Changes of major tea polyphenols and production of four new B-ring fission metabolites of catechins from post-fermented Jing-Wei Fu brick tea

Yun-Fei Zhu; Jing-Jing Chen; Xiao-Ming Ji; Xin Hu; Tie-Jun Ling; Zheng-Zhu Zhang; Guan-Hu Bao; Xiao-Chun Wan

doi:10.1016/j.foodchem.2014.08.075

Changes of major tea polyphenols and production of four new B-ring fission metabolites of catechins from post-fermented Jing-Wei Fu brick tea

Food Chem. 2015 Mar 1:170:110-7. doi: 10.1016/j.foodchem.2014.08.075. Epub 2014 Aug 23.

Authors

Yun-Fei Zhu¹, Jing-Jing Chen¹, Xiao-Ming Ji², Xin Hu², Tie-Jun Ling¹, Zheng-Zhu Zhang¹, Guan-Hu Bao³, Xiao-Chun Wan⁴

Affiliations

¹ Key Laboratory of Tea Biochemistry and Biotechnology, Anhui Agricultural University, 130 West Changjiang Road, Hefei City, Anhui Province 230036, China.
² Shaanxi Zhong Fu Tea Research Institute, Xianyang City, Shaanxi Province 712044, China.
³ Key Laboratory of Tea Biochemistry and Biotechnology, Anhui Agricultural University, 130 West Changjiang Road, Hefei City, Anhui Province 230036, China. Electronic address: baoguanhu@ahau.edu.cn.
⁴ Key Laboratory of Tea Biochemistry and Biotechnology, Anhui Agricultural University, 130 West Changjiang Road, Hefei City, Anhui Province 230036, China. Electronic address: xcwan@ahau.edu.cn.

PMID: 25306324
DOI: 10.1016/j.foodchem.2014.08.075

Abstract

HPLC analysis of samples from four major fermentation procedures of Jing-Wei Fu brick tea showed that the level of major tea catechins epigallocatechin gallate (EGCG) and epicatechin gallate (ECG) dropped increasingly to about 1/3 in the final product. Phytochemical study of the final product led to the discovery of four new B-ring fission metabolites of catechins (BRFCs) Fuzhuanin C-F (1-4) together with three known BRFCs (5-7), six known catechins (8-13), five simple phenols (14-18), seven flavones and flavone glycosides (19-25), two alkaloids (26, 27), three triterpenoids (28-30) and one steroid (31). The structures were elucidated by spectroscopic methods including 1D and 2D NMR, LC-HR-ESI-MS, IR, and CD spectra. Five compounds (16-18, 28, 29) were reported for the first time in tea. Possible pathways for the degradation of major tea catechins and the generation of BRFCs were also provided.

Keywords: (+)-Catechin (C, PubChem CID: 9064); (−)-Epiafzelechin (PubChem CID: 443639); (−)-Epicatechin (EC, PubChem CID: 72276); (−)-Epigallocatechin gallate (EGCG, PubChem CID: 65064); 2,5-Dihydroxy benzoic acid (PubChem CID: 3469); Aspergillus spp.; Astragalin (PubChem CID: 5282102); B-ring fission metabolites of catechins (BRFCs); Camellia sinensis; Canophyllol (PubChem CID: 623591); Epicatechin-3-O-(4′-O-methyl) gallate (PubChem CID: 21146794); Epicatechin-3-gallate (ECG, PubChem CID: 65056); Epigallocatechin (EGC, PubChem CID: 72277); Eurotium spp.; Fuzhuan brick tea (FBT); Fuzhuanin C–F; Gallic acid (GA, PubChem CID: 370); Gallicin (PubChem CID: 7428); Kaempferol (PubChem CID: 5280863); Myricetin (PubChem CID: 5281672); Nicotiflorin (PubChem CID: 5318767); Phloroglucinol (PubChem CID: 359); Pyrogallol (PubChem CID: 1057); Quercetin (PubChem CID: 5280343); Rutin (PubChem CID: 5280805); Theobromine (PubChem CID: 2519); Xanthocerin (PubChem CID: 5315332); α-Spinasterol (PubChem CID: 5281331).

Publication types

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

MeSH terms

Chromatography, High Pressure Liquid / methods*
Fermentation
Phenols / analysis*
Polyphenols / analysis*
Tea / chemistry*

Substances

Phenols
Polyphenols
Tea