:Theaflavin digallate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470605918
| ImageFile=theaflavin digallate.png
| ImageSize=
| SystematicName = 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)
| OtherNames = TFDG
TF-3
Theaflavin-3,3'-digallate
|Section1={{Chembox Identifiers
| 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
| InChIKey = FJYGFTHLNNSVPY-BBXLVSEPBI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FJYGFTHLNNSVPY-BBXLVSEPSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=33377-72-9
| PubChem=5748168
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=20019479
| SMILES = 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
}}
|Section2={{Chembox Properties
| C=43 | H=32 | O=20
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
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|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Theaflavin digallate (TFDG) is an antioxidant natural phenol found in black tea, and a theaflavin derivative.
Health
- TFDG is a scavenger of superoxide in vitro, even more so than EGCG.{{cite journal | doi = 10.1021/jf000066d | pmid = 10898615 | title = 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 = Journal of Agricultural and Food Chemistry | volume = 48 | issue = 7 | pages = 2736–2743 | year = 2000 | last1 = Lin | first1 = Jen-Kun | last2 = Chen | first2 = Ping-Chung | last3 = Ho | first3 = Chi-Tang | last4 = Lin-Shiau | first4 = Shoei-Yn }}
- Tea polyphenols including TFDG reduce angiogenesis,{{Cite journal |last1=Leong |first1=Hoyee |last2=Mathur |first2=Priya S. |last3=Greene |first3=Geoffrey L. |date=2009 |title=Green tea catechins inhibit angiogenesis through suppression of STAT3 activation |journal=Breast Cancer Research and Treatment |language=en |volume=117 |issue=3 |pages=505–515 |doi=10.1007/s10549-008-0196-x |issn=0167-6806 |pmc=3664280 |pmid=18821062}} which is implicated in non-liquid cancers, an area of intense current research, by decreasing vascular endothelial growth factor production and receptor phosphorylation.{{Cite journal |last1=Moyle |first1=Christina W. A. |last2=Cerezo |first2=Ana B. |last3=Winterbone |first3=Mark S. |last4=Hollands |first4=Wendy J. |last5=Alexeev |first5=Yuri |last6=Needs |first6=Paul W. |last7=Kroon |first7=Paul A. |date=2015 |title=Potent inhibition of VEGFR-2 activation by tight binding of green tea epigallocatechin gallate and apple procyanidins to VEGF: Relevance to angiogenesis |journal=Molecular Nutrition & Food Research |language=en |volume=59 |issue=3 |pages=401–412 |doi=10.1002/mnfr.201400478 |issn=1613-4125 |pmc=4681316 |pmid=25546248}}{{Cite journal |last1=Ann Beltz |first1=Lisa |last2=Kay Bayer |first2=Diana |last3=Lynn Moss |first3=Amber |last4=Mitchell Simet |first4=Ira |date=2006-09-01 |title=Mechanisms of Cancer Prevention by Green and Black Tea Polyphenols |url=https://www.eurekaselect.com/57750/article |journal=Anti-Cancer Agents in Medicinal Chemistry |language=en |volume=6 |issue=5 |pages=389–406 |doi=10.2174/187152006778226468|pmid=17017850 |url-access=subscription }}
- TFDG inhibits activity of the enzyme 3CLpro in vitro.{{cite journal|author=Chia-Nan Chen1, Coney P. C. Lin, Kuo-Kuei Huang, Wei-Cheng Chen, Hsin-Pang Hsieh, Po-Huang Liang and John T.-A. Hsu|title=Inhibition of SARS-CoV 3C-like Protease Activity by Theaflavin-3,3'-digallate (TF3)|journal=Evidence-Based Complementary and Alternative Medicine|year=2005|volume=2|issue=2|pages=209–215|doi=10.1093/ecam/neh081|pmid=15937562|pmc=1142193}}
References
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{{Thearubigin}}