Structural identification of mouse fecal metabolites of theaflavin 3,3′-digallate using liquid chromatography tandem mass spectrometry

被引:42
作者
Chen, Huadong [1 ]
Parks, Tiffany A. [1 ]
Chen, Xiaoxin [2 ]
Gillitt, Nicholas D. [3 ]
Jobin, Christian [4 ,5 ]
Sang, Shengmin [1 ]
机构
[1] N Carolina Agr & Tech State Univ, Ctr Excellence Postharvest Technol, Kannapolis, NC 28081 USA
[2] N Carolina Cent Univ, Canc Res Program, Julius L Chambers Biomed Biotechnol Res Inst, Durham, NC 27707 USA
[3] Dole Nutr Res Lab, Kannapolis, NC 28081 USA
[4] Univ N Carolina, Dept Med Pharmacol & Immunol Microbiol, Chapel Hill, NC 27599 USA
[5] Univ N Carolina, Ctr Gastrointestinal Biol & Dis, Chapel Hill, NC 27599 USA
关键词
Theaflavin 3,3 '-digallate; Mice; Metabolites; Liquid chromatography-tandem mass spectrometry; BLACK TEA THEAFLAVINS; NF-KAPPA-B; CANCER PREVENTION; GALLIC ACID; ANTIINFLAMMATORY ACTIVITY; PROTOCATECHUIC ACID; DOWN-REGULATION; TUMOR-GROWTH; IN-VIVO; POLYPHENOLS;
D O I
10.1016/j.chroma.2011.08.056
中图分类号
Q5 [生物化学];
学科分类号
070307 [化学生物学];
摘要
Black tea consumption has been associated with many health benefits including the prevention of cancer and heart disease. Theaflavins are the major bioactive polyphenols present in black tea. Unfortunately, limited information is available on their biotransformation. In the present study, we investigated the metabolic fate of theaflavin 3,3'-digallate (TFDG), one of the most abundant and bioactive theaflavins, in mouse fecal samples using liquid chromatography/electrospray ionization tandem mass spectrometry by analyzing the MSn (n = 1-3) spectra. Four metabolites theaflavin, theaflavin 3-gallate, theaflavin 3'-gallate. and gallic acid were identified as the major mouse fecal metabolites of TFDG. Glucuronidated and sulfated, instead of methylated metabolites of theaflavin 3-gallate, theaflavin 3'-gallate, and TFDG were detected and identified as the minor mouse fecal metabolites of TFDG. Our results indicate that TFDG can be degraded in mice. Further studies on the formation of those metabolites in TFDG-treated mice in germ-free conditions are warranted. To our knowledge, this is the first report on the biotransformation of TFDG in mice. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:7297 / 7306
页数:10
相关论文
共 29 条
[1]
The chemistry of tea flavonoids [J].
Balentine, DA ;
Wiseman, SA ;
Bouwens, LCM .
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION, 1997, 37 (08) :693-704
[2]
Beneficial effects of green tea: A literature review [J].
Chacko S.M. ;
Thambi P.T. ;
Kuttan R. ;
Nishigaki I. .
Chinese Medicine, 5 (1)
[3]
Metabolites Are Key to Understanding Health Effects of Wine Polyphenolics1-3 [J].
Forester, Sarah C. ;
Waterhouse, Andrew L. .
JOURNAL OF NUTRITION, 2009, 139 (09) :1824S-1831S
[4]
Thoughts on thearubigins [J].
Haslam, E .
PHYTOCHEMISTRY, 2003, 64 (01) :61-73
[5]
Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption [J].
Henning, Susanne M. ;
Aronson, William ;
Niu, Yantao ;
Conde, Francisco ;
Lee, Nicolas H. ;
Seeram, Navindra P. ;
Lee, Ru-Po ;
Lu, Jinxiu ;
Harris, Diane M. ;
Moro, Aune ;
Hong, Jenny ;
Pak-Shan, Leung ;
Barnard, R. James ;
Ziaee, Hossein G. ;
Csathy, George ;
Go, Vay L. W. ;
Wang, Hejing ;
Heber, David .
JOURNAL OF NUTRITION, 2006, 136 (07) :1839-1843
[6]
Tea catechins and polyphenols: Health effects, metabolism, and antioxidant functions [J].
Higdon, JV ;
Frei, B .
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION, 2003, 43 (01) :89-143
[7]
Gallic Acid Induces Apoptosis via Caspase-3 and Mitochondrion-Dependent Pathways in Vitro and Suppresses Lung Xenograft Tumor Growth in Vivo [J].
Ji, Bin-Chuan ;
Hsu, Wu-Huei ;
Yang, Jai-Sing ;
Hsia, Te-Chun ;
Lu, Chi-Cheng ;
Chiang, Jo-Hua ;
Yang, Jiun-Long ;
Lin, Ching-Hsiung ;
Lin, Jen-Jyh ;
Suen, Lee-Jen Wu ;
Wood, Wellington Gibson ;
Chung, Jing-Gung .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (16) :7596-7604
[8]
Breast cancer prevention by green tea catechins and black tea theaflavins in the C3(1) SV40 T,t antigen transgenic mouse model is accompanied by increased apoptosis and a decrease in oxidative DNA adducts [J].
Kaur, Siminder ;
Greaves, Peter ;
Cooke, Darren N. ;
Edwards, Richard ;
Steward, William P. ;
Gescher, Andreas J. ;
Marczylo, Timothy H. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (09) :3378-3385
[9]
ANTIINFLAMMATORY ACTIVITY OF GALLIC ACID [J].
KROES, BH ;
VANDENBERG, AJJ ;
VANUFFORD, HCQ ;
VANDIJK, H ;
LABADIE, RP .
PLANTA MEDICA, 1992, 58 (06) :499-504
[10]
Black Tea Polyphenols-Mediated In Vivo Cellular Responses During Carcinogenesis [J].
Kumar, G. ;
Pillare, S. P. ;
Maru, G. B. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2010, 10 (06) :492-505