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Prim-O-glucosylcimifugin

$116

  • Brand : BIOFRON

  • Catalogue Number : BD-D1338

  • Specification : 98%(HPLC)

  • CAS number : 80681-45-4

  • Formula : C22H28O11

  • Molecular Weight : 468.45

  • PUBCHEM ID : 14034912

  • Volume : 20MG

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Catalogue Number

BD-D1338

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

468.45

Appearance

White crystalline powder

Botanical Source

Stephania tetrandra S.Moore/Angelica, Diplolophium, Eranthis, Ledebouriella and Saposhnikovia spp

Structure Type

Chromones

Category

Standards;Natural Pytochemical;API

SMILES

CC(C)(C1CC2=C(O1)C=C3C(=C2OC)C(=O)C=C(O3)COC4C(C(C(C(O4)CO)O)O)O)O

Synonyms

5H-Furo[3,2-g][1]benzopyran-5-one, 7-[(β-D-glucopyranosyloxy)methyl]-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-4-methoxy-, (2S)-/HMS2196A10/[(2S)-2-(2-Hydroxypropan-2-yl)-4-methoxy-5-oxo-2,3-dihydro-5H-furo[3,2-g]chromen-7-yl]methyl β-D-glucopyranoside/N1606/[(2S)-2-(2-Hydroxy-2-propanyl)-4-methoxy-5-oxo-2,3-dihydro-5H-furo[3,2-g]chromen-7-yl]methyl β-D-glucopyranoside/Prim-O-glucosylcimifugin

IUPAC Name

(2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one

Applications

Prim-O-glucosylcimifugin exerts anti-inflammatory effects through the inhibition of iNOS and COX-2 expression by through regulating JAK2/STAT3 signaling.

Density

1.5±0.1 g/cm3

Solubility

Methanol

Flash Point

255.0±26.4 °C

Boiling Point

736.9±60.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:80681-45-4) 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

28839360

Abstract

BACKGROUND:
Radix Saposhnikoviae (RS) exerts anti-inflammatory, analgesic, antipyretic, antioxidation effects and has been used in traditional Chinese medicine to treat common colds, headache, and rheumatoid arthritis. Prim-O-glucosylcimifugin (POG) is the highest content chromone and one of the major active constituents in RS.

OBJECTIVE:
The study was aimed to explore the anti-inflammation effects of POG in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages.

MATERIALS AND METHODS:
Cell viability was detected by Cell Counting Kit-8 assay. Production of nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), and IL-6 was assessed by enzyme-linked immunosorbent assay. Real-time polymerase chain reaction and Western blot were performed to analyze mRNA and protein levels, respectively.

RESULTS:
During the whole experiment, 15, 50, and 100 μg/mL of POG had no cytotoxicity on RAW 264.7 cells. POG dose-dependently inhibited the production of NO, TNF-α, IL-1β, and IL-6 that were induced by LPS. POG treatment downregulated the mRNA and protein expression inducible NO synthase (iNOS) and cyclooxygenase 2 (COX-2) in LPS-activated RAW 264.7 macrophages in a concentration-dependent manner. Furthermore, LPS-induced JAK2/STAT3 activation was prevented in RAW 264.7 macrophages by POG treatment. STAT3 overexpression significantly reversed the effects of POG on LPS-activated RAW 264.7 macrophages.

CONCLUSION:
These results demonstrate that POG exerts anti-inflammatory effects through the inhibition of iNOS and COX-2 expression by inhibiting the phosphorylation of JAK2/STAT3.

SUMMARY:
POG exerts anti-inflammatory effects in RAW 264.7 macrophages through the inhibition of iNOS and COX-2 expression by inhibiting JAK2/STAT3 signaling. Abbreviations used: LPS: Lipopolyssacharide; NO: Nitric oxide; TNF-α: Tumor necrosis factor-α; IL: Interleukin; RS: Radix Saposhnikoviae; POG: Prim-O-glucosylcimifugin; iNOS: Inducible NO synthase; COX2: Cyclooxygenase; FBS: Fetal bovine serum; DMSO: Dimethylsulfoxide; CCK-8: Cell Counting Kit; RIPA: Radio immunoprecipitation assay buffer; ECL: Enhanced chemiluminescence; SD: Standard deviation; ELISA: Enzyme-Linked immunosorbent assay.

