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7,8-Dihydroxycoumarin

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-D2015

  • Specification : 98%

  • CAS number : 486-35-1

  • Formula : C9H6O4

  • Molecular Weight : 178.14

  • PUBCHEM ID : 5280569

  • Volume : 20mg

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Catalogue Number

BF-D2015

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

178.14

Appearance

Off-White crystalline powder

Botanical Source

Euphorbia lathyris,Matricaria chamomilla,Artemisia argyi,Daphne odora,Artemisia dracunculus var. turkestanica

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=C(C2=C1C=CC(=O)O2)O)O

Synonyms

Daphnetin/7,8-Dihydroxychromen-2-one/7,8-Dihydroxycoumarin/7,8-dihydroxy-coumarin/2H-1-Benzopyran-2-one, 7,8-dihydroxy-/7,8-Dihydroxy-2H-chromen-2-one/7,8-Dihydroxy-2H-1-benzopyran-2-one/TCMDC-125839

IUPAC Name

7,8-dihydroxychromen-2-one

Density

1.6±0.1 g/cm3

Solubility

Soluble to 35 mg/mL(196.47 mM) in DMSO

Flash Point

184.5±22.2 °C

Boiling Point

430.4±45.0 °C at 760 mmHg

Melting Point

265-268°C (dec.)

InChl

InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H

InChl Key

ATEFPOUAMCWAQS-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:486-35-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31521691

Abstract

AIMS:
Daphnetin (DAP) is a traditional Chinese drug usually used to treat cardiovascular diseases. Studies have confirmed the anti-inflammatory, antioxidant, anti-bacterial and insecticidal, anti-tumor and neuro-protective effects of DAP. However, its anti-arthritic potential remains unexplored. The aim of this study is to investigate the in vitro and in vivo chondroprotective effects of DAP.

MAIN METHODS:
The effect of DAP on primary rabbit chondrocytes was examined using recombinant human IL-1β for 24 h. For the in vivo studies, rabbits were randomly divided into groups: a normal control group and osteoarthritis (OA) groups. The OA groups received three different doses of DAP for 4 or 8 weeks. The anti-arthritic effect of DAP was assessed using histopathological examinations, qRT-PCR, western blotting and immunohistochemical analysis.

KEY FINDINGS:
Both in vitro and in vivo results indicate that DAP exerts a protective effect against IL-1β in chondrocytes. In vitro, DAP inhibits the expression of IL-6, IL-12, MMP-3, MMP-9 and MMP-13, induced by IL-1β in rabbit chondrocytes, and stimulates the production of IL-10. The inhibitory effect of DAP on the MMPs is partially regulated by the inhibition of the PI3K/AKT, MAPK and NF-κB signaling pathways. The effect of DAP on OA may be attributed to the suppression of inflammatory factor secretion, chondrocyte apoptosis observed by the decrease in pro-apoptotic Caspase-3 and BAX, and the activation of anti-apoptotic BCL-2.

SIGNIFICANCE:
DAP has a broad range of prospects in the treatment of OA, which provides a novel therapeutic strategy for OA.

Copyright © 2019 The Authors. Published by Elsevier Inc. All rights reserved.

KEYWORDS

Anti-arthritic; Chondrocytes; Chondroprotective; Daphnetin; Osteoarthritis

Title

Chondroprotective and antiarthritic effects of Daphnetin used in vitro and in vivo osteoarthritis models.

Author

Zhang X1, Yao J2, Wu Z1, Zou K1, Yang Z3, Huang X3, Luan Z3, Li J4, Wei Q5.

Publish date

2020 Jan 1

PMID

31198004

Abstract

OBJECTIVE:
To investigate the effect of daphnetin (DAP) combined with insulin-like growth factor 1 (IGF-1) gene transfection on chondrogenic differentiation of adipose-derived mesenchymal stem cells (ADSCs) in rats.

METHODS:
Rat ADSCs were isolated and amplified by enzymatic digestion. The third generation ADSCs were treated with IGF-1 gene transfection as experimental group and normal ADSCs as control group. The cells of the two groups were treated with different concentrations of DAP (0, 30, 60, 90 μg/mL), respectively. Cell proliferation was detected by cell counting kit 8 (CCK-8) after cultured for 72 hours. After 14 days, real-time fluorescence quantitative PCR and Western blot were used to detect the mRNA and protein expressions of chondrocyte markers (collagen type Ⅱ and Aggrecan) in each group; and toluidine blue staining and collagen type Ⅱ immunohistochemical staining were performed.

