8-O-Acetylshanzhiside methyl esterCAS# 57420-46-9 |
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Chemical structure
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| Cas No. | 57420-46-9 | SDF | Download SDF |
| PubChem ID | 162823 | Appearance | White powder |
| Formula | C19H28O12 | M.Wt | 448.4 |
| Type of Compound | Iridoids | Storage | Desiccate at -20°C |
| Synonyms | Barlerin; Umbroside | ||
| Solubility | Soluble in methan | ||
| Chemical Name | methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate | ||
| SMILES | CC(=O)OC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)C | ||
| Standard InChIKey | ARFRZOLTIRQFCI-NGQYDJQZSA-N | ||
| 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 | 8-O-Acetylshanzhiside methyl ester(ND01) has potential against cerebral ischemic injury and experimental myocardial ischemia injury, it can increase angiogenesis and improve functional recovery after stroke. ND01 protects diabetic brain against I/R injury by alleviating diabetic cerebral I/R injury and attenuating blood–brain barrier (BBB) breakdown, and its protective effects may involve HMGB-1 and NF-κB signalling pathway. |
| Targets | TNF-α | NF-kB | VEGFR | Akt | Calcium Channel | Caspase |
| In vitro | Cardioprotection with 8-O-acetylshanzhiside methylester on experimental myocardial ischemia injury.[Pubmed: 22677812 ]Eur J Pharm Sci. 2012 Aug 30;47(1):124-30.8-O-Acetylshanzhiside methyl ester (ND01) was isolated from the leaves of Lamiophlomis rotata (Benth.) Kudo. In this study, we investigated the anti-myocardial ischemia and reperfusion (I/R) injury effects of ND01 in vivo and elucidated the potential mechanism in vitro.
|
| In vivo | Effect of 8-O-acetyl shanzhiside methylester increases angiogenesis and improves functional recovery after stroke.[Pubmed: 20735376]Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):21-7.We investigated whether 8-O-Acetylshanzhiside methyl ester (ND01) regulates angiogenesis and thereby improves functional outcome after stroke.
|
| Kinase Assay | 8-O-acetyl shanzhiside methylester attenuates apoptosis and ameliorates mitochondrial energy metabolism in rat cortical neurons exposed to oxygen-glucose deprivation.[Pubmed: 19961847]Eur J Pharmacol. 2010 Mar 10;629(1-3):20-4.8-O-Acetylshanzhiside methyl ester (ND01), an iridoid glucoside compound, was isolated from the leaves of Lamiophlomis rotata (Benth.) Kudo.
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| Animal Research | 8-O-acetyl shanzhiside methylester attenuates cerebral ischaemia/reperfusion injury through an anti-inflammatory mechanism in diabetic rats.[Pubmed: 24823762 ]Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):481-7.Inflammatory activation plays a vital role in the pathophysiological mechanisms of stroke and diabetes mellitus (DM), exerts the deleterious effects on the progression of the brain and leads to vascular damage in diabetic stroke.
The objectives of this study were to investigate the effects of 8-O-Acetylshanzhiside methyl ester (ND01) on tumour necrosis factor-α (TNF-α)-stimulated SH-SY5Y cell line in vitro and the experimental ischaemic diabetic stroke model in vivo.
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8-O-Acetylshanzhiside methyl ester Dilution Calculator
8-O-Acetylshanzhiside methyl ester Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2302 mL | 11.1508 mL | 22.3015 mL | 44.603 mL | 55.7538 mL |
| 5 mM | 0.446 mL | 2.2302 mL | 4.4603 mL | 8.9206 mL | 11.1508 mL |
| 10 mM | 0.223 mL | 1.1151 mL | 2.2302 mL | 4.4603 mL | 5.5754 mL |
| 50 mM | 0.0446 mL | 0.223 mL | 0.446 mL | 0.8921 mL | 1.1151 mL |
| 100 mM | 0.0223 mL | 0.1115 mL | 0.223 mL | 0.446 mL | 0.5575 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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8-O-Acetyl shanzhiside methyl ester (ND01) is an iridoid glucoside isolated from the leaves of Lamiophlomis rotata Kudo, a Chinese folk medicinal plant in Xi-zang. 8-O-Acetyl shanzhiside methyl ester could inhibt NF-κB.
