Spinosin

CAS# 72063-39-9

Spinosin

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Catalog No. BCN1644----Order now to get a substantial discount!

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Spinosin

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Chemical Properties of Spinosin

Cas No. 72063-39-9 SDF Download SDF
PubChem ID 155692 Appearance White-beige powder
Formula C28H32O15 M.Wt 608.55
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Flavoayamenin
Solubility Soluble in water
Chemical Name 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
SMILES COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O
Standard InChIKey VGGSULWDCMWZPO-ODEMIOGVSA-N
Standard InChI InChI=1S/C28H32O15/c1-39-14-7-15-18(12(32)6-13(40-15)10-2-4-11(31)5-3-10)22(35)19(14)26-27(24(37)21(34)16(8-29)41-26)43-28-25(38)23(36)20(33)17(9-30)42-28/h2-7,16-17,20-21,23-31,33-38H,8-9H2,1H3/t16-,17-,20-,21-,23+,24+,25-,26+,27-,28+/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.
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 Spinosin

The seeds of Zizyphus jujuba

Biological Activity of Spinosin

DescriptionSpinosin has neuroprotective, anxiolytic-like and anti-inflammatory effects, it ameliorated memory impairment induced through AβO, the serotonergic neurotransmitter system, it also potentiated pentobarbital-induced sleep via the serotonergic system.
TargetsBeta Amyloid | 5-HT Receptor | cAMP | ERK | GABA Receptor
In vivo

Spinosin, a C-Glucosylflavone, from Zizyphus jujuba var. spinosa Ameliorates Aβ1-42 Oligomer-Induced Memory Impairment in Mice.[Pubmed: 25767684]

Biomol Ther (Seoul). 2015 Mar;23(2):156-64.

Alzheimer's disease (AD) is a neurodegenerative disorder associated with progressive memory loss and neuronal cell death. Although numerous previous studies have been focused on disease progression or reverse pathological symptoms, therapeutic strategies for AD are limited. Alternatively, the identification of traditional herbal medicines or their active compounds has received much attention. The aims of the present study were to characterize the ameliorating effects of Spinosin, a C-glucosylflavone isolated from Zizyphus jujuba var. spinosa, on memory impairment or the pathological changes induced through amyloid-β1-42 oligomer (AβO) in mice.
METHODS AND RESULTS:
Memory impairment was induced by intracerebroventricular injection of AβO (50 μM) and Spinosin (5, 10, and 20 mg/kg) was administered for 7 days. In the behavioral tasks, the subchronic administration of Spinosin (20 mg/kg, p.o.) significantly ameliorated AβO-induced cognitive impairment in the passive avoidance task or the Y-maze task. To identify the effects of Spinosin on the pathological changes induced through AβO, immunohistochemistry and Western blot analyses were performed. Spinosin treatment also reduced the number of activated microglia and astrocytes observed after AβO injection. In addition, Spinosin rescued the AβO-induced decrease in choline acetyltransferase expression levels.
CONCLUSIONS:
These results suggest that Spinosin ameliorated memory impairment induced through AβO, and these effects were regulated, in part, through neuroprotective activity via the anti-inflammatory effects of Spinosin. Therefore, Spinosin might be a useful agent against the amyloid b protein-induced cognitive dysfunction observed in AD patients.

Ameliorating effect of spinosin, a C-glycoside flavonoid, on scopolamine-induced memory impairment in mice.[Pubmed: 24582850]

Pharmacol Biochem Behav. 2014 May;120:88-94.

