Theaflavin digallate
Theaflavin digallate
Names
Systematic IUPAC name
3-Hydroxy-5-oxo-1,8-bis[(2R ,3R )-3,5,7-trihydroxy-3,4-dihydro-2H -1-benzopyran-2-yl]-5H -benzo[7]annulene-4,6-diyl bis(3,4,5-trihydroxybenzoate)
Other names
TFDG TF-3 Theaflavin-3,3'-digallate
Identifiers
ChemSpider
InChI=1S/C43H32O20/c44-17-7-23(46)21-12-29(52)39(60-32(21)9-17)14-1-19-20(40-30(53)13-22-24(47)8-18(45)10-33(22)61-40)11-31(54)41(63-43(59)16-4-27(50)37(56)28(51)5-16)35(19)38(57)34(6-14)62-42(58)15-2-25(48)36(55)26(49)3-15/h1-11,29-30,39-40,44-56H,12-13H2/t29-,30-,39-,40-/m1/s1
Y Key: FJYGFTHLNNSVPY-BBXLVSEPSA-N
Y InChI=1/C43H32O20/c44-17-7-23(46)21-12-29(52)39(60-32(21)9-17)14-1-19-20(40-30(53)13-22-24(47)8-18(45)10-33(22)61-40)11-31(54)41(63-43(59)16-4-27(50)37(56)28(51)5-16)35(19)38(57)34(6-14)62-42(58)15-2-25(48)36(55)26(49)3-15/h1-11,29-30,39-40,44-56H,12-13H2/t29-,30-,39-,40-/m1/s1
Key: FJYGFTHLNNSVPY-BBXLVSEPBI
Oc1cc(cc(O)c1O)C(=O)Oc5c(O)cc([C@H]2Oc3cc(O)cc(O)c3C[C@H]2O)c6\C=C(/C=C(/OC(=O)c4cc(O)c(O)c(O)c4)C(=O)c56)[C@H]7Oc8cc(O)cc(O)c8C[C@H]7O
Properties
C 43 H 32 O 20
Molar mass
868.709 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Theaflavin digallate (TFDG ) is an antioxidant natural phenol found in black tea , and a theaflavin derivative.
Health
References
^ Lin, Jen-Kun; Chen, Ping-Chung; Ho, Chi-Tang; Lin-Shiau, Shoei-Yn (2000). "Inhibition of Xanthine Oxidase and Suppression of Intracellular Reactive Oxygen Species in HL-60 Cells by Theaflavin-3,3'-digallate, (−)-Epigallocatechin-3-gallate, and Propyl Gallate". Journal of Agricultural and Food Chemistry . 48 (7): 2736–2743. doi :10.1021/jf000066d . PMID 10898615 .
^ Leong, Hoyee; Mathur, Priya S.; Greene, Geoffrey L. (2009). "Green tea catechins inhibit angiogenesis through suppression of STAT3 activation" . Breast Cancer Research and Treatment . 117 (3): 505–515. doi :10.1007/s10549-008-0196-x . ISSN 0167-6806 . PMC 3664280 . PMID 18821062 .
^ Moyle, Christina W. A.; Cerezo, Ana B.; Winterbone, Mark S.; Hollands, Wendy J.; Alexeev, Yuri; Needs, Paul W.; Kroon, Paul A. (2015). "Potent inhibition of VEGFR-2 activation by tight binding of green tea epigallocatechin gallate and apple procyanidins to VEGF: Relevance to angiogenesis" . Molecular Nutrition & Food Research . 59 (3): 401–412. doi :10.1002/mnfr.201400478 . ISSN 1613-4125 . PMC 4681316 . PMID 25546248 .
^ Ann Beltz, Lisa; Kay Bayer, Diana; Lynn Moss, Amber; Mitchell Simet, Ira (2006-09-01). "Mechanisms of Cancer Prevention by Green and Black Tea Polyphenols" . Anti-Cancer Agents in Medicinal Chemistry . 6 (5): 389–406. doi :10.2174/187152006778226468 . PMID 17017850 .
^ Chia-Nan Chen1, Coney P. C. Lin, Kuo-Kuei Huang, Wei-Cheng Chen, Hsin-Pang Hsieh, Po-Huang Liang and John T.-A. Hsu (2005). "Inhibition of SARS-CoV 3C-like Protease Activity by Theaflavin-3,3'-digallate (TF3)" . Evidence-Based Complementary and Alternative Medicine . 2 (2): 209–215. doi :10.1093/ecam/neh081 . PMC 1142193 . PMID 15937562 . {{cite journal }}
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