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Cirsimarin

$807

  • Brand : BIOFRON

  • Catalogue Number : BD-P0893

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 13020-19-4

  • Formula : C23H24O11

  • Molecular Weight : 476.43

  • PUBCHEM ID : 159460

  • Volume : 25mg

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Catalogue Number

BD-P0893

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

476.43

Appearance

Powder

Botanical Source

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O)OC

Synonyms

5-hydroxy-6,6-dimethoxy-5-methyl-1-phenyl-3-hexanone/3-Hexanone,5-hydroxy-6,6-dimethoxy-5-methyl-1-phenyl/5-hydroxy-6,7-dimethoxyflavone-4'-glucoside

IUPAC Name

5-hydroxy-6,7-dimethoxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one

Applications

Density

1.523g/cm3

Solubility

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

Flash Point

265.8ºC

Boiling Point

767.1ºC at 760 mmHg

Melting Point

InChl

InChI=1S/C23H24O11/c1-30-15-8-14-17(19(27)22(15)31-2)12(25)7-13(33-14)10-3-5-11(6-4-10)32-23-21(29)20(28)18(26)16(9-24)34-23/h3-8,16,18,20-21,23-24,26-29H,9H2,1-2H3/t16-,18-,20+,21-,23-/m1/s1

InChl Key

RETJLKUBHXTIGH-FZFRBNDOSA-N

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#:13020-19-4) 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

30053449

Abstract

Cirsium japonicum var. ussuriense (Regel) Kitam. ex Ohwi (C. ussuriense) is known as “Dae-Gye” or “Korean milk thistle”. C. ussuriense have long been used as a folk medicinal plant for inflammatory diseases such as hepatitis, nephritis, and mastitis in Korea, China, and Japan. To reveal the anti-inflammatory components of C. ussuriense, we isolated three flavone glycosides (linarin, cirsimarin, and hispidulin-7-O-neohesperidoside) from the aerial part of C. ussuriense and evaluated their inhibitory effects on LPS-induced pro-inflammatory mediators in macrophages. We also investigated the involving molecular mechanisms of cirsimarin. Among three flavone glycosides, cirsimarin showed vastly superior inhibitory potency in LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production. Cirsimarin concentration-dependently inhibited LPS-induced inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein and mRNA levels in macrophages. Cirsimarin suppressed the production and mRNA expression of tumor necrosis factor- α (TNF-α) and interleukin (IL)-6 in LPS-stimulated RAW 264.7 and bone marrow-derived macrophages. Moreover, molecular data presented that cirsimarin down-regulated the phosphorylation of Janus kinase (JAK)/signal transducer and activator of transcriptions (STATs) and p38 mitogen-activated protein kinase (MAPK), and nuclear translocation of interferon regulatory factor (IRF)-3. Collectively, cirsimarin may be an active ingredient responsible for anti-inflammatory effects of C. ussuriense and it may act as a promising therapeutic against inflammatory diseases by suppressing the JAK/STAT and IRF-3 signaling pathway.

Copyright © 2018. Published by Elsevier B.V.

KEYWORDS

Cirsium japonicum var. ussuriense (Regel) Kitam. ex Ohwi; IRF3; JAK/STAT; Macrophage; p38 cirsimarin

Title

Cirsimarin, a flavone glucoside from the aerial part of Cirsium japonicum var. ussuriense (Regel) Kitam. ex Ohwi, suppresses the JAK/STAT and IRF-3 signaling pathway in LPS-stimulated RAW 264.7 macrophages.

Author

Han HS1, Shin JS2, Lee SB1, Park JC3, Lee KT4.

Publish date

2018 Sep 25;

PMID

29689498

Abstract

Cirsitakaoside is a natural compound isolated from Premna szemaoensis. However, the anti-inflammatory effects of cirsitakaoside are poorly understood. We investigated the anti-inflammatory action of cirsitakaoside in lipopolysaccharide (LPS)-stimulated macrophages and mice in vivo. Cirsitakaoside could suppress the production of pro-inflammatory cytokines such as interleukin-1β (IL-1β), interleukin-6 (IL-6) and tumor necrosis factor alpha (TNF-α) in a dose-dependent manner in LPS-stimulated mouse peritoneal macrophages and RAW264.7 cells. Cirsitakaoside also could inhibit inducible nitric oxide synthase (iNOS) mRNA and cyclooxygenase-2 (COX-2) mRNA expression in LPS-stimulated mouse peritoneal macrophages and RAW264.7 cells. These effects were partially carried out by inactivated nuclear factor-κB (NF-κB) and Mitogen-activated protein kinases (MAPKs) pathway via inhibiting the phosphorylation of the IKKα/β, IκBα and c-Jun N-terminal kinase/stress-activated protein kinase (JNK) in LPS-stimulated murine macrophages. In vivo, we showed that cirsitakaoside could relieve LPS-induced inflammation response. These results suggest that cirsitakaoside has the potential anti-inflammatory effect for treatment of inflammation diseases.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

Cirsitakaoside; Inflammation; LPS; Macrophage; NF-κB

Title

Cirsitakaoside isolated from Premna szemaoensis reduces LPS-induced inflammatory responses in vitro and in vivo.

Author

Zhu H1, Pu D2, Di Q3, Zhao X1, Ji F4, Li H1, Zhao Z4, Gao J5, Xiao W6, Chen W7

Publish date

2018 Jun

PMID

20458325

Abstract

OBJECTIVE:
We previously reported that the flavonoid cirsimarin exerts in vitro a strong lipolytic activity on isolated adipocytes. This study was therefore designed to evaluate in vivo the effects of cirsimarin on white adipose tissue (WAT) accretion in mice.

METHODS:
Male CD1 mice were injected daily with either vehicle (intraperitoneal (i.p.)) or cirsimarin (25 or 50 mg kg(-1) per day, i.p.) for 18 days. Mice were killed and fat pads weighted. Epididymal fat pads were used for cellularity measurement. Effects of cirsimarin treatment on lipolysis and lipogenesis in WAT were assessed.

RESULTS:
Mice treated with 25 or 50 mg kg(-1) per day cirsimarin showed a decrease in retroperitoneal (-29 and -37% respectively, P<0.005) and epididymal (-25 and -28% respectively, P<0.005) fat pad weights compared with controls. This effect was restricted to intra-abdominal WAT as no difference was noticed for subcutaneous inguinal WAT. The decrease in intra-abdominal WAT accretion was due to a decrease in adipose cell diameter (-5 and -8% for 25 and 50 mg kg(-1) per day cirsimarin, respectively) resulting in a 14 and 35% decrease in adipose cell volume while no change was noticed in total adipocyte number. Direct injection of cirsimarin (50 mg kg(-1)) to rats did not trigger lipolysis. In contrast, cirsimarin showed in vivo as well as in vitro a strong antilipogenic activity, which may be the critical aspect of its effects on fat accretion in mice. The inhibitory concentration 50% of cirsimarin on lipogenic activity in isolated adipocytes was found to be 1.28±0.04 μM. Cirsimarin given orally reduced intra-abdominal fat accretion in mice. CONCLUSION: Cirsimarin exerts potent antilipogenic effect and decreases adipose tissue deposition in mice. Cirsimarin could therefore be a potential candidate for the treatment of obesity.

Title

Cirsimarin, a potent antilipogenic flavonoid, decreases fat deposition in mice intra-abdominal adipose tissue.

Author

Zarrouki B1, Pillon NJ, Kalbacher E, Soula HA, Nia N'Jomen G, Grand L, Chambert S, Geloen A, Soulage CO.

Publish date

2010 Nov