56782-99-1Relevant articles and documents
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.