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Epimagnolin A (epimagnolin A)

Cat No.:V53047 Purity: ≥98%
Epimagnolin A, a furfural lignan, has moderate anti-Plasmodium activity (IC50=5.7 μg/mL) and has no obvious toxicity to normal mammalian cells.
Epimagnolin A (epimagnolin A)
Epimagnolin A (epimagnolin A) Chemical Structure CAS No.: 41689-51-4
Product category: Parasite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Epimagnolin A, a furfural lignan, has moderate anti-Plasmodium activity (IC50=5.7 μg/mL) and has no obvious toxicity to normal mammalian cells.
Epimagnolin A is a naturally occurring furfuran lignan isolated from the flower buds of Magnolia fargesii, a plant traditionally used in Asian medicine for treating headache and nasal congestion. This compound has garnered research interest due to its anti-inflammatory, antimicrobial, and antiplasmodial properties. It has been shown to inhibit pro-inflammatory cytokines and modulate key signaling pathways such as NF-κB and MAPK. Epimagnolin A also exhibits growth inhibitory activity against larvae of Drosophila melanogaster. With an IC50 of 5.7 μg/mL against Plasmodium species and minimal toxicity to mammalian normal cells, it represents a promising lead compound for further pharmacological development.
Biological Activity I Assay Protocols (From Reference)
Targets
Epimagnolin A affects the transport activity of ABCB1, a major transmembrane efflux pump belonging to the ABC transporter superfamily. It also inhibits the enzyme activity of the matrix metalloproteinase (MMP) family, which plays a role in the degradation of extracellular matrix and cell migration. Additionally, Epimagnolin A modulates pro-inflammatory cytokines and signaling pathways including NF-κB, MAPK, p38, and AP-1. It has been shown to interact with colorectal receptors and the tumor necrosis factor receptor. These multiple targets contribute to its diverse biological activities ranging from anti-inflammatory to antimicrobial effects.
ln Vitro
Epimagnolin A demonstrates significant in vitro biological activity with an IC50 of 5.7 μg/mL against Plasmodium species, while exhibiting minimal toxicity to mammalian normal cells. In human monocytic THP-1 cells, Epimagnolin A reduced phorbol-12-myristate-13-acetate (PMA)-induced IL-6 promoter activity and IL-6 production. It also inhibits PMA-stimulated p38/NF-κB and AP-1 signaling pathways in THP-1 cells. These results suggest that Epimagnolin A can be a useful agent for the treatment of inflammatory diseases. The compound shows growth inhibitory activity against larvae of Drosophila melanogaster in cell-free assays.
ln Vivo
In vivo studies on Epimagnolin A remain limited, and its pharmacokinetics have been reported but not its detailed molecular mechanisms in living organisms. The compound has been investigated for its potential in treating conditions like allergic rhinitis, neurodegenerative disorders, and oxidative stress-related diseases based on its in vitro profile. As a natural product from Magnolia fargesii traditionally used in Asian medicine, its in vivo efficacy and safety profile require further systematic investigation through appropriate animal models to validate its therapeutic potential.
Enzyme Assay
For ABCB1 transport activity assays, membrane vesicles prepared from cells overexpressing ABCB1 are incubated with fluorescent substrate and test compound, and the accumulation of substrate is measured fluorometrically to determine inhibition of efflux transport. For MMP inhibition studies, purified MMP enzymes are incubated with fluorogenic peptide substrates in the presence of Epimagnolin A, and cleavage is monitored by fluorescence increase at specific excitation/emission wavelengths. For antiplasmodial activity, Plasmodium cultures are incubated with compound and parasite growth is assessed by microscopy or radioisotope incorporation.
Cell Assay
THP-1 human monocytic cells are cultured in RPMI 1640 medium supplemented with 10% FBS. Cells are stimulated with phorbol-12-myristate-13-acetate (PMA) and treated with Epimagnolin A at various concentrations. IL-6 promoter activity is measured using luciferase reporter assays, and IL-6 production in culture supernatants is quantified by ELISA. For cytotoxicity assessment, mammalian normal cells are treated with Epimagnolin A and cell viability is determined using MTT or similar assays to evaluate the compound's selectivity index.
Animal Protocol
Drosophila melanogaster larvae are used for in vivo growth inhibitory activity assessment. Larvae are fed with compound-containing media at various concentrations, and larval growth and development are monitored over time. For anti-inflammatory studies, appropriate animal models of inflammation (e.g., carrageenan-induced paw edema or LPS-induced systemic inflammation) would be employed. Mice or rats would be administered Epimagnolin A orally or intraperitoneally, and inflammatory markers in serum and tissues would be analyzed. However, detailed in vivo protocols for Epimagnolin A have not been extensively reported in the literature.
ADME/Pharmacokinetics
Pharmacokinetic properties of Epimagnolin A have been reported, although detailed parameters such as bioavailability, half-life, and tissue distribution are not extensively documented. As a lignan natural product with moderate lipophilicity, it is expected to be absorbed orally and distributed to various tissues. Its metabolism likely involves hepatic cytochrome P450 enzymes, and elimination may occur via biliary and renal routes. Further comprehensive pharmacokinetic studies are needed to fully characterize its absorption, distribution, metabolism, and excretion profile.
Toxicity/Toxicokinetics
Epimagnolin A exhibits minimal toxicity to mammalian normal cells, suggesting a favorable safety profile. It demonstrates significant biological activity with an IC50 of 5.7 μg/mL against Plasmodium species. The compound has been shown to have an inhibitory effect on colorectal receptors and the tumor necrosis factor receptor. As a natural product from Magnolia fargesii used traditionally in Asian medicine, it has a history of use suggesting acceptable tolerability. However, comprehensive toxicological studies including acute, subchronic, and chronic toxicity assessments have not been fully documented in the available literature.
References

