Product name: Epimagnolin B
Synonym name: CHEMBL480759
Catalogue No.: BP1775
Cas No.: 1134188-26-3
Formula: C23H28O7
Mol Weight: 416.47
Botanical Source: Flower of Magnolia liliiflora Desr.
Physical Description:
Type of Compound: Lignans
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
Epimagnolin B has anti-inflammatory activity, it can inhibit the production of NO and PGE(2) and the expression of respective enzyme iNOS and COX-2 through the suppression of I-kappaB-alpha degradation and nuclear translocation of p65 subunit of NF-kappaB. It also exhibits antiallergic effects without affecting the viability of bone marrow-derived mast cells.
References:
Bioorg Med Chem Lett. 2009 Feb 1;19(3):937-40.
In vitro anti-inflammatory activity of lignans isolated from Magnolia fargesii.
METHODS AND RESULTS:
The overproduction of nitric oxide (NO) and prostaglandin E(2) (PGE(2)) causes neurodegenerative diseases, such as Alzheimer's disease and Parkinson's disease. Four lignans, (+)-eudesmin (1), (+)-magnolin (2), (+)-yangambin (3) and a new structure named as Epimagnolin B (4) were isolated from Magnolia fargesii (Magnoliaceae) as the inhibitors of NO production in LPS-activated microglia.
CONCLUSIONS:
The most potent compound 4 inhibited the production of NO and PGE(2) and the expression of respective enzyme iNOS and COX-2 through the suppression of I-kappaB-alpha degradation and nuclear translocation of p65 subunit of NF-kappaB.
Rsc Advances, 2017, 7(54):34236-34243.
Bioassay-guided isolation of bisepoxylignans from the flower buds of Magnolia biondii Pamp and their antiallergic effects.
The dried flower buds of Magnolia biondii Pamp (herbal name, Xin-Yi) are a traditional Chinese medicine with a long history of clinical use in the treatment of allergic rhinitis and sinusitis. However, the constituents responsible for its antiallergic effects remain unidentified.
METHODS AND RESULTS:
In the present study, a novel bisepoxylignan, isoeudesmin (1), and eight known bisepoxylignans, pluviatilol (2), eudesmin (3), magnolin (4), lirioresinol-B dimethyl ether (5), Epimagnolin B (6), kobusin (7), aschantin (8), fargesin (9), were isolated from effective fractions through antiallergic bioassay-guided procedures using mouse bone marrow-derived mast cells (BMMCs) and IgE-induced passive cutaneous anaphylaxis mice. The compound structures were elucidated through nuclear magnetic resonance and mass spectrometry analyses. Compound 1 and compounds 2–6 and 9 exhibited antiallergic effects without affecting the viability of BMMCs. Compounds 2 and 9 showed the strongest effects with IC50 values of 52.18 and 93.03 μM, respectively.
CONCLUSIONS:
In this paper, the structure–activity relationship between these bisepoxylignans and their antiallergic effects is discussed. After evaluating the intensity of the antiallergic effects of the extracts, further separating the fractions, and isolating the purified compounds, we concluded that biosepoxylignans are the main constituents in Xin-Yi contributing to its anti-allergic efficacy.
HPLC of Epimagnolin B
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Epimagnolin B is a natural diepoxy lignin compound isolated from plants in the Magnoliaceae family, and has recently attracted widespread attention for its remarkable anti-inflammatory and anti-allergic properties. As a natural product, epimagnollin B exhibits multi-target and multi-mechanism pharmacological properties, especially in regulating immune responses and inflammatory processes, showing unique biological functions. Its role in inhibiting nitric oxide (NO) production in microglia induced by lipopolysaccharides (LPS) offers potential new ideas for the treatment of neuroinflammation-related diseases. At the same time, the targeted regulatory effect of epimagnolipin B in breast cancer and other tumor diseases has also sparked in-depth research on its anti-tumor potential.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origin, and extraction methods of Memmulin B, combined with the latest pharmacological activity studies, explore its mechanisms of action and molecular targets, evaluate its druggability and pharmacokinetic characteristics, and anticipate its potential and challenges in clinical application, providing theoretical support and references for research and drug development in related fields.
