Syringin

CAS# 118-34-3

Syringin

2D Structure

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Syringin

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Chemical Properties of Syringin

Cas No. 118-34-3 SDF Download SDF
PubChem ID 5316860 Appearance White powder
Formula C17H24O9 M.Wt 372.4
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms Eleutheroside B
Solubility >17.9mg/mL in DMSO
Chemical Name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
SMILES COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C=CCO
Standard InChIKey QJVXKWHHAMZTBY-GCPOEHJPSA-N
Standard InChI InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/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 Syringin

1 Daphne sp. 2 Eleutherococcus sp. 3 Fraxinus sp. 4 Globularia sp. 5 Picrasma sp. 6 Salix sp. 7 Saussurea sp. 8 Syringa sp. 9 Viscum sp. 10 Wikstroemia sp.

Biological Activity of Syringin

DescriptionSyringin (Eleutheroside B) has neuroprotective, tonic, adaptogenic, antitumour, anti- platelet aggregation, anti-inflammatory, antinociceptive ,and immune-modulating properties. It reduced the expression levels of inducible NO synthase (iNOS) ,COX,TNF-α, Beta Amyloid, and Caspase.
TargetsTNF-α | Beta Amyloid | Caspase
In vitro

Syringin from stem bark of Fraxinus rhynchophylla protects Abeta(25-35)-induced toxicity in neuronal cells.[Pubmed: 20422361]

Arch Pharm Res. 2010 Apr;33(4):531-8.

The medicinal herb Jinpi, derived from the dried stem barks of Fraxinus rhynchophylla belonging to Oleaceae is widely used as a variety of Korean folk remedies for anti-inflammatory, febricide, antidiarrhea, and antileukorrhea diseases.
METHODS AND RESULTS:
In the course of screening antidementia agents from natural products, F. rhynchophylla showed significant inhibitory activity toward Abeta(25-35)-induced neuronal cell death. An active principle was isolated and identified as Syringin.When the neuroblastoma cells were exposed to 50 microM Abeta(25-35), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction rate (survival rate) decreased to 60.21 +/- 2.16% over control while Syringin treated ones recovered cell viability up to 79.12 +/- 1.39% at 20 microM. In addition, 20 microM Syringin almost completely removed Abeta(25-35)-induced reactive oxygen species. The neuroprotective effect of Syringin seemed to be originated from the reduction of apoptosis since decrease in caspase-3 activity and expression, reduction in cleaved PARP, and DNA fragmentation were observed.
CONCLUSIONS:
These results suggest that F. rhynchophylla and Syringin are expected to be useful for preventing Abeta(25-35)-induced neuronal cell damage.

In vivo

Syringin may exert sleep-potentiating effects through the NOS/NO pathway.[Pubmed: 25377727]

Fundam Clin Pharmacol. 2015 Apr;29(2):178-84.

Sleep is essential for basic survival as well as for optimal physical and cognitive performance in both human beings and animals.
METHODS AND RESULTS:
To investigate the effect of Syringin on sleep of anesthetized mice and the potential mechanisms, 35 male Kunming mice were randomly divided into six experimental groups (n = 5) and one control group (n = 5). Sleep latency and sleep duration, as well as nitric oxide (NO) content and nitric oxide synthase (NOS) activity, were determined after Syringin administration. The NO precursor l-Arginine (l-Arg) or NOS inhibitor NG-Nitro-l-arginine methyl ester (l-NAME) was administered alone or in combination with Syringin, and time for sleep latency and duration was recorded. After intragastric administration of Syringin, sleep latency decreased in a dose- and time-dependent manner, concomitant with increased sleep duration. The optimal sleep performance was obtained when Syringin was given at a dose of 80 mg/kg for eight consecutive days. Syringin significantly reduced NO concentration and NOS activity. Administration of l-Arg prolonged sleep latency and shortened sleep duration, and the effects were fully reversed by Syringin coadministration. Administration of L-NAME induced a significant reduction in sleep latency and a corresponding increase in sleep duration, and coadministration of Syringin further enhanced the effects.
CONCLUSIONS:
The finding of our study demonstrated that Syringin could exert sleep-potentiating effects on anesthetized mice in a time- and dose-dependent manner, and these effects may be intimately correlated with the NO/NOS pathway.

Protocol of Syringin

Animal Research

Hepatoprotective effects of syringin on fulminant hepatic failure induced by D-galactosamine and lipopolysaccharide in mice.[Pubmed: 23620140]

Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin.[Pubmed: 15549657]

Planta Med. 2004 Nov;70(11):1027-32.

In the present study, Syringin, isolated by activity-guided fractionation of the ethyl acetate (EtOAc) extracts of the stem bark of Magnolia sieboldii, and sinapyl alcohol, the hydrolysate of Syringin, were evaluated for anti-inflammatory and antinociceptive activities.
METHODS AND RESULTS:
Sinapyl alcohol (20, 30 mg/kg/day, p. o.) inhibited increased vascular permeability by acetic acid in mice and reduced acute paw edema by carrageenan in rats more so than Syringin. When analgesic activity was measured using the acetic acid-induced writhing test and the hot plate test, sinapyl alcohol was much more potent than Syringin in a mouse model. In addition, sinapyl alcohol more potently inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO), prostaglandin E2 (PGE2), and tumor necrosis factor (TNF)-alpha production by macrophages than Syringin. Consistent with these observations, the expression levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 was reduced by sinapyl alcohol in a concentration-dependent manner.
CONCLUSIONS:
These results suggest that the anti-inflammatory and antinociceptive effects of Syringin after oral administration may be attributed to its in vivo transformation to sinapyl alcohol.

