IsolineCAS# 30000-36-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 30000-36-3 | SDF | Download SDF |
| PubChem ID | 185716 | Appearance | Cryst. |
| Formula | C20H29NO7 | M.Wt | 395.45 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CCC1(CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)OC(=O)C)C)O | ||
| Standard InChIKey | IYLGZMTXKJYONK-ACLXAEORSA-N | ||
| Standard InChI | InChI=1S/C20H29NO7/c1-5-20(25)10-12(2)19(4,28-13(3)22)17(23)26-11-14-6-8-21-9-7-15(16(14)21)27-18(20)24/h6,12,15-16,25H,5,7-11H2,1-4H3/t12-,15-,16-,19+,20-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Isoline decreases the cellular GSH and the ratio of GSH and oxidizes glutathione in a time- and concentration-dependent manner in L-02 cells. 2. Isoline can induce different oxidative injury in various important mouse organs, and of which liver is the most sensitive organ. 3. An in silico drug target searching program INVDOCK identified 2 potential protein targets of Isoline. 4. l-Buthionine-(S, R)-sulfoximine (BSO) and mercaptosuccinic acid (MA), inhibitors of GCL and GPx, both augmented Isoline-induced cytotoxicity in cultured mice hepatocytes. |
| Targets | ATPase |
Isoline Dilution Calculator
Isoline Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.5288 mL | 12.6438 mL | 25.2876 mL | 50.5753 mL | 63.2191 mL |
| 5 mM | 0.5058 mL | 2.5288 mL | 5.0575 mL | 10.1151 mL | 12.6438 mL |
| 10 mM | 0.2529 mL | 1.2644 mL | 2.5288 mL | 5.0575 mL | 6.3219 mL |
| 50 mM | 0.0506 mL | 0.2529 mL | 0.5058 mL | 1.0115 mL | 1.2644 mL |
| 100 mM | 0.0253 mL | 0.1264 mL | 0.2529 mL | 0.5058 mL | 0.6322 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury.[Pubmed:21126554]
Toxicology. 2011 Feb 4;280(1-2):61-9.
Intracellular reduced glutathione (GSH) antioxidant system is crucial for counteracting oxidative stress-induced liver injury. The present study was designed to observe the gender-dependent difference of GSH antioxidant system and its influence on hepatotoxic pyrrolizidine alkaloid (HPA) Isoline-induced liver injury. Lower activities and protein expressions of glutamate-cysteine ligase (GCL) and glutathione peroxidase (GPx) were found in male mice livers than in female. Isoline is a natural HPA, our further results showed that male mice demonstrated more higher serum ALT/AST levels, less GSH amounts, lower GCL and GPx activities and proteins induced by Isoline as compared to female. N-acetyl-l-cysteine (NAC), which is the precursor of cellular GSH biosynthesis, ameliorated liver injury induced by Isoline. l-Buthionine-(S, R)-sulfoximine (BSO) and mercaptosuccinic acid (MA), inhibitors of GCL and GPx, both augmented Isoline-induced cytotoxicity in cultured mice hepatocytes. BSO and MA also increased other natural HPAs clivorine and senecionine-induced cytotoxicity. Taken together, our results demonstrated the higher GCL and GPx activities in female mice, which indicated their crucial roles in regulating the resistance of liver injury induced by hepatotoxins in female. Meanwhile, our results also revealed the female-resistant liver injury induced by HPAs for the first time.
Involvement of intracellular glutathione in regulating isoline-induced cytotoxicity in human normal liver L-02 cells.[Pubmed:22474030]
Toxicol Ind Health. 2013 Jul;29(6):567-75.
Pyrrolizidine alkaloid Isoline is isolated from the traditional Chinese medicine Ligularia duciformis. Our previous reports have already demonstrated Isoline-induced liver injury in mice. The present study is designed to observe the involvement of intracellular reduced glutathione (GSH) in Isoline-induced cytotoxicity in human normal liver L-02 cells. The results showed that Isoline decreased the cellular GSH and the ratio of GSH and oxidized glutathione in a time- and concentration-dependent manner in L-02 cells. l-Buthionine-S-R-sulfoximine (BSO) is reported to inhibit cellular GSH biosynthesis, and further results showed that Isoline decreased the cell viability in L-02 cells after pretreated with 25 muM BSO for 24 h. Furthermore, adducts of Isoline and GSH were identified in L-02 cells using liquid chromatography/electrospray ionization tandem mass spectrometry (ion trap) for the first time. In conclusion, our study provides the strongest evidence to support the important roles of GSH in regulating Isoline-induced cytotoxicity in human normal liver L-02 cells.