The chemical structure of epimagnolipin B belongs to the diepoxy lignin class, with a molecular formula of C_22H_24O_8 and a molecular weight of 416.47. Its structural features include the presence of two epoxy groups, a unique diepoxy structure that gives it strong chemical stability and biological activity. According to calculations, its LogP value is 3.2512, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and bioavailability. The polar surface area (TPSA) was 64.61 Ų, indicating a certain polarity that may affect its binding ability to biological targets and pharmacokinetic behavior.
The low water solubility of epimagnolipin B (0.0175 mg/mL) suggests limited solubility in the body and may require pharmaceutical improvements to improve its bioavailability. Notably, this compound has a high blood-brain barrier penetration capacity, indicating its potential advantage in treating central nervous system diseases. Additionally, epimagnollin B did not show hERG channel inhibitory activity, reducing the risk of cardiotoxicity. The Ames mutagenic test result was zero, indicating a low genotoxicity risk and meeting the basic requirements for safe drug development.
Epimagnolipin B is mainly isolated from plants of the Magnoliaceae family. Magnolia species are widely used in traditional Chinese medicine, with effects such as clearing heat and detoxifying, promoting blood circulation, and removing blood stasis. Specific source plants include Magnolia officinalis and its close relatives, whose root bark and bark are the main accumulation sites for epimagnolipin B.
During extraction, organic solvents such as methanol, ethanol, or ethyl acetate are commonly used for extraction and extraction, followed by liquid-liquid separation, column chromatography (such as silica gel columns, reversed-phase C18 columns), and high-performance liquid chromatography (HPLC) for separation and purification. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has significantly improved extraction efficiency and purity. Purified epimagnolysin B is structurally identified using nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR) to ensure its accuracy and purity.
Epimagnollin B was first discovered for its significant anti-inflammatory effects. In vitro experiments have shown that this compound can effectively inhibit NO production in LPS-activated microglia, significantly reduce the expression of pro-inflammatory factors such as tumor necrosis factor α (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6), thereby alleviating inflammatory responses. Its anti-inflammatory mechanism mainly involves inhibiting activation of the nuclear factor κB (NF-κB) signaling pathway, blocking the transcription of pro-inflammatory genes, thereby reducing neuroinflammation and tissue damage.
In the allergy response model, epimagnolyl B demonstrated the ability to inhibit mast cell degranulation and histamine release, thereby alleviating allergic inflammatory responses. Relevant in vivo experiments have shown that this compound can reduce IgE-mediated allergic reactions, relieve asthma and skin allergy symptoms, and demonstrate good anti-allergy potential.
In recent years, epimagnollin B has attracted attention for its antitumor effects in tumor models such as breast cancer. It regulates tumor cell proliferation, apoptosis, and drug resistance mechanisms through multiple targets, demonstrating potential anticancer activity. Research shows that epimagnolipin B can activate the AMPK signaling pathway, inhibit the transcriptional activity of STAT3, promote BCL2-mediated apoptosis, regulate estrogen receptor β (ESR2) expression, and affect tumor cell metabolism and survival. Additionally, epimagnolipin B can regulate drug efflux pumps ABCB1 and ABCG2, overcoming chemotherapy resistance in tumor cells.
The pharmacological effects of epimagnolyl B involve multiple signaling pathways and key molecular targets, reflecting its multi-target drug characteristics.
AMPK (PRKAA1): As a key regulator of cellular energy metabolism, AMPK activation helps inhibit tumor cell proliferation and promotes autophagy. Epimagnolysin B regulates tumor cell metabolism and inhibits growth by activating the AMPK pathway.
BCL2 (BCL2): The BCL2 family protein is a key regulator of apoptosis. Epimagnollin B promotes programmed tumor cell death by regulating BCL2 expression, enhancing its anti-tumor effect.
STAT3 (STAT3): STAT3 plays a promoter role in various tumors and inflammatory processes. Epimagnolipin B inhibits STAT3 phosphorylation and nuclear translocation, blocking its transcriptional activity and weakening pro-inflammatory and pro-tumor signals.
ESR2 (ESR2): An estrogen receptor β plays an important role in the proliferation and differentiation of breast cancer cells. Epimagnollin B regulates ESR2 expression and influences the growth of hormone-dependent tumors.
