Diosmetin

Names

[ CAS No. ]:
520-34-3

[ Name ]:
Diosmetin

[Synonym ]:
Vitamin P
3',5,7-dihydroxy-4'-methoxyflavone
Cyanidenon-4'-methyl Ether 1479
3,3',5,7-tetrahydroxy-4'-methoxyflavone
4'-Methylluteolin
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
5,7,3'-Trihydroxy-4'-methoxyflavone
MFCD00017425
3',5,7-trihydroxy-4'-methoxy-2-phenylchromone
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
Luteolin 4'-methyl ether
3',5,7-TRIHYDROXY-4'METHOXYFLAVONE
Diosmetin
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-
Luteolin-4'-methyl Ether
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
EINECS 208-291-8
Salinigricoflavonol

Biological Activity

[Description]:

Diosmetin is a natural flavonoid which inhibits human CYP1A enzyme activity with an IC50 of 40 μM in HepG2 cell.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

IC50: 40 μM (Others, HepG2 cell)[1]

[In Vitro]

Diosmetin inhibits cell proliferation in HepG2 cells in a concentration-dependent manner. Untreated HepG2 cells grow well and are observed to have with normal skeletons, whereas cells treated with diosmetin are distorted and a number of them become round and floating[1].

[In Vivo]

Pretreatment with diosmetin significantly reduces serum levels of amylase and lipase; the histological injury; the secretion of tumor necrosis factor (TNF)-α, interleukin (IL)-1β, and IL-6; myeloperoxidase (MPO) activity, trypsinogen activation peptide (TAP) level, the expression of inducible nitric oxide synthase (iNOS); and the nuclear factor (NF)-κB activation in cerulein-induced acute pancreatitis[2].

[Cell Assay]

Diosmetin is dissolved in DMSO which is maintained at a constant concentration in control samples (2%). HepG2 cells are maintained in a humidified atmosphere of 5% CO2 at 37°C, and cultured in RPMI-1640 medium supplemented with 10% (v/v) fetal bovine serum, 100 U/mL penicillin and 100 U/mL streptomycin. HepG2 cell density is adjusted to 2×104 cells/100 μL, and the cells are seeded into 96-well plates and placed in an incubator overnight (37°C in 5% CO2) to allow for attachment and recovery. MTT analyses are performed. Briefly, cells are pretreated with 5, 10, 15 and 20 μg/mL diosmetin for 24 h. A total of 20 μL MTT solution (5 mg/mL in PBS) solution is transferred to each well to yield a final 120 μL/well and to separate wells a total of 10 μL CCK8 (5 mg/mL in PBS) is transferred. The plates are incubated for 4 h at 37°C in 5% CO2 and the absorbance is recorded at wavelengths of 595 nm and 450 nm, respectively. The half maximal inhibitory concentration (IC50) of diosmetin is calculated[1].

[Animal admin]

Experimental acute pancreatitis is induced in mice by seven intraperitoneal injection of cerulein (50 μg/kg) at hourly intervals. Diosmetin (100 mg/kg) or vehicle is pretreated 2 h before the first cerulein injection. After 6 h, 9 h, 12 h of the first cerulein injection, the severity of acute pancreatitis is evaluated biochemically and morphologically[2].

[References]

[1]. Liu B, et al. Diosmetin induces apoptosis by upregulating p53 via the TGF-β signal pathway in HepG2 hepatoma cells. Mol Med Rep. 2016 Jul;14(1):159-64.

[2]. Yu G, et al. Diosmetin ameliorates the severity of cerulein-induced acute pancreatitis in mice by inhibiting the activation of the nuclear factor-κB. Int J Clin Exp Pathol. 2014 Apr 15;7(5):2133-42.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
576.7±50.0 °C at 760 mmHg

[ Melting Point ]:
256-258ºC

[ Molecular Formula ]:
C₁₆H₁₂O₆

[ Molecular Weight ]:
300.263

[ Flash Point ]:
220.3±23.6 °C

[ Exact Mass ]:
300.063385

[ PSA ]:
100.13000

[ LogP ]:
3.10

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.697

[ Storage condition ]:
-20?C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2942000000

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Antiviral effect of methylated flavonol isorhamnetin against influenza.

PLoS ONE 10(3) , e0121610, (2015)

Influenza is an infectious respiratory disease with frequent seasonal epidemics that causes a high rate of mortality and morbidity in humans, poultry, and animals. Influenza is a serious economic conc...

Differential metabolomic analysis of the potential antiproliferative mechanism of olive leaf extract on the JIMT-1 breast cancer cell line.

J. Pharm. Biomed. Anal. 105 , 156-62, (2015)

A new differential metabolomic approach has been developed to identify the phenolic cellular metabolites derived from breast cancer cells treated with a supercritical fluid extracted (SFE) olive leaf ...

Flavonoids are inhibitors of human organic anion transporter 1 (OAT1)-mediated transport.

Drug Metab. Dispos. 42(9) , 1357-66, (2014)

Organic anion transporter 1 (OAT1) has been reported to be involved in the nephrotoxicity of many anionic xenobiotics. As current clinically used OAT1 inhibitors are often associated with safety issue...

Related Compounds

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