69655-50-1Relevant academic research and scientific papers
Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds
Kato, Eisuke,Kawabata, Jun
supporting information; experimental part, p. 4333 - 4336 (2010/09/18)
Chemical treatment of diabetes mellitus is widely studied and controlling of blood glucose level is the main course of therapy. In type 2 diabetes mellitus, insulin resistance is the major problem. An isoflavone C-glucoside, puerarin (1), is known to enhance glucose uptake into the insulin sensitive cell and is thought to be a candidate for treatment of diabetes mellitus. We synthesized 1 and several derivatives to apply for the structure-activity relationship study. The result against 3T3-L1 adipocyte indicated that the C-glucoside part of 1 is unconcerned in its activity when tested in vitro and the main structure responsible for its activity was the isoflavone moiety.
Total synthesis of puerarin, an isoflavone C-glycoside
Lee, David Y. W.,Zhang, Wu-Yan,Karnati, Vishnu Vardhan R.
, p. 6857 - 6859 (2007/10/03)
We completed the first total synthesis of puerarin (1), an isoflavone C-glycoside. The key intermediate, β-D-glucopyranosyl-2,6-dimethoxybenzene (9), was obtained by coupling of a lithiated aromatic reagent (3) with pyranolactone (2) in 56% yield. Condensation of (16) with p-methoxybenzaldehyde gave the chalcone (17). The protected chalcone (18) was cyclized to (19) in the presence of Tl(NO3)3. Demethylation of (19) was accomplished by refluxing with TMSI in CH3CN to give puerarin (1).
