Synthesis and Antioxidant Properties of Psoralen Derivatives |
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Authors: | Dang-Nan Zhou Lu Han Zhan Zhang Yun-Long Wang Xiao-Ping Zhang Yun-Jie Wu Gao-Lei Xi |
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Affiliation: | 1. Tobacco Science, Henan Agricultural University /Flavors and Fragrance Engineering & Technology Research Center of Henan Province No. 218, Ping'an Avenue, Zhengdong New District, Zhengzhou, China, 450046;2. Technology Center, China Tobacco Henan Industrial Co., Ltd., Zhengzhou, China, 450016 |
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Abstract: | Five psoralen derivatives were synthesized and the structures of them were characterized by 1H-NMR, 13C-NMR, and IR. The antioxidant properties of the compounds were tested by inhibiting the free radical-initiated DNA oxidation and scavenging the radical reaction. The results showed that the effective stoichiometric factors (n) of the compounds V and IV could reach 2.00 and 2.11 in the system of inhibiting the DNA oxidation reaction initiated by 2,2′-Azobis(2-methylpropionamidine) dihydrochloride (AAPH). In the inhibition of ⋅OH-oxidation of the DNA system, compounds I ~ V showed antioxidant properties. The thiobarbituric acid absorbance (TBARS) percentages of compounds IV and V were 76.19 % and 78.84 %. Compounds I ~ V could also inhibit Cu2+/GSH-oxidation of DNA, and all compounds exhibited good antioxidant properties except compound II (94.00 %). All the five compounds were able to trap diammonium 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) salt radical (ABTS+⋅), 2,2-diphenyl-1-picrylhydrazyl radical (DPPH⋅) and 2,6-di-tert-butyl-alpha-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-p-tolylox radical (galvinoxyl⋅). The ability of compounds I ~ V to scavenge those free radicals can be measured by the k values. The k values ranged from 0.07 to 0.82 in scavenging ABTS+⋅, galvinoxyl, and DPPH radicals, respectively. |
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Keywords: | antioxidant properties inhibiting radical-induced oxidation of DNA psoralen derivatives scavenging radicals |
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