Theaflavin-3-gallate

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.[4][5] [6] Consuming large amounts of black tea has been reported to reduce the effects of aging in female populations.[7][8]

Theaflavin-3-gallate
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
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 checkY
    Key: KMJPKUVSXFVQGZ-WQLSNUALSA-N checkY
  • 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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Infobox references

See also

References
  1. X. Hu, Z. Ping, M. Gan et al., “Theaflavin-3,3′-digallate represses osteoclastogenesis and prevents wear debris-induced osteolysis via suppression of ERK pathway,” Acta Biomaterialia 48 (2017): 479–488.
  2. Shan Z, Nisar M, Li M, Zhang C, Wan C. Theaflavin Chemistry and Its Health Benefits Oxidative Medicine and Cellular Longevity. 2021 Jan;2021. PMCID: PMC8601833.
  3. Mario A. Vermeer, Theo P. J. Mulder and Henri O. F. Molhuizen (2008). "Theaflavins from Black Tea, Especially Theaflavin-3-gallate, Reduce the Incorporation of Cholesterol into Mixed Micelles". J. Agric. Food Chem. 56 (24): 12031–12036. doi:10.1021/jf8022035. PMID 19049290.
  4. Shan Z, Nisar M, Li M, Zhang C, Wan C. Theaflavin Chemistry and Its Health Benefits Oxidative Medicine and Cellular Longevity. 2021 Jan;2021. PMCID: PMC8601833.
  5. Y. Gao, J. Yin, Y. Tu, and Y. Chen, “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, 2019
  6. H. Pan, E. Kim, G. Rankin, Y. Rojanasakul, Y. Tu, and Y. Chen, “Theaflavin-3, 3′-Digallate enhances the inhibitory effect of cisplatin by regulating the copper transporter 1 and glutathione in human ovarian cancer cells,” International Journal of Molecular Sciences 19 (1): 117, 2018.
  7. Shan Z, Nisar M, Li M, Zhang C, Wan C., "Theaflavin Chemistry and Its Health Benefits", Oxidative Medicine and Cellular Longevity 2021 Jan; 2021. PMCID: PMC8601833.
  8. Y. Oka, S. Iwai, H. Amano et al., “Tea polyphenols inhibit rat osteoclast formation and differentiation,” Journal of Pharmacological Sciences 118 (1): 55–64, 2012.
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