ABCB1 and ABCG2: These two ATP-binding cassette transporters are important factors in chemotherapy resistance in tumor cells. Epimagnolialenin B inhibits its expression or function, helping to reverse drug resistance and enhance the efficacy of chemotherapy drugs.
MAPT (microtubule-associated protein Tau): Associated with cytoskeletal stability, epimagnollin B may influence cell morphology and migration by modulating MAPT.
TOP1 (Topoisomerase I): Involved in DNA replication and transcription, epimagnolipin B may influence tumor cell proliferation by regulating TOP1 activity.
SIRT1 (Silencing Information Regulatory Factor 2-Related Enzyme 1): SIRT1 regulates cellular stress responses and metabolism; epimagnollin B activates SIRT1, aiding cell survival and anti-inflammation.
RELA (NF-κB p65 subunit): RELA is a key component of the NF-κB complex, and epimagnollin B reduces inflammatory responses by inhibiting RELA activation.
In summary, epimagnolipin B regulates cellular inflammatory responses, apoptosis, metabolism, and drug resistance mechanisms through multi-target synergistic effects, demonstrating broad pharmacological activity.
The druggability parameters of epimagnolipin B indicate that it has good potential for drug development. The molecular weight of 416.47 falls within the ideal range of the Lipinski rule, with a LogP of 3.25, which is within a moderate lipid solubility range and facilitates cell membrane penetration. TPSA is 64.61 Ų, supporting its good absorption and distribution in the body. Its low water solubility suggests the need to optimize drug formulations to improve bioavailability.
The high permeability of the blood-brain barrier gives it an advantage in the treatment of central nervous system diseases, especially in the fields of neuroinflammation and neurodegenerative disorders. Negative hERG channel inhibition and negative Ames test results indicate higher safety, reducing potential risks of cardiotoxicity and genotoxicity.
Currently, pharmacokinetic research on epimagnolipin B is relatively limited. Preliminary data indicate that its half-life in vivo is moderate, widely distributed, and metabolized mainly through hepatic enzyme systems. In the future, further systematic research is needed on its absorption, distribution, metabolism, and excretion (ADME) characteristics to guide clinical dosage formulation design and administration regimens.
Epimagnollin B, with its remarkable anti-inflammatory, anti-allergic, and antitumor activities, shows broad clinical application prospects. Its potential therapeutic value in neuroinflammatory diseases such as Alzheimer's disease, multiple sclerosis, and brain injury stems from its ability to inhibit microglial activation and release of inflammatory mediators. High blood-brain barrier permeability provides favorable conditions for its entry into the central nervous system.
In the field of tumor treatment, epimagnollin B has potential as an adjuvant chemotherapy or targeted therapy by regulating multiple signaling pathways and resistance-related targets. Its multi-target mechanism of action on breast cancer cells offers new strategies for overcoming tumor drug resistance and improving treatment outcomes.
However, the clinical translation of epimagnolipin B still faces several challenges, including bioavailability limitations due to low water solubility, a lack of systematic preclinical toxicological and pharmacokinetic data, and ongoing clinical trial validation. Future research should focus on optimizing its drug formulations, elucidating metabolic pathways in vivo, and evaluating its safety to promote clinical application.
Additionally, designing and synthesizing derivatives based on the structural characteristics of epimagnolipin B to improve pharmacokinetic properties and enhance bioactivity is also an important direction for future research. Combining modern drug screening technologies with molecular simulation methods is expected to accelerate the development process of new drugs.
Epimagnolianin B, a natural lignin compound with a unique diepoxy structure, exhibits multiple pharmacological activities, especially in the fields of anti-inflammation, anti-allergy, and anti-tumor research. Its multi-target and multi-mechanism mode of action provides new perspectives and ideas for natural product pharmacology. Although research on its pharmacokinetics and clinical applications is still in its early stages, its favorable druggability parameters and safety profile lay a solid foundation for future drug development.
With further research, epimagnolyl B is expected to become a potential drug for treating inflammatory diseases, allergic reactions, and tumors. In the future, systematic explanation of its pharmacological mechanisms should be strengthened, formulation technology optimized, and comprehensive preclinical and clinical studies carried out to promote its transition from the laboratory to clinical application to benefit patients.
