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Decursin

$392

  • Brand : BIOFRON

  • Catalogue Number : BD-P0614

  • Specification : 98.0%(HPLC)

  • CAS number : 5928-25-6

  • Formula : C19H20O5

  • Molecular Weight : 328.36

  • PUBCHEM ID : 442126

  • Volume : 20mg

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Catalogue Number

BD-P0614

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

328.36

Appearance

Powder

Botanical Source

This product is isolated and purified from the roots of Peucedanum ostruthium

Structure Type

Category

SMILES

CC(=CC(=O)OC1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C)C

Synonyms

(S)-7,8-Dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo(1,2-b:5,4-b')dipyran-7-yl 3-methyl-2-butenoate/2-Butenoic acid, 3-methyl-, 7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo(1,2-b:5,4-b')dipyran-7-yl ester, (S)-/(7S)-8,8-dimethyl-2-oxo-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-7-yl 3-methylbut-2-enoate/2-Butenoic acid, 3-methyl-, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-7-yl ester/(7S)-8,8-Dimethyl-2-oxo-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-7-yl 3-methyl-2-butenoate/(S)-8,8-Dimethyl-2-oxo-7,8-dihydro-2H,6H-pyrano(3,2-g)chromen-7-yl 3-methyl-2-butenoate

IUPAC Name

Applications

Decursin inhibits induction of inflammatory mediators by blocking nuclear factor-kappaB activation in macrophages.[Pubmed: 16510559 ]Mol Pharmacol. 2006 Jun;69(6):1783-90. In the course of screening inhibitors of matrix metalloproteinase (MMP)-9 induction in macrophages, we isolated Decursin, a coumarin compound, from the roots of Angelicae gigas. As a marker for the screening and isolation, we tested expression of MMP-9 in RAW264.7 cells and THP-1 cells after treatment with bacterial lipopolysaccharide (LPS), the TLR-4 ligand. METHODS AND RESULTS: Decursin suppressed MMP-9 expression in cells stimulated by LPS in a dose-dependent manner at concentrations below 60 microM with no sign of cytotoxicity. The suppressive effect of Decursin was observed not only in cells stimulated with ligands for TLR4, TLR2, TLR3, and TLR9 but also in cells stimulated with interleukin (IL)-1beta, and tumor necrosis factor (TNF)-alpha, indicating that the molecular target of Decursin is common signaling molecules induced by these stimulants. In addition to the suppression of MMP-9 expression, Decursin blocked nitric oxide production and cytokine (IL-8, MCP-1, IL-1beta, and TNF-alpha) secretion induced by LPS. To find out the molecular mechanism responsible for the suppressive effect of Decursin, we analyzed signaling molecules involved in the TLR-mediated activation of MMP-9 and cytokines. Decursin blocked phosphorylation of IkappaB and nuclear translocation of NF-kappaB in THP-1 cells activated with LPS. Furthermore, expression of a luciferase reporter gene under the promoter containing NF-kappaB binding sites was blocked by Decursin. CONCLUSIONS: These data indicate that Decursin is a novel inhibitor of NF-kappaB activation in signaling induced by TLR ligands and cytokines.

Density

1.2±0.1 g/cm3

Solubility

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

Flash Point

206.6±28.8 °C

Boiling Point

469.4±45.0 °C at 760 mmHg

Melting Point

93-94ºC

InChl

InChl Key

CUKSFECWKQBVED-INIZCTEOSA-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#:5928-25-6) 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

31383251

Abstract

In this study, the anti-inflammatory effects of α-lipoic acid (LA) and decursinol (Dec) hybrid compound LA-Dec were evaluated and compared with its prodrugs, LA and Dec. LA-Dec dose-dependently inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO) generation in BV2 mouse microglial cells. On the other hand, no or mild inhibitory effect was shown by the Dec and LA, respectively. LA-Dec demonstrated dose-dependent protection from activation-induced cell death in BV2 cells. LA-Dec, but not LA or Dec individually, inhibited LPS-induced increased expressions of induced NO synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins in a dosedependent manner in both BV2 and mouse macrophage, RAW264.7 cells. Furthermore, LA-Dec inhibited LPS-induced expressions of iNOS, COX-2, interleukin-6, tumor necrosis factor-α, and interleukin-1β mRNA in BV2 cells, whereas the same concentration of LA or Dec was ineffective. Signaling studies demonstrated that LA-Dec inhibited LPS-activated signal transducer and activator of transcription 3 and protein kinase B activation, but not nuclear factor-kappa B or mitogen-activated protein kinase signaling. The data implicate LA-Dec hybrid compound as a potential therapeutic agent for inflammatory diseases of the peripheral and central nervous systems. [BMB Reports 2019; 52(8): 508-513].

