Theaflavin
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| Names | |
|---|---|
| IUPAC name
3,4,5-Trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-2-chromanyl]-6-benzo[7]annulenone | |
| Identifiers | |
4670-05-7  | |
| ChEMBL | ChEMBL346119  |
| ChemSpider | 102754 |
| |
| Jmol-3D images | Image |
| PubChem | 114777 |
| |
| UNII | 1IA46M0D13 |
| Properties | |
| Molecular formula |
C29H24O12 |
| Molar mass | 564.49 g·mol−1 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Theaflavin (TF) and its derivatives, known collectively as theaflavins, are antioxidant polyphenols that are formed from the condensation of flavan-3-ols in tea leaves during the enzymatic oxidation (fermentation) of black tea. Theaflavin-3-gallate, theaflavin-3'-gallate, theaflavin-3-3'-digallate are the main theaflavins.[1] Theaflavins are types of thearubigins, and are therefore reddish in color. Epigallocatechin gallate (EGCG) will metabolize into some theaflavins in the liver.
Research into health effects
HIV
In in vitro laboratory investigations, several tea polyphenols, especially those with galloyl moiety, can inhibit HIV-1 replication with multiple mechanisms of action. Theaflavin derivatives have been found to have more potent anti-HIV-1 activity than catechin derivatives.[2]
Epigallocatechin gallate (EGCG), a catechin in green tea, binds to gp120, which works in conjunction with gp41, itself blocked by TF-3 (a theaflavin), both receptors of which HIV hijacks to enter into healthy human immune cells.
Cholesterol
In a human clinical trial published in 2003, theaflavins were found to reduce blood cholesterol levels, both total and LDL.[3]
Cancer
In in vitro laboratory investigations, theaflavins have been found to act on numerous points regulating cancer cell growth, survival, and metastasis.[4] For example, TF-3 is a potent scavenger of superoxide.[5]
See also
- List of phytochemicals and foods in which they are prominent
References
- ↑ http://www.rxlist.com/theaflavin/supplements.htm
- ↑ Liu S, Lu H, Zhao Q et al. (2005). "Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41". Biochim. Biophys. Acta 1723 (1–3): 270–81. doi:10.1016/j.bbagen.2005.02.012. PMID 15823507.
- ↑ Maron DJ, Lu GP, Cai NS et al. (2003). "Cholesterol-lowering effect of a theaflavin-enriched green tea extract: a randomized controlled trial". Arch. Intern. Med. 163 (12): 1448–53. doi:10.1001/archinte.163.12.1448. PMID 12824094.
- ↑ Bode AM and Dong Z. (2006) Molecular and Cellular Targets Mol Carcinog 45(6): 422–430.
- ↑ Journal of Agricultural and Food Chemistry: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
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