高速逆流色谱法从云南姜根茎分子蒸馏残渣中分离制备6-姜酚及姜油的体外抗氧化活性

Separation and preparation of 6-gingerol from molecular distillation residue of Yunnan ginger rhizomes by high-speed counter-current chromatography and the antioxidant activity of ginger oils in vitro.

作者信息

Gan Zhilin, Liang Zheng, Chen Xiaosong, Wen Xin, Wang Yuxiao, Li Mo, Ni Yuanying

机构信息

National Engineering Research Center for Fruits and Vegetables Processing, Beijing 100083, China; College of Food Science and Nutritional Engineering, China Agricultural University, Beijing 100083, China.

出版信息

J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Feb 1;1011:99-107. doi: 10.1016/j.jchromb.2015.12.051. Epub 2016 Jan 4.

DOI:10.1016/j.jchromb.2015.12.051

PMID:26773887

Abstract

Molecular distillation residue (MD-R) from ginger had the most total phenol content of 247.6mg gallic acid equivalents per gram (GAE/g) among the ginger oils. High-speed counter-current chromatography (HSCCC) technique in semi-preparative scale was successfully performed in separation and purification of 6-gingerol from MD-R by using a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (10:2:5:7, v/v/v/v). The target compound was isolated, collected, purified by HSCCC in the head-tail mode, and then analyzed by HPLC. A total of 90.38±0.53mg 6-gingerol was obtained from 600mg MD-R, with purity of 99.6%. In addition, the structural identification of 6-gingerol was performed by EI/MS, (1)H NMR and (13)C NMR. Moreover, the orders of antioxidant activity were vitamin E (VE)>supercritical fluid extraction oleoresin (SFE-O)=MD-R=6-gingerol>molecular distillation essential oil (MD-EO) and butylated hydroxytoluene (BHT)=VE>6-gingerol>MD-R=SFE-O>MD-EO, respectively in 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging and β-Carotene bleaching.

摘要

生姜的分子蒸馏残渣（MD-R）在生姜油中总酚含量最高，为每克247.6毫克没食子酸当量（GAE/g）。采用正己烷-乙酸乙酯-甲醇-水（10:2:5:7，v/v/v/v）组成的两相溶剂体系，通过半制备规模的高速逆流色谱（HSCCC）技术成功地从MD-R中分离纯化出6-姜酚。目标化合物通过HSCCC以头-尾模式进行分离、收集和纯化，然后用高效液相色谱法（HPLC）进行分析。从600毫克MD-R中获得了总共90.38±0.53毫克的6-姜酚，纯度为99.6%。此外，通过电子轰击质谱（EI/MS）、核磁共振氢谱（¹H NMR）和核磁共振碳谱（¹³C NMR）对6-姜酚进行了结构鉴定。此外，在2,2-二苯基-1-苦基肼自由基（DPPH）清除和β-胡萝卜素漂白实验中，抗氧化活性顺序分别为维生素E（VE）>超临界流体萃取姜辣素（SFE-O）=MD-R=6-姜酚>分子蒸馏精油（MD-EO），以及丁基羟基甲苯（BHT）=VE>6-姜酚>MD-R=SFE-O>MD-EO。