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
ChEMBL ChEMBL346119 YesY
ChemSpider 102754 YesY
Jmol interactive 3D Image
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 (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

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
This article is issued from Wikipedia - version of the Wednesday, September 02, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.