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3,6-Disinapoyl sucrose

$312

  • Brand : BIOFRON

  • Catalogue Number : BN-O1773

  • Specification : 98%(HPLC)

  • CAS number : 76656-80-9

  • Formula : C34H42O19

  • Molecular Weight : 754.7

  • PUBCHEM ID : 11968389

  • Volume : 20mg

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Catalogue Number

BN-O1773

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

754.7

Appearance

Botanical Source

Structure Type

Category

SMILES

Synonyms

3-O-[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]-beta-D-fructofuranosyl alpha-D-glucopyranoside 6-[3-(4-hydroxy-3,5-dimethoxyphenyl)-2-propenoate]

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Density

1.56±0.1 g/cm3 (20 ºC 760 Torr)

Solubility

Flash Point

Boiling Point

Melting Point

138-141 ºC

InChl

InChl Key

FHIJMQWMMZEFBL-OPSYHMPNSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:76656-80-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

24488601

Abstract

3,6′-Disinapoyl sucrose (DISS) is an oligosaccharide ester natural product originating from the root of wild Polygala tenuifolia. Our previous reports suggested that DISS can have neuroprotective effects and antidepressive activity in rats, at least in part, by increased expression of cyclic AMP response element (CRE)-binding protein (CREB) and its downstream target protein, brain-derived neurotrophic factor (BDNF). The aim of the present study was to explore the mechanism of DISS-modulated BDNF and CREB expression. In this study, we confirmed its neuroprotective effect by showing that DISS, at concentrations above 30 μM, could promote the neuron cell viability and protected the glutamate and H2O2-induced toxicity in the human neuroblastoma (SH-SY5Y) cell line. DISS treatment also increased acute (from 15 to 30 min) BDNF expression and CREB phosphorylation in a dose-dependent manner. Pharmacological inhibition of mitogen-activated protein kinase 1 (ERK1/2), CaMKII, and Trk (with U0126, KN93, or K252a, respectively) partially attenuated the stimulatory effect of DISS on phospho-CREB and BDNF expression; however, it was not inhibited by pharmacological inhibition of PKA or PI3K (with H89 and LY294002, respectively). The results are consistent with the effects of DISS on CRE-directed gene transcription, as U0126 and KN-93 treatment also blocked the DISS-induced expression of the CRE-luciferase reporter gene. The results from the present study suggest that DISS-mediated regulation of BDNF gene expression is associated with CREB-mediated transcription of BDNF and upstream activation of ERK1/2 and CaMKII. Finally, DISS may exert neuroprotective and antidepressant effects through these signaling pathways in neuronal cells.

Title

Neuroprotective effects of 3,6'-disinapoyl sucrose through increased BDNF levels and CREB phosphorylation via the CaMKII and ERK1/2 pathway.

Author

Hu Y1, Liu MY, Liu P, Dong X, Boran AD.

Publish date

2014 Aug

PMID

21585386

Abstract

OBJECTIVE:
The present study was designed to observe the effects of 3,6′-disinapoyl sucrose (DISS), an active oligosaccharide ester component obtained from the roots of Polygala tenuifolia Willd., on behavioral and biochemical aspects of depression induced by chronic mild stress (CMS) in rats. It is the first exploration of the possible association between DISS’s antidepressant-like effects and biochemical markers of depression, and involved measuring monoamine oxidase (MAO) activity, cortisol levels, superoxide dismutase (SOD) activity and malondialdehyde (MDA) levels.

METHODS:
Rats were exposed to stressor once daily for consecutive 5 weeks. DISS and a positive control drug, fluoxetine, were administered via gastric intubation to once daily for consecutive 3 weeks from the third week.

KEY FINDINGS:
The results showed that rats subjected to CMS exhibit a reduction in sucrose intake. Conversely, brain MAO-A and MAO-B activity, plasma cortisol levels, and MDA levels were increased, while SOD activity was decreased following CMS exposures. DISS significantly inhibited MAO-A and MAO-B activity and blocked plasma elevated cortisol level, an indicator of the hypothalamic-pituitary-adrenal (HPA) axis. In addition, DISS increases SOD activity, inhibits lipid peroxidation, and lessens production of MDA.

CONCLUSION:
These results suggest that DISS may possess potent and rapid antidepressant properties, which are mediated via MAO, the HPA axis and oxidative systems. These antidepressant actions make DISS a potentially valuable drug for the treatment of depression.

© 2011 The Authors. JPP © 2011 Royal Pharmaceutical Society.

Title

Possible mechanism of the antidepressant effect of 3,6'-disinapoyl sucrose from Polygala tenuifolia Willd.

Author

Hu Y1, Liu M, Liu P, Guo DH, Wei RB, Rahman K.

Publish date

2011 Jun

PMID

20018220

Abstract

Recent studies suggest that the behavioral effects of chronic antidepressant treatment are mediated by stimulation of hippocampal neuronal plasticity and neurogenesis. The present study was designed to examine the effects of 3,6′-disinapoyl sucrose (DISS), a bioactive component of Polygala tenuifolia Willd, on the expressions of four plasticity-associated genes: cell adhesion molecule L1 (CAM-L1), laminin, cAMP response element binding protein (CREB) and brain-derived neurotrophic factor (BDNF) in hippocampus, all of which are involved in neuronal plasticity and neurite outgrowth. We confirmed that chronic stress in rats caused a reduction in sensitivity to reward (sucrose consumption) and a decrease in mRNA levels of CAM-L1, laminin, and BDNF, together with a decrease in protein levels of phosphorylated CREB and BDNF. Repeated administration of DISS for 21 days at doses of 5, 10 and 20mg/kg reversed stress-induced alterations in sucrose consumption and these target mRNA and protein levels. In conclusion, increased expressions in the hippocampus of three noradrenergic-regulated plasticity genes and one neurotrophic factor may be one of the molecular and cellular mechanisms underlying the antidepressant action of DISS in chronic mild stress (CMS) rats.

Copyright (c) 2009 Elsevier Ltd. All rights reserved.

Title

Antidepressant-like effects of 3,6'-disinapoyl sucrose on hippocampal neuronal plasticity and neurotrophic signal pathway in chronically mild stressed rats.

Author

Hu Y1, Liao HB, Dai-Hong G, Liu P, Wang YY, Rahman K

Publish date

2010 Feb


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