Spinosin is a C-glycoside flavonoid isolated from the seeds of Zizyphus jujuba var. spinosa.
METHODS AND RESULTS:
This study investigated the effect of Spinosin on cholinergic blockade-induced memory impairment in mice. Behavioral tests were conducted using the passive avoidance, Y-maze, and Morris water maze tasks to evaluate the memory-ameliorating effect of Spinosin. Spinosin (10 or 20mg/kg, p.o.) significantly ameliorated scopolamine-induced cognitive impairment in these behavioral tasks with a prolonged latency time in the passive avoidance task, an increased percentage of spontaneous alternation in the Y-maze task and a lengthened swimming time in target quadrant in the Morris water maze task. In addition, a single administration of Spinosin in normal naïve mice also enhanced the latency time in the passive avoidance task. To identify the mechanism of the memory-ameliorating effect of Spinosin, receptor antagonism analysis and Western blotting were performed. The ameliorating effect of Spinosin on scopolamine-induced memory impairment was significantly antagonized by a sub-effective dose (0.5mg/kg, i.p.) of 8-hydroxy-2-(di-N-propylamino)tetralin, a 5-HT1A receptor agonist. In addition, Spinosin significantly increased the expression levels of phosphorylated extracellular signal-regulated kinases and cAMP response element-binding proteins in the hippocampus.
CONCLUSIONS:
Taken together, these results indicate that the memory-ameliorating effect of Spinosin may be, in part, due to the serotonergic neurotransmitter system, and that Spinosin may be useful for the treatment of cognitive dysfunction in diseases such as Alzheimer's disease.

Protocol of Spinosin

Animal Research

Spinosin, a C-glycoside flavonoid from semen Zizhiphi Spinozae, potentiated pentobarbital-induced sleep via the serotonergic system.[Pubmed: 18466960 ]

GABA and 5-HT systems are implicated in the anxiolytic-like effect of spinosin in mice.[Pubmed: 25449359]

Pharmacol Biochem Behav. 2015 Jan;128:41-9.


METHODS AND RESULTS:
The present study investigated the anxiolytic-like effects of Spinosin, one of the major flavonoids in Ziziphi Spinosae Semen (ZSS), in experimental models of anxiety compared with a known anxiolytic, diazepam. Repeated treatment with Spinosin (2.5 and 5mg/kg/day, p.o.) significantly increased the percentage of entries into and time spent on the open arms of the elevated plus maze compared with the control group. In the light/dark box test, Spinosin exerted an anxiolytic-like effect at 5mg/kg. In the open-field test, 5mg/kg Spinosin increased the number of central entries. Spinosin did not affect spontaneous activity. The anxiolytic-like effects of Spinosin in the elevated plus maze, light/dark box test, and open field test were blocked by the γ-aminobutyric acid-A (GABAA) receptor antagonist flumazenil (3mg/kg, i.p.) and 5-hydroxytryptamine-1A (5-HT1A) receptor antagonist WAY-100635 (1mg/kg, i.p.).
CONCLUSIONS:
These results suggest that Spinosin exerts anxiolytic-like effects, and its mechanism of action appears to be modulated by GABAA and 5-HT1A receptors.

Pharmacol Biochem Behav. 2008 Sep;90(3):399-403.

Semen Zizhiphi Spinozae has been used extensively for the treatment of insomnia.
METHODS AND RESULTS:
This study investigated the effect and possible mechanism of action of Spinosin (also known as 2''-beta-o-glucopyranosyl swertisin), a major constituent of semen Zizhiphi Spinozae, on sleep in mice. The present results showed that Spinosin significantly and dose-dependently augmented pentobarbital (45 mg/kg, i.p.)-induced sleep, reflected by increased sleep time and reduced sleep latency assessed with the loss-of-righting reflex, and these effects were potentiated by the 5-hydroxytryptamine (serotonin) precursor 5-hydroxytryptophan (5-HTP, 2.5 mg/kg,i.p.). With a subhypnotic dose of pentobarbital (28 mg/kg, i.p.), Spinosin significantly increased the rate of sleep onset and exhibited a synergistic effect with 5-HTP (2.5 mg/kg, i.p.). Pretreatment with p-chlorophenylalanine (PCPA, 300 mg/kg, s.c.), an inhibitor of tryptophan hydroxylase, significantly decreased pentobarbital-induced sleep time, and Spinosin significantly reversed this effect. The dopamine precursor L-3-(3, 4-dihydroxyphenylalanine (L-DOPA) reduced pentobarbital-induced sleep, an effect not significantly affected by Spinosin.
CONCLUSIONS:
These results suggest that Spinosin potentiated pentobarbital-induced sleep via a serotonergic mechanism.

Structure Identification
J Chromatogr Sci. 2015 Jan;53(1):97-103.

