橙皮苷衍生物的制备鉴定及抗氧化活性研究

目的:研究橙皮苷衍生物的制备、鉴定和抗氧化活性。方法:以天然橙皮苷为先导化合物,分别得到香叶木苷、香叶木素、7-O-乙氧羰亚甲基-香叶木素、7-O-羧亚甲基-香叶木素、橙皮素、3',7-O-二乙氧羰亚甲基-橙皮素、7-O-乙氧羰亚甲基-橙皮素、7-O-羧亚甲基-橙皮素共8个衍生物。比较测定了橙皮苷及其8个衍生物在同一浓度下的体外抗氧化活性,包括总抗氧化能力测定、清除自由基测定、对亚油酸自氧化和卵磷脂过氧化的抑制作用,并以橙皮苷和2,6-二叔丁基-4-甲基苯酚为对照,采用烘箱强化法测定了体外抗氧化活性较好的衍生物在不同浓度下对动物油和植物油过氧化值的影响。结果:8个衍生物的脂溶性或水溶性有所增强,在浓度为0.2 mg/mL时,橙皮苷及其8个衍生物均具有较好的体外抗氧化活性,其中化合物7-O-乙氧羰亚甲基-香叶木素对亚油酸自氧化和卵磷脂过氧化的抑制作用较强,分别为橙皮苷的2.15倍和1.92倍,它对猪油和大豆油的抗氧化效果均强于橙皮苷,并且抑制率随着浓度升高而增大,呈现出较好的量效关系,在0.2 mg/mL时,对猪油氧化的抑制率为52.17%,对大豆油氧化的抑制率为49.78%。结论:7-O-乙氧羰亚甲基-香叶木素脂溶性增强,具有比橙皮苷更强的抗氧化活性。

Study on the Preparation,Identification and Anti-oxidation Activity of Hesperidin Derivatives

Objective:To study the preparation,identification and anti-oxidation ability ofhesperidin derivatives. Methods:Using natural hesperidin as a leading compound,its eight derivatives,including diosmin,diosmetin,7-O-ethoxy-carbonyl-methylene-diosmetin,7-O-carboxy-methylene-diosmetin,hesperetin,3',7-O-di-ethoxy-carbonyl-methylene-hesperetin,7-O-ethoxy-carbonyl-methylene-hesperetin and 7-O-carboxy-methylene-hesperetin were obtained. The anti-oxidation activity of hesperidin and its eight derivatives were compared in vitro under the same concentration,including the determination of total anti-oxidant capacity and free radical scavenging activity,theinhibition on linoleic acid auto-oxidation and phosphatidylcholine peroxidation. The effects of the derivativewhich had good anti-oxidant activity in vitro on peroxide values of animal fatand vegetable oil were also determined at the different concentrations by the oven storing method using hesperidin and 2,6-di-tert-butyl-4-methylphenol ascontrasts. Results:The lipo-soluble or water-soluble properties of the 8 derivatives had been enhanced. The hesperidin and its eight derivatives had effects on different anti-oxidation models in vitro at the concentration 0.2 mg/mL,in which the compound 7-O-ethoxy-carbonyl-methylene-diosmetinhad the more significant inhibitory effect on linoleic acid auto-oxidation and phosphatidylcholine peroxidation than the others. Compared with hesperidin,the effects were 2.15 times and 1.92 times respectively.It also showed better anti-oxidation effects onlard and soybean oil than hesperidin,the inhibition rate increased with the increase of concentration and showed good dose-effect relationship trends. At 0.2 mg/mL,the inhibition rate on lard was 52.17%,and the inhibition rate on soybean was 49.78%. Conclusion:The lipo-soluble properties of 7-O-ethoxy-carbonyl-methylene-diosmetin had been enhanced and it had more significant anti-oxidant activity than hesperidin.