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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2629
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSMETIN

SMILES

COC1=CC=C(C=C1O)C2=CC(=O)C3=C(O2)C=C(O)C=C3O

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
DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells.
2003 Feb 24
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
2003 May
Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action.
2003 May 1
The beta-D-glucoside and sodium-dependent glucose transporter 1 (SGLT1)-inhibitor phloridzin is transported by both SGLT1 and multidrug resistance-associated proteins 1/2.
2003 Nov
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
Antitubercular constituents of Valeriana laxiflora.
2004 Jun
[Investigation of the hepatoprotector action of natural flavonoids].
2004 Nov-Dec
Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
2005 Aug
In vitro antioxidant activity of some Teucrium species (Lamiaceae).
2005 Jun
Determination of active components in rosemary by capillary electrophoresis with electrochemical detection.
2005 Sep 15
The efflux of flavonoids morin, isorhamnetin-3-O-rutinoside and diosmetin-7-O-beta-D-xylopyranosyl-(1-6) -beta-D-glucopyranoside in the human intestinal cell line caco-2.
2006 Aug
Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.
2006 Jul 26
Flavonoid glycosides in bergamot juice (Citrus bergamia Risso).
2006 May 31
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
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.
2007 Feb
Two new flavonoids from Origanum vulgare.
2008
Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.
2008 Apr
Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
2008 Apr 1
Effect of flavonoids on rat splenocytes, a structure-activity relationship study.
2008 Aug 15
Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists.
2008 Dec 24
Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation.
2008 Feb
Flavonoids from Galium verum L.
2008 Jul-Aug
Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.
2008 Jun
Camptothecinoids from the seeds of Taiwanese Nothapodytes foetida.
2008 Jun 16
[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].
2008 Mar
[Studies on chemical components of Lobelia chinensis].
2009 Feb
Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.
2009 Feb
Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.
2009 Feb
Aurintricarboxylic acid inhibits influenza virus neuraminidase.
2009 Feb
Stimulatory constituents of Eclipta prostrata on mouse osteoblast differentiation.
2009 Jan
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.
2009 Jan 8
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.
2009 Jul
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
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.
2009 Jun 16
The phytochemical analysis and antioxidant activity assessment of orange peel (Citrus sinensis) cultivated in Greece-Crete indicates a new commercial source of hesperidin.
2009 Mar
Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?
2009 Mar 16
[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
[Chemical constituents of Lobelia chinensis].
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
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
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
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
Diosmetin [WHO-DD]
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 Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
Code System Code Type Description
EVMPD
SUB35834
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
HSDB
8101
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
WIKIPEDIA
DIOSMETIN
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID80199966
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
DAILYMED
TWZ37241OT
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
SMS_ID
100000128590
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
PUBCHEM
5281612
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
CHEBI
4630
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
RXCUI
1314347
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY RxNorm
CAS
520-34-3
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
FDA UNII
TWZ37241OT
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
DRUG CENTRAL
4601
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-291-8
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
MERCK INDEX
m4594
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY Merck Index
MESH
C039602
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY
DRUG BANK
DB11259
Created by admin on Fri Dec 15 17:33:37 UTC 2023 , Edited by admin on Fri Dec 15 17:33:37 UTC 2023
PRIMARY