Details

Autor(en) / Beteiligte

• Xi, Gao-Lei
• Liu, Zai-Qun

Titel

Coumarin-Fused Coumarin: Antioxidant Story from N,N‑Dimethylamino and Hydroxyl Groups

Ist Teil von

• Journal of agricultural and food chemistry, 2015-04, Vol.63 (13), p.3516-3523

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2015

Quelle

MEDLINE

Beschreibungen/Notizen

• Two coumarin skeletons can form chromeno­[3,4-c]­chromene-6,7-dione by sharing with the CC in lactone. The aim of the present work was to explore the antioxidant effectiveness of the coumarin-fused coumarin via six synthetic compounds containing hydroxyl and N,N-dimethylamino as the functional groups. The abilities to quench 2,2′-azinobis­(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+•), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical revealed that the rate constant for scavenging radicals was related to the amount of hydroxyl group in the scaffold of coumarin-fused coumarin. But coumarin-fused coumarin was able to inhibit DNA oxidations caused by •OH, Cu2+/glutathione (GSH), and 2,2′-azobis­(2-amidinopropane hydrochloride) (AAPH) even in the absence of hydroxyl group. In particular, a hydroxyl and an N,N-dimethylamino group locating at different benzene rings increased the inhibitory effect of coumarin-fused coumarin on AAPH-induced oxidation of DNA about 3 times higher than a single hydroxyl group, whereas N,N-dimethylamino-substituted coumarin-fused coumarin possessed high activity toward •OH-induced oxidation of DNA without the hydroxyl group contained. Therefore, the hydroxyl group together with N,N-dimethylamino group may be a novel combination for the design of coumarin-fused heterocyclic antioxidants.