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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSMETIN

SMILES

COc1ccc(cc1O)-c2cc(=O)c3c(cc(cc3o2)O)O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI
Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

Originator

Sources: DOI: 10.1002/hlca.19250080179

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A benzoquinone and flavonoids from Cyperus alopecuroides.
2002 Jun
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
2003 May
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
2003 Sep 9
Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
2005 Aug
Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars.
2005 Feb
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005 Feb 15
Determination of active components in rosemary by capillary electrophoresis with electrochemical detection.
2005 Sep 15
Inhibition of pro-inflammatory markers in primary bone marrow-derived mouse macrophages by naturally occurring flavonoids: analysis of the structure-activity relationship.
2006 Oct 16
Raddeanalin, a new flavonoid glycoside from the leaves of Salix raddeana Laksh.
2007 Apr-Aug
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.
2007 Feb
Effect of flavonoids on rat splenocytes, a structure-activity relationship study.
2008 Aug 15
Flavonoids from Galium verum L.
2008 Jul-Aug
Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.
2008 Mar 15
Simultaneous determination of the flavonoid aglycones diosmetin and hesperetin in human plasma and urine by a validated GC/MS method: in vivo metabolic reduction of diosmetin to hesperetin.
2009 Feb
Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.
2009 Feb 8
Stimulatory constituents of Eclipta prostrata on mouse osteoblast differentiation.
2009 Jan
Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation.
2009 Jun
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
2009 Mar 25
[Chemical constituents of Galium verum].
2009 Nov
[Studies on flavones from Flos Chrysanthemi Indici].
2009 Oct
Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.
2009 Sep
Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.
2010
Flavonoids and antioxidant activity of Rosa agrestis leaves.
2010 Apr
Beta-glucuronidase from Helix pomatia origin is not suitable for diosmetin analysis.
2010 Dec 1
Effects of Various Flavonoids on the α-Synuclein Fibrillation Process.
2010 Jan 28
Effects of plant-derived polyphenols on TNF-alpha and nitric oxide production induced by advanced glycation endproducts.
2010 Jul
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.
2010 Jun
Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study.
2010 Mar 11
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
2011 May 1
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.
2015 Mar
Patents

Sample Use Guides

Mice: 50mg /kg/every other day for 6 weeks
Route of Administration: Intraperitoneal
Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.
Name Type Language
DIOSMETIN
INCI   MI   WHO-DD  
INCI  
Official Name English
4'-METHYLLUTEOLIN
Common Name English
DIOSMETIN [WHO-DD]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE
Systematic Name English
DIOSMETIN [INCI]
Common Name English
DIOSMETIN [MI]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE
Systematic Name English
DIOSMETINE
Common Name English
LUTEOLIN-4'-METHYL ETHER
Common Name English
CYANIDENON-4'-METHYL ETHER 1479
Common Name English
DIOSMETOL
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-
Systematic Name English
Classification Tree Code System Code
DSLD 4156 (Number of products:7)
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
Code System Code Type Description
EVMPD
SUB35834
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
HSDB
8101
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
WIKIPEDIA
DIOSMETIN
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
EPA CompTox
520-34-3
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
PUBCHEM
5281612
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
RXCUI
1314347
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY RxNorm
CAS
520-34-3
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
FDA UNII
TWZ37241OT
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
DRUG CENTRAL
4601
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-291-8
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
MERCK INDEX
M4594
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY Merck Index
MESH
C039602
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
DRUG BANK
DB11259
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY