Cannabisin FCAS# 163136-19-4 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 163136-19-4 | SDF | Download SDF |
| PubChem ID | 71448967 | Appearance | Powder |
| Formula | C36H36N2O8 | M.Wt | 624.69 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-[4-[(E)-3-[2-(4-hydroxyphenyl)ethylamino]-3-oxoprop-1-enyl]-2-methoxyphenoxy]prop-2-enamide | ||
| SMILES | COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CC=C(C=C2)O)OC(=CC3=CC(=C(C=C3)O)OC)C(=O)NCCC4=CC=C(C=C4)O | ||
| Standard InChIKey | JCUQMHMUDDMCSX-AADBSILNSA-N | ||
| Standard InChI | InChI=1S/C36H36N2O8/c1-44-32-22-27(7-14-30(32)41)23-34(36(43)38-20-18-25-5-12-29(40)13-6-25)46-31-15-8-26(21-33(31)45-2)9-16-35(42)37-19-17-24-3-10-28(39)11-4-24/h3-16,21-23,39-41H,17-20H2,1-2H3,(H,37,42)(H,38,43)/b16-9+,34-23- | ||
| 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. Melongenamides B-D and Cannabisin F have anti-inflammatory activity, they exhibit inhibitions of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values ranging from 16.2 to 58.5 uM. |
| Targets | Immunology & Inflammation related |
Cannabisin F Dilution Calculator
Cannabisin F Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.6008 mL | 8.004 mL | 16.0079 mL | 32.0159 mL | 40.0198 mL |
| 5 mM | 0.3202 mL | 1.6008 mL | 3.2016 mL | 6.4032 mL | 8.004 mL |
| 10 mM | 0.1601 mL | 0.8004 mL | 1.6008 mL | 3.2016 mL | 4.002 mL |
| 50 mM | 0.032 mL | 0.1601 mL | 0.3202 mL | 0.6403 mL | 0.8004 mL |
| 100 mM | 0.016 mL | 0.08 mL | 0.1601 mL | 0.3202 mL | 0.4002 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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Cannabisin F from Hemp (Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator.[Pubmed:30691004]
Int J Mol Sci. 2019 Jan 25;20(3). pii: ijms20030507.
Hemp seed (Fructus cannabis) is rich in lignanamides, and initial biological screening tests showed their potential anti-inflammatory and anti-oxidative capacity. This study investigated the possible effects and underlying mechanism of Cannabisin F, a hempseed lignanamide, against inflammatory response and oxidative stress in lipopolysaccharide (LPS)-stimulated BV2 microglia cells. Cannabisin F suppressed the production and the mRNA levels of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor alpha (TNF-alpha) in a concentration-dependent manner in LPS-stimulated BV2 microglia cell. Furthermore, Cannabisin F enhanced SIRT1 expression and blocked LPS-induced NF-kappaB (Nuclear factor kappa B) signaling pathway activation by inhibiting phosphorylation of IkappaBalpha (Inhibit proteins of nuclear factor kappaB) and NF-kappaB p65. And the SIRT1 inhibitor EX527 significantly inhibited the effect of Cannabisin F on pro-inflammatory cytokines production, suggesting that the anti-inflammatory effects of Cannabisin F are SIRT1-dependent. In addition, Cannabisin F reduced the production of cellular reactive oxygen species (ROS) and promoted the expression of Nrf2 (Nuclear factor erythroid-2 related factor 2) and HO-1 (Heme Oxygenase-1), suggesting that the anti-oxidative effects of Cannabisin F are related to Nrf2 signaling pathway. Collectively, these results suggest that the neuro-protection effect of Cannabisin F against LPS-induced inflammatory response and oxidative stress in BV2 microglia cells involves the SIRT1/NF-kappaB and Nrf2 pathway.
Characterization of enantiomeric lignanamides from Solanum nigrum L. and their neuroprotective effects against MPP(+)-induced SH-SY5Y cells injury.[Pubmed:30661806]
Phytochemistry. 2019 May;161:163-171.
Five pairs of enantiomeric lignanamides including nine undescribed compounds along with a known one were obtained from Solanum nigrum L. (Solanaceae). Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses and quantum chemical calculations of electronic circular dichroism (ECD) curves. Additionally, all isolates were evaluated for their neuroprotective activity against MPP(+) (1-methyl-4-phenylpyridinium)-induced SH-SY5Y cells injury. Among them, Cannabisin F showed the most significant neuroprotective effects at different concentrations (12.5, 25, 50muM). Further studies by Hoechst 33258 staining, monodansylcadaverine (MDC) staining and Annexin V/PI analysis demonstrated that Cannabisin F could induce protective autophagy to protect SH-SY5Y cells from MPP(+)-induced apoptosis.
Metabolites Identification of Bioactive Compounds Daturataturin A, Daturametelin I, N-Trans-Feruloyltyramine, and Cannabisin F From the Seeds of Datura metel in Rats.[Pubmed:30050436]
Front Pharmacol. 2018 Jul 9;9:731.
Datura metel L. is a widely used traditional herbal medicine, and withanolides and amides are the two groups of main bioactive constituents in Datura metel seeds. This study aimed to elucidate the metabolism of four representative bioactive compositions containing daturataturin A (1), daturametelin I (2), N-trans-feruloyltyramine (3), and Cannabisin F (4) in rats. After separately oral administration of 20 mg/kg withanolides (1, 2) and amides (3, 4) to rats, a total of 12, 24, and 21 metabolites were detected in the plasma, urine, and fecal samples, respectively. Among them, three hydroxylated metabolites, 1-M3, 2-M2, and 3-M5, were detected in plasma and rat liver microsome incubation system in high abundance. Two metabolites of 1 and 2 were unambiguously identified by comparing with reference standards. Particularly, the methylated metabolite 27alpha-methoxy-(22R)-22,26-epoxy-27-[(beta-D-glucopyranosyl)oxy]ergosta-2,4,6,24 -tetraene-1,26-dione (daturametelin L) is a new compound. The withanolides could readily get hydroxylation or methylation metabolism. Meanwhile, the phase II metabolism (glucuronidation or sulfation) was the major reaction for the amides. This is the first study on in vivo metabolism of these active compounds in seeds of Datura metel.