KEYWORDS

Anti-inflammation; JAK2/STAT3; cytokines; nitric oxide; prim-O-glucosylcimifugin

Title

Prim-O-glucosylcimifugin Attenuates Lipopolysaccharideinduced Inflammatory Response in RAW 264.7 Macrophages.

Author

Zhou J1, Sun YY2, Sun MY3, Mao WA4, Wang L1, Zhang J1, Zhang H2,4.

Publish date

2017 Jul-Sep;

PMID

28692435

Abstract

Prim-O-glucosylcimifugin is a major constituent in Radix Saposhnikovia that has been long used for the treatment of pyrexia, rheumatism, and cancer in traditional Chinese medicine. However, the molecular and cellular mechanisms remain unknown regarding the therapeutic effect of prim-O-lucosylcimifugin. Here, we investigated the effects of prim-O-glucosylcimifugin on cell cycle progression and apoptosis in human acute lymphoblastic leukemia cells. Prim-O-glucosylcimifugin treatment resulted in marked increases in cell apoptosis and cell cycle arrest at the G2/M phase. Mechanistically, prim-O-glucosylcimifugin induced the degradation of β-tubulin and downregulated phosphorylated CDK1 levels, a molecular indicator in the G2/M cell cycle arrest. Furthermore, activation of caspase-3, caspase-8, and caspase-9 was involved in the prim-O-glucosylcimifugin-induced apoptosis. Our study reveals the anticancer activity of prim-O-glucosylcimifugin and the potential underlying mechanisms.

Title

Prim-O-glucosylcimifugin induces cell cycle arrest and apoptosis in acute lymphoblastic leukemia cells.

Author

Zhang L1, Liu X, Lu X, Huang C.

Publish date

2017 Oct

PMID

31462297

Abstract

BACKGROUND:
Myeloid-derived suppressor cells (MDSCs) are immunosuppressive cells that play an important role in immune evasion, PD-1/PD-L1 inhibitor tolerance and tumour progression. Therefore, MDSCs are potential targets for cancer immunotherapy. In this study, we screened an effective polymorphonuclear MDSC (PMN-MDSC) inhibitor from the Traditional Chinese Medicine Library and evaluated its synergistic antitumour effects with PD-1 inhibitor.

METHODS:
In the present study, we found that PMN-MDSCs accumulate heavily in the spleen and bone marrow of melanoma (B16-F10) tumour-bearing mice. Then, we determined the top 10 key proteins in the upregulated KEGG pathways of PMN-MDSCs in tumour-bearing mice through proteomics and Cytoscape analysis. The key proteins were then used as targets for the screening of PMN-MDSC inhibitors from the traditional Chinese Medicine Library (20000 compounds) through molecular docking and weight calculation of the docking score. Finally, the inhibitory effect of the inhibitor was verified through proteomics and metabolomics analysis in vitro and melanoma (B16-F10) and triple-negative breast cancer (4 T1) mouse tumour models in vivo.

RESULTS:
Traditional Chinese medicine saposhnikovia root extract Prim-O-glucosylcimifugin (POG) could bind well to the target proteins and inhibit the proliferation, metabolism and immunosuppressive ability of PMN-MDSCs by inhibiting arginine metabolism and the tricarboxylic acid cycle (TCA cycle). POG could also increase CD8 T-lymphocyte infiltration in the tumours and enhance the antitumour effect of PD-1 inhibitor in B16-F10 and 4 T1 mouse tumour models.

CONCLUSIONS:
POG was successfully screened from the traditional Chinese Medicine library as a PMN-MDSC inhibitor. POG exhibited a good synergistic antitumour effect with PD-1 inhibitor. This study provided a potential option for enhancing the efficacy of PD-1 inhibitors in clinical applications.

KEYWORDS

Metabolism; Myeloid-derived suppressor cells; PD-1 inhibitor; Prim-O-glucosylcimifugin; Proliferation

Title

Prim-O-glucosylcimifugin enhances the antitumour effect of PD-1 inhibition by targeting myeloid-derived suppressor cells.

Author

Gao W1, Zhang X1, Yang W1, Dou D2, Zhang H1, Tang Y1, Zhong W1, Meng J1, Bai Y3, Liu Y4, Yang L4, Chen S4, Liu H5,6, Yang C7,8, Sun T9,10.

Publish date

2019 Aug 28