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Schizandrin A

CAS# 61281-38-7

Schizandrin A

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Quality Control of Schizandrin A

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Chemical structure

Schizandrin A

3D structure

Chemical Properties of Schizandrin A

Cas No. 61281-38-7 SDF Download SDF
PubChem ID 155256 Appearance White powder
Formula C24H32O6 M.Wt 416.51
Type of Compound Lignans Storage Desiccate at -20°C
Synonyms Schizandrin-A; Wuweizisu-A; Deoxyschizandrin
Solubility DMSO : 50 mg/mL (120.05 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name (9R,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene
SMILES CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1C)OC)OC)OC)OC)OC)OC
Standard InChIKey JEJFTTRHGBKKEI-OKILXGFUSA-N
Standard InChI InChI=1S/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14+
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.
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.
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.

Source of Schizandrin A

The seeds of Schisandra chinensis (Turcz.) Baill.

Biological Activity of Schizandrin A

DescriptionSchisandrin A , an agonist of the adiponectin receptor 2 (AdipoR2) with the IC50 value of 3.5 μM, has neuroprotective, anti-inflammatory, liver-protective, antitumor, and antioxidant activities. It alleviated microglia-mediated neuroinflammation injury through inhibiting the TRAF6-IKKβ-NF-κB and Jak2-Stat3 signaling pathways. It inhibited CYP3A activity with an IC50 of 6.60 μM and Ki of 5.83 μM, respectively.
TargetsERK | JNK | p38MAPK | Caspase | NO | TNF-α | IL Receptor | NOS | COX | JAK | STAT | NF-kB | IkB | P-gp | P450 (e.g. CYP17) | IKK
In vitro

Neuroprotective effect of schizandrin A on oxygen and glucose deprivation/reperfusion-induced cell injury in primary culture of rat cortical neurons.[Pubmed: 24986222]

J Physiol Biochem. 2014 Sep;70(3):735-47.

Brain ischemia appears to be associated with innate immunity. Recent reports showed that C3a and C5a, as potent targets, might protect against ischemia induced cell death. In traditional Chinese medicine, the fruit of Schizandra chinesis Baill (Fructus schizandrae) has been widely used as a tonic.
METHODS AND RESULTS:
In the present study, we sought to evaluate the neuroprotective effects of Schizandrin A, a composition of S. chinesis Baill, against oxygen and glucose deprivation followed by reperfusion (OGD/R)-induced cell death in primary culture of rat cortical neurons, and to test whether C3a and C5a affected cortical neuron recovery from ischemic injury after Schizandrin A treatment. The results showed that Schizandrin A significantly reduced cell apoptosis and necrosis, increased cell survival, and decreased intracellular calcium concentration ([Ca(2+)]i) and lactate dehydrogenase (LDH) release in primary culture of rat cortical neurons after OGD/R. Mechanism studies suggested that the modulation of extracellular-regulated kinase (ERK), c-Jun NH2-terminal kinases (JNK), and p38, as well as caspase-3 activity played an important role on the progress of neuronal apoptosis. C5aR participated in the neuroprotective effect of Schizandrin A in primary culture of rat cortical neurons after OGD/R.
CONCLUSIONS:
Our findings suggested that Schizandrin A might act as a candidate therapeutic target drug used for brain ischemia and related diseases.

Reversing mechanism of schizandrin A on multi-drug resistance of K562/ADR,HL60/ADR,MCF-7/ADR cell lines.[Reference: WebLink]

Chinese Pharmacological Bulletin, 2011, 27(3): 329-34.

To study the reversal effect of Schizandrin A(schA) on the K562/ADR,HL60/ADR,MCF-7/ADR,and explore its reversal mechanism.
METHODS AND RESULTS:
schA′s reversal effect was evaluated by MTT assay;accumulation of daunorubicin(DNR)and rhodamine-123(Rh123)and the expression of P-glycoprotein and multidrug resistance associated protein 1(MRP1)were evaluated by flow cytometry(FCM);the expression of intracellular mdr1 mRNA and mrp1 mRNA was detected with Real-time PCR;the changes of GSH content were detected by biochemical tests.Results The result of reversion of multidrug resistance showed schA had different reversal effects on different mechanisms of chemotherapeutic agents;the experiments of accumulation showed that the schA could significantly increase daunorubicin,rhodamine 123 contents in resistant cells,which had a good dose dependent effect;the treatment of schA could reduce remarkably the expressions of the P-gp protein and mdr1,mrp1 gene after 24 h treatment;and it could reduce GSH content after 4 h treatment in K562/ADR,HL60/ADR.
CONCLUSIONS:
schA has the reversal effect of drug resistance in different mechanisms of the two cell lines of K562/ADR and HL60/ADR.It increases the concentration of the drug resistant cells mainly by inhibiting the function and expression of P-gp,MRP1 protein and reducing mdr1,mrp1 gene expression and GSH content,and then it enhances the sensitivity and reversal effects of resistant cell lines.

