29125-80-2Relevant academic research and scientific papers
Glycosynthases from Thermotoga neapolitana β-glucosidase 1A: A comparison of α-glucosyl fluoride and in situ-generated α-glycosyl formate donors
Pozzo, Tania,Plaza, Merichel,Romero-Garcia, Javier,Faijes, Magda,Karlsson, Eva Nordberg,Planas, Antoni
, p. 132 - 139 (2014/07/21)
TnBgl1A from the thermophile Thermotoga neapolitana is a dimeric β-glucosidase that belongs to glycoside hydrolase family 1 (GH1), with hydrolytic activity through the retaining mechanism, and a broad substrate specificity acting on β-1,4-, β-1,3- and β-1,6-linkages over a range of glyco-oligosaccharides. Three variants of the enzyme (TnBgl1A-E349G, TnBgl1A-E349A and TnBgl1A-E349S), mutated at the catalytic nucleophile, were constructed to evaluate their glycosynthase activity towards oligosaccharide synthesis. Two approaches were used for the synthesis reactions, both of which utilized 4-nitrophenyl β-d-glucopyranoside (4NPGlc) as an acceptor molecule: the first using an α-glucosyl fluoride donor at low temperature (35 °C) in a classical glycosynthase reaction, and the second by in situ generation of the glycosyl donor with (4NPGlc), where formate served as the exogenous nucleophile under higher temperature (70 °C). Using the first approach, TnBgl1A-E349G and TnBgl1A-E349A synthesized disaccharides with β-1,3-linkages in good yields (up to 61%) after long incubations (15 h). However, the GH1 glycosynthase Bgl3-E383A from a mesophilic Streptomyces sp., used as reference enzyme, generated a higher yield at the same temperature with both a shorter reaction time and a lower enzyme concentration. The second approach yielded disaccharides for all three mutants with predominantly β-1,3-linkages (up to 45%) but also β-1,4-linkages (up to 12.5%), after 7 h reaction time. The TnBgl1A glycosynthases were also used for glycosylation of flavonoids, using the two described approaches. Quercetin-3-glycoside was tested as an acceptor molecule and the resultant product was quercetin-3,4′-diglycosides in significantly lower yields, indicating that TnBgl1A preferentially selects 4NPGlc as the acceptor.
Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells
Yamauchi, Kosei,Mitsunaga, Tohru,Batubara, Irmanida
, p. 937 - 944 (2014/02/14)
4′-O-β-d-Glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl- (1→4)-β-d-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells Among the synthesized quercetin glycosides, quercetin-3-O-β-d-glucopyranoside (1), quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect
Glucosylation of Quercetin by a Cell Suspension Culture of Vitis sp.
Kodama, Tohru,Ishida, Hidekatsu,Kokubo, Tetsuro,Yamakawa, Takashi,Noguchi, Hiroshi
, p. 3283 - 3288 (2007/10/02)
A cell suspension culture of a Vitis hybrid converted quercetin to six glucosides.Their structures were identified as quercetin 3-O-β-D-glucopyranoside, quercetin 3,4'-di-O-β-D-glucopyranoside, quercetin 3,7-di-O-β-D-glucopyranoside, isorhamnetin 3-O-β-D-glucopyranoside, isorhamnetin 3,4'-di-O-β-D-glucopyranoside, and isorhamnetin 3,7-di-O-β-D-glucopyranoside by UV, FD-MS, 1H-NMR, 13C-NMR spectroscopy and TLC analysis.The course of conversion was also investigated and it was shown that quercetin 3-O-glucoside reached the maximum yield of 31 percent in 24 hr and then gradually disappeared accompanied by the production of quercetin 3,4'- and 3,7-di-O-glucosides.Although the same rise and fall relationship was observed between isorhamnetin 3-O-glucoside and isorhamnetin 3,4'- or 3,7-di-O-glucoside, their conversion ratios were much lower than those of quercetin glucosides.
