固相萃取结合高效液相制备茶树没食子酸衍生物

doi:10.13305/j.cnki.jts.2012.06.001

Abstract

Abstract: Gallic acid derivatives are the chief compounds of phenolic acid in tea. They are important umami-enhancing compounds in tea beverage, and possess the effects of inhibiting IgE producton, enhancing cognition-anting depressant. A reversed-phase PHPLC coupled with SPE was developed to purify and to prepare high purity 3-O-galloyquinic acid and β-D-glucogalline from fresh tea leaves. The obtained fractions were successfully identified by LC/TOF-ESI-MS, ¹H-NMR and ¹³C-NMR. This method is simple, effective for the preparation of gallic acid derivatives.

Key words: gallic acid derivatives, SPE, PHPLC, β-D-glucogalline, 3-O-galloyquinic acid

CLC Number:

TS272
Q946.8

LU Zhong-wei, JIANG Xiao-lan, LIU Ya-jun, LIU Li, GAO Li-ping, XIA Tao. Preparation of Gallic Acid Derivatives by Solid-phase Extraction Cartridge Coupled with Preparative High Performance Liquid Chromatography from Tea Plant[J]. Journal of Tea Science, 2012, 32(6): 494-499.

References

[1] 宛晓春. 茶叶生物化学[M]. 北京: 中国农业出版社, 2003.
[2] Kaneko S, Kumazawa K, Masuda H, et al. Molecular and sensory studies on the umami taste of Japanese green tea[J]. J Agric Food Chem, 2006, 54(7): 2688-2694.
[3] Kaneko S, kumazawa K, Masuda H, et al. Sensory and structural characterisation of an umami enhancing compound in green tea[J]. J Food Science, 2006, 43: 181-184.
[4] Honma D, Tagashira M, Kanda T, et al. Identifications of inhibitors of IgE production by human lymphocytes isolated from 'Cha Chuukanbohon Nou 6' tea leaves[J]. J Sci Food Agric, 2010, 90(1): 168-174.
[5] Dimpfel W, Kler A, Kriesl E, et al. Theogallin and L-theanine as active ingredients in decaffeinated green tea extract: Ⅱ. Characterization in the freely moving rat by means of quantitative field potential analysis[J]. J Pharm Pharmacol, 2007, 59(10): 1397-1403.
[6] Cartwright RA, Roberts EAH.Theogallin, a polyphenol occuring in tea[J]. J Sci Food Agric, 1954, 34(15): 593-597.
[7] Stagg GV, Swaine D.The identification of theogallin as 3-galloyquinic acid[J]. Phytochemistry, 1971, 10(7): 1671-1673.
[8] Clifford MN, Stoupi S, Kuhnert N.Profiling and characterization by LC-MSn of the galloylquinic acids of green tea, tara tannin, and tannic acid[J]. J Agric Food Chem, 2007, 55(8): 2797-2807.
[9] Takemoto JK, Davies NM.Method development for beta-glucogallin and gallic acid analysis: application to urinary pharmacokinetic studies[J]. J Pharm Biomed Anal, 2011, 54(4): 812-816.
[10] Miyaichi Y, Nunomura N, Kawata Y, et al. Studies on nepalese crude drugs. XXVIII. Chemical constituents of Bhote Khair, the underground parts of Eskemukerjea megacarpum HARA[J]. Chem Pharm Bull (Tokyo), 2006, 54(1): 136-138.
[11] Subeki S, Matsuura H, Takahashi K, et al. Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri[J]. J Nat Prod, 2005, 68(4): 537-539.
[12] Ayoub NA.Unique phenolic carboxylic acids from Sanguisorba minor[J]. Phytochemistry, 2003, 63(4): 433-436.
[13] Ling SK, Tanaka T, Kouno I.New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia[J]. J Nat Prod, 2002, 65(2): 131-135.
[14] Niemetz R, Gross GG.Enzymology of gallotannin and ellagitannin biosynthesis[J]. Phytochemistry, 2005, 66(17): 2001-2011.
[15] Niemetz R, Gross GG.Gallotannin biosynthesis: beta-glucogallin: hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves[J]. Phytochemistry, 2001, 58(5): 657-661.
[16] Hofmann AS, Gross GG.Biosynthesis of gallotannins: formation of polygalloylglucoses by enzymatic acylation of 1,2,3,4,6-penta-O-galloylglucose[J]. Arch Biochem Biophys, 1990, 283(2): 530-532.
[17] Cammann J, Denzel K, Schilling G, et al. Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose[J]. Arch Biochem Biophys, 1989, 273(1): 58-63.
[18] Lin LZ, Chen P, Harnly JM.New phenolic components and chromatographic profiles of green and fermented teas[J]. J Agric Food Chem, 2008, 56(17): 8130-8140.
[19] Nishimura H, Nonaka G, Nishioka I.Seven quinic acid gallates from quercus stenophylla[J]. Phytochemistry, 1984, 23(11): 2621-2623.
[20] Pawlowska AM, De Leo M, Braca A.Phenolics of Arbutus unedo L. (Ericaceae) fruits: identification of anthocyanins and gallic acid derivatives[J]. J Agric Food Chem, 2006, 54(26): 10234-10238.
[21] 马耀,张建中. 微量研究没食子酸丙酯自动氧化反应[J]. 科学通报, 1993, 38(21): 1960-1961.
[22] 赵拉. 五倍子制备没食子酸的研究进展[J]. 化学与生物工程, 2008, 25(5): 5-7.

