Dynamic change in amino acids, catechins, alkaloids, and gallic acid in six types of tea processed from the same batch of fresh tea (Camellia sinensis L.) leaves

Abstract The manufacturing process plays a crucial role in influencing tea quality by altering its chemical composition. To investigate the effect of different manufacturing processes on the primary chemical components of tea, six types of traditional Chinese tea were produced from the same batch of fresh tea leaves. Dynamic changes of the major chemical components, including 22 free amino acids, 6 catechins, 2 alkaloids, and gallic acid (GA), in those six types of tea and fresh tea leaves, were analyzed. Principal component analysis (PCA) showed fresh tea leaves and the six tea types processed by different methods could be distinguished based on free amino acid chemometric analysis. The content of total free amino acids and catechins drastically decreased during fermentation, whereas GA content increased significantly. The catechin content varied greatly among different types of tea, indicating that epimerization and oxidative degradation of catechins occurred during tea processing. Caffeine content was relatively stable, whereas theobromine content fluctuated slightly according to the production process of the different teas. This study confirmed the dynamic changes in the primary characteristic metabolites during processing of different teas and demonstrated potential biomarkers to monitor the manufacturing process of different teas.

[1]  M. Clifford,et al.  Dietary phenolics: chemistry, bioavailability and effects on health. , 2009, Natural product reports.

[2]  Aysun Yilmaz,et al.  CHANGES IN CHEMICAL CONSTITUENTS AND POLYPHENOL OXIDASE ACTIVITY OF TEA LEAVES WITH SHOOT MATURITY AND COLD STORAGE , 2009 .

[3]  X. Wan,et al.  Investigation on biochemical compositional changes during the microbial fermentation process of Fu brick tea by LC-MS based metabolomics. , 2015, Food chemistry.

[4]  D. Armstrong,et al.  Varietal differences in the total and enantiomeric composition of theanine in tea , 1997 .

[5]  M. Lean,et al.  HPLC-MSn analysis of phenolic compounds and purine alkaloids in green and black tea. , 2004, Journal of agricultural and food chemistry.

[6]  Zheng-Zhu Zhang,et al.  A New Norisoprenoid and Other Compounds from Fuzhuan Brick Tea , 2012, Molecules.

[7]  R. Minocha,et al.  Transgenic manipulation of a single polyamine in poplar cells affects the accumulation of all amino acids , 2010, Amino Acids.

[8]  J. M. Jurado,et al.  Differentiation of green, white, black, Oolong, and Pu-erh teas according to their free amino acids content. , 2007, Journal of agricultural and food chemistry.

[9]  Gong Jia-shun,et al.  Effect of Different Additives on the Theabrownin and Its Formation Mechanism during Pu-erh Tea Fermentation , 2010 .

[10]  P. Tu,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. , 2014, Food chemistry.

[11]  B. C. Ghosh,et al.  Assessing biochemical changes during standardization of fermentation time and temperature for manufacturing quality black tea , 2015, Journal of Food Science and Technology.

[12]  Chung S. Yang,et al.  Cancer chemopreventive activity and bioavailability of tea and tea polyphenols. , 2003, Mutation research.

[13]  H. Tachibana,et al.  Hydrogen sulphide donors selectively potentiate a green tea polyphenol EGCG-induced apoptosis of multiple myeloma cells , 2017, Scientific Reports.

[14]  H. Shah,et al.  Withering timings affect the total free amino acids and mineral contents of tea leaves during black tea manufacturing , 2015 .

[15]  Hao Jiang,et al.  Antioxidant Activity of Leaf Extracts from Different Hibiscus sabdariffa Accessions and Simultaneous Determination Five Major Antioxidant Compounds by LC-Q-TOF-MS , 2014, Molecules.

[16]  V. Wray,et al.  New Flavonol Triglycosides from Tea (Camellia sinensis) , 2000 .

[17]  F. Wachira,et al.  Determination of Residual Catechins, Polyphenolic Contents and Antioxidant Activities of Developed Theaflavin-3,3’-Digallate Rich Black Teas , 2016 .

[18]  U. Engelhardt,et al.  Determination of amino acids in white, green, black, oolong, pu-erh teas and tea products , 2013 .

[19]  Karl Fraser,et al.  Analysis of metabolic markers of tea origin by UHPLC and high resolution mass spectrometry , 2013 .

