逆流色谱法分离纯化蒲公英中多酚类化合物

doi:10.3976/j.issn.1002-4026.2022.06.001

Abstract

Abstract:

Six polyphenolic compounds were separated and extracted from Taraxaci Herba through a combination of pH-zone-refining counter-current chromatography (pH-ZRCCC) and high-speed counter-current chromatography (HSCCC). In pH-ZRCCC,ethyl acetate-acetonitrile-water (4:1:5, V/V) was selected as the solvent system, trifluoroacetic acid (10 mmol/L) was added to the upper phase as the stationary phase, and ammonia (10 mmol/L) was added to the lower phase as the mobile phase. Caffeic acid (60.2 mg with a purity of 98.1%), p-hydroxycinnamic acid (6.3 mg with a purity of 98.8%), and mixture A (590 mg) were separated from 1.6 g of crude ethyl acetate extract of Herba Taraxaci. After further using HSCCC, petroleumether-ethyl acetate-methanol-water (1:4:1:4, V/V) was selected as the solvent system.Consequently, 1-O-caffeoylglycerol (7.7 mg with a purity of 82.2%), 3,4-dihydroxyphenylacetic acid (5.4 mgwith a purity of 24.8%), protocatechuic acid (6.2mg with a purity of 95.3%) and p-hydroxyphenylacetic acid (3.4 mgwith a purity of 89.0%) were obtained from 400 mg of mixture A.The method has a large preparation volume and good reproducibility, and is suitable for the separation and purification of Taraxaci Herba polyphenol compounds.

Key words: Taraxaci Herba, polyphenols, high-speed counter current chromatography, pH-zone-refining counter-current chromatography, separation and purification

CLC Number:

R284.2

GAO Jie, SONG Xiang-yun, MA Tian-yu, LIU Feng, ROMAN Kachan, WANG Xiao. Separation and purification of polyphenols from Taraxaci Herba by counter-current chromatography[J].Shandong Science, 2022, 35(6): 1-7.

