Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs

被引:15
|
作者
Pan, Guojun [1 ]
Li, Xuehui [1 ]
Zhao, Long [1 ]
Wu, Meng [1 ]
Su, Chao [1 ]
Li, Xuzhe [1 ]
Zhang, Yongmin [1 ,2 ]
Yu, Peng [1 ]
Teng, Yuou [1 ]
Lu, Kui [1 ]
机构
[1] Tianjin Univ Sci & Technol, China Int Sci & Technol Cooperat Base Food Nutr S, Sinofrench Joint Lab Food Nutr Safety & Med Chem, Key Lab Ind Fermentat Microbiol,Minist Educ,Tianj, Tianjin 300457, Peoples R China
[2] Univ Pierre & Marie Curie Paris 6, Inst Parisien Chim Mol, UMR CNRS 8232, 4 Pl Jussieu, F-75005 Paris, France
基金
中国国家自然科学基金;
关键词
Anastatins; Flavone; Aurone; Antioxidant; OXIDATIVE STRESS; FLAVONOIDS; LIVER;
D O I
10.1016/j.ejmech.2017.06.054
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two novel flavonoids (+/-)-Anastatins A and B as well as 14 analogs, which containing a benzofuran moiety, were synthesized by using halogenation, Suzuki coupling reaction and an oxidation/Oxa-Michael reaction cascade as the key steps. The structures of the new flavonoids were confirmed by H-1 NMR, C-13 NMR and HRMS. The antioxidant activities of them as well as the key intermediates were evaluated by ferric reducing antioxidant power (FRAP) assay and the active compounds were evaluated in the PC12 cell model of hydrogen peroxide (H2O2)-induced oxidative damage. SAR studies suggested that, for in vitro antioxidant activity, aurone derivatives showed better bioactivity than flavone counterparts. However, cyclization to benzofuran and connecting the two conjugated parts as a whole conjugated system by a double bond diminished the in vitro antioxidant activity. Among them, the most potent compound 24c was significantly decreased H2O2-caused cell injury. The apoptotic rate (Annexin V+) of H2O2-damaged PC12 cells was 60.7% while that of the compound 24c-treated cells decreased to 5.9% and 4.1% at 10 mu M and 100 mu M respectively. (C) 2017 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:577 / 589
页数:13
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