Brain tissue distribution of spinosin in rats determined by a new high-performance liquid chromatography-electrospray ionization-mass/mass spectrometry method.[Pubmed: 24771055]

Spinosin, a flavone-C-glycoside, is a bioactive ingredient isolated from a traditional Chinese herb Zizyphi Spinosi Semen.
METHODS AND RESULTS:
In this study, a new high-performance liquid chromatography-electrospray ionization-mass/mass spectrometry method was developed and validated to determine Spinosin in brain tissues including olfactory region, hippocampus, corpus striatum, cerebrum (cerebral cortex) and cerebellum, after intravenous administration with the dose of 5 mg/kg. The tissue homogenate samples were pretreated and extracted with acetonitrile by a simple protein precipitation method. The separation was performed on a YMC ODS-AQ(TM) column (250 × 2.0 mm, 3.5 μm) with the mobile phase of acetonitrile-aqueous phase (0.1% formic acid) (25 : 75, v/v) at a flow rate of 0.3 mL/min. The retention times of Spinosin and naringin (internal standard) were 3.3 and 5.1 min, respectively. Multiple reaction monitoring mode was used to monitor precursor/product ion transitions of m/z 607.2 → 427.0 for Spinosin and m/z 579.2 → 271.0 for naringin. The proposed method was successfully applied to the preclinical brain tissue distribution of Spinosin in rats.
CONCLUSIONS:
The results showed that there was a wide brain regional tissue distribution of Spinosin. The concentrations of Spinosin in corpus striatum and hippocampus were higher than that in other areas.

Spinosin Dilution Calculator

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Preparing Stock Solutions of Spinosin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6433 mL 8.2163 mL 16.4325 mL 32.865 mL 41.0813 mL
5 mM 0.3287 mL 1.6433 mL 3.2865 mL 6.573 mL 8.2163 mL
10 mM 0.1643 mL 0.8216 mL 1.6433 mL 3.2865 mL 4.1081 mL
50 mM 0.0329 mL 0.1643 mL 0.3287 mL 0.6573 mL 0.8216 mL
100 mM 0.0164 mL 0.0822 mL 0.1643 mL 0.3287 mL 0.4108 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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References on Spinosin

Augmentative effect of spinosin on pentobarbital-induced loss of righting reflex in mice associated with presynaptic 5-HT1A receptor.[Pubmed:22221104]

J Pharm Pharmacol. 2012 Feb;64(2):277-82.

OBJECTIVES: This study investigated whether Spinosin potentiates pentobarbital-induced loss of righting reflex (LORR) in mice via 5-HT(1A) receptors. METHODS: Our primary endpoint for sedation was LORR. In addition, the basal rectal temperature was measured. KEY FINDINGS: The results demonstrated that the 5-HT(1A) agonist 8-OH-DPAT (s.c.) induced reductions in duration of LORR at 0.1, 0.5 and 1.0 mg/kg (P < 0.01), and prolongation of LORR latency at 0.5 and 1.0 mg/kg (s.c., P < 0.01) in pentobarbital (45 mg/kg, i.p.)-treated mice. This effect of 8-OH-DPAT was antagonized either by 5-HT(1A) antagonist p-MPPI (5 mg/kg, i.p.) or by Spinosin (15 mg/kg, i.g.) with significance, respectively. Co-administration of Spinosin and p-MPPI both at ineffective doses (Spinosin at 5.0 mg/kg, i.g. and p-MPPI at 1.0 mg/kg, i.p.) showed significant augmentative effects in reducing latency to LORR, and increasing LORR duration (P < 0.01) in pentobarbital-treated mice. On the other hand, Spinosin inhibited 8-OH-DPAT-induced hypothermia, which has been generally attributed to the activation of somatodendritic 5-HT(1A) autoreceptors in mice. CONCLUSIONS: Based on our previous results and the present data, it should be presumed that presynaptic 5-HT(1A) autoreceptor mechanisms may be involved in the inhibitory effect of Spinosin on 8-OH-DPAT-induced hypothermia and also in the potentiating effect of Spinosin on pentobarbital-induced LORR in mice.

