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| Targets |
Usaramine N-oxide does not have a well-defined specific molecular target; it is a natural product with broad biological activities. As a pyrrolizidine alkaloid N-oxide, the compound may exert its effects through modulation of cellular signaling pathways involved in inflammation and cell proliferation. Pyrrolizidine alkaloids are known to cause hepatotoxicity through metabolic activation to reactive pyrrolic intermediates that form DNA and protein adducts. However, N-oxidation generally reduces toxicity compared to the parent alkaloid. Usaramine N-oxide's weak inhibitory activity against Caco-2 cells suggests potential interactions with cellular targets involved in proliferation or survival. The anti-inflammatory activity may involve modulation of cytokine production or inflammatory mediator release.
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| ln Vitro |
In vitro, usaramine N-oxide exhibits weak inhibitory activity against Caco-2 human colorectal adenocarcinoma cells with an IC₅0 of 42.35 microM. This indicates modest cytotoxicity or anti-proliferative activity against this cell line. The compound also possesses anti-inflammatory activities, as demonstrated in various in vitro models. The exact mechanism of action for the anti-inflammatory effect is not fully elucidated but may involve suppression of pro-inflammatory cytokines (e.g., TNF-alpha, IL-6, IL-1beta) or inhibition of inflammatory mediators such as nitric oxide or prostaglandins. The weak cytotoxicity and anti-inflammatory properties make usaramine N-oxide a compound of interest for studying natural product pharmacology.
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| ln Vivo |
In vivo data for usaramine N-oxide are limited. As a natural product isolated from Crotalaria pallida, the compound has not been extensively studied in animal models. Pyrrolizidine alkaloids and their N-oxides are known to be hepatotoxic in vivo, causing veno-occlusive disease and liver damage following metabolic activation. However, N-oxides are generally less toxic than the parent alkaloids due to reduced metabolic activation. The compound's anti-inflammatory activity observed in vitro may translate to in vivo effects, but specific animal studies have not been reported in the literature. The pharmacokinetic properties, bioavailability, and tissue distribution of usaramine N-oxide have not been characterized.
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| Enzyme Assay |
In vitro assays for usaramine N-oxide typically involve cell viability and cytotoxicity testing. Caco-2 cells are cultured in DMEM or MEM medium supplemented with 10% FBS, 1% non-essential amino acids, and 1% penicillin-streptomycin in a humidified atmosphere of 5% CO2 at 37degC. Cells are seeded in 96-well plates at a density of 1-5 × 10⁴ cells/well and allowed to attach overnight. Cells are treated with serial dilutions of usaramine N-oxide (typically 0.1-200 microM) for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or CellTiter-Glo assays. IC₅0 values are calculated from dose-response curves using nonlinear regression. For anti-inflammatory activity, macrophages (e.g., RAW 264.7) are stimulated with LPS (1 microg/mL) in the presence or absence of the compound, and inflammatory mediators (NO, TNF-alpha, IL-6) are measured.
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| Cell Assay |
In vitro cellular assays for usaramine N-oxide are performed using Caco-2 cells for cytotoxicity assessment and RAW 264.7 macrophages for anti-inflammatory evaluation. For Caco-2 cytotoxicity assays, cells are cultured in MEM or DMEM with 20% FBS and 1% penicillin-streptomycin. Cells are seeded in 96-well plates at 2.5 × 10⁴ cells/well and grown to 70-80% confluence. Cells are treated with usaramine N-oxide (0-200 microM) for 48 hours. Cell viability is measured using the MTT assay: MTT (5 mg/mL) is added to each well and incubated for 4 hours at 37degC. Formazan crystals are dissolved in DMSO and absorbance is read at 570 nm. IC₅0 values are calculated using GraphPad Prism. For anti-inflammatory assays, RAW 264.7 cells are seeded in 96-well plates and stimulated with LPS (1 microg/mL) with or without compound treatment for 24 hours.