Title

An alpha-lipoic acid-decursinol hybrid compound attenuates lipopolysaccharide-mediated inflammation in BV2 and RAW264.7 cells.

Author

Kwon MY1, Park J1, Kim SM1, Lee J1, Cho H2, Park JH3, Han IO1.

Publish date

2019 Aug

PMID

31351099

Abstract

Decursinol angelate (DA) is a pyranocoumarin purified from the roots of Angelica gigas. Here, we synthesized DA and determined its anti-inflammatory potential on TPA-induced mice ear inflammation. First, we evaluated the non-toxic behaviour of DA on HaCaT cells. Additionally, we observed the free radical scavenging potential of DA at 60 μM to be 50%. This finding was further supported by nitric oxide assay, malondialdehyde assay, H2DCFDA staining and western blotting analysis of antioxidant enzymes. DA also suppressed the activation and polarization of macrophage phagocytic activity on RAW 264.7 cells. We further evaluated the expression of ICAM-1, MCP-1, MIP-2 and MIP-1β on in-vivo model system. Consequently, DA significantly reduced the production of NF-κB and COX-2 induced proinflammatory cytokine levels on TPA induced ear edema. Inhibition of MAPK and transcriptional factor NF-κB was also validated by western blotting analysis of p-ERK, p-p38, IKKα, IKKγ, IκBα, NF-κB-p65. Immunohistochemistry and immunofluorescence staining of NFκB-p65, TNF-α and IL-1β were also performed to support the findings. Conclusively, these results suggest that topical administration of DA significantly inhibited the expression of pro-inflammatory cytokines by blocking the canonical NF-κB and MAPK pathway. Therefore, we suggest DA as a potent therapeutic compound against skin inflammation related diseases.

Copyright © 2019 Elsevier Ltd. All rights reserved.

KEYWORDS

12-O-Tetradecanoylphorbol-13-acetate; Decursinol angelate; Macrophage activation; NF-κB; Oxidative stress

Title

Decursinol angelate ameliorates 12-O-tetradecanoyl phorbol-13-acetate (TPA) -induced NF-κB activation on mice ears by inhibiting exaggerated inflammatory cell infiltration, oxidative stress and pro-inflammatory cytokine production.

Author

Chang SN1, Khan I2, Dey DK1, Cho KH3, Hwang BS4, Bae KB5, Kang SC6, Park JG5.

Publish date

2019 Oct

PMID

31261662

Abstract

Ionic liquids (ILs) have gained much attention as alternative solvents to volatile organic solvents due to their attractive properties. This study aimed to develop an efficient method for the selective separation of decursin (D) and decursinol angelate (DA) from Angelica gigas Nakai (A. gigas) using ILs and crystallization. The IL 1-butyl-3-methylimidazolium tetrafluoroborate ((BMIm)BF4) was the most efficient at extracting D and DA. Parameters including solid-to-liquid ratio, time, and temperature were optimized by response surface methodology (RSM). Under optimal extraction conditions (1 g/6.5 mL solid-to-liquid ratio, 60 °C temperature, and 120 min time), the extraction yields of D and DA were 43.32 mg/g (97.06%) and 17.87 mg/g (97.12%), respectively. Moreover, drowning out crystallization using deionized water (DW) as an anti-solvent offered an excellent ability to recover D and DA from the A. gigas-(BMIm)BF4 extraction solution. The rates of recovery and the total purity of D and DA were found to be greater than 97%. Therefore, a rapid and efficient method of combining ILs with crystallization was effectively achieved for the selective separation of D and DA. This approach is assumed to be beneficial in the pharmaceutical industry for the effective obtention of D- and DA-enriched products.

KEYWORDS

Angelica gigas Nakai; crystallization; decursin; decursinol angelate; ionic liquids

Title

Rapid and Efficient Separation of Decursin and Decursinol Angelate from Angelica gigas Nakai using Ionic Liquid, (BMIm)BF4, Combined with Crystallization.

Author

Kiyonga AN1, An JH1, Lee KY2, Lim C1, Suh YG1, Chin YW3, Jung K4.

Publish date

2019 Jun 28