Catalogue Number
BF-F2002
Analysis Method
HPLC,NMR,MS
Specification
98%
Storage
2-8°C
Molecular Weight
208.17
Appearance
Light Yellow crystalline powder
Botanical Source
Datura metel,Xanthoceras sorbifolium,Sarcandra glabra,Fraxinus chinensis,Actinidia chinensis
Structure Type
Phenylpropanoids
Category
Standards;Natural Pytochemical;API
SMILES
COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)O
Synonyms
Coumarin, 7,8-dihydroxy-6-methoxy-/6-methoxy-7,8-dihydroxycoumarin/7,8-Dihydroxy-6-methoxy-2H-chromen-2-one/2H-1-Benzopyran-2-one,7,8-dihydroxy-6-methoxy/7,8-Dihydroxy-6-methoxycoumarin/2H-1-Benzopyran-2-one, 7,8-dihydroxy-6-methoxy-/7,8-dihydroxy-6-methoxy-benzopyran-2-one/7,8-Dihydroxy-6-methoxy-2H-1-benzopyran-2-one/Fraxetin
IUPAC Name
7,8-dihydroxy-6-methoxychromen-2-one
Density
1.5±0.1 g/cm3
Solubility
Methanol; Ethanol
Flash Point
196.0±22.2 °C
Boiling Point
472.0±45.0 °C at 760 mmHg
Melting Point
230-232°C
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#:574-84-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
COA
31080186
Lung cancer represents the leading cause of cancer-associated mortality, and non-small-cell lung cancer (NSCLC) is the most frequent histologic sub-type. It is therefore urgent to develop novel agents for the treatment of NSCLC. Fraxetin (FXT) is a potent plant-derived product and has been recognized as a promising anticancer agent for breast cancer and osteosarcoma. However, the anti-cancer potential of FXT for NSCLC remains to be elucidated. Accordingly, in the present study, we evaluated the inhibitory effect of FXT on the proliferation and growth of NSCLC cells using six human NSCLC cell lines: A549, H460, HCC827, H1650, PC-9 and H1975. FXT exhibited significant inhibitory effects on the proliferation of these cancer cell lines. By contrast, no inhibitory effect was observed on the viability of non-cancer lung cell lines even at the highest concentration of FXT (100 μM). Among the NSCLC cell lines, HCC827 and H1650 cells showed the most sensitive to FXT. Accordingly, HCC827 and H1650 cells were used for the subsequent experiments. Flow cytometric analysis revealed that FXT caused a significant cell cycle arrest and pro-apoptotic effects. Mechanistically, FXT suppressed the IL-6-induced phosphorylation of tyrosine residue (Tyr705) of signal transducer and activator of transcription 3 (STAT3) probably by binding to STAT3. Molecular docking and molecular dynamic simulations studies indicated that FXT interacts with STAT3 through hydrogen bond and hydrophobic interaction. In conclusion, these findings suggest that FXT could be a promising lead compound to be used as a novel STAT3 inhibitor and potential antitumor agent for the treatment of NSCLC.
coumarin; fraxetin; hydrogen bond and hydrophobic interaction; non-small-cell lung cancer; signal transducer and activator of transcription 3
Fraxetin Suppresses Proliferation of Non-Small-Cell Lung Cancer Cells via Preventing Activation of Signal Transducer and Activator of Transcription 3.
Zhang Y1, Wang L2, Deng Y1, Zhao P1, Deng W1, Zhang J1, Luo J1, Li R1.
2019 May
31003150
BACKGROUND:
Liver fibrosis is a chronic lesion which ultimately results in cirrhosis and possible death. Although the high incidence and lethality, few therapies are effective for liver fibrosis. Fraxetin (7,8-dihydroxy-6-methoxy coumarin), a natural product extracted from cortex fraxini, has exhibited a significant hepatoprotective and anti-fibrotic properties. However, the underlying mechanism of the anti-hepatic fibrotic property remains unknown.
METHODS:
48 Male Sprague Dawley rats were divided into four groups at random which were named as normal group, model group, fraxetin 25 mg/kg and 50 mg/kg group. The experimental model of liver fibrosis was founded by carbon tetrachloride (CCl4) rats which were simultaneously treated with fraxetin (25 mg/kg or 50 mg/kg). Normal groups received equal volumes of saline and peanut oil.
RESULTS:
Results showed that fraxetin ameliorated CCl4 induced liver damage and fibrosis. Furthermore, histopathology examinations revealed that fraxetin improved the morphology and alleviated collagen deposition in fibrotic liver. Fraxetin inhibited inflammation and hepatocytes apoptosis by modulating the NF-κB/IκBα, MAPKs and Bcl-2/Bax signaling pathways.
CONCLUSION:
Our findings indicate that fraxetin is effective in preventing liver fibrosis through inhibiting inflammation and hepatocytes apoptosis which is associated with regulating NF-κB/IκBα, MAPKs and Bcl-2/Bax signaling pathways in rats.
Copyright © 2019 Institute of Pharmacology, Polish Academy of Sciences. Published by Elsevier B.V. All rights reserved.
Fraxetin; Inflammation; Liver fibrosis; MAPKs; NF-κB
Antifibrotic effects of Fraxetin on carbon tetrachloride-induced liver fibrosis by targeting NF-κB/IκBα, MAPKs and Bcl-2/Bax pathways.
Wu B1, Wang R1, Li S1, Wang Y1, Song F1, Gu Y1, Yuan Y2.
2019 Jun
30832436
This paper reports the successive isolation and purification of bioactive compounds from the stem bark of Jatropha podagrica, a widely known medicinal plant. The ethyl acetate extract of the stem bark exhibited the strongest antioxidant activity assessed by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, and ferric reducing antioxidant power (FRAP) assays (IC50 = 46.7, 66.0, and 492.6, respectively). By column chromatography (CC) with elution of hexane and ethyl acetate at 8:2, 7:3, and 6:4 ratios, the isolation of this active extract yielded five fractions (C1⁻C5). Chemical structures of the constituents included in C1⁻C5 were elucidated by gas chromatography-mass spectrometry (GC-MS), electrospray ionization-mass spectrometry (ESI-MS), and nuclear magnetic resonance (NMR) and resolved as methyl gallate (C1, C2, C3, C4), gallic acid (C1, C2), fraxetin (C2, C3, C4, C5), and tomentin (C3). Mixture C2 (IC50 DPPH and ABTS = 2.5 µg/mL) and C3 (IC50 FRAP = 381 µg/mL) showed the highest antioxidant properties. Among the isolated fractions, C4 was the most potential agent in growth inhibition of six bacterial strains including Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Listeria monocytogenes, Bacillus subtilis, and Proteus mirabilis (MIC = 5, 20, 30, 20, 25, and 20 mg/mL, respectively). All identified constituents exerted an inhibitory activity on the growth of Lactuca sativa, of which the mixture C3 performed the maximal inhibition on shoot (IC50 = 49.4 µg/mL) and root (IC50 = 47.1 µg/mL) growth. Findings of this study suggest that gallic acid, methyl gallate, fraxetin, and tomentin isolated from J. podagrica possessed antioxidant, antibacterial, and growth inhibitory potentials.
Jatropha podagrica; allelopathic activity; antibacterial; antioxidant; fraxetin; gallic acid; methyl gallate; stem bark; tomentin
Isolation and Purification of Bioactive Compounds from the Stem Bark of Jatropha podagrica.
Minh TN1, Xuan TD2, Tran HD3, Van TM4, Andriana Y5, Khanh TD6,7, Quan NV8, Ahmad A9.
2019 Mar 3
