EudesminCAS# 526-06-7 |
- Pinoresinol dimethyl ether
Catalog No.:BCN6767
CAS No.:29106-36-3
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| Cas No. | 526-06-7 | SDF | Download SDF |
| PubChem ID | 325601 | Appearance | Powder |
| Formula | C22H26O6 | M.Wt | 386.4 |
| Type of Compound | Lignans | Storage | Desiccate at -20°C |
| Synonyms | (-)-Eudesmin;Eudesmine | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3R,3aS,6R,6aS)-3,6-bis(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan | ||
| SMILES | COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC)OC)OC | ||
| Standard InChIKey | PEUUVVGQIVMSAW-DJDZNOHASA-N | ||
| Standard InChI | InChI=1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21+,22+/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Eudesmin shows antiinflammatory, neuritogenic, anticonvulsant and sedative effects, the mechanism of eudesmin may be related to up-regulation of GABAA and GAD65 expressions, and anti-apoptosis of neuron the in brain.50 microM (+)-eudesmin can induce neurite outgrowth and enhance nerve growth factor (NGF)-mediated neurite outgrowth from PC12 cells by stimulating up-stream MAPK, PKC and PKA pathways. |
| Targets | TNF-α | MAPK | PKC | PKA | GABA Receptor | NGF |
| In vitro | Eudesmin inhibits tumor necrosis factor-alpha production and T cell proliferation.[Pubmed: 10489872]Arch Pharm Res. 1999 Aug;22(4):348-53.Possible antiinflammatory effects of Eudesmin were examined by assessing the effects on tumor necrosis factor (TNF)-alpha production and lymphocyte proliferation as well as cytotoxicity against murine and human macrophages. Effects of (+)-eudesmin from the stem bark of magnolia kobus DC. var. borealis Sarg. on neurite outgrowth in PC12 cells.[Pubmed: 17225460]Arch Pharm Res. 2006 Dec;29(12):1114-8.
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| In vivo | Anticonvulsant and Sedative Effects of Eudesmin isolated from Acorus tatarinowii on mice and rats.[Pubmed: 25851178 ]Phytother Res. 2015 Jul;29(7):996-1003This paper was designed to investigate anticonvulsant and sedative effects of Eudesmin isolated from Acorus tatarinowii. |
| Kinase Assay | The lignan eudesmin extracted from Piper truncatum induced vascular relaxation via activation of endothelial histamine H1 receptors.[Pubmed: 19374838 ]Eur J Pharmacol. 2009 Mar 15;606(1-3):150-4.In Brazilian folk medicine, extracts from Piper species are used to reduce blood pressure. Previously, we demonstrated the vasodilatory activity of crude extracts from leaves of Piper truncatum explaining their possible use in the treatment of hypertension in traditional medicine. |
Eudesmin Dilution Calculator
Eudesmin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.588 mL | 12.94 mL | 25.8799 mL | 51.7598 mL | 64.6998 mL |
| 5 mM | 0.5176 mL | 2.588 mL | 5.176 mL | 10.352 mL | 12.94 mL |
| 10 mM | 0.2588 mL | 1.294 mL | 2.588 mL | 5.176 mL | 6.47 mL |
| 50 mM | 0.0518 mL | 0.2588 mL | 0.5176 mL | 1.0352 mL | 1.294 mL |
| 100 mM | 0.0259 mL | 0.1294 mL | 0.2588 mL | 0.5176 mL | 0.647 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Eudesmin inhibits tumor necrosis factor-alpha production and T cell proliferation.[Pubmed:10489872]
Arch Pharm Res. 1999 Aug;22(4):348-53.
Possible antiinflammatory effects of Eudesmin were examined by assessing the effects on tumor necrosis factor (TNF)-alpha production and lymphocyte proliferation as well as cytotoxicity against murine and human macrophages. The compound significantly inhibited TNF-alpha production by lipopolysaccharide (LPS)-stimulated murine macrophage RAW264.7 without displaying cytotoxicity suggesting that Eudesmin may inhibit TNF-alpha production without any interference of normal cell function. It also significantly attenuated T cell proliferation stimulated by concanavalin A (Con A) in a dose-dependent manner.
Effects of (+)-eudesmin from the stem bark of magnolia kobus DC. var. borealis Sarg. on neurite outgrowth in PC12 cells.[Pubmed:17225460]
Arch Pharm Res. 2006 Dec;29(12):1114-8.