Spinosin, a C-glycoside flavonoid from semen Zizhiphi Spinozae, potentiated pentobarbital-induced sleep via the serotonergic system.[Pubmed:18466960]

Pharmacol Biochem Behav. 2008 Sep;90(3):399-403.

Semen Zizhiphi Spinozae has been used extensively for the treatment of insomnia. This study investigated the effect and possible mechanism of action of Spinosin (also known as 2''-beta-o-glucopyranosyl swertisin), a major constituent of semen Zizhiphi Spinozae, on sleep in mice. The present results showed that Spinosin significantly and dose-dependently augmented pentobarbital (45 mg/kg, i.p.)-induced sleep, reflected by increased sleep time and reduced sleep latency assessed with the loss-of-righting reflex, and these effects were potentiated by the 5-hydroxytryptamine (serotonin) precursor 5-hydroxytryptophan (5-HTP, 2.5 mg/kg,i.p.). With a subhypnotic dose of pentobarbital (28 mg/kg, i.p.), Spinosin significantly increased the rate of sleep onset and exhibited a synergistic effect with 5-HTP (2.5 mg/kg, i.p.). Pretreatment with p-chlorophenylalanine (PCPA, 300 mg/kg, s.c.), an inhibitor of tryptophan hydroxylase, significantly decreased pentobarbital-induced sleep time, and Spinosin significantly reversed this effect. The dopamine precursor L-3-(3, 4-dihydroxyphenylalanine (L-DOPA) reduced pentobarbital-induced sleep, an effect not significantly affected by Spinosin. These results suggest that Spinosin potentiated pentobarbital-induced sleep via a serotonergic mechanism.

Ameliorating effect of spinosin, a C-glycoside flavonoid, on scopolamine-induced memory impairment in mice.[Pubmed:24582850]

Pharmacol Biochem Behav. 2014 May;120:88-94.

Spinosin is a C-glycoside flavonoid isolated from the seeds of Zizyphus jujuba var. spinosa. This study investigated the effect of Spinosin on cholinergic blockade-induced memory impairment in mice. Behavioral tests were conducted using the passive avoidance, Y-maze, and Morris water maze tasks to evaluate the memory-ameliorating effect of Spinosin. Spinosin (10 or 20mg/kg, p.o.) significantly ameliorated scopolamine-induced cognitive impairment in these behavioral tasks with a prolonged latency time in the passive avoidance task, an increased percentage of spontaneous alternation in the Y-maze task and a lengthened swimming time in target quadrant in the Morris water maze task. In addition, a single administration of Spinosin in normal naive mice also enhanced the latency time in the passive avoidance task. To identify the mechanism of the memory-ameliorating effect of Spinosin, receptor antagonism analysis and Western blotting were performed. The ameliorating effect of Spinosin on scopolamine-induced memory impairment was significantly antagonized by a sub-effective dose (0.5mg/kg, i.p.) of 8-hydroxy-2-(di-N-propylamino)tetralin, a 5-HT1A receptor agonist. In addition, Spinosin significantly increased the expression levels of phosphorylated extracellular signal-regulated kinases and cAMP response element-binding proteins in the hippocampus. Taken together, these results indicate that the memory-ameliorating effect of Spinosin may be, in part, due to the serotonergic neurotransmitter system, and that Spinosin may be useful for the treatment of cognitive dysfunction in diseases such as Alzheimer's disease.

GABA and 5-HT systems are implicated in the anxiolytic-like effect of spinosin in mice.[Pubmed:25449359]

Pharmacol Biochem Behav. 2015 Jan;128:41-9.

The present study investigated the anxiolytic-like effects of Spinosin, one of the major flavonoids in Ziziphi Spinosae Semen (ZSS), in experimental models of anxiety compared with a known anxiolytic, diazepam. Repeated treatment with Spinosin (2.5 and 5mg/kg/day, p.o.) significantly increased the percentage of entries into and time spent on the open arms of the elevated plus maze compared with the control group. In the light/dark box test, Spinosin exerted an anxiolytic-like effect at 5mg/kg. In the open-field test, 5mg/kg Spinosin increased the number of central entries. Spinosin did not affect spontaneous activity. The anxiolytic-like effects of Spinosin in the elevated plus maze, light/dark box test, and open field test were blocked by the gamma-aminobutyric acid-A (GABAA) receptor antagonist flumazenil (3mg/kg, i.p.) and 5-hydroxytryptamine-1A (5-HT1A) receptor antagonist WAY-100635 (1mg/kg, i.p.). These results suggest that Spinosin exerts anxiolytic-like effects, and its mechanism of action appears to be modulated by GABAA and 5-HT1A receptors.