[1]	. [J]. Journal of Tea Science, 1965, 2(04): 59 -63 .
[2]	. [J]. Journal of Tea Science, 1965, 2(03): 18 -21 .
[3]	. [J]. Journal of Tea Science, 1965, 2(03): 22 -24 .
[4]	. [J]. Journal of Tea Science, 1966, 3(02): 55 -57 .
[5]	. [J]. Journal of Tea Science, 1966, 3(02): 82 -83 .
[6]	. [J]. Journal of Tea Science, 1986, 6(01): 1 -8 .
[7]	. [J]. Journal of Tea Science, 1987, 7(02): 29 -34 .
[8]	. [J]. Journal of Tea Science, 1988, 8(01): 37 -42 .
[9]	. [J]. Journal of Tea Science, 1995, 15(02): 154 .
[10]	. [J]. Journal of Tea Science, 1999, 19(01): 73 -76 .

Preparation of Gallic Acid Derivatives by Solid-phase Extraction Cartridge Coupled with Preparative High Performance Liquid Chromatography from Tea Plant

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 10

[1]	LI Ziqiang, YANG Mei, ZHANG Xinzhong, LUO Fengjian, ZHOU Li, LOU Zhengyun, SUN Hezhi, WANG Xinru, CHEN Zongmao. Residue Determination of Sixteen Pesticides in Green Tea by UPLC-MS/MS [J]. Journal of Tea Science, 2022, 42(4): 537-548.
[2]	LIU Qi, OUYANG Jian, LIU Changwei, CHEN Hongyu, LI Juan, XIONG Ligui, LIU Zhonghua, HUANG Jian'an. Research Progress of Tea Quality Evaluation Technology [J]. Journal of Tea Science, 2022, 42(3): 316-330.
[3]	CHEN Xiaomin, ZHAO Feng, WANG Shuyan, SHAO Shuxian, WU Wenxi, LIN Qin, WANG Pengjie, YE Naixing. Purine Alkaloid Evaluation and Excellent Resources Screening of Fujian Wild Tea [J]. Journal of Tea Science, 2022, 42(1): 18-28.
[4]	LIU Yanan, LIU Mengyuan, HUANG Liyun, KANG Zhiwei, XU Yongyu, CHEN Zhenzhen. Analysis of Diversity and Temporal Patterns of the Insect Communities in Tea Gardens [J]. Journal of Tea Science, 2022, 42(1): 109-119.
[5]	MA Jiali, WANG Chen, CHEN Hongping, CHAI Yunfeng, ZHU Li, LIU Xin. Rapid Determination of 24 Pesticide Residues in Tea by in-Syringe Dispersive Solid Phase Extraction-Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry [J]. Journal of Tea Science, 2021, 41(5): 717-730.
[6]	LYU Haitao, WU Wenjun, LIAO Shengxi, WANG Zizhi, ZHOU Junhong, LI Li, CUI Kai. Analysis of Ground-based Spectral Reflection Characteristics and Differences of Three Types of Yunnan Puer Tea [J]. Journal of Tea Science, 2021, 41(2): 184-192.
