357194-03-7Relevant articles and documents
Quercetin-3-oleoyl derivatives as new GPR40 agonists: Molecular docking studies and functional evaluation
Carullo, Gabriele,Perri, Mariarita,Manetti, Fabrizio,Aiello, Francesca,Caroleo, Maria Cristina,Cione, Erika
, p. 1761 - 1764 (2019)
The G-protein-coupled receptor 40 (GPR40)is an attractive molecular target for the treatment of type 2 diabetes mellitus. Previously, based on the natural oleic acid substrate, an exogenous ligand for this receptor, named AV1, was synthesized. In this context, here we validated the activity of AV1 as a full agonist, while the corresponding catechol analogue, named AV2, was investigated for the first time. The ligand-protein interaction between this new molecule and the receptor was highlighted in the lower portion of the GPR40 groove that generally accommodates DC260126. The functional assays performed have demonstrated that AV2 is a suitable GPR40 partial agonist, showing a therapeutic potential and representing a useful tool in the management of type 2 diabetes.
New lipophenols prevent carbonyl and oxidative stresses involved in macular degeneration
Moine, Espérance,Boukhallat, Manel,Cia, David,Jacquemot, Nathalie,Guillou, Laurent,Durand, Thierry,Vercauteren, Joseph,Brabet, Philippe,Crauste, Céline
, p. 367 - 382 (2020/11/13)
Dry age-related macular degeneration and Stargardt disease undergo a known toxic mechanism caused by carbonyl and oxidative stresses (COS). This is responsible for accumulation in the retinal pigment epithelium (RPE) of A2E, a main toxic pyridinium bis-retinoid lipofuscin component. Previous studies have shown that carbonyl stress in retinal cells could be reduced by an alkyl-phloroglucinol-DHA conjugate (lipophenol). Here, we performed a rational design of different families of lipophenols to conserve anti-carbonyl stress activities and improve antioxidant properties. Five synthetic pathways leading to alkyl-(poly)phenol derivatives, with phloroglucinol, resveratrol, catechin and quercetin as the main backbone, linked to poly-unsaturated fatty acid, are presented. These lipophenols were evaluated in ARPE-19 cell line for their anti-COS properties and a structure-activity relationship study is proposed. Protection of ARPE-19 cells against A2E toxicity was assessed for the four best candidates. Finally, interesting anti-COS properties of the most promising quercetin lipophenol were confirmed in primary RPE cells.
Synthesis, characterization and antioxidant activity of quercetin derivatives
Sun, Lei,Lu, Bo,Liu, Yandan,Wang, Qian,Li, Gao,Zhao, Longxuan,Zhao, Chunhui
supporting information, p. 2944 - 2953 (2021/08/25)
A series of quercetin derivatives were synthesized via Williamson etherification, Steglich esterification or Koenigs–Knorr glycosylation reaction at 3 and 7 position hydroxyl groups selectively. The structures of the synthesized compounds were characteriz