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Osajin (CID 95168; NSC 21565), a naturally-occurring compound, is the major bioactive isoflavone isolated from the fruit of Maclura pomifera with antitumor, antioxidant and anti-inflammatory activities. Osajin was found to significantly induce apoptosis of NPC cells in a dose- and time-dependent manner. Multiple molecular effects were observed during osajin treatment including a significant loss of mitochondrial transmembrane potential, release of cytochrome c into the cytosol, enhanced expression of Fas ligand (FasL), suppression of glucose-regulated protein 78 kDa (GRP78), and activation of caspases-9, -8, -4 and -3. In addition, up-regulation of proapoptotic Bax protein and down-regulation of antiapoptotic Bcl-2 protein were also observed. Taken together, 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. Thus, osajin could be developed as a new effective and chemopreventive compound for human NPC.
Physicochemical Properties
| Molecular Formula | C25H5O5 |
| Molecular Weight | 385.304206609726 |
| Exact Mass | 404.162 |
| Elemental Analysis | C, 74.24; H, 5.98; O, 19.78 |
| CAS # | 482-53-1 |
| PubChem CID | 95168 |
| Appearance | White to off-white solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 632.3±55.0 °C at 760 mmHg |
| Melting Point | 189° (uncorr), 193° (corr) |
| Flash Point | 218.7±25.0 °C |
| Vapour Pressure | 0.0±1.9 mmHg at 25°C |
| Index of Refraction | 1.628 |
| LogP | 7.62 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 30 |
| Complexity | 752 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | [C]/C(=[C]/[C]C1C2=C([C]=[C]C(O2)([C])[C])C2OC=C(C(C=2C=1[O])=O)C1C=CC([O])=CC=1)/[C] |^1:0,2,7,8,11,12,20,26,29,^4:3| |
| InChi Key | DCTLJGWMHPGCOS-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3 |
| Chemical Name | 4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI) |
| Synonyms | CID 95168; NSC 21565; CID95168; Osajin; 482-53-1; 3'-DEOXYPOMIFERIN; 5'-O-DEMETHYLSCANDINONE; 83R5N9X74B; 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one; NSC-21,565; 4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-; NSC21565; CID-95168; NSC-21565 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
- Apoptotic pathways (e.g., activation of caspases and regulation of Bcl-2 family proteins). - Histone deacetylase (HDAC) inhibition (possibly shared with pomiferin, but specific data for osajin not confirmed). |
| ln Vitro |
In a dose-dependent manner, Osajin dramatically decreased the viability of human NPC cells (TW076, CG1, and TW04 cells). Osajin causes human nasopharyngeal cancer cells to undergo apoptosis by means of a number of apoptotic mechanisms, including as the intrinsic pathway, which depends on endoplasmic reticulum stress and mitochondria, and the extrinsic death receptor pathway [1]. Six human cancer cell lines, including those from the kidney, lung, prostate, breast, melanoma, and colon, are susceptible to growth inhibition by astaxanthin [2]. - Antiproliferative activity: Osajin induces apoptosis in human nasopharyngeal carcinoma cells via activation of multiple apoptotic pathways, including caspase-3, -8, and -9, and downregulation of anti-apoptotic proteins Bcl-2 and Bcl-xL. [1] - Oxidative stress regulation: May modulate reactive oxygen species (ROS) levels to trigger apoptotic signaling. [1] - HDAC inhibition potential: As a prenylated isoflavone, osajin may share structural similarity with pomiferin, a known HDAC inhibitor, but specific IC50 values for osajin were not identified in the available data. [2] |
| ln Vivo |
Osajin and pomiferin treatment provides a cardioprotective effect by suppressing oxidative stress, which is linked to improvements in ventricular function. Osajin and pomiferin attenuate ischemia-reperfusion-induced myocardial dysfunction. This was confirmed by the increase in antioxidant enzyme values and total antioxidant activity [3]. - In a heart ischemia-reperfusion model, premedication with osajin was observed to reduce myocardial infarct size compared to the control group. It also improved cardiac function indices such as left ventricular ejection fraction (LVEF) and left ventricular fractional shortening (LVFS) after reperfusion. [3] - Osajin pretreatment decreased the levels of oxidative stress markers (e.g., malondialdehyde, MDA) in myocardial tissue and increased the activity of antioxidant enzymes (e.g., superoxide dismutase, SOD; glutathione peroxidase, GSH-Px), indicating a protective effect against oxidative damage induced by ischemia-reperfusion. [3] - Inflammatory response in the heart was alleviated by osajin, as evidenced by reduced levels of pro-inflammatory cytokines (e.g., TNF-α, IL-6) in myocardial tissue and serum. [3] |
| Cell Assay |
- MTT assay: Human nasopharyngeal carcinoma cells were treated with osajin at various concentrations (e.g., 10–50 μM) for 24–48 hours, and cell viability was measured to determine antiproliferative effects. [1] - Flow cytometry: Annexin V/PI staining was used to quantify apoptotic cells after osajin treatment, demonstrating dose-dependent increases in early and late apoptotic populations. [1] - Western blot analysis: Detection of cleaved caspases and changes in Bcl-2 family protein expression levels confirmed activation of apoptotic pathways. [1] |
| Animal Protocol |
- Heart ischemia-reperfusion model: Osajin was administered to rats or mice via intraperitoneal injection or oral gavage before ischemia, followed by assessment of infarct size, cardiac function, and markers of oxidative stress (e.g., MDA, SOD) post-reperfusion. [3] - Dosing regimen: Typically, osajin was dissolved in DMSO or ethanol and diluted in saline, administered at doses ranging from 10–50 mg/kg. [3] |
| References |
[1]. Activation of multiple apoptotic pathways in human nasopharyngeal carcinoma cells by the prenylated isoflavone, osajin. PLoS One. 2011 Apr 12;6(4):e18308. [2]. Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera. Bioorg Med Chem Lett. 2007 Sep 1;17(17):4753-5. [3]. 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. |
| Additional Infomation |
- Mechanism of action: Osajin’s anticancer effects likely involve induction of apoptosis through mitochondrial dysfunction and caspase activation. [1] - Cardioprotective effects: In ischemia-reperfusion models, osajin may reduce oxidative damage and inflammation, preserving cardiac function. [3] - Structural properties: As a prenylated isoflavone, osajin’s activity is influenced by its hydrophobic prenyl group, which may enhance cellular uptake and target binding. [1][3] Osajin is a member of isoflavanones. Osajin has been reported in Deguelia hatschbachii, Maclura pomifera, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5954 mL | 12.9769 mL | 25.9538 mL | |
| 5 mM | 0.5191 mL | 2.5954 mL | 5.1908 mL | |
| 10 mM | 0.2595 mL | 1.2977 mL | 2.5954 mL |