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Eupalinolide B

Cat No.:V28978 Purity: ≥98%
Eupalinolide B is a naturally occuring germacrane sesquiterpene extracted from Eupatorium lindleyanum.
Eupalinolide B
Eupalinolide B Chemical Structure CAS No.: 877822-41-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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10mg
25mg
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Product Description
Eupalinolide B is a naturally occuring germacrane sesquiterpene extracted from Eupatorium lindleyanum. Eupalinolide B displays potent cytotoxicity against A-549, BGC-823 and HL-60 tumour cell lines.
V28978 Eupalinolide B (CAS: 877822-41-8) is a naturally occurring germacrane sesquiterpene lactone extracted from Eupatorium lindleyanum. With the molecular formula C24H30O9 and a molecular weight of 462.49 g/mol, it is a bioactive compound with significant anticancer properties. It has been the subject of research for its potent cytotoxicity against various tumor cell lines.
Biological Activity I Assay Protocols (From Reference)
Targets
Eupalinolide B targets multiple signaling pathways involved in cancer cell survival and proliferation. It has been shown to inhibit tumor cell proliferation and induce apoptosis by disrupting key signaling pathways such as STAT3 and NF-κB. By interfering with these pathways, it effectively suppresses the growth and survival of cancer cells.
ln Vitro
In vitro, Eupalinolide B demonstrates potent cytotoxicity against several tumor cell lines. It is particularly effective against A-549 (lung cancer), BGC-823 (gastric cancer), and HL-60 (leukemia) cells. This broad-spectrum activity highlights its potential as a lead compound for anticancer drug development. Its activity is likely mediated by the induction of apoptosis and cell cycle arrest.
ln Vivo
In vivo, the efficacy of Eupalinolide B has not been extensively reported. However, its strong in vitro activity and its mechanism of inhibiting key survival pathways like STAT3 and NF-κB suggest that it could be effective in vivo as well. Further studies in animal models are needed to confirm its therapeutic potential and pharmacokinetic properties.
Enzyme Assay
The in vitro cytotoxicity assay for Eupalinolide B is the primary method for evaluating its activity. Tumor cell lines, such as A-549, BGC-823, and HL-60, are cultured in 96-well plates and treated with varying concentrations of the compound. After 48-72 hours of incubation, cell viability is assessed using a standard colorimetric assay like MTT or SRB, from which the IC50 value is determined.
Cell Assay
In vitro cell culture studies for Eupalinolide B involve detailed mechanistic investigations. Treated cancer cells are analyzed for apoptosis using Annexin V/PI staining and flow cytometry. Cell cycle distribution is assessed by propidium iodide staining. The expression of signaling pathway proteins like STAT3 and NF-κB, as well as apoptotic markers like caspases and PARP, is analyzed by Western blotting to confirm the mechanism of action.
Animal Protocol
In vivo animal experiments for Eupalinolide B would typically involve xenograft models. Immunodeficient mice are implanted with human tumor cells (e.g., A-549 lung cancer cells). Once tumors are established, Eupalinolide B is administered, typically via intraperitoneal injection. Tumor growth is monitored over time, and at the end of the study, tumors are excised and analyzed for histopathology and molecular markers.
ADME/Pharmacokinetics
Eupalinolide B has a molecular weight of 462.49 g/mol and is a solid compound. It is slightly soluble in water (3.6 g/L at 25°C) and is more soluble in organic solvents like DMSO. It is typically stored as a powder at -20°C. For in vitro studies, stock solutions are prepared in DMSO and diluted in cell culture media.
Toxicity/Toxicokinetics
Toxicological data for Eupalinolide B are limited to in vitro cytotoxicity assessments. Its potent effects on cancer cells suggest it could be toxic to normal cells at high concentrations. As a research compound, it is not intended for human use, and comprehensive in vivo toxicity studies are not available. Standard safety precautions should be followed.
References

[1]. Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum. J Asian Nat Prod Res. 2007 Apr-Aug;9(3-5):339-45.

Additional Infomation
Reports indicate that Eupalinolide A has been discovered in Eupatorium lindleyanum, and relevant data is available for reference.
Eupalinolide B is a research compound with no clinical approval. It is a valuable natural product for studying the anticancer mechanisms of sesquiterpene lactones. Its ability to inhibit STAT3 and NF-κB, two major oncogenic pathways, makes it a promising lead compound for drug discovery, particularly for cancers that are dependent on these pathways for survival and growth.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₂₄H₃₀O₉
Molecular Weight
462.49
Exact Mass
462.188
CAS #
877822-41-8
PubChem CID
71463992
Appearance
White to off-white solid powder
Density
1.24±0.1 g/cm3 (20 ºC 760 Torr)
Boiling Point
618.6±55.0 °C at 760 mmHg
Flash Point
205.4±25.0 °C
Vapour Pressure
0.0±4.1 mmHg at 25°C
Index of Refraction
1.541
LogP
2.5
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
9
Heavy Atom Count
33
Complexity
909
Defined Atom Stereocenter Count
4
SMILES
C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/C[C@@H]1OC(=O)C)/COC(=O)C)OC(=O)/C(=C/CO)/C)C(=C)C(=O)O2
InChi Key
HPWMABTYJYZFLK-FHEQDPKSSA-N
InChi Code
InChI=1S/C24H30O9/c1-13(8-9-25)23(28)32-21-11-18(12-30-16(4)26)6-7-19(31-17(5)27)14(2)10-20-22(21)15(3)24(29)33-20/h6,8,10,19-22,25H,3,7,9,11-12H2,1-2,4-5H3/b13-8+,14-10+,18-6-/t19-,20+,21+,22-/m0/s1
Chemical Name
[(3aR,4R,6Z,9S,10E,11aR)-9-acetyloxy-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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)
DMSO : ~100 mg/mL (~216.22 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.41 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.41 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1622 mL 10.8110 mL 21.6221 mL
5 mM 0.4324 mL 2.1622 mL 4.3244 mL
10 mM 0.2162 mL 1.0811 mL 2.1622 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.

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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?
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  • 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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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