Figures/Tables 5

Table 1

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Table 2

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References 22

[1]	袁昌齐. 蒲公英的本草论证和种类鉴定[J]. 中国野生植物资源, 2001, 20(3): 6-8.
[2]	谢沈阳, 杨晓源, 丁章贵, 等. 蒲公英的化学成份及其药理作用[J]. 天然产物研究与开发, 2012, 24(S1): 141-151. DOI:10.16333/j.1001-6880.2012.s1.030. doi: 10.16333/j.1001-6880.2012.s1.030
[3]	MIŁEK M, MARCINČÁKOVÁ D, LEGÁTH J. Polyphenols content, antioxidant activity, and cytotoxicity assessment of Taraxacum officinale extracts prepared through the micelle-mediated extraction method[J]. Molecules (Basel, Switzerland), 2019, 24(6): 1025. DOI:10.3390/molecules24061025. doi: 10.3390/molecules24061025
[4]	FARIA T C, NASCIMENTO C C H C, DE VASCONCELOS S D D, et al. Literature review on the biological effects of Taraxacum officinale plant in therapy[J]. Asian Journal of Pharmaceutical Research and Development, 2019, 7(3): 94-99. DOI:10.22270/ajprd.v7i3.502. doi: 10.22270/ajprd.v7i3.502
[5]	ALMAJANO M P, CARBÓ R, DELGADO M E, et al. Effect of pH on the antimicrobial activity and oxidative stability of oil-in-water emulsions containing caffeic acid[J]. Journal of Food Science, 2007, 72(5): C258-C263. DOI:10.1111/j.1750-3841.2007.00387.x. doi: 10.1111/j.1750-3841.2007.00387.x
[6]	PARK C M, JIN K S, LEE Y W, et al. Luteolin and chicoric acid synergistically inhibited inflammatory responses via inactivation of PI3K-Akt pathway and impairment of NF-κB translocation in LPS stimulated RAW 264.7 cells[J]. European Journal of Pharmacology, 2011, 660(2/3): 454-459. DOI:10.1016/j.ejphar.2011.04.007. doi: 10.1016/j.ejphar.2011.04.007
[7]	聂文佳, 徐帅师, 张咏梅. 蒲公英有效成分及其药理作用研究进展[J]. 辽宁中医药大学学报, 2020, 22(7): 140-145. DOI:10.13194/j.issn.1673-842x.2020.07.034. doi: 10.13194/j.issn.1673-842x.2020.07.034
[8]	段红波, 梁引库. 蒲公英多酚的提取及其活性研究[J]. 中国食品添加剂, 2017(3): 80-86.
[9]	HU W C, ZHOU J, SHEN T, et al. Target-guided isolation of three main antioxidants from Mahonia bealei (fort.) carr. leaves using HSCCC[J]. Molecules (Basel, Switzerland), 2019, 24(10): 1907. DOI:10.3390/molecules24101907. doi: 10.3390/molecules24101907
[10]	DONG H J, ZHANG Y Q, FANG L, et al. Combinative application of pH-zone-refining and conventional high-speed counter-current chromatography for preparative separation of alkaloids from Stephania kwangsiensis[J]. Journal of Chromatography B, Analytical Technologies in the Biomedical and Life Sciences, 2011, 879(13/14): 945-949. DOI:10.1016/j.jchromb.2011.02.051. doi: 10.1016/j.jchromb.2011.02.051
[11]	岳亚文, 田振, 张劲松, 等. 利用高速逆流色谱技术制备灵芝酮三醇[J]. 食用菌学报, 2020, 27(2): 77-83. DOI:10.16488/j.cnki.1005-9873.2020.02.010. doi: 10.16488/j.cnki.1005-9873.2020.02.010
[12]	李芙蓉, 施文正, 李燕. 高速逆流色谱法分离制备南极磷虾虾粉抗氧化肽[J]. 上海海洋大学学报, 2019, 28(2): 305-312.
[13]	施树云, 张宇平, 赵昱, 等. 高速逆流色谱分离制备蒲公英中的黄酮苷[C]// 中国药学会.第九届全国中药和天然药物学术研讨会大会报告及论文集. 南昌: 中国药学会, 2007.
[14]	张天佑, 王晓. 高速逆流色谱技术[M]. 北京: 化学工业出版社, 2011.
[15]	ITO Y. pH-zone-refining counter-current chromatography: Origin, mechanism, procedure and applications[J]. Journal of Chromatography A, 2013, 1271(1): 71-85. DOI:10.1016/j.chroma.2012.11.024. doi: 10.1016/j.chroma.2012.11.024 pmid: 23219480
[16]	马天宇. pH区带逆流色谱分离纯化金银花等四种中药材中酚酸类化合物的研究[D]. 济南: 山东中医药大学, 2020.
[17]	LEE K H, WHANG W K. Inhibitory effects of bioassay-guided isolation of anti-glycation components fromTaraxacum coreanum and simultaneous quantification[J]. Molecules (Basel, Switzerland), 2018, 23(9): 2148. DOI:10.3390/molecules23092148. doi: 10.3390/molecules23092148
[18]	TALAPATRA B, DAS A K, TALAPATRA S K. Defuscin, a new phenolic ester from Dendrobium fuscescens: Conformation of shikimic acid[J]. Phytochemistry, 1989, 28(1): 290-292. DOI:10.1016/0031-9422(89)85065-4. doi: 10.1016/0031-9422(89)85065-4
[19]	李定祥, 侴桂新, 王峥涛. 川西千里光中酚酸类化学成分研究[J]. 河南中医, 2014, 34(9): 1847-1849. DOI:10.16367/j.issn.1003-5028.2014.09.001. doi: 10.16367/j.issn.1003-5028.2014.09.001
[20]	李骅轩, 崔淑君, 肖朝江, 等. 厚皮香酚性成分及其镇痛活性[J]. 中成药, 2019, 41(7): 1582-1586.
[21]	梁永红, 叶敏, 张灵芝, 等. 骨碎补中的两个新酚酸类化合物[J]. 药学学报, 2010, 45(7): 874-878. DOI:10.16438/j.0513-4870.2010.07.004. doi: 10.16438/j.0513-4870.2010.07.004
[22]	段礼新, 余正江, 冯宝民, 等. 复方三子养亲汤中酚酸类成分[J]. 沈阳药科大学学报, 2007, 24(11): 679-681. DOI:10.3969/j.issn.1006-2858.2007.11.005. doi: 10.3969/j.issn.1006-2858.2007.11.005

时间/min	流量/mL	甲醇体积分数(A)/%	0.1%甲酸水体积分数(B)/%
0.01	1.00	20.0	80.0
10.00	1.00	24.0	76.0
20.00	1.00	24.0	76.0
21.00	1.00	34.0	66.0
30.00	1.00	40.0	60.0
35.00	1.00	100.0	0

分配系数	目标化合物
分配系数	Ⅰ	Ⅱ	Ⅲ	Ⅳ	Ⅴ	Ⅵ
K_acid	29.92	6.43	9.29	4.61	0.20	1.94
K_base	0.00	0.75	0.00	0.05	0.02	0.00

Separation and purification of polyphenols from Taraxaci Herba by counter-current chromatography

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