137790-51-3Relevant academic research and scientific papers
Synthesis and Biological Evaluation of 4-Substituted Kaempfer-3-ols
Kim, Sugyeom,Lannigan, Deborah A.,Li, Yu,Lin, Lin,O'Doherty, George A.,Sayasith, Peyton R.,Tarr, Ariel T.,Wright, Eric B.,Yasmin, Sharia
, p. 4279 - 4288 (2020/04/09)
The synthesis of two series of five kaempfer-3-ols was described. The first set all have a C-3 hydroxyl group and the second has a carboxymethoxy ether at the C-3 position. Both series have variable substitution at the C-4 position (i.e., OH, Cl, F, H, OMe). Both kaempferols and carboxymethoxy ethers were evaluated for their ability to inhibit ribosomal s6 kinase (RSK) activity and cancer cell proliferation.
Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins
Hao,Caulfield,Hamilton,Pickett,Midega,Khan,Wang,Hooper
, p. 73 - 87 (2016/04/06)
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.
Isotopic labelling of quercetin 3-glucoside
Caldwell, Stuart T.,Petersson, Hanna M.,Farrugia, Louis J.,Mullen, William,Crozier, Alan,Hartley, Richard C.
, p. 7257 - 7265 (2007/10/03)
The potentially important dietary antioxidant, quercetin 3-O-β-d-glucoside, has been 13C-labelled at C-2 of the flavonoid unit by synthesis in 15% yield over five steps from [13C]carbon dioxide. The route is appropriate for radiochemical synthesis. Formation of the protected 3-glucosylated flavonol appears to result from [1,7]-sigmatropic rearrangement with migration of a benzyl group followed by cyclisation. A free 5-OH results even when a phosphazene superbase is used.