(+)-Eudesmin [4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane] was isolated from the stem bark of Magnolia kobus DC. var. borealis Sarg. and found to have neuritogenic activity. 50 microM (+)-Eudesmin induced neurite outgrowth and enhanced nerve growth factor (NGF)-mediated neurite outgrowth from PC12 cells. At this concentration, (+)-Eudesmin also enhanced NGF-induced neurite-bearing activity and this activity was partially blocked by various protein kinase inhibitors. These included PD98059, a mitogen-activated protein kinase (MAPK) kinase inhibitor. GF109203X, a protein kinase C (PKC) inhibitor and H89, a protein kinase A (PKA) inhibitor. These results suggest that (+)-Eudesmin can induce neurite outgrowth from PC12 cells by stimulating up-stream MAPK, PKC and PKA pathways.
Anticonvulsant and Sedative Effects of Eudesmin isolated from Acorus tatarinowii on mice and rats.[Pubmed:25851178]
Phytother Res. 2015 Jul;29(7):996-1003.
This paper was designed to investigate anticonvulsant and sedative effects of Eudesmin isolated from Acorus tatarinowii. The Eudesmin (5, 10, and 20 mg/kg) was administered intraperitoneally (i.p.). The maximal electroshock test (MES) and pentylenetertrazole (PTZ)-induced seizures in male mice were used to evaluate anticonvulsant activities of Eudesmin, and sedative effects of Eudesmin were evaluated by pentobarbital sodium-induced sleeping time (PST) and locomotor activity in mice. Finally, the mechanisms of Eudesmin were investigated by determining contents of glutamic acid (Glu) and gamma-aminobutyric acid (GABA) in epileptic mice, and expressions of glutamate decarboxylase 65 (GAD65), GABAA , Bcl-2, and caspase-3 in the brain of chronic epileptic rats. Results of MES and PTZ tests revealed that Eudesmin possesses significant anticonvulsant effects, and the PST and locomotor activity tests demonstrated that Eudesmin has significant sedative effects. Furthermore, our study revealed that after treatment with Eudesmin, GABA contents increased, whereas Glu contents decreased, and ratio of Glu/GABA decreased. Our results also indicated that expressions of GAD65, GABAA, and Bcl-2 were up-regulated by treating with Eudesmin, whereas the caspase-3 obviously was down-regulated. In conclusion, Eudesmin has significant anticonvulsant and sedative effects, and the mechanism of Eudesmin may be related to up-regulation of GABAA and GAD65 expressions, and anti-apoptosis of neuron the in brain.
The lignan eudesmin extracted from Piper truncatum induced vascular relaxation via activation of endothelial histamine H1 receptors.[Pubmed:19374838]
Eur J Pharmacol. 2009 Mar 15;606(1-3):150-4.
In Brazilian folk medicine, extracts from Piper species are used to reduce blood pressure. Previously, we demonstrated the vasodilatory activity of crude extracts from leaves of Piper truncatum explaining their possible use in the treatment of hypertension in traditional medicine. In the present study, we investigated the effects of Eudesmin, a lignan isolated from hexane extract of leaves from Piper truncatum, on the contractility of rat aortas and the possible mechanisms involved in its vascular action. Eudesmin induced an intense concentration-dependent relaxation of aortic rings precontracted with phenylephrine. The concentration of Eudesmin necessary to reduce phenylephrine-induced aortic contraction by 50% (IC(50)) was 10.69+/-0.67 microg/ml. Eudesmin-induced vasodilation required an intact endothelium since vascular relaxation was inhibited by mechanic removal of endothelium, and by pretreatment with nitric oxide synthase inhibitor and soluble guanylate cyclase inhibitor. Relaxation induced by Eudesmin was also impaired in the presence of indomethacin and diphenhydramine, a cyclooxygenase inhibitor and an antagonist of type 1 histamine receptor (H(1)), respectively. IC(50) was increased to 18.1+/-1.8 and 18.1+/-2.6 microg/ml (P<0.05; n=6) after exposure to indomethacin and diphenhydramine, respectively. Atropine (muscarinic receptor antagonist), propranolol (beta-adrenoceptor antagonist) and glibenclamide (ATP-sensitive K(+) channel blocker) did not alter the effect of Eudesmin. These results indicate that Eudesmin-induced vascular relaxation in rat aorta is mediated by release of nitric oxide and prostanoid through the involvement of histamine receptor present in the endothelial cells.
