-C-(2''-O-galloyl-6''-O-p-hydroxybenzoyl)-β-D-glucoside (3), maclurin 3-C-(2''-O-p-hydroxybenzoyl-6''-O-galloyl)-β-D-glucoside (4), maclurin 3-C-(2'',3'',6''-tri-O-galloyl)-β-D-glucoside (5), iriflophenone 3-C(2'',6''-di-O-galloyl)-β-D-glucoside (6) and iriflophenone 3-C-(2'',3'',6''-tri-O-galloyl)-β-D-glucoside (7). (-)-Epicatechin 3-O-gallate (9), mangiferin (10), isomangiferin (11) and a new xanthone C-glucoside gallate, mangiferin 6'-O-gallate (8), have also been isolated and their structures have been similarly characterized.Furthermore, the above plant source contained polygalloylglucoses which were characterized on the basis of chemical and high performance liquid chromatographic analyses as a mixture of penta- to undecagalloylglucoses based on a 1,2,3,4,6-penta-O-galloyl-β-D-glucose core.Maclurin 3-C-glucoside (1) has been transformed enzymatically to mangiferin (10) and isomangiferin (11), and it has become clear that 1 is a key intermediate in the biosynthesis of 10 and 11. Keywords - Mangifera indica; Anacardiaceae; galloyl maclurin 3-C-glucoside p-hydroxybenzoate; galloyl iriflopenone 3-C-glucoside; galloyl mangiferin; benzophenone C-glucoside; biosynthesys; mangiferin; isomangiferin; galloylglucose