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| 5mg |
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| Targets |
Human Endogenous Metabolite
Matairesinol targets multiple signaling pathways involved in inflammation, oxidative stress, and cancer. It effectively inhibits the phosphorylation of MAPK, JNK, and NF-κB, while downregulating RANKL-induced NFATc1 expression and activity, and suppressing the activation of the PI3K/AKT/FOXO1 pathway. Matairesinol functions as an inflammatory pathway, oxidative stress, and cancer pathway inhibitor. As a lignan, it is believed to function as an antioxidant, effectively scavenging free radicals and mitigating oxidative stress. It also possesses anti-inflammatory properties, which contribute to the reduction of inflammation and promotion of healing processes. Matairesinol is recognized for its potential as a neuroprotective agent, shielding neurons from damage and fostering optimal neurological function. The compound acts as an inhibitor of Mdr-1, suggesting it may modulate multidrug resistance in cancer cells. Its ability to inhibit angiogenesis via suppression of mitochondrial reactive oxygen species further supports its role in cancer prevention and treatment. |
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| ln Vitro |
In vitro, Matairesinol has demonstrated a wide range of biological activities. It inhibits the phosphorylation of MAPK, JNK, and NF-κB, key signaling pathways involved in inflammation and cell survival. Matairesinol downregulates RANKL-induced NFATc1 expression and activity, which is important for osteoclast differentiation and bone resorption. It suppresses the activation of the PI3K/AKT/FOXO1 pathway, which is involved in cell proliferation and survival. The compound has been shown to inhibit angiogenesis via suppression of mitochondrial reactive oxygen species. Matairesinol exhibits cytotoxicity against the T-cell lymphoma cell line CCRF-CEM. It also demonstrates radical and superoxide scavenging activities. In studies of immunomodulation, matairesinol has shown effects in vivo and ex vivo. The compound's anti-allergic effects have also been reported. Matairesinol's ability to inhibit multiple inflammatory and cancer-related pathways makes it a valuable tool for in vitro studies of inflammation, oxidative stress, and cancer.
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| ln Vivo |
In vivo, Matairesinol is an orally active bioactive compound. It has been studied in various animal models of disease. Matairesinol exerts anti-inflammatory and antioxidant effects in sepsis-mediated brain injury by repressing the MAPK and NF-κB pathways through up-regulating AMPK. The compound is applicable in research on sepsis-mediated brain injury, osteoporosis, heart failure, atopic dermatitis, and various cancer models. Serum enterolactone levels (a metabolite of matairesinol) show an inverse association with serum isoprostane levels, suggesting a potential protective effect against oxidative injury in vivo. Matairesinol has been studied for its immunomodulatory effects in vivo. The compound's ability to inhibit angiogenesis and suppress mitochondrial reactive oxygen species suggests potential therapeutic applications in cancer and cardiovascular diseases. However, comprehensive in vivo pharmacokinetic and toxicology studies have not been extensively reported. Further in vivo studies are needed to fully characterize the compound's therapeutic potential and safety profile.
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| Enzyme Assay |
In vitro enzyme and receptor binding assays for Matairesinol typically involve the use of isolated kinases and signaling proteins to study its mechanism of action. For MAPK inhibition assays, the compound is incubated with purified MAPK enzymes or cell lysates, and the phosphorylation of substrate proteins is measured by western blotting or ELISA. For NF-κB assays, the compound is tested for its ability to inhibit NF-κB activation in cell-free systems using electrophoretic mobility shift assays (EMSA) or reporter gene assays. For PI3K/AKT/FOXO1 pathway assays, the compound is incubated with purified kinases or cell lysates, and the phosphorylation of downstream targets is measured. Antioxidant activity is assessed using cell-free assays such as DPPH radical scavenging or superoxide scavenging assays. For Mdr-1 inhibition studies, the compound is tested for its ability to inhibit the efflux activity of P-glycoprotein using membrane vesicle assays or fluorescence-based transport assays. Typical assay conditions include incubation at 25-37°C in appropriate buffer systems (pH 7.4), with reaction products measured by spectrophotometry, fluorometry, or radiometric detection.
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| Cell Assay |
In vitro cell-based assays for Matairesinol are performed using various cell lines to study its effects on inflammation, oxidative stress, and cancer. Cells are cultured in appropriate medium and treated with Matairesinol at various concentrations (typically 1-100 μM) for 24-72 hours. Following treatment, cell viability is assessed using MTT, CCK-8, or trypan blue exclusion assays. Apoptosis is measured by flow cytometry using Annexin V/propidium iodide staining or by measuring caspase activity. For studies of inflammation, immune cells (e.g., macrophages) are stimulated with LPS in the presence or absence of Matairesinol, and the production of pro-inflammatory cytokines (TNF-α, IL-6, IL-1β) is measured by ELISA or multiplex bead-based assays. For studies of oxidative stress, cells are treated with Matairesinol and an oxidative stress inducer (e.g., H₂O₂), and the levels of reactive oxygen species (ROS) and lipid peroxidation products are measured. For studies of cancer, various cancer cell lines (e.g., CCRF-CEM T-cell lymphoma) are treated with Matairesinol, and cell proliferation, migration, and invasion are assessed. Each experiment includes appropriate controls and is performed in triplicate to ensure statistical reliability.
