osajin

Names

[ CAS No. ]:
482-53-1

[ Name ]:
osajin

[Synonym ]:
UNII-83R5N9X74B
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
4H,8H-Benzo[1,2-b:3,4-b']dipyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-buten-1-yl)-
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-buten-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
osajin

Biological Activity

[Description]:

Osajin is the major bioactive isoﬂavone present in the fruit of Maclura pomifera with antitumor, antioxidant and anti-inflammatory activities.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Natural Products >> Flavonoids

Research Areas >> Metabolic Disease

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Inflammation/Immunology

[Target]

Apoptosis[1]

[In Vitro]

Osajin significantly decreases the viability of human NPC cells (TW076, CG1 and TW04 cells) in a dose-dependent manner. Osajin induces apoptosis in human NPC cells through multiple apoptotic pathways, including the extrinsic death receptor pathway, and intrinsic pathways relying on mitochondria and endoplasmic reticulum stress[1]. Osajin exhibits growth inhibitory activity on six human cancer cell lines, including kidney, lung, prostate, breast, melanoma and colon cancer cells[2].

[In Vivo]

Osajin and pomiferin attenuates the myocardial dysfunction provoked by ischemia reperfusion. This is confirmed by an increase in both antioxidant enzyme values and total antioxidant activity. The cardioprotection provided by osajin and pomiferin treatment results from the suppression of oxidative stress and this correlates with improved ventricular function[3].

[Cell Assay]

NPC cells are seeded in 96-well plates (5000/well) and allowed to adhere for 24 h. The medium is then substituted by a fresh one containing different concentrations (0.01–10 µM) of osajin for another 24 h. For the time-course assay, the incubation times with 5 µM of osajin are 6, 12, 24, 36 and 48 h. After incubation, 10 µl of 5 mg/ml of MTT is added to each well and incubated for 4 h at 37°C. Cell viability is determined using the MTT-based assay[1].

[Animal admin]

Rats[1] The Wistar rats are divided into four groups. The first treatment group receives osajin (5 mg/kg/day in 0.5% Avicel); the second treatment group receives pomiferin (5 mg/kg/day in 0.5% Avicel); the placebo group receives only 0.5 Avicel; the last is an untreated control group. Biochemical indicator of oxidative damage-lipid peroxidation product malondialdehyde, antioxidant enzymes-superoxide dismutase, glutathione peroxidase, total antioxidant activity in serum and myocardium are evaluated. The effect of osajin and pomiferin on cardiac function, left ventricular end-diastolic pressure, left ventricular pressure and peak positive +dP/dt ischemia and reperfusion, also is examined[1].

[References]

[1]. Huang TT, et al. Activation of multiple apoptotic pathways in human nasopharyngeal carcinoma cells by the prenylated isoflavone, osajin. PLoS One. 2011 Apr 12;6(4):e18308.

[2]. Son IH, et al. Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera. Bioorg Med Chem Lett. 2007 Sep 1;17(17):4753-5.

[3]. Florian T, et al. Effects of prenylated isoflavones osajin and pomiferin in premedication on heart ischemia-reperfusion. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2006 Jul;150(1):93-100.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
632.3±55.0 °C at 760 mmHg

[ Melting Point ]:
189° (uncorr), 193° (corr)

[ Molecular Formula ]:
C₂₅H₂₄O₅

[ Molecular Weight ]:
404.455

[ Flash Point ]:
218.7±25.0 °C

[ Exact Mass ]:
404.162384

[ PSA ]:
79.90000

[ LogP ]:
7.62

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.628

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Interactions of genistein and related isoflavones with lipid micelles.

Langmuir 22(17) , 7175-84, (2006)

Genistein (5,7,4'-trihydroxyisoflavone) modulates the function of several transmembrane ion-channel proteins by mechanisms that are unrelated to phosphorylation events. Daidzein (7,4'-dihydroxy-isofla...

Electrochemical and spectrometric study of antioxidant activity of pomiferin, isopomiferin, osajin and catalposide.

J. Pharm. Biomed. Anal. 48(1) , 127-33, (2008)

The antioxidant properties of pomiferin, isopomiferin, osajin and catalposide are evaluated. The electrochemical behaviour of these compounds at a carbon paste electrode was studied using square wave ...

Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera.

Bioorg. Med. Chem. Lett. 17(17) , 4753-5, (2007)

The major constituents from the fruits of Maclura pomifera are the prenylated isoflavones, osajin (1) and pomiferin (2). Their structures were elucidated using NMR spectroscopic techniques and mass sp...