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(-)-Syringaresinol di-O-glucoside

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-S4005

  • Specification : 98%(HPLC)

  • CAS number : 66791-77-3

  • Formula : C34H46O18

  • Molecular Weight : 742.71

  • PUBCHEM ID : 442830

  • Volume : 25mg

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Catalogue Number

BF-S4005

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

742.71

Appearance

Powder

Botanical Source

Eucommia ulmoides,Pittosporum illicioides,Sargentodoxa cuneata,Kalopanax septemlobus

Structure Type

Lignanoids

Category

SMILES

COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C3C4COC(C4CO3)C5=CC(=C(C(=C5)OC)OC6C(C(C(C(O6)CO)O)O)O)OC

Synonyms

(2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-6-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

IUPAC Name

(2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-6-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Applications

(+)-Syringaresinol-di-O-beta-D-glucoside, a phenolic compound from Acanthopanax senticosus Harms, suppresses proinflammatory mediators in SW982 human synovial sarcoma cells by inhibiting activating protein-1 and/or nuclear factor-kappaB activities. PUMID/DOI:DOI: 10.1016/j.tiv.2007.04.016 Toxicol In Vitro. 2007 Dec;21(8):1530-7. (+)-Syringaresinol-di-O-beta-D-glucoside (SR), syringin, and isofraxidin isolated from the stem bark of Acanthopanax senticosus Harms are its major constituents. The present work was undertaken to analyze effects of these compounds on inflammatory functions in SW982 human synovial sarcoma cell system. When cells were exposed to SR, syringin, or isofraxidin, only isofraxidin had significant inhibitory effects on cell growth, although a slight inhibition was observed at the highest concentration of SR. SR suppressed the production of IL-6 at lower concentrations than syringin and isofraxidin. SR and syringin significantly suppressed the production of prostaglandin E(2), while isofraxidin suppressed only slightly. SR was more potent than syringin and isofraxidin at inhibiting the expression of IL-1beta, IL-6, cyclooxygenase (COX)-2 and matrix metalloproteinases (MMP)-1 mRNA, but was less potent than syringin at inhibiting the expression of MMP-2. We further demonstrated that SR significantly reduced MMP-1 promoter luciferase activity and DNA-binding activity of transcriptional factors AP-1 and NF-kappaB. Taken together, these results suggest that SR, an active component of the stem bark of A. senticosus, modulates the inflammatory process involved in arthritis by suppressing various gene expression through inhibiting AP-1 and/or NF-kappaB activities.

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

519.7±34.3 °C

Boiling Point

935.7±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C34H46O18/c1-43-17-5-13(6-18(44-2)31(17)51-33-27(41)25(39)23(37)21(9-35)49-33)29-15-11-48-30(16(15)12-47-29)14-7-19(45-3)32(20(8-14)46-4)52-34-28(42)26(40)24(38)22(10-36)50-34/h5-8,15-16,21-30,33-42H,9-12H2,1-4H3/t15-,16-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30+,33+,34+/m1/s1

InChl Key

FFDULTAFAQRACT-NYYYOYJKSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:66791-77-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28941417

Abstract

Sargentodoxa cuneata, containing syringaresinol and its glycoside liriodendrin as the main bioactive compounds, is a well-known traditional Chinese medicine for treating intestinal inflammation. In our preliminary study, liriodendrin inhibited NF-kB activation in sepsis-induced acute lung injury. The present study was designed to investigate its effect on dextran sulfate sodium (DSS)-induced colitis in a mouse model and to explore the possible related mechanisms. Experimental colitis was established by giving mice drinking water containing 3% (w/v) DSS for 7days. The mice were pretreated with liriodendrin (100mg/kg/day, intragastrically) 3days before DSS treatment. We determined the effects of liriodendrin on disease activity index (DAI), colon length, histopathological examination, antioxidants, and anti-inflammatory activities. Our results showed that liriodendrin greatly decreased MPO and MDA activities and significantly increased SOD and GPx activities in the colon. Moreover, liriodendrin improved DAI, colon length and histological damage in colon and reduced the levels of pro-inflammatory cytokines, such as TNF-a, IL-1β and IL-6. Meanwhile, assessments by western blot revealed that liriodendrin significantly suppressed the activation of Akt and NF-κB pathways and up-regulated the expression of ERβ in the colon. In vitro, liriodendrin down-regulated production of pro-inflammatory cytokines and suppressed NF-κB signalling pathways in LPS-induced RAW 264.7 macrophages in a concentration-dependent manner. In addition, syringaresinol, the hydrolysate of liriodendrin, more potently down-regulated production of pro-inflammatory cytokines and suppressed NF-κB and Akt signalling pathways in LPS-induced RAW 264.7 macrophages,which were abolished by using a pure ER antagonist, ICI182, 780. Taken together, liriodendrin-mediated suppression of inflammatory damage in the colon may be attributable to the in vivo transformation to syringaresinol and liriodendrin may be a promising therapeutic approach preventive agent for colitis treatment.

