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Investigation of epigallocatechin-3-O-caffeoate and epigallocatechin-3-O-p-coumaroate in tea leaves by LC/MS-MS analysis.
Food Res Int. 2017 12; 102:77-83.FR

Abstract

(-)-Epigallocatechin-3-O-gallate (EGCG), the major catechin present in green tea, exhibits potent antioxidant activity. We thereby investigated the presence of unknown components bearing the (-)-epigallocatechin (EGC) moiety in fresh tea leaf samples. Initially, liquid chromatography tandem mass spectrometry (LC-MS/MS) was employed to examine fresh tea leaves of the Yabukita, the most popular tea cultivar in Japan, which suggested the presence of the EGC phenylpropanoid derivatives, (-)-epigallocatechin-3-O-p-coumaroate (EGCpCA) and (-)-epigallocatechin-3-O-caffeoate (EGCCA). The structures of the detected EGCpCA and EGCCA were then confirmed by LC-MS/MS using synthesized EGCpCA and EGCCA as standards. In addition, EGCpCA and EGCCA were evaluated for their antioxidant activity in the ORAC (oxygen radical antioxidant capacity) and DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assays, where EGCCA (8.60μmolTE/μmol, TE=Trolox equivalents) exhibited a stronger antioxidant activity than EGCG (5.52μmolTE/μmol) in the ORAC assay. Finally, EGCpCA and EGCCA were quantitated in several tea leaf samples using LC-MS/MS, and it was found that these compounds were present in lower quantities (EGCpCA, 16.8-345.8μg/g, EGCCA, 4.3-75.1μg/g in the dry tea leaves) than the major catechins. In this study, we found the potent antioxidant EGCCA using LC-MS/MS and revealed its wide existence in various tea leaves.

Authors+Show Affiliations

Research and Development Department, Health and Wellness Headquarters, Morinaga and Company Limited, 2-1-1 Shimosueyoshi, Tsurumi-ku, Yokohama, Kanagawa 230-8504, Japan. Electronic address: m-umehara-ji@morinaga.co.jp.Research and Development Department, Health and Wellness Headquarters, Morinaga and Company Limited, 2-1-1 Shimosueyoshi, Tsurumi-ku, Yokohama, Kanagawa 230-8504, Japan.Research and Development Department, Health and Wellness Headquarters, Morinaga and Company Limited, 2-1-1 Shimosueyoshi, Tsurumi-ku, Yokohama, Kanagawa 230-8504, Japan.Research and Development Department, Health and Wellness Headquarters, Morinaga and Company Limited, 2-1-1 Shimosueyoshi, Tsurumi-ku, Yokohama, Kanagawa 230-8504, Japan.

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29196011

Citation

Umehara, Masahiro, et al. "Investigation of epigallocatechin-3-O-caffeoate and epigallocatechin-3-O-p-coumaroate in Tea Leaves By LC/MS-MS Analysis." Food Research International (Ottawa, Ont.), vol. 102, 2017, pp. 77-83.
Umehara M, Yanae K, Maruki-Uchida H, et al. Investigation of epigallocatechin-3-O-caffeoate and epigallocatechin-3-O-p-coumaroate in tea leaves by LC/MS-MS analysis. Food Res Int. 2017;102:77-83.
Umehara, M., Yanae, K., Maruki-Uchida, H., & Sai, M. (2017). Investigation of epigallocatechin-3-O-caffeoate and epigallocatechin-3-O-p-coumaroate in tea leaves by LC/MS-MS analysis. Food Research International (Ottawa, Ont.), 102, 77-83. https://doi.org/10.1016/j.foodres.2017.09.086
Umehara M, et al. Investigation of epigallocatechin-3-O-caffeoate and epigallocatechin-3-O-p-coumaroate in Tea Leaves By LC/MS-MS Analysis. Food Res Int. 2017;102:77-83. PubMed PMID: 29196011.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Investigation of epigallocatechin-3-O-caffeoate and epigallocatechin-3-O-p-coumaroate in tea leaves by LC/MS-MS analysis. AU - Umehara,Masahiro, AU - Yanae,Koji, AU - Maruki-Uchida,Hiroko, AU - Sai,Masahiko, Y1 - 2017/09/28/ PY - 2017/06/28/received PY - 2017/09/26/revised PY - 2017/09/27/accepted PY - 2017/12/3/entrez PY - 2017/12/3/pubmed PY - 2019/8/20/medline KW - Antioxidant activity KW - EGC derivative KW - Epigallocatechin-3-O-caffeoate KW - Epigallocatechin-3-O-p-coumaroate KW - Tea SP - 77 EP - 83 JF - Food research international (Ottawa, Ont.) JO - Food Res Int VL - 102 N2 - (-)-Epigallocatechin-3-O-gallate (EGCG), the major catechin present in green tea, exhibits potent antioxidant activity. We thereby investigated the presence of unknown components bearing the (-)-epigallocatechin (EGC) moiety in fresh tea leaf samples. Initially, liquid chromatography tandem mass spectrometry (LC-MS/MS) was employed to examine fresh tea leaves of the Yabukita, the most popular tea cultivar in Japan, which suggested the presence of the EGC phenylpropanoid derivatives, (-)-epigallocatechin-3-O-p-coumaroate (EGCpCA) and (-)-epigallocatechin-3-O-caffeoate (EGCCA). The structures of the detected EGCpCA and EGCCA were then confirmed by LC-MS/MS using synthesized EGCpCA and EGCCA as standards. In addition, EGCpCA and EGCCA were evaluated for their antioxidant activity in the ORAC (oxygen radical antioxidant capacity) and DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assays, where EGCCA (8.60μmolTE/μmol, TE=Trolox equivalents) exhibited a stronger antioxidant activity than EGCG (5.52μmolTE/μmol) in the ORAC assay. Finally, EGCpCA and EGCCA were quantitated in several tea leaf samples using LC-MS/MS, and it was found that these compounds were present in lower quantities (EGCpCA, 16.8-345.8μg/g, EGCCA, 4.3-75.1μg/g in the dry tea leaves) than the major catechins. In this study, we found the potent antioxidant EGCCA using LC-MS/MS and revealed its wide existence in various tea leaves. SN - 1873-7145 UR - https://www.unboundmedicine.com/medline/citation/29196011/Investigation_of_epigallocatechin_3_O_caffeoate_and_epigallocatechin_3_O_p_coumaroate_in_tea_leaves_by_LC/MS_MS_analysis_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0963-9969(17)30670-1 DB - PRIME DP - Unbound Medicine ER -