姜黄醇提物化学成分及其抗氧化活性分析

doi:10.7506/spkx1002-6630-20180704-057

食品科学 ›› 2019, Vol. 40 ›› Issue (12): 226-231.doi: 10.7506/spkx1002-6630-20180704-057

姜黄醇提物化学成分及其抗氧化活性分析

刘宇1,2，熊亮1,2，彭成1，李小翠1,2，蒙春旺1,2，刘菲1,2,*，郭力1,2,*

1.成都中医药大学药学院，中药材标准化教育部重点实验室，中药资源系统研究与开发利用省部共建国家重点实验室培育基地，四川成都 611137；2.成都中医药大学，西南特色药材创新药物成分研究所，四川成都 611137

出版日期:2019-06-25 发布日期:2019-06-28
基金资助:
四川省青年科技创新研究团队专项计划项目（2016TD0006；2017TD0001）

Chemical Constituents from Ethanol Extract of Curcuma longa L. Rhizoma and Their Antioxidant Activity

LIU Yu1,2, XIONG Liang1,2, PENG Cheng1, LI Xiaocui1,2, MENG Chunwang1,2, LIU Fei1,2,*, GUO Li1,2,*

1. Key Laboratory of Standardization of Chinese Herbal Medicine, Ministry of Education, State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine Resources, College of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; 2. Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China

Online:2019-06-25 Published:2019-06-28

摘要/Abstract

摘要： 目的：研究姜黄（Curcuma longa L.）的化学成分及其抗氧化活性。方法：应用硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及高效液相制备色谱等方法进行分离纯化，根据高分辨质谱、核磁共振谱鉴定化合物的结构；同时采用1,1-二苯基-2-三硝基苯肼（1,1-diphenyl-2-picrylhydrazyl，DPPH）法、2,2’-联氮双(3-乙基苯并噻唑啉-6-磺酸)（2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)，ABTS）法和铁氰化钾还原法对分离得到的化合物进行抗氧化活性筛选。结果：从姜黄中分离鉴定了7 个合物，分别为Zingerol（1）、Dihydroferulic acid ethyl ester（2）；乙基-3-(4-羟基-苯基)-丙酸乙酯（3）、Zingerone dimer [4,4’-(6,6’-dihydroxy-5,5’-dimethoxy-[1,1’-biphenyl]-3,3’-diyl) bis(butan-2-one)]（4）、姜酮（5）、4-(3,4-二甲氧基苯基)丁烷-2-酮（6）、香草醛（7）。其中，化合物1～5均具有一定的抗氧化活性，ABTS阳离子自由基清除实验中，化合物1和化合物2的IC50值分别为（3±0.2）μmol/L和（12±1.0）μmol/L，化合物1优于阳性对照VC（VC的IC50值（13±1.1）μmol/L），化合物2与VC效果相当，还原力实验中，化合物1活性优于VC，浓度低于0.125 μmol/mL时化合物2活性强于VC。结论：化合物4为新的天然产物，化合物1、2、3和6为姜黄属中首次发现，化合物1抗氧化活性较强可能与其脂肪链2位上羟基取代有关，姜黄醇提物中的酚类成分是姜黄抗氧化活性的物质基础之一。

关键词: 姜黄, 化学成分, 抗氧化活性

Abstract: Objective: To identify the chemical constituents from the rhizome of Curcuma longa L. and to assess their antioxidant activity. Methods: The chemical constituents were purified consecutively by silica gel column chromatography, Sephadex LH-20 gel column chromatography, and preparative high performance liquid chromatography (HPLC). Their structures were identified by spectroscopic analyses, and their antioxidant activity were evaluated by 2,2’-azinobis-(3- ethylbenzthiazoline-6-sulphonate) (ABTS) radical cation scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, and potassium ferricyanide reduction assays. Results: Seven compounds were isolated from C. longa L. and were identified as zingerol (1), dihydroferulic acid ethyl ester (2), ethyl 3-(4-hydroxy-phenyl)-propionate (3), zingerone dimer [4,4’-(6,6’-dihydroxy-5,5’-dimethoxy-[1,1’-biphenyl]-3,3’-diyl)bis(butan-2-one)] (4), zingiberone (5), 4-(3,4-dimethoxyphenyl) butan-2-one (6), and vanillin (7). Among them, compounds 1–5 showed antioxidant activity. The IC50 of compounds 1 and 2 were (3 ± 0.2) and (12 ± 1.0) μmol/L, respectively, in ABTS assay. Compound 1 was found to exhibit higher antioxidant activity than the positive drug, VC (VC, IC50 value = (13 ± 1.1) μmol/L), while the activity of compound 2 was equivalent to VC. In the reducing power assay, compound 1 showed higher activity than VC at all investigated concentrations, while compound 2 had higher activity than VC only when the concentration was lower than 0.125 μmol/mL. Conclusion: Compound 4 is a new natural product, and compounds 1, 2, 3 and 6 are found from this plant for the first time. The stronger antioxidant activity of compound 1 may be related to hydroxyl substitution at C-2, In addition, the phenols from the ethanol extract may be one of the material bases for the antioxidant activity of C. longa L..

Key words: Curcuma longa L., chemical constituents, antioxidant activity

中图分类号:

R282.5

刘宇，熊亮，彭成，李小翠，蒙春旺，刘菲，郭力. 姜黄醇提物化学成分及其抗氧化活性分析[J]. 食品科学, 2019, 40(12): 226-231.

LIU Yu, XIONG Liang, PENG Cheng, LI Xiaocui, MENG Chunwang, LIU Fei, GUO Li. Chemical Constituents from Ethanol Extract of Curcuma longa L. Rhizoma and Their Antioxidant Activity[J]. FOOD SCIENCE, 2019, 40(12): 226-231.

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姜黄醇提物化学成分及其抗氧化活性分析

Chemical Constituents from Ethanol Extract of Curcuma longa L. Rhizoma and Their Antioxidant Activity

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