Theaflavin-3-gallate

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
CAS Number	30462-34-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3039319;
ChemSpider	147959 ;
PubChem CID	169167;
UNII	S6469PF6TK ;
CompTox Dashboard (EPA)	DTXSID30951233 ;
	InChI 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 Key: KMJPKUVSXFVQGZ-WQLSNUALSA-N ;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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
^ 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.
^ 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.
^ 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.

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

[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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

v t e Thearubigins and their glycosides
Theaflavins	Theaflavin Theaflavin-3-gallate Theaflavin 3'-gallate Theaflavin 3,3' digallate Theasinensin A and B
Oxidated theaflavins	Bistheaflavin-A Bistheaflavin-B Theacitrin

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
CAS Number	30462-34-1^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3039319
ChemSpider	147959^Y
PubChem CID	169167
UNII	S6469PF6TK^Y
CompTox Dashboard (EPA)	DTXSID30951233
InChI 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
SMILES 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
Chemical formula	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

Theaflavin-3-gallate

See also

References