Protocol of Schizandrin A

Kinase Assay

Effects of schizandrin A on the activity of CYP3A in rat liver microsomes.[Reference: WebLink]

Chinese Journal of Clinical Pharmacology & Therapeutics, 2009, 14(11):1275-80.

To study the effects of Schizandrin A on CYP3A by in vitro drug metabolism experiments.
METHODS AND RESULTS:
:Midazolam(MDZ)was adopted as a drug "probe" and a detection method of high-performance liquid chromatography(HPLC)was established,the rat liver microsome was as a carrier.The IC50 value of Schizandrin A by in vitro administration and related enzyme kinetic parameters on CYP3A were detected.The endogenous substances did not interfere with the determination in the incubation system.The method was fast,stable and had high sensitivity.The IC50 of Schizandrin A on MDZ metabolism in liver microsomes was 6.26 μmol/mL,and the enzyme kinetic parameters were as follows:Km=15.77 μmol/L,Ki=5.5 μmol/mL.
CONCLUSIONS:
Schizandrin A is able to inhibit CYP3A activity in rat liver microsomes.The inhibition is mixed type,non-competitive and anti-competitive inhibition.

Cell Research

Schizandrin A Inhibits Microglia-Mediated Neuroninflammation through Inhibiting TRAF6-NF-κB and Jak2-Stat3 Signaling Pathways.[Pubmed: 26919063]

PLoS One. 2016 Feb 26;11(2):e0149991.

Microglial-mediated neuroinflammation has been established as playing a vital role in pathogenesis of neurodegenerative disorders. Thus, rational regulation of microglia functions to inhibit inflammation injury may be a logical and promising approach to neurodegenerative disease therapy. The purposes of the present study were to explore the neuroprotective effects and potential molecular mechanism of Schizandrin A (Sch A), a lignin compound isolated from Schisandra chinesnesis.
METHODS AND RESULTS:
Our observations showed that Sch A could significantly down-regulate the increased production of nitric oxide (NO), tumor necrosis factor (TNF)-α and interleukin (IL)-6 induced by lipopolysaccharide (LPS) both in BV-2 cells and primary microglia cells. Moreover, Sch A exerted obvious neuroprotective effects against inflammatory injury in neurons when exposed to microglia-conditioned medium. Investigations of the mechanism showed the anti-inflammatory effect of Sch A involved the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) expression levels and inhibition of the LPS-induced TRAF6-IKKβ-NF-κB pathway. Furthermore, inhibition of Jak2-Stat3 pathway activation and Stat3 nuclear translocation also was observed.
CONCLUSIONS:
SchA can exert anti-inflammatory and neuroprotective effects by alleviating microglia-mediated neuroinflammation injury through inhibiting the TRAF6-IKKβ-NF-κB and Jak2-Stat3 signaling pathways.

Schizandrin A Dilution Calculator

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Preparing Stock Solutions of Schizandrin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4009 mL 12.0045 mL 24.009 mL 48.0181 mL 60.0226 mL
5 mM 0.4802 mL 2.4009 mL 4.8018 mL 9.6036 mL 12.0045 mL
10 mM 0.2401 mL 1.2005 mL 2.4009 mL 4.8018 mL 6.0023 mL
50 mM 0.048 mL 0.2401 mL 0.4802 mL 0.9604 mL 1.2005 mL
100 mM 0.024 mL 0.12 mL 0.2401 mL 0.4802 mL 0.6002 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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Background on Schizandrin A

Schisandrin A inhibits CYP3A activity with an IC50 of 6.60 μM and Ki of 5.83 μM, respectively.

In Vitro:Schisandrin A (Sch A) strongly inhibits microsomal midazolam 1-hydroxylation catalyzed by CYP3A, with an IC50 of 6.60 μM. The recovery of enzyme activity in the absence or presence of Schisandrin A is shown in dilution assay plots. The Ki value for Schisandrin A is obtained from the Dixon plots and is 5.83 μM. The inactivation of rat liver microsomal midazolam 1-hydroxylation activity by Schisandrin A in the presence of NADPH is found to be time- and concentration-dependent. The Kinact and Ki are estimated to be 0.134/min and 4.51 μM, respectively for Schisandrin A[1].

