3种橙皮素酯类化合物的合成、鉴定与抗氧化性研究

Synthesis, indentification and antioxidant activity of three hesperitin ester derivatives

分别以食品添加剂苯甲酸、山梨酸和肉桂酸为原料,经过酰氯化与天然二氢黄酮化合物橙皮素反应得到3种橙皮素酯类衍生物,并鉴定了它们的结构。体外比较测定了它们在多个浓度下清除羟自由基(·OH)、2,2-二苯基-1-苦味酰基自由基(DPPH)和2,2’-联氨-双(3-乙基苯并噻唑啉-6-磺酸)二胺盐(ABTS)自由基的活性,并研究了它们对亚油酸自氧化、脂质体过氧化的抑制作用及抗植物油氧化能力。实验结果表明,此3种橙皮素酯类衍生物在体外自由基测试模型中均具有清除活性,并且与浓度呈正相关性,橙皮素-7-苯甲酸酯(化合物2)和橙皮素-7-山梨酸酯(化合物3)对亚油酸自氧化、脂质体过氧化的抑制作用及抗植物油氧化能力均强于橙皮素,可作为食品抗氧化剂进一步研究。

Three hesperitin ester derivatives were synthesized by the reactions of food additives benzoic acid, sorbic acid and cinnamic acid as the raw materials respectively via acylation with dihydroflavone compound hesperitin, and their structures were identified. Their scavenging effects on hydroxyl radical（·OH）, diphenyl picryl hydrazinyl radical（DPPH） and 2,2＇-azino-bis（3-ethylbenzthiazoline-6-sulfonic acid）（ABTS） radical were compared in vitro with hesperitin at various concentrations. Their inhibiting effects on linoleic acid autooxidation, liposome peroxidation and oxidation of plant oil were also studied. The results showed that the three hesperitin ester derivatives had inhibitory activity in the different free radical test models in vitro, and the effects positively correlated with their concentrations. At the determined concentrations, hesperitin-7-benzoate（compound 2） and hesperitin-7-sorbate（compound 3） had stronger antioxidant effects on linoleic acid autooxidation, liposome peroxidation and oxidation of plant oil than those of the hesperitin, and can be further studied as food antioxidants.