StylopineCAS# 84-39-9 |
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| Cas No. | 84-39-9 | SDF | Download SDF |
| PubChem ID | 440583 | Appearance | Cryst. |
| Formula | C19H17NO4 | M.Wt | 323.1 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | C1CN2CC3=C(CC2C4=CC5=C(C=C41)OCO5)C=CC6=C3OCO6 | ||
| Standard InChIKey | UXYJCYXWJGAKQY-HNNXBMFYSA-N | ||
| Standard InChI | InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m0/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. Stylopine can serve as a model compound for the design and future development of structurally related AKR1C3 inhibitors. 2. Stylopine suppresses the NO and PGE2 production in macrophages by inhibiting the iNOS and COX-2 expressions, may contribute to the anti-inflammatory activity of Chelidonium majus. |
| Targets | NO | PGE | TNF-α | IL Receptor | COX | NOS |
Stylopine Dilution Calculator
Stylopine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.095 mL | 15.4751 mL | 30.9502 mL | 61.9003 mL | 77.3754 mL |
| 5 mM | 0.619 mL | 3.095 mL | 6.19 mL | 12.3801 mL | 15.4751 mL |
| 10 mM | 0.3095 mL | 1.5475 mL | 3.095 mL | 6.19 mL | 7.7375 mL |
| 50 mM | 0.0619 mL | 0.3095 mL | 0.619 mL | 1.238 mL | 1.5475 mL |
| 100 mM | 0.031 mL | 0.1548 mL | 0.3095 mL | 0.619 mL | 0.7738 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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Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica.[Pubmed:17250743]
FEBS J. 2007 Feb;274(4):1019-35.
(S)-Stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine. Stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges. Although the methylenedioxy bridge-forming P450 (CYP719) involved in berberine biosynthesis has been cloned from Coptis japonica[Ikezawa N, Tanaka M, Nagayoshi M, Shinkyo R, Sakaki T, Inouye K & Sato F (2003) J Biol Chem278, 38557-38565], no information is available regarding the genes for methylenedioxy bridge-forming enzymes in Stylopine biosynthesis. Two cytochrome P450 cDNAs involved in Stylopine biosynthesis were isolated using degenerate primers designed for C. japonica CYP719 from cultured Eschscholzia californica cells. Heterologous expression in Saccharomyces cerevisiae showed that both CYP719A2 and CYP719A3 had Stylopine synthase activity to catalyze methylenedioxy bridge-formation from cheilanthifoline to Stylopine, but not cheilanthifoline synthase activity to convert scoulerine to cheilanthifoline. Functional differences and expression patterns of CYP719A2 and CYP719A3 were examined to investigate their physiological roles in Stylopine biosynthesis. Enzymatic analysis showed that CYP719A2 had high substrate affinity only toward (R,S)-cheilanthifoline, whereas CYP719A3 had high affinity toward three similar substrates (R,S)-cheilanthifoline, (S)-scoulerine, and (S)-tetrahydrocolumbamine. An expression analysis in E. californica plant tissues showed that CYP719A2 and CYP719A3 exhibited expression patterns similar to those of three Stylopine biosynthetic genes (CYP80B1, berberine bridge enzyme, and S-adenosyl-l-methionine : 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase), whereas the specific expression of CYP719A3 in root was notable. Treatment of E. californica seedlings with methyl jasmonate resulted in the coordinated induction of CYP719A2 and CYP719A3 genes. The physiological roles of CYP719A2 and CYP719A3 in Stylopine biosynthesis are discussed.
Isoquinoline alkaloids as a novel type of AKR1C3 inhibitors.[Pubmed:24769118]
J Steroid Biochem Mol Biol. 2014 Sep;143:250-8.
AKR1C3 is an important human enzyme that participates in the reduction of steroids and prostaglandins, which leads to proliferative signalling. In addition, this enzyme also participates in the biotransformation of xenobiotics, such as drugs and procarcinogens. AKR1C3 is involved in the development of both hormone-dependent and hormone-independent cancers and was recently demonstrated to confer cell resistance to anthracyclines. Because AKR1C3 is frequently upregulated in various cancers, this enzyme has been suggested as a therapeutic target for the treatment of these pathological conditions. In this study, nineteen isoquinoline alkaloids were examined for their ability to inhibit a recombinant AKR1C3 enzyme. As a result, Stylopine was demonstrated to be the most potent inhibitor among the tested compounds and exhibited moderate selectivity towards AKR1C3. In the follow-up cellular studies, Stylopine significantly inhibited the AKR1C3-mediated reduction of daunorubicin in intact cells without considerable cytotoxic effects. This inhibitor could therefore be used as a model AKR1C3 inhibitor in research or evaluated as a possible therapeutic anticancer drug. Furthermore, based on our results, Stylopine can serve as a model compound for the design and future development of structurally related AKR1C3 inhibitors.
Stylopine from Chelidonium majus inhibits LPS-induced inflammatory mediators in RAW 264.7 cells.[Pubmed:15473662]
Arch Pharm Res. 2004 Sep;27(9):923-9.
Stylopine is a major component of the leaf of Chelidonium majus L. (Papaveraceae), which has been used for the removal of warts, papillomas and condylomas, as well as the treatment of liver disease, in oriental countries. Stylopine per se had no cytotoxic effect in unstimulated RAW 264.7 cells, but concentration-dependently reduced nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-1beta), and the IL-6 production and cyclooxygenase-2 (COX-2) activity caused by the LPS stimulation. The levels of inducible nitric oxide synthase (iNOS) and COX-2 protein expressions were markedly suppressed by Stylopine in a concentration dependent manner. These results suggest that Stylopine suppress the NO and PGE2 production in macrophages by inhibiting the iNOS and COX-2 expressions. These biological activities of Stylopine may contribute to the anti-inflammatory activity of Chelidonium majus.
