Methyl kulonateCAS# 22611-37-6 |
Quality Control & MSDS
3D structure
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| Cas No. | 22611-37-6 | SDF | Download SDF |
| PubChem ID | 44567123 | Appearance | Powder |
| Formula | C31H48O4 | M.Wt | 484.71 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl (2R)-2-[(5R,9R,10R,13S,14S,16S,17S)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoate | ||
| SMILES | CC(=CCCC(C1C(CC2(C1(CCC3C2=CCC4C3(CCC(=O)C4(C)C)C)C)C)O)C(=O)OC)C | ||
| Standard InChIKey | ZLOYHDGVJFCYJK-RLIKWOGQSA-N | ||
| Standard InChI | InChI=1S/C31H48O4/c1-19(2)10-9-11-20(27(34)35-8)26-23(32)18-31(7)22-12-13-24-28(3,4)25(33)15-16-29(24,5)21(22)14-17-30(26,31)6/h10,12,20-21,23-24,26,32H,9,11,13-18H2,1-8H3/t20-,21+,23+,24+,26-,29-,30+,31-/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. Methyl kulonate shows interesting antimycobacterial activity (with MIC value of 70 uM ). 2. Methyl kulonate exhibits potent cytotoxicities against HL60 cells with IC50 values in the range of 2.8-5.8 uM. 3. Methyl kulonate inhibits production of nitric oxide (NO) in mouse macrophage RAW 264.7 cells induced by lipopolysaccharide (LPS). |
| Targets | NO | NOS | COX | Antifection |
Methyl kulonate Dilution Calculator
Methyl kulonate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0631 mL | 10.3154 mL | 20.6309 mL | 41.2618 mL | 51.5772 mL |
| 5 mM | 0.4126 mL | 2.0631 mL | 4.1262 mL | 8.2524 mL | 10.3154 mL |
| 10 mM | 0.2063 mL | 1.0315 mL | 2.0631 mL | 4.1262 mL | 5.1577 mL |
| 50 mM | 0.0413 mL | 0.2063 mL | 0.4126 mL | 0.8252 mL | 1.0315 mL |
| 100 mM | 0.0206 mL | 0.1032 mL | 0.2063 mL | 0.4126 mL | 0.5158 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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Cytotoxic and nitric oxide production-inhibitory activities of limonoids and other compounds from the leaves and bark of Melia azedarach.[Pubmed:25146759]
Chem Biodivers. 2014 Aug;11(8):1121-39.
Nine limonoids, 1-9, one apocarotenoid, 11, one alkaloid, 12, and one steroid, 13, from the leaf extract; and one triterpenoid, 10, five steroids, 14-18, and two flavonoids, 19 and 20, from the bark extract of Melia azedarach L. (Chinaberry tree; Meliaceae) were isolated. Among these compounds, three compounds, 4-6, were new, and their structures were established as 3-deacetyl-28-oxosalannolactone, 3-deacetyl-28-oxosalanninolide, and 3-deacetyl-17-defurano-17,28-dioxosalannin, respectively, on the basis of extensive spectroscopic analyses and comparison with literature data. All of the isolated compounds were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK-BR-3) cancer cell lines. 3-Deacetyl-4'-demethyl-28-oxosalannin (3) against HL60 and AZ521 cells, and Methyl kulonate (10) against HL60 cells exhibited potent cytotoxicities with IC50 values in the range of 2.8-5.8 muM. In addition, upon evaluation of compounds 1-13 against production of nitric oxide (NO) in mouse macrophage RAW 264.7 cells induced by lipopolysaccharide (LPS), seven, i.e., trichilinin B (1), 4, ohchinin (7), 23-hydroxyohchininolide (8), 21-hydroxyisoohchininolide (9), 10, and methyl indole 3-carboxylate (12), inhibited production of NO with IC50 values in the range of 4.6-87.3 muM with no, or almost no, toxicity to the cells (IC50 93.2-100 muM). Western blot analysis revealed that compound 7 reduced the expression levels of the inducible NO synthase (iNOS) and COX-2 proteins in a concentration-dependent manner. Furthermore, compounds 5, 6, 13, and 18-20 exhibited potent inhibitory effects (IC50 299-381 molar ratio/32 pmol TPA) against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cell line.
Limonoids from Melia azedarach Fruits as Inhibitors of Flaviviruses and Mycobacterium tubercolosis.[Pubmed:26485025]
PLoS One. 2015 Oct 20;10(10):e0141272.
The biological diversity of nature is the source of a wide range of bioactive molecules. The natural products, either as pure compounds or as standardized plant extracts, have been a successful source of inspiration for the development of new drugs. The present work was carried out to investigate the cytotoxicity, antiviral and antimycobacterial activity of the methanol extract and of four identified limonoids from the fruits of Melia azedarach (Meliaceae). The extract and purified limonoids were tested in cell-based assays for antiviral activity against representatives of ssRNA, dsRNA and dsDNA viruses and against Mycobacterium tuberculosis. Very interestingly, 3-alpha-tigloyl-melianol and melianone showed a potent antiviral activity (EC50 in the range of 3-11muM) against three important human pathogens, belonging to Flaviviridae family, West Nile virus, Dengue virus and Yellow Fever virus. Mode of action studies demonstrated that title compounds were inhibitors of West Nile virus only when added during the infection, acting as inhibitors of the entry or of a very early event of life cycle. Furthermore, 3-alpha-tigloyl-melianol and Methyl kulonate showed interesting antimycobacterial activity (with MIC values of 29 and 70 muM respectively). The limonoids are typically lipophilic compounds present in the fruits of Melia azeradach. They are known as cytotoxic compounds against different cancer cell lines, while their potential as antiviral and antibacterial was poorly investigated. Our studies show that they may serve as a good starting point for the development of novel drugs for the treatment of infections by Flaviviruses and Mycobacterium tuberculosis, for which there is a continued need.
Cytotoxic tirucallane triterpenoids from Melia azedarach fruits.[Pubmed:20802401]
Molecules. 2010 Aug 27;15(9):5866-77.
The phytochemical investigation of the dichloromethane-soluble part of the methanol extract obtained from the fruits of Melia azedarach afforded one new tirucallane-type triterpene, 3-alpha-tigloylmelianol and three known tirucallanes, melianone, 21-beta-acetoxy-melianone, and Methyl kulonate. The structure of the isolated compounds was mainly determined by 1D and 2D NMR experiments as well as HPLC-Q-TOF mass spectrometry. The cytotoxicity of the isolated compounds toward the human lung adenocarcinoma epithelial cell line A549 was determined, while no activity was observed against the phytonematode Meloidogyne incognita.
