Theaflavin

Theaflavin
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 N
3D model (Jmol) Interactive image
ChEMBL ChEMBL346119 YesY
ChemSpider 102754 YesY
PubChem 114777
UNII 1IA46M0D13 YesY
Properties
C29H24O12
Molar mass 564.50 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 YesYN ?)
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 (sometimes erroneously referred to as 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. Those molecules contain a tropolone moiety.

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

References

  1. ↑ http://www.rxlist.com/theaflavin/supplements.htm
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ Bode AM and Dong Z. (2006) Molecular and Cellular Targets Mol Carcinog 45(6): 422–430.
  5. ↑ 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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