THEAFLAVIN

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

Structure Search

SMILES

[H][C@@]1(OC2=CC(O)=CC(O)=C2C[C@H]1O)C3=CC(O)=C(O)C4=C(O)C(=O)C=C(C=C34)[C@@]5([H])OC6=CC(O)=CC(O)=C6C[C@H]5O

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22351658 | https://www.ncbi.nlm.nih.gov/pubmed/15483420 | https://www.ncbi.nlm.nih.gov/pubmed/22138428

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
20S proteosome, human, CHEMBL3831201 1 Target ID: 20S proteosome, human, CHEMBL3831201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22351658	Inhibitor 8297
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15341993	Inhibitor 8297	4.17 µM [IC50]
Influenza A virus (A/PR/8/34(H1N1)) 5 Target ID: CHEMBL612610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24370660	Inhibitor 8297
Influenza B virus (B/Lee/40) 1 Target ID: CHEMBL612452 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24370660	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22138428 https://www.ncbi.nlm.nih.gov/pubmed/22634505	Primary	Preclinical	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27237789 https://www.ncbi.nlm.nih.gov/pubmed/27756182	Primary	Phase I 428	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17499812 https://www.ncbi.nlm.nih.gov/pubmed/22202062 https://www.ncbi.nlm.nih.gov/pubmed/26586942	Primary	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100713	https://www.001chemical.com/chem/search?q=DY100713
1PlusChem LLC	1P003V8C	https://www.1pchem.com/search?query=1P003V8C
A2B Chem	AB79644	http://a2bchem.com/prod/AB79644
AK Scientific	Y0203	https://aksci.com/item_detail.php?cat=Y0203
Ambeed	A218957	http://www.ambeed.com/search/Search.html?keyword=A218957
AstaTech	41837	http://astatechinc.com/CPSResult.php?CRNO=41837
Biopurify Phytochemicals	BP1384	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP1384&searchhtmp=simplesearch&t=1
Chem Scene	CS-5885	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5885
Matrix Scientific	97965	http://www.matrixscientific.com/097965.html
MedChem Express	HY-N0243	https://www.medchemexpress.com/search.html?q=HY-N0243&ft=&fa=&fp=
MolPort	MolPort-027-720-916	https://www.molport.com/shop/molecule-link/MolPort-027-720-916
MolPort	MolPort-039-052-353	https://www.molport.com/shop/molecule-link/MolPort-039-052-353
Molcore	MC100713	http://www.molcore.com/CatMC100713.html
PI Chemicals	PI-36373	http://www.pipharm.com/catalog_products/PI-36373.html
Toronto Research Chemicals	T340200	https://www.trc-canada.com/product-detail/?CatNum=T340200
eMolecules	276215480	https://orderbb.emolecules.com/search/#?query=276215480
eMolecules	5851757	https://orderbb.emolecules.com/search/#?query=5851757
eMolecules	95716391	https://orderbb.emolecules.com/search/#?query=95716391
mcule	MCULE-6543286448	https://mcule.com/MCULE-6543286448/

PubMed

Title	Date	PubMed
Analysis of black tea theaflavins by non-aqueous capillary electrophoresis.	2001 Jun 1	11459305
Black tea is a powerful chemopreventor of reactive oxygen and nitrogen species: comparison with its individual catechin constituents and green tea.	2001 Jun 1	11374887
Effects of purified green and black tea polyphenols on cyclooxygenase- and lipoxygenase-dependent metabolism of arachidonic acid in human colon mucosa and colon tumor tissues.	2001 Nov 1	11705450
Anticlastogenic effects of black tea (World blend) and its two active polyphenols theaflavins and thearubigins in vivo in Swiss albino mice.	2001 Oct 26	11720078
Analysis of theaflavins in biological fluids using liquid chromatography-electrospray mass spectrometry.	2001 Sep 5	11530986
Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced inflammatory skin edema and ornithine decarboxylase activity by theaflavin-3,3'-digallate in mouse.	2002	12416263
[Protective effect of tea pigments on mice skin photoaging induced by UV irradiation].	2002 Jan	12583239
Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays.	2002 Nov	12410547
Tea enhances insulin activity.	2002 Nov 20	12428980
Black tea represents a major source of dietary phenolics among regular tea drinkers.	2002 Oct	12516885
Cancer chemoprevention by tea polyphenols through modulating signal transduction pathways.	2002 Oct	12433185
Signal transduction pathways: targets for green and black tea polyphenols.	2003 Jan 31	12542977
Cholesterol-lowering effect of a theaflavin-enriched green tea extract: a randomized controlled trial.	2003 Jun 23	12824094
Antimicrobial activity of 10 different plant polyphenols against bacteria causing food-borne disease.	2004 Dec	15577214
Ellipsometry analysis of the in vitro adsorption of tea polyphenols onto salivary pellicles.	2004 Dec	15560834
Modulation of phosphatidylinositol-3-kinase/protein kinase B- and mitogen-activated protein kinase-pathways by tea polyphenols in human prostate cancer cells.	2004 Feb 1	14743383
Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities.	2004 Jan 15	14723964
Theaflavin, a black tea extract, is a novel anti-inflammatory compound.	2004 Oct	15483420
Optimization of theaflavin biosynthesis from tea polyphenols using an immobilized enzyme system and response surface methodology.	2005 Feb	15742149
The signal transduction networks required for phosphorylation of STAT1 at Ser727 in mouse epidermal JB6 cells in the UVB response and inhibitory mechanisms of tea polyphenols.	2005 Feb	15550455
[Effect of tea polyphenols on oxidative metabolism of polymorphonuclear neutrophils in healthy and obese people].	2005 Jul	16194025
Creaming in black tea.	2005 Oct 5	16190662
Modulation of the oxidative stress and nuclear factor kappaB activation by theaflavin 3,3'-gallate in the rats exposed to cerebral ischemia-reperfusion.	2007	17976306
Black tea polyphenols mimic insulin/insulin-like growth factor-1 signalling to the longevity factor FOXO1a.	2008 Jan	18005251

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Fri Dec 15 17:14:50 GMT 2023` Edited by `admin` on `Fri Dec 15 17:14:50 GMT 2023`
Record UNII	1IA46M0D13
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THEAFLAVIN

Common Name

English

1,8-BIS(3-ALPHA,5,7-TRIHYDROXY-2-ALPHA-CHROMANYL)-5H-BENZOCYCLOHEPTEN-5-ONE

Common Name

English

3,4,5-TRIHYDROXY-1,8-BIS((2R,3R)-3,5,7-TRIHYDROXY-2-CHROMANYL)-6-BENZO(7)ANNULENONE

Common Name

English

THEAFLAVINE [MI]

Common Name

English

1,8-BIS((2R,3R)-3,5,7-TRIHYDROXY-2H-1-BENZOPYRAN-2-YL)-3,4,6-TRIHYDROXY-5H-BENZOCYCLOHEPTEN-5-ONE

Common Name

English

5H-BENZOCYCLOHEPTEN-5-ONE, 1,8-BIS(3-ALPHA,5,7-TRIHYDROXY-2-ALPHA-CHROMANYL)-3,4,6-TRIHYDROXY-

Common Name

English

5H-BENZOCYCLOHEPTEN-5-ONE, 1,8-BIS((2R,3R)-3,5,7-TRIHYDROXY-2H-1-BENZOPYRAN-2-YL)-3,4,6-TRIHYDROXY

Common Name

English

Classification Tree Code System Code

DSLD

3126 (Number of products:1)