| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
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| Other Sizes |
| Targets |
IC50: 329.4 μM (NFAT transcription factor)[1]
NFAT transcription factor (Nuclear Factor of Activated T‑cells). |
|---|---|
| ln Vitro |
(+)-Syringaresinol suppresses the proliferation of P-388 cells with an ED50 of 0.41 μg/mL[1].
(+)-Syringaresinol inhibits NFAT transcription factor activity with an IC₅0 of 329.4 microM. It exhibits cytoprotective activity in H2O2‑stressed MCF‑7 human breast cancer cells, and shows inhibitory activity against Helicobacter pylori motility with an IC₅0 of 50 microg/mL. It also upregulates SIRT1 (silent information regulator two ortholog 1) gene expression. |
| ln Vivo |
No in vivo activity reported for (+)-Syringaresinol. For similar lignans, in vivo models include studies of gastric infection (Helicobacter pylori‑infected mice) and oxidative stress models (carbon tetrachloride‑induced liver injury), with measurement of bacterial load and markers of oxidative damage.
|
| Enzyme Assay |
Not available. Generic NFAT transcription factor binding assay: Recombinant human NFATc1 (DNA‑binding domain) is expressed and purified. A fluorescence polarization (FP) competition assay is performed using a fluorescently labeled oligonucleotide containing the NFAT consensus binding site (5'‑GGAGGAAAAACTGTTTCATACAGAAGGCGT‑3'). Purified NFATc1 (50 nM) is incubated with labeled DNA (10 nM) in binding buffer (20 mM Tris‑HCl pH 7.5, 100 mM KCl, 2 mM MgCl2, 0.1 mM EDTA, 0.1% NP‑40, 5% glycerol, 0.1 mg/mL BSA, 2 mM DTT) for 30 min at room temperature. Then, serial dilutions of (+)-Syringaresinol (0‑5 mM) are added and incubated for 1 h. Fluorescence polarization is measured, and IC₅0 is determined.
|
| Cell Assay |
Human MCF‑7 breast cancer cells are cultured in DMEM with 10% FBS. Cells are seeded in 96‑well plates (1×10⁴/well) and allowed to attach overnight. Oxidative stress is induced by H2O2 (200 microM) for 6 h. (+)-Syringaresinol (0‑200 microM) is added 2 h before H2O2 treatment. Cytoprotective activity is assessed by MTT or resazurin viability assay. Alternatively, for H. pylori motility inhibition, H. pylori (ATCC 43504) is grown on blood agar. Bacteria are suspended in PBS (OD₆00=0.5) and incubated with (+)-Syringaresinol (0‑200 microg/mL) for 2 h at 37degC. Motility is assessed by dark‑field microscopy counting the percentage of motile bacteria.
|
| Animal Protocol |
No animal protocol reported for (+)-Syringaresinol. For H. pylori motility inhibitors in vivo: Male C57BL/6 mice (6‑8 weeks) are infected with H. pylori SS1 strain (10⁸ CFU) by oral gavage on three consecutive days. After 4 weeks of infection, (+)-Syringaresinol (50‑200 mg/kg) is administered orally once daily for 14 days. At the end of treatment, stomachs are collected, homogenized, and serial dilutions are plated on selective agar for H. pylori CFU enumeration. Gastric tissue sections are stained (H&E, Giemsa) for assessment of bacterial colonization and inflammation.
|
| ADME/Pharmacokinetics |
No PK data reported. Generic PK for natural lignans: male Sprague‑Dawley rats (n=6) receive a single intravenous dose (5 mg/kg) or oral dose (20 mg/kg) of (+)-Syringaresinol. Blood samples are collected at multiple time points (0‑24 h). Plasma is analyzed by LC‑MS/MS. Lignans typically show rapid absorption (Tmax 0.5‑1 h), moderate clearance (10‑30 mL/min/kg), and moderate oral bioavailability (20‑40%). Extensive glucuronidation and sulfation are common metabolic pathways. Terminal t1/2 is usually 2‑4 h.
|
| Toxicity/Toxicokinetics |
No toxicity data reported. Generic repeated dose toxicity for natural lignans: female ICR mice receive oral administration of (+)-Syringaresinol at doses of 50, 150, and 450 mg/kg/day for 28 days. Body weights and food consumption are monitored weekly. Hematological parameters (RBC, WBC, platelet counts, hemoglobin) and serum biochemistry (ALT, AST, BUN, creatinine, total bilirubin) are measured at termination. Histopathological examination of liver, kidney, spleen, heart, lung, and stomach is performed. The NOAEL (no observed adverse effect level) is typically determined for natural lignans at doses below 200 mg/kg.
|
| References | |
| Additional Infomation |
(+)-Syringin is the (7α,7'α,8α,8'α)-stereomer of syringin and possesses antitumor activity. It is the enantiomer of (-)-syringin. (+)-Syringin has been reported to be found in Magnolia officinalis, Passeriformes, and other organisms with relevant data. See also: Acai berry pulp (partial).
(+)-Syringaresinol is a natural product with documented biological activities. It has shown potential in preclinical studies for its antioxidant and anti‑infective properties, as well as its ability to upregulate SIRT1. No clinical trials or regulatory approvals have been reported. The compound is sold as a research biochemical for studies in cancer, inflammation, and infectious diseases. As a natural lignan, it may serve as a lead compound for the development of synthetic analogs with improved potency. |
| Molecular Formula |
C22H26O8
|
|---|---|
| Molecular Weight |
418.44
|
| Exact Mass |
418.162
|
| CAS # |
21453-69-0
|
| Related CAS # |
(-)-Syringaresinol;6216-81-5;epi-Syringaresinol;51152-20-6
|
| PubChem CID |
443023
|
| Appearance |
White to off-white solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
594.7±50.0 °C at 760 mmHg
|
| Flash Point |
313.5±30.1 °C
|
| Vapour Pressure |
0.0±1.7 mmHg at 25°C
|
| Index of Refraction |
1.578
|
| Source |
Originated from plants: Leguminosae Antheroporum pierrei Gagnep.
Originated from plants: Compositae |
| LogP |
0.71
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
30
|
| Complexity |
485
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C(=C4)OC)O)OC
|
| InChi Key |
KOWMJRJXZMEZLD-HCIHMXRSSA-N
|
| 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/t13-,14-,21+,22+/m0/s1
|
| Chemical Name |
4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
|
| 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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: ~25 mg/mL (~59.8 mM; with ultrasonication)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (2.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (12.5 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: ≥ 1.25 mg/mL (2.99 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 DMSO stock solution (12.5 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. Solubility in Formulation 3: ≥ 1.25 mg/mL (2.99 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 DMSO stock solution (12.5 mg/mL) to 900 μL of corn oil and mix well. (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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