In Vitro:Treatment of SH-SY5Y cells with ND01 blocks TNF-α-induced nuclear transcription factor κB (NF-κB) activation and decreases high-mobility group box-1 (HMGB-1) expression. [1]. Treatment of H9c2 cells with ND01 9 μM blocks TNF-α-induced NF-κB phosphorylation by blocking High-mobility group box1 (HMGB1) expression[2].
In Vivo:8-O-Acetyl shanzhiside methyl ester 40 mg/kg demonstrates significant neuroprotective effect even after delayed administration at 4 hr after I/R. 8-O-Acetyl shanzhiside methyl ester 40 mg/kg attenuates the histopathological damage, decreases brain swelling, inhibits NF-κB activation and reduces HMGB-1 expression in ischaemic brain tissue[1]. 8-O-Acetyl shanzhiside methyl ester significantly promotes angiogenesis in the ischaemic brain and improves functional outcome after stroke. 8-O-Acetyl shanzhiside methyl ester also significantly increases vascularization compared with vehicle treatment. It increases the expression of VEGF, Ang1, phosphorylation of Tie2 and Akt VEGF[3]. 8-O-Acetyl shanzhiside methyl ester significantly shortens capillary blood clotting time and reduces blood loss volume, but does not influence mice activated partial thromboplastin time, prothrombin time or thrombin time. It significantly prolongs euglobulin clot lysis time in hyperfibrinolysis mice[4].
References:
[1]. Zhang L, et al. 8-O-acetyl shanzhiside methylester attenuates cerebral ischaemia/reperfusion injury through an anti-inflammatory mechanism in diabetic rats. Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):481-7.
[2]. Kang ZC, et al. Cardioprotection with 8-O-acetyl shanzhiside methylester on experimental myocardial ischemia injury. Eur J Pharm Sci. 2012 Aug 30;47(1):124-30.
[3]. Jiang WL, et al. Effect of 8-O-acetyl shanzhiside methylester increases angiogenesis and improves functional recovery after stroke. Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):21-7.
[4]. Fan PC, et al. A new anti-fibrinolytic hemostatic compound 8-O-acetyl shanzhiside methylester extracted from Lamiophlomis rotata. J Ethnopharmacol. 2016 Jul 1;187:232-8.
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8-O-acetyl shanzhiside methylester attenuates apoptosis and ameliorates mitochondrial energy metabolism in rat cortical neurons exposed to oxygen-glucose deprivation.[Pubmed:19961847]
Eur J Pharmacol. 2010 Mar 10;629(1-3):20-4.
8-O-acetyl shanzhiside methylester (ND01), an iridoid glucoside compound, was isolated from the leaves of Lamiophlomis rotata (Benth.) Kudo. The present study elucidated the effects of ND01 on the cultured rat cortical neuron injury induced by oxygen-glucose deprivation. The results showed that ND01 treatment obviously attenuated apoptosis and ameliorated mitochondrial energy metabolism in rat cortical neurons by increasing cell survival rate, mitochondrial respiratory enzyme activities, mitochondrial respiratory control ratio and adenosine triphosphate (ATP) content, and by attenuating lactate dehydrogenase (LDH) leakage, intracellular Ca(2+) level and caspase-3 activity in a concentration-dependent manner. These findings indicated that ND01 has potential against cerebral ischemic injury, and its protective effect on oxygen-glucose deprivation-induced injury might be due to the suppression of intracellular Ca(2+) elevation and caspase-3 activity, and improvement of mitochondrial energy metabolism.
Effect of 8-O-acetyl shanzhiside methylester increases angiogenesis and improves functional recovery after stroke.[Pubmed:20735376]
Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):21-7.