J Appl Toxicol. 2014 Mar;34(3):265-71.

Animal Models: BALB/c mice
Formulation: ---
Dosages:10, 30 and 100 mg/kg
Administration: i.p.

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Preparing Stock Solutions of Syringin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6853 mL 13.4264 mL 26.8528 mL 53.7057 mL 67.1321 mL
5 mM 0.5371 mL 2.6853 mL 5.3706 mL 10.7411 mL 13.4264 mL
10 mM 0.2685 mL 1.3426 mL 2.6853 mL 5.3706 mL 6.7132 mL
50 mM 0.0537 mL 0.2685 mL 0.5371 mL 1.0741 mL 1.3426 mL
100 mM 0.0269 mL 0.1343 mL 0.2685 mL 0.5371 mL 0.6713 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 Syringin

Syringin from stem bark of Fraxinus rhynchophylla protects Abeta(25-35)-induced toxicity in neuronal cells.[Pubmed:20422361]

Arch Pharm Res. 2010 Apr;33(4):531-8.

The medicinal herb Jinpi, derived from the dried stem barks of Fraxinus rhynchophylla belonging to Oleaceae is widely used as a variety of Korean folk remedies for anti-inflammatory, febricide, antidiarrhea, and antileukorrhea diseases. In the course of screening antidementia agents from natural products, F. rhynchophylla showed significant inhibitory activity toward Abeta(25-35)-induced neuronal cell death. An active principle was isolated and identified as Syringin. When the neuroblastoma cells were exposed to 50 microM Abeta(25-35), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction rate (survival rate) decreased to 60.21 +/- 2.16% over control while Syringin treated ones recovered cell viability up to 79.12 +/- 1.39% at 20 microM. In addition, 20 microM Syringin almost completely removed Abeta(25-35)-induced reactive oxygen species. The neuroprotective effect of Syringin seemed to be originated from the reduction of apoptosis since decrease in caspase-3 activity and expression, reduction in cleaved PARP, and DNA fragmentation were observed. These results suggest that F. rhynchophylla and Syringin are expected to be useful for preventing Abeta(25-35)-induced neuronal cell damage.

Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin.[Pubmed:15549657]

Planta Med. 2004 Nov;70(11):1027-32.

In the present study, Syringin, isolated by activity-guided fractionation of the ethyl acetate (EtOAc) extracts of the stem bark of Magnolia sieboldii, and sinapyl alcohol, the hydrolysate of Syringin, were evaluated for anti-inflammatory and antinociceptive activities. Sinapyl alcohol (20, 30 mg/kg/day, p. o.) inhibited increased vascular permeability by acetic acid in mice and reduced acute paw edema by carrageenan in rats more so than Syringin. When analgesic activity was measured using the acetic acid-induced writhing test and the hot plate test, sinapyl alcohol was much more potent than Syringin in a mouse model. In addition, sinapyl alcohol more potently inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO), prostaglandin E2 (PGE2), and tumor necrosis factor (TNF)-alpha production by macrophages than Syringin. Consistent with these observations, the expression levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 was reduced by sinapyl alcohol in a concentration-dependent manner. These results suggest that the anti-inflammatory and antinociceptive effects of Syringin after oral administration may be attributed to its in vivo transformation to sinapyl alcohol.

Syringin may exert sleep-potentiating effects through the NOS/NO pathway.[Pubmed:25377727]

Fundam Clin Pharmacol. 2015 Apr;29(2):178-84.

Sleep is essential for basic survival as well as for optimal physical and cognitive performance in both human beings and animals. To investigate the effect of Syringin on sleep of anesthetized mice and the potential mechanisms, 35 male Kunming mice were randomly divided into six experimental groups (n = 5) and one control group (n = 5). Sleep latency and sleep duration, as well as nitric oxide (NO) content and nitric oxide synthase (NOS) activity, were determined after Syringin administration. The NO precursor l-Arginine (l-Arg) or NOS inhibitor NG-Nitro-l-arginine methyl ester (l-NAME) was administered alone or in combination with Syringin, and time for sleep latency and duration was recorded. After intragastric administration of Syringin, sleep latency decreased in a dose- and time-dependent manner, concomitant with increased sleep duration. The optimal sleep performance was obtained when Syringin was given at a dose of 80 mg/kg for eight consecutive days. Syringin significantly reduced NO concentration and NOS activity. Administration of l-Arg prolonged sleep latency and shortened sleep duration, and the effects were fully reversed by Syringin coadministration. Administration of L-NAME induced a significant reduction in sleep latency and a corresponding increase in sleep duration, and coadministration of Syringin further enhanced the effects. The finding of our study demonstrated that Syringin could exert sleep-potentiating effects on anesthetized mice in a time- and dose-dependent manner, and these effects may be intimately correlated with the NO/NOS pathway.

Description

Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy.

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