基于离心分配色谱技术制备Oleocanthal,Oleacein及其抗氧化活性研究  

Preparation of Oleocanthal and Oleacein Based on Centrifugal Partition Chromatography Technology and Their Antioxidant Activities

作　　者：李文君[1,2,3] 王成章 雷建都[2] 唐凤霞[1,2,3] LI Wenjun;WANG Chengzhang;LEI Jiandu;TANG Fengxia(Institute of Chemistry Industry of Forest Products,CAF,National Engineering Lab.for Biomass Chemical Utilization,Key Lab.of Chemical Engineering of Forest Products,National Forestry and Grassland Administration,Key Lab.of Biomass Energy and Material,Jiangsu Province,Nanjing 210042,China;College of Materials Science and Technology,Beijing Forestry University,Beijing 100083,China;Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources,Nanjing Forestry University,Nanjing 210037,China)

机构地区：[1]中国林业科学研究院林产化学工业研究所,生物质化学利用国家工程实验室,国家林业和草原局林产化学工程重点实验室,江苏省生物质能源与材料重点实验室,江苏南京210042 [2]北京林业大学材料科学与技术学院,北京100083 [3]南京林业大学江苏省林业资源高效加工利用协同创新中心,江苏南京210037

出　　处：《林产化学与工业》2022年第2期39-46,共8页Chemistry and Industry of Forest Products

基　　金：中国林科院中央级公益性科研院所基本科研业务费专项资金(CAFYBB2017ZA004-2);江苏省生物质能源与材料重点实验室基本科研业务费项目(JSBEM-S-201810)。

摘　　要：以从特级初榨橄榄油中提取的橄榄油总多酚浸膏(TPF)为原料,基于离心分配色谱(CPC)技术进行快速分离,并利用薄层层析色谱(TLC)、制备高效液相色谱(Pre-HPLC)等纯化、制备2-(4-羟基苯基)乙基(E)-4-甲酰基-3-(2-氧代乙基)己基-4-烯酸酯(oleocanthal,OLEO)和2-(3,4-二羟基苯基)乙基(Z)-4-甲酰基-3-(2-氧代乙基)己基-4-烯酸酯(oleacein,OLEA)单体化合物,并采用^(1)H NMR进行结构表征,同时考察其抗氧化活性。研究结果表明:9 g浸膏溶于20 mL甲醇中,在以正己烷/乙酸乙酯/乙醇/水体积比为3∶2∶3∶2为溶剂系统的CPC中分离得到14组馏分,经过纯化,分别得到纯度95%以上的OLEO 422.3 mg和OLEA 163.0 mg。不同质量浓度(0~1 g/L)的OLEO和OLEA对ABTS^(+)·、DPPH·清除率能力和总抗氧化能力(T-AOC)评价发现,OLEA具有比OLEO更强的抗氧化活性,其中OLEO和OLEA对DPPH·的半数抑制质量浓度(IC_(50))值分别为0.029和1.85×10^(-11)g/L,OLEO和OLEA对ABTS^(+)·的清除能力最高分别为0.7655和0.8942 mmol/L(以Trolox溶液的浓度计),OLEO和OLEA的T-AOC最高分别达到0.1571和0.6462 mmol/L(以FeSO_(4)浓度计)。Based on centrifugal partition chromatography(CPC)and thin-layer chromatography(TLC),preparative high performance liquid chromatography(Pre-HPLC)and so on,the total polyphenol extract(TPF)of olive oil was extracted from extra virgin olive oil,and then TPF was used as raw material to separate and prepare 2-(4-hydroxyphenyl)ethyl(E)-4-formyl-3-(2-oxoethyl)hex-4-enoate(oleocanthal,OLEO)and 2-(3,4-dihydroxyphenyl)ethyl(Z)-4-formyl-3-(2-oxoethyl)hex-4-enoate(oleacein,OLEA)monomer compounds.Their structures were characterized by ^(1)H NMR and their antioxidant activities were also investigated.The results showed that 14 fractions were obtained during the process of CPC with the solvent system of n-hexane/ethyl acetate/ethanol/water volume ratio of 3∶2∶3∶2 from 9 g extract in 20 mL of methanol.After purification,422.3 mg OLEO and 163.0 mg OLEA with the purity of≥95%were obtained,respectively;the antioxidant activities of OLEO and OLEA at different concentrations(0-1 g/L)were evaluated by their free radical scavenging capacity on ABTS^(+)·,DPPH·and total antioxidant capacity(T-AOC),it indicated that OLEA had stronger antioxidant activity than OLEO,and the 50%inhibition concentration(IC_(50))values of OLEO and OLEA for DPPH·were 0.029 and 1.85×10^(-11)g/L,respectively,the scavenging capacties of OLEO and OLEA against ABTS^(+)·were 0.7655 and 0.8942 mmol/L(calculated by the concentration of Trolox);and their total antioxidant capacities reached 0.1571 and 0.6462 mmol/L(calculated by the concentration of FeSO_(4)),respectively.

关 键 词：馏分 梯度洗脱 刺激醛 油精 评价 

分 类 号：TQ35[化学工程]