Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C29H24O12 |
| Molecular Weight | 564.4937 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1CC2=C(O[C@@H]1C3=CC(O)=C(O)C4=C(O)C(=O)C=C(C=C34)[C@H]5OC6=C(C[C@H]5O)C(O)=CC(O)=C6)C=C(O)C=C2O
InChI
InChIKey=IPMYMEWFZKHGAX-ZKSIBHASSA-N
InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22-,28-,29-/m1/s1
| Molecular Formula | C29H24O12 |
| Molecular Weight | 564.4937 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Theaflavin is a black tea polyphenol, which possesses a wide variety of pharmacological properties including potent antioxidative, anti-apoptotic, anti-cancer and anti-inflammatory effects. Theaflavin (TF-1) can bind to, and inhibit the purified 20S proteasome, accompanied by suppression of tumour cell proliferation, suggesting that the tumour proteasome is an important target whose inhibition is at least partially responsible for the anticancer effects of black tea. Theaflavin is a potent inhibitor of interleukin-8 gene expression in vitro. The proximal mechanism of this effect involves, in part, inhibition of IkappaB kinase activation and activator protein-1 pathway. Theaflavin has been known to possess neuroprotective effects against ischemia, Alzheimer's disease and other neurodegenerative disorders.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22138428 | https://www.ncbi.nlm.nih.gov/pubmed/22634505
Curator's Comment: Theaflavin has been known to possess neuroprotective effects against ischemia, Alzheimer's disease and other neurodegenerative disorders in animal models.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: 20S proteosome, human, CHEMBL3831201 |
|||
Target ID: CHEMBL1978 |
4.17 µM [IC50] | ||
Target ID: CHEMBL612610 |
|||
Target ID: CHEMBL612452 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Combination of HSCCC and Sephadex LH-20 methods An approach to isolation and purification of the main individual theaflavins from black tea. | 2008-01-01 |
|
| Black tea polyphenols mimic insulin/insulin-like growth factor-1 signalling to the longevity factor FOXO1a. | 2008-01 |
|
| Identification of a PKCepsilon-dependent regulation of myocardial contraction by epicatechin-3-gallate. | 2008-01 |
|
| Monitoring the binding processes of black tea thearubigin to the bovine serum albumin surface using quartz crystal microbalance with dissipation monitoring. | 2007-12-12 |
|
| Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3. | 2007-12 |
|
| Theaflavins attenuate hepatic lipid accumulation through activating AMPK in human HepG2 cells. | 2007-11 |
|
| Theaflavins induce G2/M arrest by modulating expression of p21waf1/cip1, cdc25C and cyclin B in human prostate carcinoma PC-3 cells. | 2007-10-13 |
|
| Determination of theaflavins including methylated theaflavins in black tea leaves by solid-phase extraction and HPLC analysis. | 2007-09-05 |
|
| Inhibition of 17alpha-hydroxylase/C17,20-lyase (CYP17) from rat testis by green tea catechins and black tea theaflavins. | 2007-09 |
|
| Inhibitory activities of dietary phenolic compounds on heterocyclic amine formation in both chemical model system and beef patties. | 2007-08 |
|
| Effects of infusion time and addition of milk on content and absorption of polyphenols from black tea. | 2007-06-13 |
|
| Theaflavins induced apoptosis of LNCaP cells is mediated through induction of p53, down-regulation of NF-kappa B and mitogen-activated protein kinases pathways. | 2007-05-16 |
|
| Breast cancer prevention by green tea catechins and black tea theaflavins in the C3(1) SV40 T,t antigen transgenic mouse model is accompanied by increased apoptosis and a decrease in oxidative DNA adducts. | 2007-05-02 |
|
| Black tea polyphenols restrict benzopyrene-induced mouse lung cancer progression through inhibition of Cox-2 and induction of caspase-3 expression. | 2007-01-26 |
|
| Structure-activity relationships of tea compounds against human cancer cells. | 2007-01-24 |
|
| Theanaphthoquinone inhibits fatty acid synthase expression in EGF-stimulated human breast cancer cells via the regulation of EGFR/ErbB-2 signaling. | 2007-01-15 |
|
| alpha-Glucosidase inhibitory profile of catechins and theaflavins. | 2007-01-10 |
|
| Comparison of plants used for skin and stomach problems in Trinidad and Tobago with Asian ethnomedicine. | 2007-01-05 |
|
| Effects of a combination of thyme and oregano essential oils on TNBS-induced colitis in mice. | 2007 |
|
| Modulation of the oxidative stress and nuclear factor kappaB activation by theaflavin 3,3'-gallate in the rats exposed to cerebral ischemia-reperfusion. | 2007 |
|
| Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions. | 2006-12 |
|
| High-throughput analysis of catechins and theaflavins by high performance liquid chromatography with diode array detection. | 2006-11-03 |
|
| [Simultaneous analysis of theaflavins and catechins by capillary electrophoresis]. | 2006-11 |
|
| Chemopreventive potential of diallylsulfide, lycopene and theaflavin during chemically induced colon carcinogenesis in rat colon through modulation of cyclooxygenase-2 and inducible nitric oxide synthase pathways. | 2006-08 |
|
| Anticlastogenic effects of black tea polyphenols theaflavins and thearubigins in human lymphocytes in vitro. | 2006-08 |
|
| In vitro cytotoxicity of a theaflavin mixture from black tea to malignant, immortalized, and normal cells from the human oral cavity. | 2006-08 |
|
| Epicatechins Purified from Green Tea (Camellia sinensis) Differentially Suppress Growth of Gender-Dependent Human Cancer Cell Lines. | 2006-06 |
|
| Molecular and cellular targets. | 2006-06 |
|
| Analytical separation of tea catechins and food-related polyphenols by high-speed counter-current chromatography. | 2006-04-21 |
|
| Potent inhibitory effects of black tea theaflavins on off-odor formation from citral. | 2006-04-19 |
|
| Inhibition of CWR22Rnu1 tumor growth and PSA secretion in athymic nude mice by green and black teas. | 2006-04 |
|
| Theaflavin-3, 3'-digallate induces epidermal growth factor receptor downregulation. | 2006-03 |
|
| Antimicrobial activities of tea catechins and theaflavins and tea extracts against Bacillus cereus. | 2006-02 |
|
| Inhibitory effects of black tea theaflavin derivatives on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and arachidonic acid metabolism in mouse ears. | 2006-02 |
|
| Theaflavin ameliorates cerebral ischemia-reperfusion injury in rats through its anti-inflammatory effect and modulation of STAT-1. | 2006 |
|
| Induction of apoptosis in human leukemia cells by black tea and its polyphenol theaflavin. | 2005-12-08 |
|
| Creaming in black tea. | 2005-10-05 |
|
| Stability of black tea polyphenol, theaflavin, and identification of theanaphthoquinone as its major radical reaction product. | 2005-07-27 |
|
| [Effect of tea polyphenols on oxidative metabolism of polymorphonuclear neutrophils in healthy and obese people]. | 2005-07 |
|
| Molecular definition of black tea taste by means of quantitative studies, taste reconstitution, and omission experiments. | 2005-06-29 |
|
| Black tea polyphenols suppress cell proliferation and induce apoptosis during benzo(a)pyrene-induced lung carcinogenesis. | 2005-06 |
|
| Antioxidative properties of black tea. | 2005-06 |
|
| The theaflavin fraction is responsible for the facilitatory effect of black tea at the skeletal myoneural junction. | 2005-05-13 |
|
| Black tea theaflavins suppress dioxin-induced transformation of the aryl hydrocarbon receptor. | 2005-05 |
|
| [Study on the effect of theaflavins on the adhesion between monocyte and endothelial cells]. | 2005-04 |
|
| Black tea extract can modulate protein expression of H-ras, c-Myc, p53, and Bcl-2 genes during pulmonary hyperplasia, dysplasia, and carcinoma in situ. | 2005 |
|
| Amelioration of sodium arsenite-induced clastogenicity by tea extracts in Chinese hamster v79 cells. | 2005 |
|
| Correlation of apoptosis with comet formation induced by tea polyphenols in human leukemia cells. | 2005 |
|
| [Studies on antioxidant constituents from black tea]. | 2004-10 |
|
| Improvement of tea leaves fermentation with Aspergillus spp. pectinase. | 2002 |
Sample Use Guides
30 male and female Japanese were enrolled and participants were randomly allocated to receive placebo, theaflavin (50 or 100 mg/day), or catechin (400 mg/ml) for 10 weeks.
Route of Administration:
Oral
Incubation of rat microsomal tissue preparation with 0.1 umol [1b-
3H] androstenedione as a substrate were performed in the presence of EGCG, TF-1 (Theaflavin-1), TF-2 (Theaflavin-2) and TF-3 (Theaflavin-3) with concentrations ranging from 5 to 40 uM. EGCG, TF-1, TF-2 and TF-3 induced a concentrationdependent inhibition of rat ovarian and human placental aromatase activities. the IC50 of EGCG, TF-1, TF-2 and TF-3 inhibited aromatase activity of rat ovarian microsomes were 18.27± 1.26, 5.72± 0.61, 7.33± 0.22, and 20.37± 2.57 uM, respectively. EGCG, TF-1, TF-2 and TF-3 also inhibited the activity of aromatase obtained from human placenta and the IC50 were 13.79± 0.89, 4.17± 0.84, 3.23± 0.08 and 3.45± 0.18 uM, respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:42:46 GMT 2025
by
admin
on
Mon Mar 31 18:42:46 GMT 2025
|
| Record UNII |
1IA46M0D13
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
DSLD |
3126 (Number of products:1)
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
||
|
NCI_THESAURUS |
C275
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
4670-05-7
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
114777
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
DTXSID40196916
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
38021
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | RxNorm | ||
|
THEAFLAVIN
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
C056068
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
m10693
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | Merck Index | ||
|
C29855
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
1IA46M0D13
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY | |||
|
136609
Created by
admin on Mon Mar 31 18:42:46 GMT 2025 , Edited by admin on Mon Mar 31 18:42:46 GMT 2025
|
PRIMARY |