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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
140.0 nM [IC50] | ||
Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
2.4 µM [IC50] | ||
Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
29.0 nM [IC50] | ||
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383 |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28101238 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. | 2003 May |
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Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action. | 2003 May 1 |
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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 |
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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 |
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Antitubercular constituents of Valeriana laxiflora. | 2004 Jun |
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[Investigation of the hepatoprotector action of natural flavonoids]. | 2004 Nov-Dec |
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Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones. | 2005 Aug |
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In vitro antioxidant activity of some Teucrium species (Lamiaceae). | 2005 Jun |
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Determination of active components in rosemary by capillary electrophoresis with electrochemical detection. | 2005 Sep 15 |
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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 |
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Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece. | 2006 Jul 26 |
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Flavonoid glycosides in bergamot juice (Citrus bergamia Risso). | 2006 May 31 |
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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 |
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Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo. | 2007 Feb |
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Two new flavonoids from Origanum vulgare. | 2008 |
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Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages. | 2008 Apr |
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Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones. | 2008 Apr 1 |
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Effect of flavonoids on rat splenocytes, a structure-activity relationship study. | 2008 Aug 15 |
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Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists. | 2008 Dec 24 |
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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 |
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Flavonoids from Galium verum L. | 2008 Jul-Aug |
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Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway. | 2008 Jun |
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Camptothecinoids from the seeds of Taiwanese Nothapodytes foetida. | 2008 Jun 16 |
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[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)]. | 2008 Mar |
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[Studies on chemical components of Lobelia chinensis]. | 2009 Feb |
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Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana. | 2009 Feb |
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Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana. | 2009 Feb |
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Aurintricarboxylic acid inhibits influenza virus neuraminidase. | 2009 Feb |
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Stimulatory constituents of Eclipta prostrata on mouse osteoblast differentiation. | 2009 Jan |
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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 |
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Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation. | 2009 Jul |
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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 |
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Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention. | 2009 Jun 16 |
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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 |
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Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action? | 2009 Mar 16 |
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[Chemical constituents of Galium verum]. | 2009 Nov |
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[Studies on flavones from Flos Chrysanthemi Indici]. | 2009 Oct |
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Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells. | 2009 Sep |
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[Chemical constituents of Lobelia chinensis]. | 2009 Sep |
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Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro. | 2010 |
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Flavonoids and antioxidant activity of Rosa agrestis leaves. | 2010 Apr |
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Beta-glucuronidase from Helix pomatia origin is not suitable for diosmetin analysis. | 2010 Dec 1 |
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Effects of Various Flavonoids on the α-Synuclein Fibrillation Process. | 2010 Jan 28 |
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Effects of plant-derived polyphenols on TNF-alpha and nitric oxide production induced by advanced glycation endproducts. | 2010 Jul |
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Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents. | 2010 Jun |
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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 |
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Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. | 2010 Mar 2 |
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Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids. | 2011 May 1 |
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In vitro effects of some flavones on human pyruvate kinase isoenzyme M2. | 2015 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383
Mice: 50mg /kg/every other day for 6 weeks
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19424633
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.
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DSLD |
4156 (Number of products:7)
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SUB35834
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8101
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DIOSMETIN
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DTXSID80199966
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TWZ37241OT
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100000128590
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5281612
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4630
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1314347
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520-34-3
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TWZ37241OT
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4601
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208-291-8
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m4594
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C039602
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DB11259
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ACTIVE MOIETY