[20]  J. Chen,et al.  Changes of major tea polyphenols and production of four new B-ring fission metabolites of catechins from post-fermented Jing-Wei Fu brick tea. , 2015, Food chemistry.

[21]  Lei Li,et al.  Simultaneous determination of free amino acids in Pu-erh tea and their changes during fermentation. , 2016, Food chemistry.

[22]  F. Wachira,et al.  Effect of Sunlight Exposure and Different Withering Durations on Theanine Levels in Tea ( Camellia sinensis ) , 2015 .

[23]  Jiewen Zhao,et al.  Determination of caffeine content and main catechins contents in green tea (Camellia sinensis L.) using taste sensor technique and multivariate calibration. , 2010 .

[24]  Masato Kazusaki,et al.  Validation of analytical procedures by high−performance liquid chromatography for pharmaceutical analysis , 2012 .

[25]  Hubiao Chen,et al.  Comparison of ten major constituents in seven types of processed tea using HPLC-DAD-MS followed by principal component and hierarchical cluster analysis , 2015 .

[26]  L. Terry,et al.  Variation of theanine, phenolic, and methylxanthine compounds in 21 cultivars of Camellia sinensis harvested in different seasons. , 2017, Food chemistry.

[27]  Jun-feng Tan,et al.  Study of the dynamic changes in the non-volatile chemical constituents of black tea during fermentation processing by a non-targeted metabolomics approach , 2016 .

[28]  Wang Li-l.  Changes on Catechin and Alkaloid Contents in Fresh Tea Leaves During Withering , 2015 .

[29]  Yuko Yoshida,et al.  Simultaneous analysis of individual catechins and caffeine in green tea , 1996 .

[30]  Yuerong Liang,et al.  Screening the cultivar and processing factors based on the flavonoid profiles of dry teas using principal component analysis , 2018 .

[31]  S. Baldermann,et al.  Recent studies of the volatile compounds in tea , 2013 .

[32]  B. Mackey,et al.  Structure-activity relationships of tea compounds against human cancer cells. , 2007, Journal of agricultural and food chemistry.

[33]  L. Mannina,et al.  Untargeted and targeted methodologies in the study of tea (Camellia sinensis L.) , 2014 .

[34]  Chenggang Yang,et al.  Inhibition of green tea polyphenol EGCG((−)-epigallocatechin-3-gallate) on the proliferation of gastric cancer cells by suppressing canonical wnt/β-catenin signalling pathway , 2016, International journal of food sciences and nutrition.

[35]  K. Fraser,et al.  Analysis of Low Molecular Weight Metabolites in Tea Using Mass Spectrometry-Based Analytical Methods , 2014, Critical reviews in food science and nutrition.

[36]  J. Bennetzen,et al.  Draft genome sequence of Camellia sinensis var. sinensis provides insights into the evolution of the tea genome and tea quality , 2018, Proceedings of the National Academy of Sciences.

[37]  Y. Kakùda,et al.  Production, Quality, and Biological Effects of Oolong Tea (Camellia sinensis) , 2010 .

[38]  Ying-Jun Zhang,et al.  Puerins A and B, two new 8-C substituted flavan-3-ols from Pu-er tea. , 2005, Journal of agricultural and food chemistry.

[39]  D. Hou,et al.  A Genome-Wide Microarray Highlights the Antiinflammatory Genes Targeted by Oolong Tea Theasinensin A in Macrophages , 2011, Nutrition and cancer.

[40]  V. Pawar,et al.  Investigation of processes in black tea manufacture through model fermentation (oxidation) experiments. , 2014, Journal of agricultural and food chemistry.

[41]  Ferda Sari,et al.  Changes in theanine and caffeine contents of black tea with different rolling methods and processing stages , 2013, European Food Research and Technology.

[42]  Tianfeng Chen,et al.  Structure-Activity Relationship Analysis on Antioxidant and Anticancer Actions of Theaflavins on Human Colon Cancer Cells. , 2018, Journal of agricultural and food chemistry.

[43]  Eun-hee Kim,et al.  Metabolic phenotyping of various tea (Camellia sinensis L.) cultivars and understanding of their intrinsic metabolism. , 2017, Food chemistry.

[44]  H. Fujiki,et al.  Human cancer stem cells are a target for cancer prevention using (−)-epigallocatechin gallate , 2017, Journal of Cancer Research and Clinical Oncology.

[45]  R. Gavara,et al.  Antioxidant and antimicrobial properties of ethylene vinyl alcohol copolymer films based on the release of oregano essential oil and green tea extract components , 2015 .

[46]  Yu Huang,et al.  Degradation of green tea catechins in tea drinks. , 2001, Journal of agricultural and food chemistry.

[47]  S. Kallithraka,et al.  Evaluation of bitterness and astringency of (+)-catechin and (-)-epicatechin in red wine and in model solution , 1997 .

[48]  M. Narukawa,et al.  L-Theanine Elicits an Umami Taste with Inosine 5′-Monophosphate , 2008, Bioscience, biotechnology, and biochemistry.

[49]  B. Logue,et al.  The analysis of aroma/flavor compounds in green tea using ice concentration linked with extractive stirrer. , 2017, Journal of chromatography. A.

[50]  B. Nelson,et al.  Separation and identification of twelve catechins in tea using liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry. , 2000, Analytical chemistry.

[51]  M. Pinto.  Tea: A new perspective on health benefits , 2013 .

[52]  Chi-Tang Ho,et al.  Quantification of ascorbyl adducts of epigallocatechin gallate and gallocatechin gallate in bottled tea beverages. , 2018, Food chemistry.

[53]  Yead Morshed Nibir,et al.  Comparative assessment of total polyphenols, antioxidant and antimicrobial activity of different tea varieties of Bangladesh , 2017 .

[54]  H. Tong,et al.  Dynamic changes in amino acids, catechins, caffeine and gallic acid in green tea during withering , 2018 .

[55]  Jingming Ning,et al.  Safety and anti-hyperglycemic efficacy of various tea types in mice , 2016, Scientific Reports.

[56]  Mark D Kellogg,et al.  Effects of Theobromine and Caffeine on Mood and Vigilance , 2013, Journal of clinical psychopharmacology.

[57]  Ashu Gulati,et al.  Characterization of volatile components of Kangra orthodox black tea by gas chromatography-mass spectrometry , 2007 .

[58]  R. Bino,et al.  Structural annotation and elucidation of conjugated phenolic compounds in black, green, and white tea extracts. , 2012, Journal of agricultural and food chemistry.

[59]  Dongfeng Zhang,et al.  Coffee and tea consumption and risk of lung cancer: a dose-response analysis of observational studies. , 2012, Lung cancer.

[60]  Chi-Tang Ho,et al.  Impact of Six Typical Processing Methods on the Chemical Composition of Tea Leaves Using a Single Camellia sinensis Cultivar, Longjing 43. , 2018, Journal of agricultural and food chemistry.

[61]  V. Gökmen,et al.  Flavor characteristics of seven grades of black tea produced in Turkey. , 2012, Journal of agricultural and food chemistry.

[62]  X. Wan,et al.  Chemical constituents analysis of white tea of different qualities and different storage times , 2016, European Food Research and Technology.

[63]  Yueming Jiang,et al.  Compositional analysis of teas from Australian supermarkets , 2006 .

[64]  Pei Chen,et al.  Tentative identification, quantitation, and principal component analysis of green pu-erh, green, and white teas using UPLC/DAD/MS. , 2011, Food chemistry.

[65]  Luca Tiano,et al.  Antioxidant activity of white, green and black tea obtained from the same tea cultivar , 2013 .

[66]  P. Sporns,et al.  MALDI-TOF MS analysis of food flavonol glycosides. , 2000, Journal of agricultural and food chemistry.

[67]  M. El-Shahawi,et al.  Analysis of some selected catechins and caffeine in green tea by high performance liquid chromatography. , 2012, Food chemistry.

[68]  T. Hofmann,et al.  Molecular and sensory studies on the umami taste of Japanese green tea. , 2006, Journal of agricultural and food chemistry.

[69]  Weidong Dai,et al.  Characterization of white tea metabolome: Comparison against green and black tea by a nontargeted metabolomics approach. , 2017, Food research international.

[70]  P. Tu,et al.  Change in tea polyphenol and purine alkaloid composition during solid-state fungal fermentation of postfermented tea. , 2012, Journal of agricultural and food chemistry.

[71]  Ying-Jun Zhang,et al.  Plant Resources, Chemical Constituents, and Bioactivities of Tea Plants from the Genus Camellia Section Thea. , 2018, Journal of agricultural and food chemistry.