Purification and HPLC Analysis of Caffeoylquinic Acids from Kudingcha Made from Ilex kudingcha C.J. Tseng

doi:10.7506/spkx1002-6630-201322024

Abstract

Abstract:

Six caffeoylquinic acid (CQA) derivatives were separated by column chromatography and semi-preparative
high performance liquid chromatography (HPLC) from the crude extract of Ilex kudingcha C.J. Tseng. An HPLC method
with DAD and TSKgel ODS-80 TsQA column was developed for the simultaneous determination of CQAs in Kudingcha
made from Ilex kudingcha C.J. Tseng. The results demonstrated that six CQA derivatives with 95% purity, 3-CQA,
4-CQA, 5-CQA, 3,4-diCQA, 3,5-diCQA and 4,5-diCQA, could be obtained through the purification of Ilex kudingcha
C.J. Tseng by semi-preparative high performance liquid chromatography (HPLC). The chromatographic conditions were
determined as follows: oven temperature set at 40 ℃, gradient elution with methanol/formic acid (5‰) with a flow rate
0.5 mL/min, and detection at a wavelength of 326 nm. As results, good linearity was observed with correlation coefficients of
0.9992–0.9999, the average recovery of the CQA derivatives from spiked samples was 96.34%, with relative standard
deviations (RSD) less than 3% (n = 3).

Key words: Kudingcha, Ilex kudingcha C.J. Tseng, caffeoylquinic acids, purification, high performance liquid chromatography(HPLC)

CLC Number:

TS201.4

WANG Qing-chuan，ZHANG Xin，ZHANG Wen-qin，SUN Xin-qi，HU Bing，SUN Yi，ZENG Xiao-xiong. Purification and HPLC Analysis of Caffeoylquinic Acids from Kudingcha Made from Ilex kudingcha C.J. Tseng[J]. FOOD SCIENCE, 2013, 34(22): 119-122.

References

[1] 陈杖洲. 苦丁茶的开发及其利用[J]. 中国茶叶加工, 1998, (4): 29-31.

[2] 刘瑾，丁平. 冬青属药用植物资源、化学成分及药理作用研究进展[J]. 广州中医药大学学报, 2008, 25 (3): 277-280.

[3] LIU L, SUN Y, LAURA T, et al. Determination of polyphenolic content and antioxidant activity of kudingcha made from Ilex kudingcha C.J.Tseng [J]. Food Chemistry, 2009, 112, 35-42.

[4] LI Li, PENG Yong, MA Guizhi, et al. Quantitative Analysis of Five Kudinosides in the Large-leaved Kudingcha and Related Species from the Genus Ilex by UPLC–ELSD [J]. Phytochemical Analysis, 2012, 23: 677-683.

[5] 刘丽香，梁兴飞，孙怡，等. 苦丁茶提取物多酚含量与抗氧化活性的测定[J]. 茶叶科学, 2008, 28(4): 289-293.

[6] 刘丽香，LAURA T，梁兴飞，等. Folin-Ciocalteu比色法测定苦丁茶中多酚含量[J]. 茶叶科学, 2008, 28(2): 101-106.

[7] 孙怡. 苦丁冬青苦丁茶中多酚类物质的分离纯化与结构解析[J]. 食品科学, 2011, 32(11): 60-63.

[8] CLIFFORD M N. Chlorogenic acids and other cinnamates-nature, occurrence, dietary burden, absorption and metabolism [J]. Journal of the Science of Food and Agriculture, 2000, 80(7): 1033-1043.

[9] 孟伟，温亚男，魏永巨. 金银花中绿原酸含量的荧光法测定[J]. 分析化学, 2009, 37(z1).

[10] 李文龙，张文明，薛东升，等. 测定金银花中6种有机酸化合物含量的一种新方法[J]. 浙江大学学报（医学版）, 2012, 41(1): 13-18.

[11] IWAI K, KISHIMOTO N, KAKINO Y, et al. In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans [J]. Journal of Agriculture and Food Chemistry, 2004, 52(15) : 4893-4898.

[12] 刘颖，郭明哗，白根本. 绿原酸的研究进展[J]. 中药材, 2012, 35(7): 1180-1185.

[13] ROBINSON W E Jr, CORDEIRO M, ABDEL-MALEK S, et al. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase [J]. Molecular Pharmacology, 1996, 50(4): 846-855.

[14] Gó1ngora L, Giner RM, Má?ez S, et al. Effects of caffeoyl conjugates of isoprenyl-hydroquinone glucoside and quinic acid on leukocyte function [J]. Life Science, 2002, 71(25): 2995-3004.

[15] MATSUI T, EBUCHI S, FUJISE T, et a1. Strong antihyperglycemic effects of water-soluble fraction of Brazilian propolis and its bioactive constituent, 3, 4, 5-tri-O-caffeoylquinic acid [J]. Biological and Pharmaceutical Bulletin, 2004, 27(11): 1797-1803.

[16] XIANG T, XIONG Q B, KETUT A I, et al. Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei [J]. Planta Medica, 2001, 67(4): 322-325.

[17] CLIFFORD M N, JOHNSTON K L, KNIGHT S, et al. Hierarchical scheme for LC-MSn identification of chlorogenic acids [J]. Journal of Agricultural and Food Chemistry, 2003, 51: 2900-2911.

[18] CLIFFORD M N, KNIGHT S, KUHNERT N. Discriminating between the six isomers of dicaffeoylquinic acid by LC-MSn [J]. Journal of Agricultural and Food Chemistry, 2005, 53: 3821-3832.

[19] BRAVO L, GOYA L, LECUMBERRI E. LC/MS Characterization of phenolic constituents of mate (Ilex paraguariensis, St. Hil.) and its antioxidant activity compared to commonly consumed beverages [J]. Food Research International, 2007, 40: 393-405.

[20] INBARAJ B S, LU H, KAO T H, et al. Simultaneous determination of phenolic acids and flavonoids in Lycium barbarum Linnaeus by HPLC–DAD–ESI-MS [J]. Journal of Pharmaceutical and Biomedical Analysis, 2010, 51: 549-556.

[21] NEGISHI O, NEGISHI Y, YAMAGUCHI F, et al. Deodorization with ku-ding-cha containing a large amount of caffeoylquinic acid derivatives [J]. Agricultural and Food Chemistry, 2004, 52: 5513-5518.