We investigated whether 8-O-acetyl shanzhiside methylester (ND01) regulates angiogenesis and thereby improves functional outcome after stroke. Adult male rats were subjected to 1 hr of middle cerebral artery occlusion (MCAO) and reperfusion, and treated with or without different doses (5 and 10 mg/kg) of ND01, starting 24 hr after ischaemia and reperfusion (I/R) and by intravenous injection daily for 14 days. Neurological functional tests were performed and cerebral Evans blue extravasation was measured. Angiogenesis and angiogenic factor expression were measured by immunohistochemistry and Western blot, respectively. The results indicated that ND01 significantly promoted angiogenesis in the ischaemic brain and improved functional outcome after stroke. ND01 also significantly increased vascularization compared with vehicle treatment. ND01 increased the expression of VEGF, Ang1, phosphorylation of Tie2 and Akt VEGF. The Ang1/Tie2 axis and Akt pathways appear to mediate ND01-induced angiogenesis.
Cardioprotection with 8-O-acetyl shanzhiside methylester on experimental myocardial ischemia injury.[Pubmed:22677812]
Eur J Pharm Sci. 2012 Aug 30;47(1):124-30.
8-O-acetyl shanzhiside methylester (ND01) was isolated from the leaves of Lamiophlomis rotata (Benth.) Kudo. In this study, we investigated the anti-myocardial ischemia and reperfusion (I/R) injury effects of ND01 in vivo and elucidated the potential mechanism in vitro. The results indicated that ND01 significantly attenuated hypoxia-induced cytotoxicity in a concentration-dependent manner in H9c2 cells. Treatment of H9c2 cells with ND01 9 muM blocked TNF-alpha-induced nuclear factor kappaB (NF-kappaB) phosphorylation by blocking High-mobility group box1 (HMGB1) expression. Treatment of rats with ND01 10mg/kg, (i.v.) protected the animals from myocardial I/R injury as indicated by a decrease in infarct volume, improvement in hemodynamics and reduction of myocardial damage severity. Treatment with ND01 also lowered serum levels of pro-inflammatory factors and reduced High mobility group box-1 protein (HMGB1) and phosphorylated NF-kappaB expression in ischemic myocardial tissue. Additionally, continuous i.v. of ND01 14 days attenuated cardiac remodeling. These protective effects suggested that ND01 might be due to block of myocardial inflammatory cascades through an HMGB1-dependent NF-kappaB signaling pathway.
8-O-acetyl shanzhiside methylester attenuates cerebral ischaemia/reperfusion injury through an anti-inflammatory mechanism in diabetic rats.[Pubmed:24823762]
Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):481-7.
Inflammatory activation plays a vital role in the pathophysiological mechanisms of stroke and diabetes mellitus (DM), exerts the deleterious effects on the progression of the brain and leads to vascular damage in diabetic stroke. The objectives of this study were to investigate the effects of 8-O-acetyl shanzhiside methylester (ND01) on tumour necrosis factor-alpha (TNF-alpha)-stimulated SH-SY5Y cell line in vitro and the experimental ischaemic diabetic stroke model in vivo. TNF-alpha-stimulated SH-SY5Y cells were pre-incubated with ND01, then analysed protein expression. For in vivo experiment, the diabetic rats were subjected to middle cerebral artery occlusion (MCAO) for 30 min. followed by reperfusion for 23 hr. Treatment of SH-SY5Y cells with ND01 blocked TNF-alpha-induced nuclear transcription factor kappaB (NF-kappaB) activation and decreased high-mobility group box-1 (HMGB-1) expression. ND01 40 mg/kg demonstrated significant neuroprotective effect even after delayed administration at 4 hr after I/R. ND01 40 mg/kg attenuated the histopathological damage, decreased brain swelling, inhibited NF-kappaB activation and reduced HMGB-1 expression in ischaemic brain tissue. These data show that ND01 protects diabetic brain against I/R injury with a favourable therapeutic time-window by alleviating diabetic cerebral I/R injury and attenuating blood-brain barrier (BBB) breakdown, and its protective effects may involve HMGB-1 and NF-kappaB signalling pathway.
