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Bergapten

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-B3008

  • Specification : 98%

  • CAS number : 484-20-8

  • Formula : C12H8O4

  • Molecular Weight : 216.19

  • PUBCHEM ID : 2355

  • Volume : 100mg

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Catalogue Number

BF-B3008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

216.19

Appearance

White needle shaped crystal

Botanical Source

Leonurus japonicus,Notopterygium incisum,Peucedanum praeruptorum,Saposhnikovia divaricata,Glehnia littoralis

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C2C=CC(=O)OC2=CC3=C1C=CO3

Synonyms

Geralen/Heraclin/Bergapten/4-MOP/5-19-06-00004/Bergaptan/4-Methoxyfuro[3,2-g]benzopyrane-7-one,5-Methoxypsoralen,Bergapten/7H-Furo[3,2-g][1]benzopyran-7-one, 4-methoxy-/MAJUDIN/4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one/5-Methoxypsoralen/4-Methoxyfuro[3,2-g]Benzopyran-7-One/5-MOP/5-19-06-00004 (Beilstein Handbook Reference)/4-Methoxy-furo[3,2-g]chromen-7-one/Psoraderm/4-Methoxy-7H-furo[3,2-g]chromen-7-one

IUPAC Name

4-methoxyfuro[3,2-g]chromen-7-one

Density

1.4±0.1 g/cm3

Solubility

Methanol; Acetontrile; Ethyl Acetate; DMSO

Flash Point

203.2±28.7 °C

Boiling Point

412.4±45.0 °C at 760 mmHg

Melting Point

190-193 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2935000000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:484-20-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30227322

Abstract

Oxysterol receptors LXRs (α and β) are recently reported to be one of the novel and potential therapeutic targets in reducing cell proliferation and tumor growth in different system model. Activation of LXRs is correlated with modification of PI3K/Akt pathway. LXRs are also found to play a critical role in maintaining lipid homeostatais by regulating ABCA1, IDOL, SREBP1, LDLR and also certain lipogenic genes such as FASN and SCD1. In the present study a potential furanocoumarin, Bergapten (BeG) has been evaluated for its anticancer property on Hepatocellular Carcinoma (HCC) on LXR axis. The molecular docking analysis was carried out for BeG on LXR (α & β) using Maestro tool and compared with reference ligands. This was followed by in vitro (HepG2 cell lines) and in vivo (on NDEA induced HCC in Wistar albino rats) anticancer evaluation of BeG. The docking results revealed polar and hydrophobic interactions of BeG with LXR (α,β). The in vitro studies revealed the potential of BeG in lowering the accumulation of lipid droplets in HepG2 cells which was correlated with increase in LXR (α,β) protein expressions. Furthermore, the in vivo studies demonstrated the potential of BeG in ameliorating the cancer induced alterations in body weight, liver weight and significant restoration of the changes in mRNA and protein expressions of LXR(α,β), ABCA1, IDOL, SREBP1 and LDLR. BeG also modulated the expressions of PI3K, Akt and certain lipogenic genes like FASN and SCD1 and reduced the lipid droplets level in liver cancer cells. These results provide evidence and validates the critical role of BeG in maintaining the lipid homeostasis and justifies its anticancer potential against NDEA-induced HCC.
Copyright © 2018 Elsevier Masson SAS. All rights reserved.

KEYWORDS

Akt; Bergapten; Hepaotocellular carcinoma; IDOL; LDLR; LXR (α and β); Lipid metabolism; PI3K

Title

Bergapten inhibits liver carcinogenesis by modulating LXR/PI3K/Akt and IDOL/LDLR pathways.

Author

Pattanayak SP1, Bose P2, Sunita P3, Siddique MUM4, Lapenna A5.

Publish date

2018 Dec

PMID

30628674

Abstract

The principal subtype of lung cancer, non‑small cell lung cancer (NSCLC) is a life‑threatening malignancy that causes high mortality rates. Bergapten (5‑methoxypsoralen) has been identified to possess anticancer activity against a number of carcinomas. In the present study, the effects of bergapten on NSCLC cells were investigated. The cell viability was determined by MTT assay. Cell cycle distribution was analyzed using flow cytometry. Protein expression and kinase cascade were demonstrated using western blot analysis. The results demonstrated that treatment with bergapten (50 µM for 48 h) inhibited the viability of A549 and NCI‑H460 NSCLC cells to 79.1±2.8% and 74.5±3.1%, respectively, compared with the controls. It was identified that bergapten induced G1 phase accumulation in A549 and NCI‑H460 cells between ~58 and 75% (P<0.01). In addition, bergapten significantly increased the sub‑G1 phase ratio to ~9% (P<0.05) in the two cell types. Further investigation demonstrated that bergapten upregulated the expression of cellular tumor antigen p53 (p53) and its downstream proteins cyclin‑dependent kinase inhibitor 1 and cyclin‑dependent kinase inhibitor 1B, whereas, it downregulated the expression of cyclin D1 and CDK4. Overall, these results suggested that bergapten may inhibit cell viability and trigger G1 arrest and apoptosis in A549 and NCI‑H460 cells, which may be attributed to the activation of p53‑mediated cascades. Therefore, bergapten may be beneficial for NSCLC treatment.

Title

Bergapten induces G1 arrest of non‑small cell lung cancer cells, associated with the p53‑mediated cascade.

Author

Chiang SR1, Lin CS2, Lin HH3, Shieh PC2, Kao SH2.

Publish date

2019 Mar

PMID

31037830

Abstract

Osteoarthritis (OA) is a chronic degenerative disease that commonly affects the elderly. Current drug therapies for treating OA may cause adverse side effects, and so there remains a need to develop alternative treatments. Bergapten (BG) is a coumarin phytohormone that is widely found in fruits and has antioxidative and anti-inflammatory effects. Here, we tested the hypothesis that BG may restrict the progression of OA by examining its effect on OA chondrocytes. We observed that BG significantly ameliorated interleukin (IL)-1β-induced expression of inflammatory cytokines and mediators, including interleukin 1 (Il-1), interleukin 6 (Il-6), tumor necrosis factor α (Tnf-α), cyclooxygenase 2 (Cox-2) and matrix metalloproteinase 13 (Mmp-13), maintained chondrocyte phenotype, and promoted the secretion of cartilage-specific extracellular matrix. We provide evidence that BG exerts its anti-inflammatory effect by activating the ANP32A/ATM signaling pathway, which was recently verified to be associated with OA. In conclusion, these findings indicate that BG may be a potential candidate for treatment of OA.
© 2019 The Authors. Published by FEBS Press and John Wiley & Sons Ltd.

KEYWORDS

ANP32A/ATM signal; IL-1β; bergapten; chondrocytes; osteoarthritis

Title

Bergapten alleviates osteoarthritis by regulating the ANP32A/ATM signaling pathway.

Author

He Y1,2, Zisan Z3, Lu Z1,2, Zheng L1,2, Zhao J1,2,4,5.

Publish date

2019 Jun


Description :

Bergapten is a natural anti-inflammatory and anti-tumor agent isolated from bergamot essential oil, other citrus essential oils and grapefruit juice. Bergapten is inhibitory towards mouse and human CYP isoforms.