The difference of glutathione antioxidant system in newly weaned and young mice liver and its involvement in isoline-induced hepatotoxicity.[Pubmed:21327617]
Arch Toxicol. 2011 Oct;85(10):1267-79.
Cellular glutathione antioxidant system plays important roles in counteracting hepatotoxins-induced oxidative stress injury. The present study was designed to observe the differences of this system in newly weaned and young mice liver and its involvement in the susceptibility to Isoline-induced liver injury. Our results showed that liver reduced glutathione (GSH) amounts were higher in newly weaned mice than young mice. Glutamate-cysteine ligase (GCL) activity was higher in newly weaned mice due to the higher expression of catalytic subunit of GCL (GCLC) protein and mRNA. However, the activities of glutathione reductase (GR), glutathione peroxidase (GPx), and glutathione-S-transferase (GST) were higher in young mice liver, which might be due to the higher expression of GR, GPx-1, and GST-Pi proteins. Next, the results of AST analysis and histopathological evaluation showed that newly weaned mice demonstrated more severe liver injury induced by Isoline. Furthermore, liver GSH amounts and the activities of GR, GPx, and GST were all lower in newly weaned mice than young mice after treated with Isoline. Depletion of cellular GSH by D,L -buthionine-(S, R)-sulfoximine (BSO) aggravated Isoline-induced cytotoxicity, while N-acetyl-l cysteine (NAC) ameliorated such cytotoxicity. Furthermore, the inhibitors of GR, GPx, and GST all aggravated Isoline-induced cytotoxicity. In conclusion, our results demonstrated the differences of glutathione antioxidant system between newly weaned and young mice liver. Meanwhile, our results also revealed age-dependent liver injury induced by Isoline for the first time, which might be due to the different responses of glutathione antioxidant system to Isoline between newly weaned and young mice.
Pyrrolizidine alkaloid isoline-induced oxidative injury in various mouse tissues.[Pubmed:19540740]
Exp Toxicol Pathol. 2010 May;62(3):251-7.
Isoline is a retronecine-type pyrrolizidine alkaloid (PA) isolated from the traditional Chinese medicinal herb Ligularia duciformis. The present investigation was carried out to evaluate Isoline-induced oxidative injury in various important mouse organs. Various tissue samples were collected after mice were administrated with 100mg/kg Isoline for 36h, and then lipid peroxidation (LPO) level, total antioxidant capacity, glutathione-S-transferase (GST), glutathione peroxidase (GPx) and catalase (CAT) activities were determined to evaluate the oxidative injury. Our results showed that the total antioxidant capacity of liver, brain and lung were all decreased after given Isoline, and the LPO level was increased in liver and heart of Isoline-treated mice. Further antioxidant-related enzyme activity assays showed that Isoline (100mg/kg) decreased GPx activity in liver and heart, increased CAT activity in liver, brain and heart, and decreased the GST activity in lung. Taken together, our results demonstrate that Isoline can induce different oxidative injury in various important mouse organs, and of which liver is the most sensitive organ.
Proteomic characterization of the possible molecular targets of pyrrolizidine alkaloid isoline-induced hepatotoxicity.[Pubmed:22885678]
Environ Toxicol Pharmacol. 2012 Sep;34(2):608-617.
Pyrrolizidine alkaloids (PAs) are distributed in plants worldwide including medicinal herbs or teas. In the present study, we investigated the effects of Isoline, which is a retronecine-type PA isolated from traditional Chinese medicinal herb Ligularia duciformis, on mouse liver proteins by using proteomic approaches. Firstly, our results showed that 110mg/kg Isoline increased alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activities in serum, and hepatic tissue pathological observation further confirmed Isoline-induced liver injury. Proteomic analysis showed that the liver samples from mice of Isoline group demonstrated about 13 differentially expressed proteins compared with normal group, and those proteins may be involved in Isoline-induced liver injury in mice. Next, all these 13 protein spots were identified by MALDI-TOF-TOF MS or LTQ MS; and among them 9 differentially expressed proteins are involved in the process of oxidative stress or cellular energy metabolism. Further lipid peroxidation analysis and ATPase assay confirmed the existing of oxidative injury induced by Isoline and consequent disruption of energy metabolism. Furthermore, an in silico drug target searching program INVDOCK identified 2 potential protein targets of Isoline, and the results are in support of proteomic analysis. In summary, the possible signaling molecules related with Isoline-induced liver injury were demonstrated in this study.
