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Decursinol angelate

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-D1007

  • Specification : 98%

  • CAS number : 130848-06-5

  • Formula : C19H20O5

  • Molecular Weight : 328.364

  • PUBCHEM ID : 776123

  • Volume : 20mg

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Catalogue Number

BF-D1007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

328.364

Appearance

Powder

Botanical Source

Peucedanum purpurea

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

2-Butenoic acid, 2-methyl-, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-7-yl ester, (2Z)-/(7S)-8,8-Dimethyl-2-oxo-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-7-yl (2Z)-2-methyl-2-butenoate/LXU5241LCL/Decursinol angelate

IUPAC Name

[(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate

Applications

Decursinol angelate, a cytotoxic and protein kinase C (PKC) activating agent from the root of Angelica gigas, possesses anti-tumor and anti-inflammatory activities[1][2].

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

93-94 ºC

InChl

InChI=1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/b11-5-/t16-/m0/s1

InChl Key

AGABNGOXUSXQDD-XKGFZTIGSA-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#:130848-06-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30060484

Abstract

Inflammation is considered the root cause of various inflammatory diseases, including cancers. Decursinol angelate (DA), a pyranocoumarin compound obtained from the roots of Angelica gigas, has been reported to exhibit potent anti-inflammatory effects. In this study, the anti-inflammatory effects of DA on the MAP kinase and NFκB signaling pathways and the expression of pro-inflammatory cytokines were investigated in phorbol 12-myristate 13-acetate (PMA)-activated human promyelocytic leukemia (HL-60) and lipopolysaccharide (LPS)-stimulated macrophage (Raw 264.7) cell lines. PMA induced the activation of the MAP kinase-NFκB pathway and the production of pro-inflammatory cytokines in differentiated monocytes. Treatment with DA inhibited the activation of MAP kinases and the translocation of NFκB, and decreased the expression and exogenous secretion of IL-1β and IL-6. Furthermore, LPS-stimulated Raw 264.7 cells were found to have increased expression of M1 macrophage-associated markers, such as NADPH oxidase (NOX) and inducible nitric oxide synthase (iNOS), and the M2 macrophage-associated marker CD11b. LPS also activated pro-inflammatory cytokines and Erk-NFκB. Treatment with DA suppressed LPS-induced macrophage polarization and the inflammatory response by blocking Raf-ERK and the translocation of NFκB in Raw 264.7 cells. Treatment with DA also inhibited the expression of pro-inflammatory cytokines, such as IL-1β and IL-6, NOX, and iNOS in Raw 264.7 cells. These results suggest that DA has the potential to inhibit macrophage polarization and inflammation by blocking the activation of pro-inflammatory signals. These anti-inflammatory effects of DA may contribute to its potential use as a therapeutic strategy against various inflammation-induced cancers.

KEYWORDS

MAP kinase; NFκB; cytokines; decursinol angelate; inflammation

Title

Decursinol Angelate Inhibits LPS-Induced Macrophage Polarization through Modulation of the NFκB and MAPK Signaling Pathways.

Author

Islam SU1, Lee JH2, Shehzad A3, Ahn EM4, Lee YM5, Lee YS6.

Publish date

2018 Jul 27

PMID

29134229

Abstract

Epidemiological studies have shown that inflammation plays a critical role in the development and progression of various chronic diseases, including cancers, neurological diseases, hepatic fibrosis, diabetic retinopathy, and vascular diseases. Decursin and decursinol angelate (DA) are pyranocoumarin compounds obtained from the roots of Angelica gigas. Several studies have described the anti-inflammatory effects of decursin and DA. Decursin and DA have shown potential anti-inflammatory activity by modulating growth factors such as vascular endothelial growth factor, transcription factors such as signal transducer and activator of transcription 3 and nuclear factor kappa-light-chain-enhancer of activated B cells, cellular enzymes including matrix metalloproteinases cyclooxygenase, and protein kinases such as extracellular receptor kinase, phosphatidylinositol-3-kinase, and protein kinase C. These compounds have the ability to induce apoptosis by activating pro-apoptotic proteins and the caspase cascade, and reduced the expression of anti-apoptotic proteins such as B-cell lymphoma 2 and B-cell lymphoma-extra-large. Interaction with multiple molecular targets and cytotoxic effects, these two compounds are favorable candidates for treating various chronic inflammatory diseases such as cancers (prostate, breast, leukemia, cervical, and myeloma), rheumatoid arthritis, diabetic retinopathy, hepatic fibrosis, osteoclastogenesis, allergy, and Alzheimer’s disease. We have summarized the preliminary studies regarding the biological effects of decursin and DA. In this review, we will also highlight the functions of coumarin compounds that can be translated to a clinical practice for the treatment and prevention of various inflammatory ailments.

KEYWORDS

Cancer; Decursin; Decursinol angelate; Disease; Inflammation

Title

Decursin and decursinol angelate: molecular mechanism and therapeutic potential in inflammatory diseases.

Author

Shehzad A1, Parveen S1, Qureshi M1, Subhan F2, Lee YS3.

Publish date

2018 Mar

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