143724-75-8

Upstream product

• 117-39-5 quercetol 
• 780724-90-5 dimethylallyl diphosphate 
• 143724-67-8 2-(3,4-bis(methoxymethoxy)phenyl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 143724-71-4 5-O-prenyl-3,3',7,4'-tetrakis-O-methoxymethylquercetin 
• 1383545-66-1 2-(3,4-diacetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-4H-chromene-3,5,7-triyl triacetate 
• 1383545-61-6 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate 
• 1064-06-8 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 
• 115-18-4 2-methyl-3-buten-2-ol 
• 157650-20-9 2-(3,4-bis(pivaloyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromene-3,7-diyl bis(2,2-dimethylpropanoate) 
• 153-18-4 rutin 
• 870-63-3 prenyl bromide 
• 143724-77-0 2-(3,4-bis(methoxymethoxy)phenyl)-5-hydroxy-3,7-bis(methoxymethoxy)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one 

Downstream Products

• 40073-88-9 3,3',4',7-tetramethoxy-8-C-prenylquercetin 

Relevant academic research and scientific papers

Hypoglycemic and hypolipidemic dual activities of extracts and flavonoids from Desmodium caudatum and an efficient synthesis of the most potent 8-prenylquercetin

Since glucolipid metabolism disorders is often the mono-target therapy fails in managing blood glucose and lipid levels and the other complications, it is urgent and necessary to seek for the new potential drugs or functional food acting on multi-targets.

Effects of quercetin and artemetin prenylation on bioavailability and bioactivity

Flavonoids are a huge class of polyphenolic compounds ubiquitous in higher plants, in most food and beverages of natural origin. They could be considered as dietary phenols, which exert many health-promoting effects on human and animal physiology with a w

Microbial transformation of prenylquercetins by mucor hiemalis

Quercetin, one of the most widely distributed flavonoids, has been found to show various biological activities including antioxidant, anticancer, and anti-inflammatory effects. It has been reported that bioactivity enhancement of flavonoids has often been closely associated with nuclear prenylation, as shown in 8-prenylquercetin and 5′-prenylquercetin. It has also been revealed in many studies that the biological activities of flavonoids could be improved after glucosylation. Three prenylated quercetins were prepared in this study, and microbial transformation was carried out in order to identify derivatives of prenylquercetins with increased water solubility and improved bioavailability. The fungus M. hiemalis was proved to be capable of converting prenylquercetins into more polar metabolites and was selected for preparative fermentation. Six novel glucosylated metabolites were obtained and their chemical structures were elucidated by NMR and mass spectrometric analyses. All the microbial metabolites showed improvement in water solubility.

Regioselective synthesis of C-prenylated flavonoids via intramolecular [1,3] or [1,5] shift reaction catalyzed by acidic clays

Prenyl side chain and dihydropyrano skeleton exists in many natural and synthetic biologically active flavonoids. A highly efficient and regioselective method for the synthesis of C-prenylated flavonoids via intramolecular [1,3] or [1,5] shift reaction of

Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones

Three series of prenylated and/or geranylated flavonoids were synthesized and evaluated for their α-glucosidase inhibitory activity. The 3′,5′-digeranylated chalcone (16) was identified as a new α-glucosidase inhibitor whose activity (IC50 = 0.

An efficient method for C8-prenylation of flavonols and flavanones

Synthesis of C8-prenylated flavonols and flavanones via the palladium-catalyzed 7-O-1,1-dimethylprop-2-enylation, followed by Claisen rearrangement is described. Two regioselectivities (carbon-carbon bond formation at either the tail or head of the prenyl

Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: An SAR study

A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.

Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures

Dimethylallyl diphosphate: naringenin 8-dimethylallyltransferase (EC 2.5.1) was characterized. The enzyme was enantiospecific for (-)-(2S)-naringenin and utilized 3,3-dimethylallyl diphosphate as sole prenyl donor. It required Mg2+ (optimum concentration, 10 mM), and has an optimum pH of 9-10. The apparent K(m) values for 3,3-dimethylallyl diphosphate and naringenin were 120 and 36 μM, respectively. The microsomal fraction prenylated several other flavanones at the C-8 position less effectively as compared with naringenin. Interestingly, when 2'-hydroxynaringenin was used as a prenyl acceptor, the 8-lavandulyl (sophoraflavanone G) and the 6-dimethylallyl derivatives were formed, together with the 8-dimethylallyl derivative, leachianone G. These results suggest that the 2'-hydroxy group of naringenin plays an important role for the formation of a lavandulyl group. (C) 2000 Elsevier Science Ltd.

1H-NMR CHEMICAL SHIFT OF THE FLAVONOL 5-HYDROXY PROTON AS A CHARACTERIZATION OF 6- OR 8-ISOPRENOID SUBSTITUTION

1H Nmr examination of 6- or 8-isoprenoid substituted flavonols has shown that the location of isoprenoid side chain on A ring can be deduced from the chemical shift of the 5-hydroxy proton.The application of this 1H nmr technique to identification of the