[7]	REN Guangxin, JIN Shanshan, LI Luqing, NING Jingming, ZHANG Zhengzhu. Research Progress of Near-infrared Spectroscopy in Tea Quality Control and Equipment Development [J]. Journal of Tea Science, 2020, 40(6): 707-714.
[8]	CHEN Lin, ZHANG Yinggen, CHEN Jian, SONG Zhenshuo, XIANG Lihui, YU Wenquan, YOU Zhiming. Aroma Profiling of Fresh Leaves of Oolong Tea Cultivars during White Tea Processing [J]. Journal of Tea Science, 2020, 40(6): 771-781.
[9]	QIAO Li, HONG Feng, JIN Yinli, GENG Shubao, GUO Shibao. Effects on the Photoreaction Behavior of Ectropis Grisescens Warren to Different Light Spectrum [J]. Journal of Tea Science, 2020, 40(5): 617-624.
[10]	LU Li, CHENG Xi, ZHANG Bo, SHEN Xiaoxia, LIU Yan, XIONG Li, YUAN Xiao, LI Yuanhua, LI Xinghui. Establishment of Predictive Model for Quantitative Analysis of Tea Polyphenols and Caffeine of Souchong by Near Infrared Spectroscopy [J]. Journal of Tea Science, 2020, 40(5): 689-695.
[11]	ZHENG Chengqin, MA Cunqiang, ZHANG Zhengyan, LI Xiaohong, WU Tingting, ZHOU Binxing. A Preliminary Study on the Degradation Pathway of Caffeine in Tea Microbial Solid-state Fermentation [J]. Journal of Tea Science, 2020, 40(3): 386-396.
[12]	YANG Jie, ZHOU Li, YU Huan, SUN Hezhi, WANG Xinru, ZHANG Xinzhong, YANG Mei, CHEN Zongmao, LUO Fengjian. Determination of Pesticide Residue in Fresh Tea Leaves and Dry Tea by Solid Extraction and Dispersive Solid Extraction Cleanup Coupled with Tandem Mass Spectrum [J]. Journal of Tea Science, 2020, 40(3): 397-406.
[13]	YANG Yaqin, FENG Shuhui, HU Yongjian, LI Yuanyuan, WANG Huifeng, LIU Jinxi, ZHONG Hongjian. Determination of Glyphosate and Aminomethyl Phosphonic Acid Residue in Green Tea by Gas Chromatography-Mass Spectrometry [J]. Journal of Tea Science, 2020, 40(1): 125-132.
[14]	LIU Peng, AI Shirong, YANG Puxiang, LI Wenjin, XIONG Aihua, TONG Yang, HU Xiao, WU Ruimei. Nonlinear Manifold Dimensionality Reduction Methods for Quick Discrimination of Tea at Different Altitude by Near Infrared Spectroscopy [J]. Journal of Tea Science, 2019, 39(6): 715-722.
[15]	WU Huiping, QI Meng, LI Yeyun, MA Huiqin, WU Xun. Proposal to Replace the Illegitimate Name of Tea Garden Weeds in China [J]. Journal of Tea Science, 2019, 39(3): 247-256.