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Schisantherin B

CAS# 58546-55-7

Schisantherin B

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Quality Control of Schisantherin B

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Chemical structure

Schisantherin B

3D structure

Chemical Properties of Schisantherin B

Cas No. 58546-55-7 SDF Download SDF
PubChem ID 6438572 Appearance White powder
Formula C28H34O9 M.Wt 514.57
Type of Compound Lignans Storage Desiccate at -20°C
Synonyms Gomisin-B; Schizantherin-B; Wuweizi ester-B; Schisantherin-B
Solubility DMSO : 250 mg/mL (485.85 mM; Need ultrasonic)
SMILES CC=C(C)C(=O)OC1C2=CC(=C(C(=C2C3=C(C4=C(C=C3CC(C1(C)O)C)OCO4)OC)OC)OC)OC
Standard InChIKey BKGUPIVDQHHVMV-RZGKOBFOSA-N
Standard InChI InChI=1S/C28H34O9/c1-9-14(2)27(29)37-26-17-12-18(31-5)22(32-6)25(34-8)21(17)20-16(10-15(3)28(26,4)30)11-19-23(24(20)33-7)36-13-35-19/h9,11-12,15,26,30H,10,13H2,1-8H3/b14-9-/t15-,26-,28-/m0/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.
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 Schisantherin B

The seeds of Schisandra chinensis (Turcz.) Baill.

Biological Activity of Schisantherin B

DescriptionSchisantherin B may protect against cognitive deficits and neurodegeneration induced by Aβ1-42 in mice by regulating the glutamate transporter type 1 (GLT-1) restoration as well as the capacity of Glycogen synthase kinase3β(GSK3β), it also shows good effect in lowering the serum glutamic-pyruvic transaminase level of the patients suffering from chronic virus hepatitis.
TargetsP450 (e.g. CYP17) | GSK-3 | Beta Amyloid
In vivo

Effect of Tacrolimus on the pharmacokinetics of bioactive lignans of Wuzhi tablet (Schisandra sphenanthera extract) and the potential roles of CYP3A and P-gp.[Pubmed: 24462213]

Phytomedicine. 2014 Apr 15;21(5):766-72.

We recently reported that Wuzhi tablet (WZ), a preparation of the ethanol extract of Wuweizi (Schisandra sphenanthera), had significant effects on blood concentrations of Tacrolimus (FK506) in renal transplant recipients and rats. The active lignans in WZ are schisandrin A, schisandrin B, schisandrin C, schisandrol A, schisandrol B, schisantherin A, and Schisantherin B. Until now, whether the pharmacokinetics of these lignans in WZ would be affected by FK506 remained unknown.
METHODS AND RESULTS:
Therefore, this study aimed to investigate whether and how FK506 affected pharmacokinetics of lignans in WZ in rats and the potential roles of CYP3A and P-gp. After a single oral co-administration of FK506 and WZ, the blood concentration of lignans in WZ was decreased by FK506; furthermore, the AUC of schisantherin A, schisandrin A, schisandrol A and schisandrol B was only 64.5%, 47.2%, 55.1% and 57.4% of that of WZ alone group, respectively. Transport study in Caco-2 cells showed that these lignans were not substrates of P-gp, suggesting decreased blood concentration of lignans by FK506 was not via P-gp pathway. Metabolism study in the human recombinant CYP 3A showed that these lignans had higher affinity to CYP3A than that of FK506, and thus had a stronger CYP3A-mediated metabolism.
CONCLUSIONS:
It was concluded that the blood concentrations of these lignans were decreased and their CYP3A-mediated metabolisms were increased in the presence of FK506 since these lignans had higher affinity to CYP3A.

Protocol of Schisantherin B

Animal Research

Schisantherin B ameliorates Aβ1-42-induced cognitive decline via restoration of GLT-1 in a mouse model of Alzheimer's disease.[Pubmed: 27660034]

Physiol Behav. 2016 Dec 1;167:265-273.

Accumulation of amyloid beta (Aβ) peptide and hyperphosphorylated tau protein has been proposed to play roles in neural destruction which induce Alzheimer's disease (AD) progresses, glutamate transporter type 1 (GLT-1) and Glycogen synthase kinase3β (GSK3β) may be the pathological links between Aβ and tau pathology. Schisantherin B (STB) is one bioactive of lignans isolated from Schisandra chinensis (Turcz.) Baill which has been commonly used as a traditional herbal medicine for thousands of years.
METHODS AND RESULTS:
This paper was designed to investigate the effects of STB on improving the cognitive function and neurodegeneration in the mouse model of Alzheimer's disease induced by Aβ1-42, and its possible mechanism were Glutamate transporter GLT-1, tau and GSK3β. It was found that successive intracerebroventricular (ICV) administration of STB (0.15mg/kg) for 5days significantly attenuated Aβ1-42-induced learning and memory impairment as measured by the Locomotor activity test, Y-maze test and Morris water maze test. Furthermore, STB at a dose of 0.15mg/kg restored the activities of GLT-1 and GSK3β while decreasing the levels of hyperphosphorylated tau protein in the hippocampus and cerebral cortex.
CONCLUSIONS:
The results suggested that STB might protect against cognitive deficits and neurodegeneration induced by Aβ1-42 in mice by regulating the GLT-1 restoration as well as the capacity of GSK3β.

