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8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity.
Food Chem. 2014; 152:539-45.FC

Abstract

Phytochemical investigation of the aqueous extract of pu-erh tea afforded eight novel 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols (puerins I-VIII) by (1)H, (13)C, two-dimensional nuclear magnetic resonance (NMR) and high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry (HPLC-DAD-ESI/MS) analysis. Comparative chemical analysis of green tea, black tea and Chinese dark teas confirmed that these compounds were the marker compounds of Chinese dark teas. Furthermore, fungal fermentation was indispensable for the biosynthesis of these novel compounds. Through single fungal fermentation, it was proved that catechins and theanine were the precursors of puerins I-VIII. HPLC-DAD-ESI/MS analysis elucidated the biosynthetic pathway for puerins I-VIII. Puerins I-IV have potential protective effects for the human micro-vascular endothelial cells (HMEC) injury induced by hydrogen dioxide compared to other tea polyphenols. 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols could be used in the quality control and authentication of Chinese dark teas.

Authors+Show Affiliations

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China.State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China.State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China.State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China.State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China.State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China.State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China. Electronic address: pengfeitu@bjmu.edu.cn.

Pub Type(s)

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

Language

eng

PubMed ID

24444972

Citation

Wang, Weinan, et al. "8-C N-ethyl-2-pyrrolidinone Substituted Flavan-3-ols as the Marker Compounds of Chinese Dark Teas Formed in the Post-fermentation Process Provide Significant Antioxidative Activity." Food Chemistry, vol. 152, 2014, pp. 539-45.
Wang W, Zhang L, Wang S, et al. 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity. Food Chem. 2014;152:539-45.
Wang, W., Zhang, L., Wang, S., Shi, S., Jiang, Y., Li, N., & Tu, P. (2014). 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity. Food Chemistry, 152, 539-45. https://doi.org/10.1016/j.foodchem.2013.10.117
Wang W, et al. 8-C N-ethyl-2-pyrrolidinone Substituted Flavan-3-ols as the Marker Compounds of Chinese Dark Teas Formed in the Post-fermentation Process Provide Significant Antioxidative Activity. Food Chem. 2014;152:539-45. PubMed PMID: 24444972.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity. AU - Wang,Weinan, AU - Zhang,Liang, AU - Wang,Shu, AU - Shi,Shepo, AU - Jiang,Yong, AU - Li,Ning, AU - Tu,Pengfei, Y1 - 2013/11/01/ PY - 2013/07/25/received PY - 2013/09/06/revised PY - 2013/10/21/accepted PY - 2014/1/22/entrez PY - 2014/1/22/pubmed PY - 2014/9/6/medline KW - Antioxidant KW - Aspergillus niger KW - Chinese dark tea KW - Flavan-3-ols KW - Post-fermentation SP - 539 EP - 45 JF - Food chemistry JO - Food Chem VL - 152 N2 - Phytochemical investigation of the aqueous extract of pu-erh tea afforded eight novel 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols (puerins I-VIII) by (1)H, (13)C, two-dimensional nuclear magnetic resonance (NMR) and high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry (HPLC-DAD-ESI/MS) analysis. Comparative chemical analysis of green tea, black tea and Chinese dark teas confirmed that these compounds were the marker compounds of Chinese dark teas. Furthermore, fungal fermentation was indispensable for the biosynthesis of these novel compounds. Through single fungal fermentation, it was proved that catechins and theanine were the precursors of puerins I-VIII. HPLC-DAD-ESI/MS analysis elucidated the biosynthetic pathway for puerins I-VIII. Puerins I-IV have potential protective effects for the human micro-vascular endothelial cells (HMEC) injury induced by hydrogen dioxide compared to other tea polyphenols. 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols could be used in the quality control and authentication of Chinese dark teas. SN - 1873-7072 UR - https://www.unboundmedicine.com/medline/citation/24444972/8_C_N_ethyl_2_pyrrolidinone_substituted_flavan_3_ols_as_the_marker_compounds_of_Chinese_dark_teas_formed_in_the_post_fermentation_process_provide_significant_antioxidative_activity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0308-8146(13)01566-5 DB - PRIME DP - Unbound Medicine ER -