Structural identification of theaflavin trigallate and tetragallate from black tea using liquid chromatography/electrospray ionization tandem mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 43, 2012, Pages 10850-10857

  Chen, Huadong ^a   Shurlknight, Kelly ^a   Leung, Tinchung ^b   Sang, Shengmin ^a  

^a NORTH CAROLINA A AND T STATE UNIVERSITY   (United States)

^b NORTH CAROLINA CENTRAL UNIVERSITY   (United States)

Author keywords

Black tea; LC MS; theaflavin tetragallate; theaflavin trigallate; thearubigins

Indexed keywords

BLACK TEA; EPIGALLOCATECHIN-3-GALLATE; GALLATE; HEALTH BENEFITS; HEART DISEASE; IONIZATION MASS SPECTROMETRY; LC-MS; POLYPHENOLS; STRUCTURAL ASPECTS; STRUCTURAL IDENTIFICATION; TANDEM MASS SPECTROMETRY; THEAFLAVINS; THEARUBIGINS;

CHROMATOGRAPHY; DISEASES; FLAVONOIDS; LIQUIDS; MASS SPECTROMETRY; PHENOLS;

IONIZATION OF LIQUIDS;

BIFLAVONOID; CATECHIN; PLANT EXTRACT; THEAFLAVIN;

ARTICLE; CAMELLIA SINENSIS; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY;

BIFLAVONOIDS; CAMELLIA SINENSIS; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; PLANT EXTRACTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

CAMELLIA SINENSIS;

EID: 84868160199     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf303749z     Document Type: Article

References (19)

1. Ross, I. A. Medicinal Plants of the World: Chemical Constituents, Traditional and Modern Medicinal Uses; Humana Press Inc: Totowa, NJ, 2005; pp 1-27.
2. Gallenkemper, G. About the effect of (black) tea compresses on the skin-Application study of inflammatory lesions on the legs in particular in connection with venous blood flow disturbance and literature review Phlebologie 2009, 38, 276-294
3. Naito, Y.; Yoshikawa, T. Green tea and heart health J. Cardiovasc. Pharmacol. 2009, 54, 385-90
4. Gardner, E. J.; Ruxton, C. H.; Leeds, A. R. Black tea-Helpful or harmful? A review of the evidence Eur J Clin Nutr 2007, 61, 3-18
5. Yang, C. S.; Wang, H.; Li, G. X.; Yang, Z.; Guan, F.; Jin, H. Cancer prevention by tea: Evidence from laboratory studies Pharmacol. Res. 2011, 64, 113-22
6. Kumar, G.; Pillare, S. P.; Maru, G. B. Black tea polyphenols-mediated in vivo cellular responses during carcinogenesis Mini-Rev. Med. Chem. 2010, 10, 492-505
7. Sang, S.; Lambert, J. D.; Ho, C. T.; Yang, C. S., The chemistry and biotransformation of tea constituents. Pharmacol. Res. 2011.
8. Sang, S.; Lambert, J. D.; Tian, S.; Hong, J.; Hou, Z.; Ryu, J. H.; Stark, R. E.; Rosen, R. T.; Huang, M. T.; Yang, C. S.; Ho, C. T. Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities Bioorg. Med. Chem. 2004, 12, 459-67
9. Haslam, E. Thoughts on thearubigins Phytochemistry 2003, 64, 61-73
10. Kuhnert, N.; Drynan, J. W.; Obuchowicz, J.; Clifford, M. N.; Witt, M. Mass spectrometric characterization of black tea thearubigins leading to an oxidative cascade hypothesis for thearubigin formation Rapid Commun. Mass Spectrom.: RCM 2010, 24, 3387-404
11. Ozawa, T.; Kataoka, M.; Morikawa, K.; Negishi, O. Elucidation of the partial structure of polymeric thearubigins from black tea by chemical degradation Biosci., Biotechnol., Biochem. 1996, 60, 2023-2027
12. Kuhnert, N. Unraveling the structure of the black tea thearubigins Arch. Biochem. Biophys. 2010, 501, 37-51
13. Lorenz, M.; Urban, J.; Engelhardt, U.; Baumann, G.; Stangl, K.; Stangl, V. Green and black tea are equally potent stimuli of NO production and vasodilation: New insights into tea ingredients involved Basic Res Cardiol 2009, 104, 100-110
14. Yang, G. Y.; Liu, Z.; Seril, D. N.; Liao, J.; Ding, W.; Kim, S.; Bondoc, F.; Yang, C. S. Black tea constituents, theaflavins, inhibit 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis in A/J mice Carcinogenesis 1997, 18, 2361-5
15. Patel, R.; Ingle, A.; Maru, G. B. Polymeric black tea polyphenols inhibit 1,2-dimethylhydrazine induced colorectal carcinogenesis by inhibiting cell proliferation via Wnt/beta-catenin pathway Toxicol. Appl. Pharmacol. 2008, 227, 136-46
16. Kumar, G.; Pillare, S. P.; Maru, G. B. Black tea polyphenols-mediated in vivo cellular responses during carcinogenesis Mini-Rev. Med. Chem. 2010, 10, 492-505
17. Coxon, D. T.; Vora, V. C.; Tee, J. L.; Grant, M. S.; Ollis, W. D.; Holmes, A. Flavanol digallates in green tea leaf Tetrahedron 1972, 28, 2819-2826
18. Lihu, Y.; Yueming, J.; Nivedita, D.; Riantong, S.; Xu, L.; Jun, D.; Katherine, R.; Alan, L.; Ying, X. HPLC analyses of flavanols and phenolic acids in the fresh young shoots of tea (Camellia sinensis) grown in Australia Food Chem. 2004, 84, 253-263
19. Sang, S.; Tian, S.; Stark, R. E.; Yang, C. S.; Ho, C. T. New dibenzotropolone derivatives characterized from black tea using LC/MS/MS Bioorg. Med. Chem. 2004, 12, 3009-17