[1]. Furfuran lignans and a flavone from Artemisia gorgonum Webb and their in vitro activity against Plasmodium falciparum. J Ethnopharmacol. 2011 Nov 18;138(2):637-40.

Additional Infomation
Magnolin has been reported in Geranium platyanthum, Annona mucosa, and other organisms with relevant data. See also: Flower apex (partial) of Centipeda minima.
Epimagnolin A is a furfuran lignan obtained from the flower buds of Magnolia fargesii, traditionally used in Asian medicine for treating headache and nasal congestion. It has been investigated for its potential in treating inflammatory diseases, allergic rhinitis, neurodegenerative disorders, and oxidative stress-related diseases. The compound's mechanism involves modulation of NF-κB, MAPK, p38, and AP-1 signaling pathways, as well as inhibition of MMP enzymes and ABCB1 transport activity. Epimagnolin A is currently in preclinical research stages and has not been approved for clinical use or received FDA approval for any indication. It remains an investigational compound primarily used for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H28O7
Molecular Weight
416.464
Exact Mass
416.183
CAS #
41689-51-4
PubChem CID
169234
Appearance
White to off-white solid powder
LogP
2.9
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
7
Heavy Atom Count
30
Complexity
532
Defined Atom Stereocenter Count
4
SMILES
COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC)OC)OC
InChi Key
MFIHSKBTNZNJIK-RZTYQLBFSA-N
InChi Code
InChI=1S/C23H28O7/c1-24-17-7-6-13(8-18(17)25-2)21-15-11-30-22(16(15)12-29-21)14-9-19(26-3)23(28-5)20(10-14)27-4/h6-10,15-16,21-22H,11-12H2,1-5H3/t15-,16-,21+,22+/m0/s1
Chemical Name
(3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
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: 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)
Solubility Data
Solubility (In Vitro)
DMSO : 100 mg/mL (240.12 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.00 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 (6.00 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 (6.00 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 2.4012 mL 12.0060 mL 24.0119 mL
5 mM 0.4802 mL 2.4012 mL 4.8024 mL
10 mM 0.2401 mL 1.2006 mL 2.4012 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 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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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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