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| Animal Protocol |
In vivo animal experiments with Matairesinol are conducted in mouse or rat models of sepsis-mediated brain injury, osteoporosis, heart failure, atopic dermatitis, and various cancer models. Typically, 6-8 week old rodents are used, and the compound is administered via oral gavage at doses ranging from 1-100 mg/kg. In models of sepsis-mediated brain injury, Matairesinol is administered before or after the induction of sepsis (e.g., by cecal ligation and puncture or LPS injection), and markers of brain injury and inflammation are assessed. In models of osteoporosis, the compound is administered to ovariectomized mice, and bone density and bone turnover markers are measured. In models of heart failure, the compound is administered to mice with cardiac injury, and cardiac function and markers of heart failure are assessed. In models of atopic dermatitis, the compound is administered topically or systemically, and skin inflammation and itch are assessed. In cancer models, tumor-bearing mice are treated with Matairesinol, and tumor growth and metastasis are assessed. Blood samples are collected to measure compound concentrations and biomarkers of efficacy and toxicity. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines, with appropriate sample sizes (typically n=6-10 per group) to ensure statistical power.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Matairesinol are characteristic of a plant lignan. The compound is orally active and is absorbed directly, in addition to being further metabolized by enteric bacteria to enterolactone and enterodiol. Following oral administration, Matairesinol is absorbed in the intestine and distributed to tissues. The compound undergoes extensive metabolism by the gut microbiota, which converts it to the mammalian lignans enterolactone and enterodiol. These metabolites are then absorbed and circulated in the plasma. Serum enterolactone levels are used as a biomarker of lignan intake and have been associated with reduced oxidative stress. The compound's pharmacokinetics are influenced by gut microbiota composition and dietary factors. The elimination half-life is determined by the rate of metabolism and excretion. As with all research chemicals, appropriate pharmacokinetic studies should be conducted to fully characterize the compound's absorption, distribution, metabolism, and excretion.
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| Toxicity/Toxicokinetics |
The toxicological profile of Matairesinol has not been extensively characterized in formal toxicology studies. As a principle plant lignan constituent of dietary fiber, the compound is naturally present in the diet and is generally recognized as safe at dietary levels. Matairesinol is classified as a polyphenol and is found in various foods, including flaxseed, sesame seeds, and whole grains. The compound has been studied for its potential protective effects against oxidative injury, inflammation, and cancer. In cell-based assays, Matairesinol has been shown to inhibit cancer cell growth and induce apoptosis without causing significant cytotoxicity to normal cells at low concentrations. However, comprehensive toxicology studies including acute, subchronic, and chronic toxicity assessments, as well as genotoxicity and reproductive toxicity evaluations, have not been reported. The compound is classified as a research chemical and is not approved for human use. Standard safety precautions should be observed when handling the compound, including the use of appropriate personal protective equipment.
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| References | |
| Additional Infomation |
(-)-Mataterecinol is a lignan belonging to the γ-butyrolactone class, with its 3 and 4 positions substituted by 4-hydroxy-3-methoxybenzyl groups (3R,4R-diastereomers). It possesses phytoestrogen, plant metabolite, angiogenesis inhibitor, and anti-asthmatic effects. It is a polyphenol, lignan, and γ-lactone. Mataterecinol has been reported in tea (Camellia sinensis), radish (Raphanus sativus var. sativus), and other organisms with relevant data. See also: Lignans (subclass); Burdock fruit (part); Pumpkin seed (part).
Matairesinol is a valuable research tool for studying inflammation, oxidative stress, cancer, and lignan metabolism. It is a principle plant lignan constituent of dietary fiber. Matairesinol is an orally active bioactive compound that functions as an inflammatory pathway, oxidative stress, and cancer pathway inhibitor. It undergoes metabolism by enteric bacteria to yield enterolactone and enterodiol. Matairesinol is abundantly present in the bark and needles of various coniferous trees. It is classified as a lignan, which falls under the category of polyphenols. Matairesinol acts as an inhibitor of Mdr-1 and has been studied for its immunomodulatory effects. It is applicable in research on sepsis-mediated brain injury, osteoporosis, heart failure, atopic dermatitis, and various cancer models. The compound is not approved for any clinical indication and is strictly for research use only. Its diverse range of biochemical and physiological effects makes it a valuable tool for studying the role of lignans in health and disease. |
| Molecular Formula |
C20H22O6
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|---|---|
| Molecular Weight |
358.39
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| Exact Mass |
358.141
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| CAS # |
580-72-3
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| PubChem CID |
119205
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| Appearance |
White to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
593.0±45.0 °C at 760 mmHg
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| Melting Point |
119 °C
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| Flash Point |
212.3±22.2 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.605
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| LogP |
1.7
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
26
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| Complexity |
469
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| Defined Atom Stereocenter Count |
2
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| SMILES |
COC1=C(C=CC(=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O)OC)O
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| InChi Key |
MATGKVZWFZHCLI-LSDHHAIUSA-N
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| InChi Code |
InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
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| Chemical Name |
(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
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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: 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)
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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 | 2.7903 mL | 13.9513 mL | 27.9026 mL | |
| 5 mM | 0.5581 mL | 2.7903 mL | 5.5805 mL | |
| 10 mM | 0.2790 mL | 1.3951 mL | 2.7903 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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