In Vivo:Schisandrin A (SchA) significantly inhibits CYP3A activity in rat hepatic microsomes and Vmax value of each group in a concentration-dependent manner. The double-reciprocal plots and the secondary plot show that Schisandrin A inhibits CYP3A activity, with an apparent Ki value of 30.67 mg/kg. In each Schisandrin A-treated group, Schisandrin A also significantly decreases 1-hydroxymidazolam plasma concentrations compared with the negative group (to levels similar to the positive group)[2].

References:
[1]. Li WL, et al. Inhibitory effects of Schisandrin A and Schisandrin B on CYP3A activity. Methods Find Exp Clin Pharmacol. 2010 Apr;32(3):163-9. [2]. Li WL, et al. Inhibitory effects of continuous ingestion of Schisandrin A on CYP3A in the rat. Basic Clin Pharmacol Toxicol. 2012 Feb;110(2):187-92.

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References on Schizandrin A

Neuroprotective effect of schizandrin A on oxygen and glucose deprivation/reperfusion-induced cell injury in primary culture of rat cortical neurons.[Pubmed:24986222]

J Physiol Biochem. 2014 Sep;70(3):735-47.

Brain ischemia appears to be associated with innate immunity. Recent reports showed that C3a and C5a, as potent targets, might protect against ischemia induced cell death. In traditional Chinese medicine, the fruit of Schizandra chinesis Baill (Fructus schizandrae) has been widely used as a tonic. In the present study, we sought to evaluate the neuroprotective effects of Schizandrin A, a composition of S. chinesis Baill, against oxygen and glucose deprivation followed by reperfusion (OGD/R)-induced cell death in primary culture of rat cortical neurons, and to test whether C3a and C5a affected cortical neuron recovery from ischemic injury after Schizandrin A treatment. The results showed that Schizandrin A significantly reduced cell apoptosis and necrosis, increased cell survival, and decreased intracellular calcium concentration ([Ca(2+)]i) and lactate dehydrogenase (LDH) release in primary culture of rat cortical neurons after OGD/R. Mechanism studies suggested that the modulation of extracellular-regulated kinase (ERK), c-Jun NH2-terminal kinases (JNK), and p38, as well as caspase-3 activity played an important role on the progress of neuronal apoptosis. C5aR participated in the neuroprotective effect of Schizandrin A in primary culture of rat cortical neurons after OGD/R. Our findings suggested that Schizandrin A might act as a candidate therapeutic target drug used for brain ischemia and related diseases.

Schizandrin A Inhibits Microglia-Mediated Neuroninflammation through Inhibiting TRAF6-NF-kappaB and Jak2-Stat3 Signaling Pathways.[Pubmed:26919063]

PLoS One. 2016 Feb 26;11(2):e0149991.

Microglial-mediated neuroinflammation has been established as playing a vital role in pathogenesis of neurodegenerative disorders. Thus, rational regulation of microglia functions to inhibit inflammation injury may be a logical and promising approach to neurodegenerative disease therapy. The purposes of the present study were to explore the neuroprotective effects and potential molecular mechanism of Schizandrin A (Sch A), a lignin compound isolated from Schisandra chinesnesis. Our observations showed that Sch A could significantly down-regulate the increased production of nitric oxide (NO), tumor necrosis factor (TNF)-alpha and interleukin (IL)-6 induced by lipopolysaccharide (LPS) both in BV-2 cells and primary microglia cells. Moreover, Sch A exerted obvious neuroprotective effects against inflammatory injury in neurons when exposed to microglia-conditioned medium. Investigations of the mechanism showed the anti-inflammatory effect of Sch A involved the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) expression levels and inhibition of the LPS-induced TRAF6-IKKbeta-NF-kappaB pathway. Furthermore, inhibition of Jak2-Stat3 pathway activation and Stat3 nuclear translocation also was observed. In conclusion, SchA can exert anti-inflammatory and neuroprotective effects by alleviating microglia-mediated neuroinflammation injury through inhibiting the TRAF6-IKKbeta-NF-kappaB and Jak2-Stat3 signaling pathways.

Description

Schisandrin A inhibits CYP3A activity with an IC50 of 6.60 μM and Ki of 5.83 μM, respectively.

Keywords:

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