31025-53-3

Usage

InChI:InChI=1/C21H20O9/c22-9-16-18(25)19(26)20(27)21(30-16)28-11-6-12(23)17-13(24)8-14(29-15(17)7-11)10-4-2-1-3-5-10/h1-8,16,18-23,25-27H,9H2/t16-,18-,19+,20-,21-/m1/s1

Upstream product

• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 2816-24-2 2-nitrophenyl β-D-glucopyranoside 
• 1350535-30-6 chrysin 7-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 62055-04-3 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one 

Downstream Products

• 122472-95-1 5-acetoxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-chromen-4-one 
• 72963-83-8 7-β-D-glucopyranosyloxy-5-methoxy-2-phenyl-chromen-4-one 
• 62055-04-3 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

A new flavone glycoside from the aerial part of Scutellaria schachristanica

The new flavone glycoside schachristanoside was isolated from the aerial part of Scutellaria schachristanica Zuz. (Lamiaceae). Spectral data and chemical transformations found that schachristanoside had the structure chrysin-7-O-[α-L-arabinopyranosyl-(1∈→∈6)] -β-D-glucopyranoside.

Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca

In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3′. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3′ positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.

Identification and Characterization of Two New 1- O-Acyl-glucose-ester Forming Glucosyltransferases from Erigeron breviscapus

Two versatile UDP-glucosyltransferases, UGT75L25 and UGT75X1, were isolated from Erigeron breviscapus. The enzymes display high sequence identity to flavonoid 7-O-glucosyltransferase from Malus species and cluster to the phylogenetic group L of plant glucosyltransferases, also involved in the formation of hydroxycinnamoyl glucose esters, which are used as bifunctional donors in the glucosylation or acylation of anthocyanins. The enzymes, functionally expressed in Escherichia coli, exhibit broad substrate specificity toward 21 structurally diverse types of phenolic acids, including (hydroxy)cinnamates, vanillic acid, 3-hydroxycoumarin, and 7-hydroxyflavonoids. The catalytic characteristics of UGT75L25 and UGT75X1 were exploited to generate the corresponding acyl-glucose-esters or glucosides with high efficiency. These findings demonstrate the significant potential of acyl-glucose-esters in the further enzymatic synthesis of bioactive anthocyanins.

Acylated flavone glucosides: Synthesis, conformational investigation, and complexation properties

Acylated flavonoid glycosides are ubiquitous in plants; however, the possible influence of the acyl groups on the typical properties of flavonoids is rather poorly documented. In this work, a series of chrysin (= 5,7 dihydroxyflavone) glucosides acylated with aromatic and aliphatic acid residues has been synthesized in a simple three-step procedure. Aromatic acyl groups are shown to impose folded conformations on the chrysin glucosides owing to their ability to stack on the polyphenolic nucleus. The acyl groups may also cause significant changes in the ability of the flavonoid glucosides to bind hard metal ions and proteins, as demonstrated in this work in the case of Al3+ and bovine serum albumin.