160880-89-7

Basic information

• Product Name: 8-(β-D-glucopyranosyl)-5,7-dihydroxyflavone
• Synonyms: 8-(β-D-glucopyranosyl)-5,7-dihydroxyflavone
• CAS NO: 160880-89-7
• Molecular Weight: 416.384
• Mol File: 160880-89-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 8-(β-D-glucopyranosyl)-5,7-dihydroxyflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(β-D-glucopyranosyl)-5,7-dihydroxyflavone(160880-89-7)
• EPA Substance Registry System: 8-(β-D-glucopyranosyl)-5,7-dihydroxyflavone(160880-89-7)

Safety Data

• Hazardous Substances Data: 160880-89-7(Hazardous Substances Data)

Upstream product

• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 40489-17-6 2-hydroxypinocembrin 
• 137790-51-3 2-acetyl-3,5-bis(benzyloxy)phenyl benzoate 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 

Relevant articles and documents

Design and Synthesis of CNb-targeted Flavones and Analogues with Neuroprotective Potential Against H2O2- and Aβ1-42-Induced Toxicity in SH-SY5Y Human Neuroblastoma Cells

With the lack of available drugs able to prevent the progression of Alzheimer’s disease (AD), the discovery of new neuroprotective treatments able to rescue neurons from cell injury is presently a matter of extreme importance and urgency. Here, we were inspired by the widely reported potential of natural flavonoids to build a library of novel flavones, chromen-4-ones and their C-glucosyl derivatives, and to explore their ability as neuroprotective agents with suitable pharmacokinetic profiles. All compounds were firstly evaluated in a parallel artificial membrane permeability assay (PAMPA) to assess their effective permeability across biological membranes, namely the blood-brain barrier (BBB). With this test, we aimed not only at assessing if our candidates would be well-distributed, but also at rationalizing the influence of the sugar moiety on the physicochemical properties. To complement our analvsis logD7.4 was determined. From all screened compounds, the p-morpholinyl flavones stood out for their ability to fully rescue SH-SY5Y human neuroblastoma cells against both H2O2 A β1-42-induced cell death. Cholinesterase inhibition was also evaluated, and modest inhibitory activities were found. This work highlights the potential of C-glucosylflavones as neuroprotective agents, and presents the p-morpholinyl C-glucosylflavone 37, which did not show any cytotoxicity towards HepG2 and Caco-2 cells at 100 ΜM, as a new lead structure for further development against AD.

Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins

The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus.