Theaflavin

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Theaflavin
Theaflavin.svg
Identifiers
CAS number 4670-05-7 N
PubChem 114777
ChemSpider 102754 YesY
UNII 1IA46M0D13 YesY
ChEMBL CHEMBL346119 YesY
Jmol-3D images Image 1
Properties
Molecular formula C29H24O12
Molar mass 564.49 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 principle of theaflavins.[1] Theaflavins are types of thearubigins, and are therefore reddish in color. Epigallocatechin gallate (EGCG) will metabolize into some theaflavins in the liver.[citation needed]

Research into health effects[edit]

HIV[edit]

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.[citation needed]

Cholesterol[edit]

In a human clinical trial published in 2003, theaflavins were found to reduce blood cholesterol levels, both total and LDL.[3]

Cancer[edit]

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[edit]

References[edit]

  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