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| Animal Protocol |
In vivo animal studies for usaramine N-oxide have not been extensively reported in the literature. Pyrrolizidine alkaloids are typically studied in rodent models to assess hepatotoxicity. In such studies, compounds are administered orally or intraperitoneally at doses ranging from 1-100 mg/kg. Animals are monitored for signs of toxicity, and liver function is assessed by measuring serum ALT, AST, and bilirubin levels. Liver histopathology is performed to evaluate tissue damage. For anti-inflammatory evaluation, animal models of inflammation (e.g., carrageenan-induced paw edema, LPS-induced systemic inflammation) could be used. However, specific protocols for usaramine N-oxide have not been published. Researchers should consult the primary literature for the most current information.
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| ADME/Pharmacokinetics |
Usaramine N-oxide (CAS#: 117020-54-9) has molecular formula C1₈H2₅NO₇ and molecular weight 367.39. The compound is a solid powder and should be stored at -20degC for long-term stability. It is a pyrrolizidine alkaloid N-oxide isolated from Crotalaria pallida. The compound is soluble in DMSO and methanol. It exhibits weak inhibitory activity against Caco-2 cells (IC₅0 = 42.35 microM) and possesses anti-inflammatory properties. The compound is intended for research use only and is not for human therapeutic applications. As a natural product, usaramine N-oxide serves as a tool for studying pyrrolizidine alkaloid pharmacology and natural product-based anti-inflammatory agents.
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| Toxicity/Toxicokinetics |
Toxicological information for usaramine N-oxide is limited. Pyrrolizidine alkaloids are known hepatotoxins that cause veno-occlusive disease, liver fibrosis, and hepatocellular carcinoma following chronic exposure. The toxicity is mediated by metabolic activation to reactive pyrrolic intermediates that form covalent adducts with DNA and proteins. N-oxides are generally less toxic than the parent alkaloids due to reduced metabolic activation. However, N-oxides can be reduced back to the parent alkaloid in the gut by intestinal microbiota, potentially leading to toxicity. The compound should be handled with standard laboratory precautions including the use of personal protective equipment and working in a fume hood. Avoid inhalation, ingestion, and skin contact. The compound should be stored at -20degC and disposed of according to institutional guidelines.
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| References | |
| Additional Infomation |
Usalamine N-oxide is a pyrrolizine alkaloid belonging to the Senecio alkaloid class. It has two hydroxyl substituents at positions 12 and 18, two carbonyl substituents at positions 11 and 16, and one N-oxide substituent. It is a metabolite of plants in the genus Jacobaea. It is a diol, macrolide, alkene, organic heterocyclic compound, primary alcohol, pyrrolizine alkaloid, tertiary alcohol, and tertiary amine oxide. Its function is related to usalamine.
See also: Isosatidine (note moved to). Usaramine N-oxide (CAS#: 117020-54-9) is a natural pyrrolizidine alkaloid N-oxide isolated from Crotalaria pallida (smooth rattlebox). The compound exhibits weak inhibitory activity against Caco-2 human colorectal adenocarcinoma cells with an IC₅0 of 42.35 microM, and possesses anti-inflammatory activities. Pyrrolizidine alkaloids are a large class of plant secondary metabolites known for their hepatotoxicity, and their N-oxides are often less toxic due to reduced metabolic activation. Usaramine N-oxide is used in research to study the pharmacology of natural products, plant-derived alkaloids, and their potential therapeutic applications in inflammation and cancer. The compound is supplied for research use only and is not approved for any clinical indication. |
| Molecular Formula |
C18H25NO7
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|---|---|
| Molecular Weight |
367.394
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| Exact Mass |
367.163
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| CAS # |
117020-54-9
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| PubChem CID |
22524560
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| Appearance |
Off-white to light yellow solid powder
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| LogP |
0
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
26
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| Complexity |
673
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1[C@H]2OC(=O)/C(/C[C@H](C)[C@@](CO)(O)C(OCC3[C@@]2([H])[N+]([O-])(CC=3)C1)=O)=C\C
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| InChi Key |
IDIMIWQPUHURPV-BEPQMMTDSA-N
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| InChi Code |
InChI=1S/C18H25NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-,19?/m1/s1
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| Chemical Name |
(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| 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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7219 mL | 13.6095 mL | 27.2190 mL | |
| 5 mM | 0.5444 mL | 2.7219 mL | 5.4438 mL | |
| 10 mM | 0.2722 mL | 1.3610 mL | 2.7219 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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