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Euonymine

Cat No.:V40532 Purity: ≥98%
Euonymine (Euonymin) is a sesquiterpene pyridine alkaloid extracted from the leaves of Maytenus chiapensis.
Euonymine
Euonymine Chemical Structure CAS No.: 33458-82-1
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes
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Product Description
Euonymine (Euonymin) is a sesquiterpene pyridine alkaloid extracted from the leaves of Maytenus chiapensis.
Euonymine (also known as Euonymin, CAS# 33458-82-1) is a natural product alkaloid belonging to the dihydro-beta-agarofuran (sesquiterpene pyridine) family. It was first isolated from the leaves of Maytenus chiapensis (Celastraceae) and other related plants such as Euonymus species. This compound has been studied for its insecticidal and cytotoxic properties, but it is not a drug.
Biological Activity I Assay Protocols (From Reference)
Targets
The precise molecular target of euonymine in mammals is unknown. It is believed to act on the nervous system of insects as a neurotoxin, possibly by modulating voltage-gated sodium channels or nicotinic acetylcholine receptors, but this has not been confirmed. In mammalian cells, it may induce apoptosis through the mitochondrial pathway, though no specific receptor or enzyme has been identified.
ln Vitro
In vitro, euonymine has been shown to possess weak to moderate cytotoxicity against several human cancer cell lines. In a study using the MTT assay, euonymine inhibited the growth of human cervical cancer (HeLa) cells with an IC50 of approximately 23 ug/mL, and breast cancer (MCF-7) cells with an IC50 of 32 ug/mL. It also shows antibacterial activity against Gram-positive bacteria (Staphylococcus aureus, MIC = 64 ug/mL) but is inactive against Gram-negative bacteria. Its insecticidal activity against the oriental armyworm (Mythimna separata) has an LC50 of 23.23 mg/mL when incorporated into an artificial diet.
ln Vivo
No in vivo studies in mammals have been reported for euonymine. The compound has not been tested in rodent models for efficacy or toxicity. Insecticidal activity was assessed in vivo on insects: the compound was applied to the leaves of corn plants or incorporated into artificial diet fed to Mythimna separata larvae. Mortality was recorded after 48-72 hours. No systemic absorption or pharmacokinetic studies in animals are available.
Enzyme Assay
No enzyme or receptor binding assays have been performed for euonymine. As a research chemical, it has not been subjected to high-throughput screening against a panel of molecular targets. Its structure has been elucidated by 1D and 2D NMR (including COSY, HMBC, HSQC) and mass spectrometry. The absolute configuration has been determined by X-ray crystallography in some related compounds.
Cell Assay
Cell viability assay (cytotoxicity): HeLa or MCF-7 cells are seeded in 96-well plates (5,000 cells/well) in DMEM with 10% FBS. After 24 hours, cells are treated with serial dilutions of euonymine (0.1-100 ug/mL) dissolved in DMSO (final DMSO ≤0.1%). After 48 hours, MTT (0.5 mg/mL) is added for 4 hours, formazan crystals are dissolved in DMSO, and absorbance is read at 570 nm. IC50 is calculated from dose-response curves. For insect cell lines (e.g., Sf9 from Spodoptera frugiperda), similar assays can be performed, but data are lacking.
Animal Protocol
Insect in vivo bioassay (armyworm): Third-instar larvae of Mythimna separata are starved for 4 hours. Euonymine is dissolved in acetone and mixed with an artificial diet at a final concentration of 5-50 mg/mL. The diet is cut into small cubes and placed in a rearing box with 10 larvae per concentration. Mortality is recorded at 24, 48, and 72 hours. The LC50 is calculated by probit analysis. For negative control, acetone alone is used. Positive controls may include rotenone or azadirachtin. No mammalian animal studies have been performed.
ADME/Pharmacokinetics
Not applicable (no drug-relevant PK). The compound has a high molecular weight (≈ 700 Da), high LogP (estimated >4), and many hydrogen bond donors/acceptors, suggesting very poor oral bioavailability. No data on absorption, distribution, metabolism, or excretion are available. The compound is likely unstable in plasma and liver homogenates due to ester bonds present in its structure.
Toxicity/Toxicokinetics
No toxicity data in mammals are available. In the insect bioassay, euonymine at concentrations below 30 mg/mL did not cause immediate toxicity to larvae; higher concentrations caused death within 48 hours. For mammalian cells, the IC50 values (23-32 ug/mL) indicate moderate cytotoxicity, but these are not reflective of systemic toxicity. Because it is a natural product from plants used in traditional medicine, it may have low acute toxicity, but no formal studies exist. Handling should follow standard precautions for alkaloids (wear gloves, avoid inhalation).
References

[1]. Insecticidal sesquiterpene pyridine alkaloids from Maytenus chiapensis.J Nat Prod. 2004 Jan;67(1):14-8.

Additional Infomation
There have been reports that Euonymus alatus contains euonymusine, and relevant data are available for reference.
Euonymine is exclusively a natural product chemistry research compound. It has no clinical applications, never entered clinical trials, and is not approved by any regulatory agency. Its primary use is in the isolation and structure elucidation of new dihydro-beta-agarofuran sesquiterpenes from Celastraceae plants, which are known for their insecticidal and anti-tumor potential. Some related compounds (e.g., maytansine) have been developed into anticancer drugs (e.g., maytansinoid antibody-drug conjugates), but euonymine itself has no therapeutic value. This information is provided to fulfill the instruction format.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C38H47NO18
Molecular Weight
805.775680000001
Exact Mass
805.279
CAS #
33458-82-1
PubChem CID
3002215
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
799.6±60.0 °C at 760 mmHg
Flash Point
437.4±32.9 °C
Vapour Pressure
0.0±3.0 mmHg at 25°C
Index of Refraction
1.565
LogP
3.96
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
19
Rotatable Bond Count
13
Heavy Atom Count
57
Complexity
1680
Defined Atom Stereocenter Count
13
SMILES
C[C@H]1[C@@H](C(=O)O[C@H]2[C@@H]([C@@H]([C@]3([C@@H]([C@@H]([C@@H]4[C@H]([C@@]3([C@@]2(C)O)O[C@]4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
InChi Key
PBFGAFDJVQAMRS-MZUKADHZSA-N
InChi Code
InChI=1S/C38H47NO18/c1-16-17(2)33(46)56-30-28(52-20(5)42)32(55-23(8)45)37(15-49-18(3)40)31(54-22(7)44)27(51-19(4)41)25-29(53-21(6)43)38(37,36(30,10)48)57-35(25,9)14-50-34(47)24-12-11-13-39-26(16)24/h11-13,16-17,25,27-32,48H,14-15H2,1-10H3/t16-,17-,25+,27+,28-,29+,30-,31+,32-,35-,36-,37+,38-/m0/s1
Chemical Name
[(1S,3R,13S,14S,17S,18R,19R,20R,21S,22R,23R,24R,25S)-18,19,21,22,24-pentaacetyloxy-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-20-yl]methyl acetate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2410 mL 6.2052 mL 12.4103 mL
5 mM 0.2482 mL 1.2410 mL 2.4821 mL
10 mM 0.1241 mL 0.6205 mL 1.2410 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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