Spinosin, a C-Glucosylflavone, from Zizyphus jujuba var. spinosa Ameliorates Abeta1-42 Oligomer-Induced Memory Impairment in Mice.[Pubmed:25767684]

Biomol Ther (Seoul). 2015 Mar;23(2):156-64.

Alzheimer's disease (AD) is a neurodegenerative disorder associated with progressive memory loss and neuronal cell death. Although numerous previous studies have been focused on disease progression or reverse pathological symptoms, therapeutic strategies for AD are limited. Alternatively, the identification of traditional herbal medicines or their active compounds has received much attention. The aims of the present study were to characterize the ameliorating effects of Spinosin, a C-glucosylflavone isolated from Zizyphus jujuba var. spinosa, on memory impairment or the pathological changes induced through amyloid-beta1-42 oligomer (AbetaO) in mice. Memory impairment was induced by intracerebroventricular injection of AbetaO (50 muM) and Spinosin (5, 10, and 20 mg/kg) was administered for 7 days. In the behavioral tasks, the subchronic administration of Spinosin (20 mg/kg, p.o.) significantly ameliorated AbetaO-induced cognitive impairment in the passive avoidance task or the Y-maze task. To identify the effects of Spinosin on the pathological changes induced through AbetaO, immunohistochemistry and Western blot analyses were performed. Spinosin treatment also reduced the number of activated microglia and astrocytes observed after AbetaO injection. In addition, Spinosin rescued the AbetaO-induced decrease in choline acetyltransferase expression levels. These results suggest that Spinosin ameliorated memory impairment induced through AbetaO, and these effects were regulated, in part, through neuroprotective activity via the anti-inflammatory effects of Spinosin. Therefore, Spinosin might be a useful agent against the amyloid b protein-induced cognitive dysfunction observed in AD patients.

Brain tissue distribution of spinosin in rats determined by a new high-performance liquid chromatography-electrospray ionization-mass/mass spectrometry method.[Pubmed:24771055]

J Chromatogr Sci. 2015 Jan;53(1):97-103.

Spinosin, a fl avone-C-glycoside, is a bioactive ingredient isolated from a traditional Chinese herb Zizyphi Spinosi Semen. In this study, a new high-performance liquid chromatography-electrospray ionization-mass/mass spectrometry method was developed and validated to determine Spinosin in brain tissues including olfactory region, hippocampus, corpus striatum, cerebrum (cerebral cortex) and cerebellum, after intravenous administration with the dose of 5 mg/kg. The tissue homogenate samples were pretreated and extracted with acetonitrile by a simple protein precipitation method. The separation was performed on a YMC ODS-AQ(TM) column (250 x 2.0 mm, 3.5 mum) with the mobile phase of acetonitrile-aqueous phase (0.1% formic acid) (25 : 75, v/v) at a fl ow rate of 0.3 mL/min. The retention times of Spinosin and naringin (internal standard) were 3.3 and 5.1 min, respectively. Multiple reaction monitoring mode was used to monitor precursor/product ion transitions of m/z 607.2 --> 427.0 for Spinosin and m/z 579.2 --> 271.0 for naringin. The proposed method was successfully applied to the preclinical brain tissue distribution of Spinosin in rats. The results showed that there was a wide brain regional tissue distribution of Spinosin. The concentrations of Spinosin in corpus striatum and hippocampus were higher than that in other areas.

Description

Spinosyn a C-glycoside flavonoid isolated from the seeds of Zizyphus jujube, with neuroprotective effects. Spinosin inhibits Aβ1-42 production and aggregation via activating Nrf2/HO-1 pathway.

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