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] Theaflavin-3-gallate has been studied as a cancer-fighting chemical; specifically when combined with cisplatin against ovarian cancer cells.[4][5] [6] It has been reported that consuming large amounts of black tea reduces the effects of aging in female populations.[7][8]

Theaflavin-3-gallate
Names
Preferred 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
  • 30462-34-1 Y
3D model (JSmol)
ChEMBL
ChemSpider
  • 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 Y
    Key: KMJPKUVSXFVQGZ-WQLSNUALSA-N Y
  • 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).
N verify (what is YN ?)
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, vol. 48, pp. 479–488, 2017.
  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, vol. 24, no. 4, p. 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, vol. 19, no. 1, p. 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 Pharma- cological Sciences, vol. 118, no. 1, pp. 55–64, 2012.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.