Theaflavin
From Wikipedia, the free encyclopedia
| Theaflavin | |
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| IUPAC name | 3,4,5-trihydroxy-1,8-bis[(2R,3R)-3,5,7- trihydroxy-2-chromanyl]-6-benzo[7]annulenone |
| Identifiers | |
| CAS number | [4670-05-7] |
| PubChem | |
| SMILES | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C (=CC(=C4O)O)C5C(CC6=C(C=C(C=C6O5)O)O)O)O)O |
| Properties | |
| Molecular formula | C29H24O12 |
| Molar mass | 564.494 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Theaflavin and its derivatives, known collectively as theaflavins, are polyphenols Flavan-3-ols that are formed from catechins such as in tea leaves during the enzymatic oxidation (called fermentation by the tea trade) of tea leaves, such as in black tea. 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 in laboratory investigations.[1]
- Theaflavin-3'-monogallate (TF-2) causes apoptosis in colon cancer cells.[2]
- Theaflavin-3,3'-digallate (TF3) binds to gp41 of HIV as well as inhibit 3CLPro of severe acute respiratory syndrome (SARS).[3]
- 3-Isotheaflavin-3-gallate (TF2B) inhibits 3CLPro of SARS.[3]
Epigallocatechin gallate (EGCG), a catechin in green tea, binds to gp120, which works in conjunction with gp41 of HIV to enter into healthy human immune cells. Like EGCG, Theaflavins and Thearubigins compounds found in black teas penetrate the blood brain barrier, and have been shown to be effective against dementia in aging as well as AIDS related dementia plaques in vitro.
Theaflavins have also been found to reduce blood cholesterol levels.[4]
[edit] See also
[edit] References
- ^ 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:. PMID 15823507.
- ^ AnnieAppleseedProject.org
- ^ a b Chia-Nan Chen1, Coney P. C. Lin, Kuo-Kuei Huang, Wei-Cheng Chen, Hsin-Pang Hsieh, Po-Huang Liang and John T.-A. Hsu (2005). "Inhibition of SARS-CoV 3C-like Protease Activity by Theaflavin-3,3'-digallate (TF3)". Evidence-based Compl. and Alt. Medicine 2 (2): 209–215. doi:.
- ^ 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:. PMID 12824094.
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