化学
抗氧化剂
自动氧化
DPPH
乙酸乙酯
咖啡酸
立体化学
有机化学
作者
V. D. Kancheva,Luciano Saso,Petya V. Boranova,Abdullah Khan,Manju K. Saroj,Mukesh K. Pandey,Shashwat Malhotra,Jordan Z. Nechev,Sunil Sharma,Ashok K. Prasad,Maya Georgieva,Carleta Joseph,Anthony L. DePass,R. C. Rastogi,Virinder S. Parmar
出处
期刊:Biochimie
[Elsevier]
日期:2010-09-01
卷期号:92 (9): 1089-1100
被引量:37
标识
DOI:10.1016/j.biochi.2010.06.012
摘要
The chain-breaking antioxidant activities of eight coumarins [7-hydroxy-4-methylcoumarin (1), 5,7-dihydroxy-4-methylcoumarin (2), 6,7-dihydroxy-4-methylcoumarin (3), 6,7-dihydroxycoumarin (4), 7,8-dihydroxy-4-methylcoumarin (5), ethyl 2-(7,8-dihydroxy-4-methylcoumar-3-yl)-acetate (6), 7,8-diacetoxy-4-methylcoumarin (7) and ethyl 2-(7,8-diacetoxy-4-methylcoumar-3-yl)-acetate (8)] during bulk lipid autoxidation at 37 °C and 80 °C in concentrations of 0.01–1.0 mM and their radical scavenging activities at 25 °C using TLC–DPPH test have been studied and compared. It has been found that the o-dihydroxycoumarins 3–6 demonstrated excellent activity as antioxidants and radical scavengers, much better than the m-dihydroxy analogue 2 and the monohydroxycoumarin 1. The substitution at the C-3 position did not have any effect either on the chain-breaking antioxidant activity or on the radical scavenging activity of the 7,8-dihydroxy- and 7,8-diacetoxy-4-methylcoumarins 6 and 8. The comparison with DL-α-tocopherol (TOH), caffeic acid (CA) and p-coumaric acid (p-CumA) showed that antioxidant efficiency decreases in the following sequence: TOH > CA > 3 > 4 > 6 > 5 > 2 > 1 = 7 = 8 = p-CumA. Theoretical calculations and the “Lipinski’s Rule of Five” were used for explaining the structure–activity relationships and pharmacokinetic behavior. A higher TGSO oxidation stability was observed in the presence of equimolar (1:1) binary mixtures of coumarins with TOH (1 + TOH, 3 + TOH and 5 + TOH). However, the synergism (14%) was observed only for the binary mixture of 5 + TOH.
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