Synthesis and Hypoglycemic Activity of Novel Quercetin Conjugates

Abstract

Eight novel quercetin conjugates 20～27 were successfully synthesized through a concise procedure with 15%～ 46% overall yields by using Rutin as the starting material. After O-benzylation, glycoside hydrolysis and O-propargylation, rutin was converted to the key intermediate 5,7,3',4'-tetrabenzyloxy-3-O-propargylquercetin, which subsequently 'clicked' with azido containing glycosides, poly(ethylene glycol) (PEG) or oligo(ethylene glycol) (OEG) to provide the fully protected quercetin conjugates 12～19. After global deprotection, the resulting quercetin conjugates were evaluated on hypoglycemic activities at 3T3-L1 adipocyte level. The results showed that conjugates 24, 26 and 27 exhibited good hypoglycemic effects.

Quercetin-1,2,3-Triazole Hybrids as Multifunctional Anti-Alzheimer’s Agents

“…In the literature, a wide variety of flavonoid-1,2,3-triazole hybrids are known to exhibit a wide range of biological properties, such as antitumor, antimicrobial, antidiabetic, neuroprotective, anti-inflammatory, and antioxidant properties, among others [22]. However, only a few examples of quercetin derivatives functionalized with a 1,2,3-triazole heterocyclic in the 3-OH position are reported; see Figure 1 [23][24][25][26]. Quercetin-1,2,3-triazole hybrids reported in the literature with antitumor, anti-inflammatory, and hypoglycemic effects [23][24][25][26].…”

“…However, only a few examples of quercetin derivatives functionalized with a 1,2,3-triazole heterocyclic in the 3-OH position are reported; see Figure 1 [23][24][25][26]. Quercetin-1,2,3-triazole hybrids reported in the literature with antitumor, anti-inflammatory, and hypoglycemic effects [23][24][25][26]. Quercetin-1,2,3-triazole hybrids reported in the literature with antitumor, anti-inflammatory, and hypoglycemic effects [23][24][25][26].…”

“…Quercetin-1,2,3-triazole hybrids reported in the literature with antitumor, anti-inflammatory, and hypoglycemic effects [23][24][25][26]. Quercetin-1,2,3-triazole hybrids reported in the literature with antitumor, anti-inflammatory, and hypoglycemic effects [23][24][25][26].…”

“…Figure 1.Quercetin-1,2,3-triazole hybrids reported in the literature with antitumor, anti-inflammatory, and hypoglycemic effects[23][24][25][26].…”