Structure Identification
J Nat Prod. 2006 Dec;69(12):1697-701.

Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora.[Pubmed: 17190445]


METHODS AND RESULTS:
Bioactivity-directed fractionation of an ethanolic extract of the fruits of Schisandra rubriflora led to the isolation and identification of dibenzocyclooctadiene lignans including the new lignans rubrisandrins A (1a + 1b) and B (2) and the known lignans gomisin J (3), (+/-)-gomisin M1 (4), (+)-gomisin M2 (5), schisanhenol (6), deoxyschisandrin, Schisantherin B, schisandrin, tigloylgomisin P, gomisin O, angeloylgomisin P, and epigomisin O. Their structure and stereochemistry were determined by spectroscopic methods, including 2D-NMR techniques.
CONCLUSIONS:
Compounds 1 and 3-6 were active as anti-HIV agents. (+/-)-Gomisin M1 (4) exhibited the most potent anti-HIV activity, with EC50 and therapeutic index (TI) values of <0.65 microM and >68, respectively.

Sci Sin. 1978 Jul-Aug;21(4):483-502.

Studies on the active principles of Schisandra sphenanthera Rehd. et Wils. The structures of schisantherin A, B, C, D, E, and the related compounds.[Pubmed: 233922]


METHODS AND RESULTS:
Deoxyschisandrin (VIII) and five new lignans, named schisantherin A, Schisantherin B, C, D, and E, were isolated from the active fraction of the fruits of Schisandra sphenanthera Rehd. et Wils. Their configurations and conformations were established by exhaustive spectral analysis as well as chemical degradations as shown in Ia, Ib; IIa, IIb; IIIa, IIIb; IVa, IVb, and Va, Vb respectively, and their absolute configurations at biphenyl, at C6, C7, and C8 were all assigned to be S form. The position of the methylenedioxyl group in the structures of gamma-schisandrin and Wuweizisu C (as described in the literature), isolated from Schisandra chinensis, must be corrected as shown in VI and VII respectively.
CONCLUSIONS:
In pharmacologica studies and preliminary clinical trials, schisantherin A,Schisantherin B, C, and D showed good effect in lowering the serum glutamic-pyruvic transaminase level of the patients suffering from chronic virus hepatitis. Schisantherin E and deoxyschisandrin were not effective.

Schisantherin B Dilution Calculator

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Schisantherin B Molarity Calculator

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Preparing Stock Solutions of Schisantherin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9434 mL 9.7169 mL 19.4337 mL 38.8674 mL 48.5843 mL
5 mM 0.3887 mL 1.9434 mL 3.8867 mL 7.7735 mL 9.7169 mL
10 mM 0.1943 mL 0.9717 mL 1.9434 mL 3.8867 mL 4.8584 mL
50 mM 0.0389 mL 0.1943 mL 0.3887 mL 0.7773 mL 0.9717 mL
100 mM 0.0194 mL 0.0972 mL 0.1943 mL 0.3887 mL 0.4858 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 Schisantherin B

Schisantherin B is a natural product.

References:
[1]. Liu Jiasen, et al. STUDIES ON THE ACTIVE PRINCIPLES OF SCHISANDRA SPHENANTHERA REHD. ET WILS. THE STRUCTURES OF SCHISANTHERIN A, B, C, D, E, AND THE RELATED COMPOUNDS. Science China Mathematics, 1978, (4)

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References on Schisantherin B

Studies on the active principles of Schisandra sphenanthera Rehd. et Wils. The structures of schisantherin A, B, C, D, E, and the related compounds.[Pubmed:233922]

Sci Sin. 1978 Jul-Aug;21(4):483-502.

Deoxyschisandrin (VIII) and five new lignans, named schisantherin A, B, C, D, and E, were isolated from the active fraction of the fruits of Schisandra sphenanthera Rehd. et Wils. Their configurations and conformations were established by exhaustive spectral analysis as well as chemical degradations as shown in Ia, Ib; IIa, IIb; IIIa, IIIb; IVa, IVb, and Va, Vb respectively, and their absolute configurations at biphenyl, at C6, C7, and C8 were all assigned to be S form. The position of the methylenedioxyl group in the structures of gamma-schisandrin and Wuweizisu C (as described in the literature), isolated from Schisandra chinensis, must be corrected as shown in VI and VII respectively. In pharmacologica studies and preliminary clinical trials, schisantherin A, B, C, and D showed good effect in lowering the serum glutamic-pyruvic transaminase level of the patients suffering from chronic virus hepatitis. Schisantherin E and deoxyschisandrin were not effective.

Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora.[Pubmed:17190445]

J Nat Prod. 2006 Dec;69(12):1697-701.

Bioactivity-directed fractionation of an ethanolic extract of the fruits of Schisandra rubriflora led to the isolation and identification of dibenzocyclooctadiene lignans including the new lignans rubrisandrins A (1a + 1b) and B (2) and the known lignans gomisin J (3), (+/-)-gomisin M1 (4), (+)-gomisin M2 (5), schisanhenol (6), deoxyschisandrin, Schisantherin B, schisandrin, tigloylgomisin P, gomisin O, angeloylgomisin P, and epigomisin O. Their structure and stereochemistry were determined by spectroscopic methods, including 2D-NMR techniques. Compounds 1 and 3-6 were active as anti-HIV agents. (+/-)-Gomisin M1 (4) exhibited the most potent anti-HIV activity, with EC50 and therapeutic index (TI) values of <0.65 microM and >68, respectively.

Effect of Tacrolimus on the pharmacokinetics of bioactive lignans of Wuzhi tablet (Schisandra sphenanthera extract) and the potential roles of CYP3A and P-gp.[Pubmed:24462213]

Phytomedicine. 2014 Apr 15;21(5):766-72.

We recently reported that Wuzhi tablet (WZ), a preparation of the ethanol extract of Wuweizi (Schisandra sphenanthera), had significant effects on blood concentrations of Tacrolimus (FK506) in renal transplant recipients and rats. The active lignans in WZ are schisandrin A, schisandrin B, schisandrin C, schisandrol A, schisandrol B, schisantherin A, and Schisantherin B. Until now, whether the pharmacokinetics of these lignans in WZ would be affected by FK506 remained unknown. Therefore, this study aimed to investigate whether and how FK506 affected pharmacokinetics of lignans in WZ in rats and the potential roles of CYP3A and P-gp. After a single oral co-administration of FK506 and WZ, the blood concentration of lignans in WZ was decreased by FK506; furthermore, the AUC of schisantherin A, schisandrin A, schisandrol A and schisandrol B was only 64.5%, 47.2%, 55.1% and 57.4% of that of WZ alone group, respectively. Transport study in Caco-2 cells showed that these lignans were not substrates of P-gp, suggesting decreased blood concentration of lignans by FK506 was not via P-gp pathway. Metabolism study in the human recombinant CYP 3A showed that these lignans had higher affinity to CYP3A than that of FK506, and thus had a stronger CYP3A-mediated metabolism. It was concluded that the blood concentrations of these lignans were decreased and their CYP3A-mediated metabolisms were increased in the presence of FK506 since these lignans had higher affinity to CYP3A.

Schisantherin B ameliorates Abeta1-42-induced cognitive decline via restoration of GLT-1 in a mouse model of Alzheimer's disease.[Pubmed:27660034]

Physiol Behav. 2016 Dec 1;167:265-273.

Accumulation of amyloid beta (Abeta) peptide and hyperphosphorylated tau protein has been proposed to play roles in neural destruction which induce Alzheimer's disease (AD) progresses, glutamate transporter type 1 (GLT-1) and Glycogen synthase kinase3beta (GSK3beta) may be the pathological links between Abeta and tau pathology. Schisantherin B (STB) is one bioactive of lignans isolated from Schisandra chinensis (Turcz.) Baill which has been commonly used as a traditional herbal medicine for thousands of years. This paper was designed to investigate the effects of STB on improving the cognitive function and neurodegeneration in the mouse model of Alzheimer's disease induced by Abeta1-42, and its possible mechanism were Glutamate transporter GLT-1, tau and GSK3beta. It was found that successive intracerebroventricular (ICV) administration of STB (0.15mg/kg) for 5days significantly attenuated Abeta1-42-induced learning and memory impairment as measured by the Locomotor activity test, Y-maze test and Morris water maze test. Furthermore, STB at a dose of 0.15mg/kg restored the activities of GLT-1 and GSK3beta while decreasing the levels of hyperphosphorylated tau protein in the hippocampus and cerebral cortex. The results suggested that STB might protect against cognitive deficits and neurodegeneration induced by Abeta1-42 in mice by regulating the GLT-1 restoration as well as the capacity of GSK3beta.

Description

Schisantherin B (Gomisin-B; Wuweizi ester-B; Schisantherin-B) is a natural product.

Keywords:

Schisantherin B,58546-55-7,Gomisin-B; Schizantherin-B; Wuweizi ester-B; Schisantherin-B,Natural Products, buy Schisantherin B , Schisantherin B supplier , purchase Schisantherin B , Schisantherin B cost , Schisantherin B manufacturer , order Schisantherin B , high purity Schisantherin B

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