| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
Purity: =98.14%
| Targets |
Syringaresinol targets multiple signaling pathways and proteins, including the NF-κB and AKT signaling pathways. It also modulates AMPK, eNOS, calcium channels, and NO synthase. Syringaresinol acts as an inhibitor of the NFAT transcription factor (IC₅₀ = 329.4 μM) and has been shown to activate FOXO3, leading to the degradation of HIF-1α. These diverse targets underlie its anti-inflammatory, anticancer, and vasorelaxant properties.
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| ln Vitro |
In vitro, syringaresinol exhibits potent anticancer activity against various cancer cell lines, with IC₅₀ values of 75.74±8.42 μM (HeLa), 34.78±1.77 μM (MCF-7), and 23.08±2.22 μM (U251). The (+)-enantiomer suppresses the proliferation of P-388 cells with an ED₅₀ of 0.41 μg/mL. Syringaresinol also demonstrates significant anti-inflammatory activity by inhibiting NF-κB and AKT signaling in IL-1β-activated mouse chondrocytes. Additionally, it enhances NO production in endothelial cells via PI3K/Akt- and PLC/Ca²⁺/CaMKKβ-dependent eNOS phosphorylation.
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| ln Vivo |
In vivo, syringaresinol has been shown to attenuate osteoarthritis progression in mouse models of DMM-induced osteoarthritis. It protects against hypoxia/reoxygenation-induced cardiomyocyte injury and death by destabilizing HIF-1α in a FOXO3-dependent manner. Syringaresinol also alleviates early diabetic retinopathy by downregulating HIF-1α/VEGF via activating the Nrf2 antioxidant pathway. Furthermore, it has demonstrated antidepressant-like activity in mice through noncompetitive inhibition of the serotonin transporter.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for syringaresinol typically involve competition binding studies with radiolabeled ligands. For NFAT inhibition, a standard protocol uses a reporter gene assay in cells transfected with NFAT-luciferase constructs. Cells are treated with varying concentrations of syringaresinol (typically 1-1000 µM) for 24-48 hours, and luciferase activity is measured. IC₅₀ values are calculated from dose-response curves. For kinase inhibition studies (e.g., Akt, AMPK), purified enzymes are incubated with the compound and specific substrates, and phosphorylation is detected by ELISA or Western blotting.
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| Cell Assay |
In vitro cell culture experiments with syringaresinol typically involve cancer cell lines (e.g., HeLa, MCF-7, U251) or chondrocytes. Cells are cultured in appropriate media and treated with syringaresinol at concentrations ranging from 1-100 µM for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. For anti-inflammatory studies, chondrocytes are stimulated with IL-1β in the presence of syringaresinol, and cytokine production (e.g., TNF-α, IL-6) is measured by ELISA. Apoptosis is measured using Annexin V/PI staining or caspase activity assays.
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| Animal Protocol |
In vivo animal studies with syringaresinol typically involve mouse models of osteoarthritis (DMM-induced) or myocardial ischemia/reperfusion injury. A standard protocol for osteoarthritis involves administering syringaresinol orally or intraperitoneally at doses of 10-50 mg/kg daily for 4-8 weeks. For ischemia studies, mice are subjected to hypoxia/reoxygenation, and syringaresinol is administered before or after the insult. At study termination, tissues are collected for histopathological examination, and biomarkers of inflammation, apoptosis, and oxidative stress are measured.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of syringaresinol are not fully characterized. As a lignan with a molecular weight of 418.44 and moderate lipophilicity (LogP 0.71), it is expected to have moderate oral bioavailability. The compound is soluble in DMSO, ethanol, and other organic solvents. Syringaresinol is likely metabolized in the liver via phase I and phase II reactions, and it may undergo enterohepatic circulation. However, formal pharmacokinetic studies including half-life, volume of distribution, and clearance have not been reported.
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| Toxicity/Toxicokinetics |
Syringaresinol has low toxicity for laboratory use. The compound is not classified as hazardous under normal handling conditions. In vitro studies have shown that syringaresinol exhibits selective cytotoxicity against cancer cells with relatively low toxicity to normal cells. The compound is not known to be mutagenic, carcinogenic, or reproductively toxic. Standard laboratory precautions (gloves, safety glasses) are recommended. Syringaresinol is not intended for human or veterinary use and has not undergone rigorous toxicological evaluation for therapeutic applications.
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| References |
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| Additional Infomation |
Syringaresinol is a lignan with the structure 7,9':7',9-diepoxylignanane, where hydroxyl groups are substituted at positions 4 and 4', and methoxy groups are substituted at positions 3, 3', 5, and 5'. It is a plant metabolite. Syringaresinol is a lignan, polyphenol, aromatic ether, furan, and polyether. It has been reported to be found in Sarcopyramis nepalensis, Raphanus sativus var. sativus, and other organisms with relevant data.
Syringaresinol is a naturally occurring lignan found in various plants, including the branch of Liriodendron chinensis. It has been studied for its potential in treating cancer, ischemia-related diseases, and osteoarthritis. (-)-Syringaresinol has been identified as a potential chemotherapeutic agent. Syringaresinol has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action involves modulation of multiple signaling pathways, including NF-κB, AKT, AMPK, and FOXO3/HIF-1α. |
| Molecular Formula |
C22H26O8
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| Molecular Weight |
418.44
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| Exact Mass |
418.163
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| CAS # |
487-35-4
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| Related CAS # |
(-)-Syringaresinol;6216-81-5;epi-Syringaresinol;51152-20-6
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| PubChem CID |
100067
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| Appearance |
White to off-white solid powder
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| Melting Point |
210 - 211 °C
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| LogP |
3.207
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
30
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| Complexity |
485
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
KOWMJRJXZMEZLD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3
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| Chemical Name |
4-[6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
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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 | 2.3898 mL | 11.9491 mL | 23.8983 mL | |
| 5 mM | 0.4780 mL | 2.3898 mL | 4.7797 mL | |
| 10 mM | 0.2390 mL | 1.1949 mL | 2.3898 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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