KEYWORDS

Anti-Inflammatory activities; Antioxidants; ERβ; Liriodendrin; Ulcerative colitis.

Title

Protective role of liriodendrin in mice with dextran sulphate sodium-induced ulcerative colitis

Author

Zhen Zhang 1, Lei Yang 2, Botao Wang 1, Lanqiu Zhang 2, Qi Zhang 2, Dihua Li 2, Shukun Zhang 2, Hongwei Gao 3, Ximo Wang 4

Publish date

2017 Nov

PMID

27498121

Abstract

In current study, we investigated the role of liriodendrin, a constituent isolated from Sargentodoxa cuneata (Oliv.) Rehd. Et Wils (Sargentodoxaceae), in cecal ligation and puncture (CLP)-induced acute lung inflammatory response and injury (ALI). The inflammatory mediator levels in bronchoalveolar lavage fluid (BALF) were determined by enzyme-linked immunosorbent assay (ELISA). Pathologic changes in lung tissues were evaluated via pathological section with hematoxylin and eosin (H&E) staining. To investigate the mechanism whereby liriodendrin regulates lung inflammation, the phosphorylation of the NF-kB (p65) and expression of vascular endothelial growth factor (VEGF) were determined by western blot assay. We show that liriodendrin treatment significantly improved the survival rate of mice with CLP-induced sepsis. Pulmonary histopathologic changes, alveolar hemorrhage, and neutrophil infiltration were markedly decreased by liriodendrin. In addition, liriodendrin decreased the production of the proinflammatory mediators including (TNF-α, IL-1β, MCP-1, and IL-6) in lung tissues. Vascular permeability and lung myeloperoxidase (MPO) accumulation in the liriodendrin-treated mice were substantially reduced. Moreover, liriodendrin treatment significantly suppressed the expression of VEGF and activation of NF-kB in the lung. We further show that liriodendrin significantly reduced the production of proinflammatory mediators and downregulated NF-kB signaling in LPS-stimulated RAW 264.7 macrophage cells. Moreover, liriodendrin prevented the generation of reactive oxygen species (ROS) by upregulating the expression of SIRT1 in RAW 264.7 cells. These findings provide a novel theoretical basis for the possible application of liriodendrin in clinic.

KEYWORDS

ALI; NF-kB; VEGF; liriodendrin; sepsis.

Title

Protective Role of Liriodendrin in Sepsis-Induced Acute Lung Injury

Author

Lei Yang 1, Dihua Li 1, Yuzhen Zhuo 1, Shukun Zhang 1, Ximo Wang 1 2, Hongwei Gao 3

Publish date

2016 Oct

PMID

26236742

Abstract

The preparative purification of liriodendrin from Sargentodoxa cuneata using macroporous resin combined with crystallization process was evaluated. The properties of adsorption/desorption of liriodendrin on eight macroporous resins were investigated systematically. X-5 resin was selected as the most suitable medium for liriodendrin purification. The adsorption of liriodendrin on X-5 resin fitted well with the pseudo-second-order kinetic model and Langmuir isotherm model. Dynamic adsorption/desorption tests were performed using a glass column packed with X-5 resin to optimize the separation process of liriodendrin. After one treatment with X-5 resin, the content of liriodendrin in the product was increased 48.73-fold, from 0.85% to 41.42%, with a recovery yield of 88.9%. 97.48% liriodendrin was obtained by further crystallization and determined by HPLC. The purified product possessed strong antioxidant activity. In conclusion, purification of liriodendrin might expend its further pharmacological researches and further applications in pharmacy.

Title

Preparative Purification of Liriodendrin from Sargentodoxa cuneata by Macroporous Resin

Author

Di-Hua Li 1, Yan Wang 2, Yuan-Shan Lv 1, Jun-Hong Liu 1, Lei Yang 1, Shu-Kun Zhang 1, Yu-Zhen Zhuo 1

Publish date

2015