Theaflavin

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Theaflavin
Theaflavin.svg
Names
IUPAC name
3,4,5-Trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-2-chromanyl]-6-benzo[7]annulenone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
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).
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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, and 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.[citation needed] Those molecules contain a tropolone moiety.

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. ^ "Theaflavin Effectiveness, Safety, and Drug Interactions on RxList". rxlist.com. Archived from the original on 4 September 2017. Retrieved 24 April 2018. 
  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, Dong Z (2006). "Molecular and Cellular Targets". Mol Carcinog. 45 (6): 422–430. doi:10.1002/mc.20222. PMC 2238808Freely accessible. PMID 16688728. 
  5. ^ Lin JK (2000). "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". Journal of Agricultural and Food Chemistry. 48 (7): 2736–2743. doi:10.1021/jf000066d.