Theaflavin-3-gallate

Last updated
Theaflavin-3-gallate
Theaflavin 3-gallate.svg
Names
Systematic IUPAC name
(2R,3R)-5,7-Dihydroxy-2-{3,4,6-trihydroxy-5-oxo-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-5H-benzo[7]annulen-2-yl}-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Other names
Theaflavin-3-monogallate; Theaflavin monogallate A; Theaflavin 2A; TFMG
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C36H28O16/c37-14-5-20(39)18-10-26(45)35(51-27(18)7-14)17-9-25(44)33(48)30-16(17)1-12(2-24(43)32(30)47)34-29(11-19-21(40)6-15(38)8-28(19)50-34)52-36(49)13-3-22(41)31(46)23(42)4-13/h1-9,26,29,34-35,37-42,44-46,48H,10-11H2,(H,43,47)/t26-,29-,34-,35-/m1/s1 Yes check.svgY
    Key: KMJPKUVSXFVQGZ-WQLSNUALSA-N Yes check.svgY
  • c1c(cc(=O)c(c2c1c(cc(c2O)O)[C@@H]3[C@@H](Cc4c(cc(cc4O3)O)O)O)O)[C@@H]5[C@@H](Cc6c(cc(cc6O5)O)O)OC(=O)c7cc(c(c(c7)O)O)O
Properties
C36H28O16
Molar mass 716.604 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Theaflavin-3-gallate is a theaflavin derivative. It can be found in abundance in black tea and is produced during fermentation. [1] [2] [3] It has been studied as a cancer-fighting chemical when combined with cisplatin against ovarian cancer cells. [2] [4] [5] Consuming large amounts of black tea has been reported to reduce the effects of aging in female populations. [2] [6]

See also

References

  1. ↑ Hu X, Ping Z, Gan M, Tao Y, Wang L, Shi J, Wu X, Zhang W, Yang H, Xu Y, Wang Z, Geng D (January 2017). "Theaflavin-3,3'-digallate represses osteoclastogenesis and prevents wear debris-induced osteolysis via suppression of ERK pathway". Acta Biomater. 48: 479–488. doi:10.1016/j.actbio.2016.11.022. PMID   27838465.
  2. 1 2 3 Oxidative Medicine and Cellular Longevity (2024). "Retracted: Theaflavin Chemistry and Its Health Benefits". Oxid Med Cell Longev. 2024: 9893267. doi: 10.1155/2024/9893267 . PMC   10791473 . PMID   38234551.
  3. ↑ Vermeer MA, Mulder TP, Molhuizen HO (December 2008). "Theaflavins from black tea, especially theaflavin-3-gallate, reduce the incorporation of cholesterol into mixed micelles". J Agric Food Chem. 56 (24): 12031–6. doi:10.1021/jf8022035. PMID   19049290.
  4. ↑ Gao Y, Yin J, Tu Y, Chen YC (February 2019). "Theaflavin-3,3'-Digallate Suppresses Human Ovarian Carcinoma OVCAR-3 Cells by Regulating the Checkpoint Kinase 2 and p27 kip1 Pathways". Molecules. 24 (4): 673. doi: 10.3390/molecules24040673 . PMC   6412557 . PMID   30769778.
  5. ↑ Pan H, Kim E, Rankin GO, Rojanasakul Y, Tu Y, Chen YC (January 2018). "Theaflavin-3,3'-Digallate Enhances the Inhibitory Effect of Cisplatin by Regulating the Copper Transporter 1 and Glutathione in Human Ovarian Cancer Cells". Int J Mol Sci. 19 (1): 117. doi: 10.3390/ijms19010117 . PMC   5796066 . PMID   29301278.
  6. ↑ Oka Y, Iwai S, Amano H, Irie Y, Yatomi K, Ryu K, Yamada S, Inagaki K, Oguchi K (2012). "Tea polyphenols inhibit rat osteoclast formation and differentiation". J Pharmacol Sci. 118 (1): 55–64. doi:10.1254/jphs.11082fp. PMID   22186621.
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