欢迎访问《林产化学与工业》,

林产化学与工业 ›› 2022, Vol. 42 ›› Issue (2): 39-46.doi: 10.3969/j.issn.0253-2417.2022.02.006

• 研究报告 • 上一篇    下一篇

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

李文君1,2,3, 王成章1,*(), 雷建都2, 唐凤霞1,2,3   

  1. 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
  • 收稿日期:2021-10-11 出版日期:2022-04-28 发布日期:2022-05-06
  • 通讯作者: 王成章 E-mail:wangczlhs@sina.com
  • 作者简介:王成章, 研究员, 博士生导师, 研究领域为天然植物资源加工; E-mail: wangczlhs@sina.com
    李文君(1989-), 女, 河南周口人, 助理研究员, 博士生, 主要从事木本油脂成分分析及应用的研究工作
  • 基金资助:
    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)

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

Wenjun LI1,2,3, Chengzhang WANG1,*(), Jiandu LEI2, Fengxia TANG1,2,3   

  1. 1. 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
    2. College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China
    3. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
  • Received:2021-10-11 Online:2022-04-28 Published:2022-05-06
  • Contact: Chengzhang WANG E-mail:wangczlhs@sina.com

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1H 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(IC50)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0.765 5和0.894 2 mmol/L (以Trolox溶液的浓度计),OLEO和OLEA的T-AOC最高分别达到0.157 1和0.646 2 mmol/L (以FeSO4浓度计)。

关键词: 馏分, 梯度洗脱, 刺激醛, 油精, 评价

Abstract:

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 1H 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(IC50) 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 0.765 5 and 0.894 2 mmol/L(calculated by the concentration of Trolox); and their total antioxidant capacities reached 0.157 1 and 0.646 2 mmol/L(calculated by the concentration of FeSO4), respectively.

Key words: fractions, gradient elution, oleocanthal, oleacein, evaluation

中图分类号: