TRICETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O7
Molecular Weight	302.2357
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C(=O)C=C(O2)C3=CC(O)=C(O)C(O)=C3)C(O)=C1

InChI

InChIKey=ARSRJFRKVXALTF-UHFFFAOYSA-N

InChI=1S/C15H10O7/c16-7-3-8(17)14-9(18)5-12(22-13(14)4-7)6-1-10(19)15(21)11(20)2-6/h1-5,16-17,19-21H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19705844 | https://www.ncbi.nlm.nih.gov/pubmed/21067180 | https://www.ncbi.nlm.nih.gov/pubmed/28731287 | https://www.ncbi.nlm.nih.gov/pubmed/11052728 | https://www.ncbi.nlm.nih.gov/pubmed/25790236 | http://www.hmdb.ca/metabolites/HMDB29620

Tricetin is a dietary flavonoid found in cereals and cereal products, ginkgo nuts, pulses, and tea. It has demonstrated anti-inflammatory and anticancer effects in a number of in vitro model.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Matrix metalloproteinase-9 3 Target ID: P14780 Gene ID: 4318.0 Gene Symbol: MMP9 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28731287	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19705844	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25738754	Primary	Preclinical	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21067180	Primary	Basic research	Unknown Approved Use Unknown
Oral cancer 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28731287	Primary	Basic research	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25790236	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A distinctive flavonoid chemistry for the anomalous genus Biebersteinia.	2001 Jan	11198823
The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen.	2002 Sep-Oct	12440738
Identification of lipophilic flavones and flavonols by comparative HPLC, TLC and UV spectral analysis.	2003 Mar-Apr	12693635
Flavone glucosides with immunomodulatory activity from the leaves of Pleioblastus amarus.	2004 Apr	15081303
Quantitative high-performance liquid chromatography analyses of flavonoids in Australian Eucalyptus honeys.	2004 Jan 28	14733497
Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica.	2004 May	15184009
Sequential O-methylation of tricetin by a single gene product in wheat.	2006 Jul	16730127
Dietary flavones and flavonoles are inhibitors of poly(ADP-ribose)polymerase-1 in pulmonary epithelial cells.	2007 Oct	17884996
Cation dependent O-methyltransferases from rice.	2008 Feb	17943312
Nanocapsule@xerogel microparticles containing sodium diclofenac: a new strategy to control the release of drugs.	2008 Jun 24	18358650
Structure-activity relationships of wheat flavone O-methyltransferase: a homodimer of convenience.	2008 May	18397325
Antimicrobial activity of Inga fendleriana extracts and isolated flavonoids.	2009 Dec	20120106
Inhibition of LPS-induced pulmonary inflammation by specific flavonoids.	2009 May 8	19292976
[Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense].	2009 Sep	19943487
Tricetin, a dietary flavonoid, inhibits proliferation of human breast adenocarcinoma mcf-7 cells by blocking cell cycle progression and inducing apoptosis.	2009 Sep 23	19705844
Effects of Various Flavonoids on the α-Synuclein Fibrillation Process.	2010 Jan 28	20976092
Structure-function relationships of wheat flavone O-methyltransferase: Homology modeling and site-directed mutagenesis.	2010 Jul 29	20670441
Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.	2012 Jun	22445328

Patents

Sample Use Guides

In Vivo Use Guide

Tricetin was administered to four rats at an oral dose of 100 mg which resulted in the urinary excretion of unchanged tricetin, accompanied by small amounts of 3,5-dihydroxyphenylpropionic acid.

Route of Administration: Oral

In Vitro Use Guide

Human MCF-7 breast cancer cells were maintained in monolayer cultures at 37 deg-C under a 5% CO2 atmosphere in DMEM supplemented with 10% FCS, 5 micro-g/mL insulin, 100 units/mL of penicillin G, 100 micro-g/mL of streptomycin, and 0.25 micro-g/mL of amphotericin B. Cells were plated in 96-well culture plates, and incubated for 24 hours prior to treatment with various concentrations of triceten and a further 48 hour incubation period. Inhibition of cell proliferation by tricetin was measured by XTT assay. Triceten inhibited the growth of MCF-7 cells in a dose-dependent manner with an IC50 value of 32.17 micro-M.

Name

Type

Language

TRICETIN

Common Name

English

5,7,3',4',5'-PENTAHYDROXYFLAVONE

Systematic Name

English

5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)CHROMEN-4-ONE

Systematic Name

English

Code System Code Type Description

DAILYMED

5627PY99ZO