RESULTS:
CCK-8 assay showed that with the increase of DAP concentration, the cell absorbance ( A) value of the control group and the experimental group increased gradually ( P<0.05). At the same DAP concentration, the cell A value of the experimental group was significantly higher than that of the control group ( P<0.05). Real-time fluorescence quantitative PCR and Western blot showed that with the increase of DAP concentration, the relative mRNA and protein expressions of collagen type Ⅱ and Aggrecan in the control group did not change significantly, and there was no significant difference among the different concentration groups ( P>0.05). But the mRNA and protein expressions of collagen type Ⅱ and Aggrecan in the experimental group increased gradually, and the 60 and 90 μg/mL DAP concentration groups were significantly higher than 0 μg/mL DAP concentration group ( P<0.05). At the same DAP concentration, the relative mRNA and protein expressions of collagen type Ⅱ and Aggrecan were significantly higher in the experimental group than in the control group ( P<0.05). Toluidine blue staining showed that with the increase of DAP concentration, there was no significant difference in cell staining between the control group and the experimental group. At the same DAP concentration, the cells in the experimental group were slightly darker than those in the control group. Immunohistochemical staining of collagen type Ⅱ showed that with the increase of DAP concentration, there was no significant difference in the cytoplasmic brown-yellow coloring of the cells in the control group. The cytoplasmic brown-yellow coloring of the cells in the experimental group gradually deepened, with 60 and 90 μg/mL DAP concentration groups significantly deeper than 0 μg/mL DAP concentration group. At the same DAP concentration, the color of the cells in the experimental group was significantly deeper than that in the control group.

CONCLUSION:
DAP can promote the proliferation of ADSCs in rats. The differentiation of ADSCs into chondrocytes induced by DAP alone was slightly, but DAP combined with IGF-1 gene transfection has obvious synergistic effect to promote chondrogenic differentiation of ADSCs.

KEYWORDS

Adipose-derived mesenchymal stem cells; chondrogenic differentiation; daphnetin; insulin-like growth factor 1; rat

Title

[Effects of daphnetin combined with insulin-like growth factor 1 on chondrogenic differentiation of adipose-derived mesenchymal stem cells in rats].

Author

Shen N1, Xi X1, Li F2, Lu C3, Zhang P4.

Publish date

2019 Jun

PMID

30991161

Abstract

The bacterial pneumonia caused by methicillin-resistant Staphylococcus aureus (MRSA) is a potentially fatal disease, featured with extensive infection, inflammation, and airway dysfunction. With the increasing emerging of drug-resistant strains, new therapeutic strategies beyond canonical antibiotic treatment are pressingly needed. Daphnetin (DAPH) is a natural coumarin derivative with anti-inflammation, anti-microorganism and anti-oxidative properties. However, the protective effect of DAPH on S. aureus-caused pneumonia and the mechanism involved are never explored. Here we show that DAPH treatment conferred substantial protection against S. aureus-induced pneumonia, characterized by the reduced inflammatory responses, the augmented bacterial clearance and the alleviated tissue damage. Our study indicates that DAPH significantly enhanced mTOR-dependent autophagic pathway, leading to the boosted microphage bactericidal activity and the suppressed inflammatory responses. Inhibition of autophagic pathway therefore largely abolished DAPH-elicited repression of inflammatory response and macrophage anti-bacterial capability. Together, we herein not only identify a novel, natural agent to combat bacterial pneumonia, but also underscore the significance of autophagic pathway in orchestrating antimicrobial and anti-inflammatory responses, which may have important implication for the treatment of the infectious diseases, particularly that caused by obstinate, antibiotic-resistant pathogens such as MRSA.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Autophagy; Daphnetin; Pneumonia; Staphylococcus aureus

Title

Daphnetin prevents methicillin-resistant Staphylococcus aureus infection by inducing autophagic response.

Author

Zhang W1, Zhuo S2, He L1, Cheng C1, Zhu B1, Lu Y3, Wu Q4, Shang W5, Ge W2, Shi L6.

Publish date

2019 Jul;


Description :

Daphnetin (7,8-dihydroxycoumarin), one coumarin derivative isolated from plants of the Genus Daphne, is a protein kinase inhibitor, with IC50s of 7.67 μM, 9.33 μM and 25.01 μM for EGFR, PKA and PKC in vitro, respectively[1][2]. Daphnetin (7,8-dihydroxycoumarin) is a secondary metabolite of plants used in folk medicine to counter inflammatory and allergic diseases, also has been clinically used in the treatment of coagulation disorders, rheumatoid arthritis with anti-malarian and anti-pyretic properties[3].