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Oxypeucedanin

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-O1005

  • Specification : 98%

  • CAS number : 737-52-0

  • Formula : C16H14O5

  • Molecular Weight : 286.28

  • PUBCHEM ID : 160544

  • Volume : 20mg

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Catalogue Number

BF-O1005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

286.28

Appearance

White powder

Botanical Source

root of Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C(O1)COC2=C3C=CC(=O)OC3=CC4=C2C=CO4)C

Synonyms

4-(3,3-Dimethyl-oxiranylmethoxy)-furo[3,2-g]chromen-7-one/7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,3-dimethyloxiranyl)methoxy)-/5-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g]chromen-7-one/4-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g]chromen-7-one/7H-Furo[3,2-g][1]benzopyran-7-one, 5-[(3,3-dimethyloxiranyl)methoxy]-/7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(3,3-dimethyloxiranyl)methoxy]-/Oxypencedanin/5-[(3,3-Dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one/oxypeucadanin

IUPAC Name

4-[(3,3-dimethyloxiran-2-yl)methoxy]furo[3,2-g]chromen-7-one

Density

1.4±0.1 g/cm3

Solubility

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

Flash Point

237.8±28.7 °C

Boiling Point

469.6±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H14O5/c1-16(2)13(21-16)8-19-15-9-3-4-14(17)20-12(9)7-11-10(15)5-6-18-11/h3-7,13H,8H2,1-2H3

InChl Key

QTAGQHZOLRFCBU-UHFFFAOYSA-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#:737-52-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30042338

Abstract

P-glycoprotein affects the transport of numerous drugs including chemotherapeutic drugs vincristine sulfate (VCR) and docetaxel (DTX), and is one of the main causes for multidrug resistance. Our previous studies have shown that oxypeucedanin (OPD) can enhance the intestinal transit of puerarin and VCR. However, the underlying mechanism is unclear. This study investigated the potential mechanism by which OPD improves P-gp-mediated drug transport. Molecular docking was performed to predict the binding force between OPD and P-gp and the contribution of OPD on P-gp activity. We observed the effect of OPD on the transport of VCR in MDCK-MDR1 cell monolayer and also measured the plasma pharmacokinetic parameters of DTX in the presence and absence of OPD by LC-MS/MS. Moreover, we further investigated the reversal mechanism of OPD on P-gp-mediated drug transport by determining the intracellular accumulation of Rhodamine-123 (Rh123) and P-gp ATPase activity as well as protein expression and mRNA level of P-gp. Our molecular docking results revealed that the binding force between OPD and P-gp was much lower than that between P-gp and verapamil (a P-gp substrate). The transport study in vitro indicated that OPD increased the flux of VCR across MDCK-MDR1 cell monolayer. The in vivo pharmacokinetic parameters data showed OPD increased the absorption of DTX. OPD activated P-gp ATPase activity and enhanced intracellular accumulation of Rh123 in MDCK-MDR1 cells. Western blotting and qRT-PCR outcomes indicated that OPD suppressed P-gp protein expression as well as downregulated P-gp mRNA level. Thus, OPD reverse P-gp-mediated drug transport via inhibition of P-gp activity and P-gp protein expression as well as downregulation of P-gp mRNA level. Our results suggest that OPD could reverse P-gp-mediated drug resistance in tumor cells.

KEYWORDS

P-glycoprotein (P-gp); oxypeucedanin (OPD); reversal effect; transmembrane transport

Title

Reversal Effect of Oxypeucedanin on P-glycoprotein-mediated Drug Transport.

Author

Dong W1, Liao ZG2, Zhao GW3, Guan XJ4, Zhang J5, Liang XL6, Yang M7.

Publish date

2018 Jul 24;

PMID

29493160

Abstract

The study was aimed to establish a liquid chromatography-tandem mass spectrometric method for the determination of the docetaxel concentration in rat plasma, and study the effect of coumarin constituents (imperatorin, isoimperatorin and oxypeucedanin) in Angelica dahurica on pharmacokinetics of docetaxel.Plasma was precipitated with acetonitrile and determined by LC-MS method with Paclitaxel as an internal standard. The specificity, linearity, range, accuracy, precision and stability of the method were suitable for the determination of docetaxel in plasma.Six sprague-dawley rats in each group received intragastric administration of docetaxel (50 mg•kg⁻¹), oxypeucedanin (8 mg•kg⁻¹) combined with docetaxel (50 mg•kg⁻¹), imperatorin (15 mg•kg⁻¹) combined with docetaxel (50 mg•kg⁻¹), and isoimperatorin(15 mg•kg⁻¹) combined with docetaxel (50 mg•kg⁻¹).Their drug plasma concentration was determined by LC-MS with Paclitaxel as an internal standard to draw plasma concentration-time curve, and the phamacokinetic parameters were calculated by DAS 2.0. The results showed that the phamacokinetic parameters of docetaxel all had notable changes when combined with imperatorin, isoimperatorin, and oxypeucedanin, respectively. The phamacokinetic parameters AUC and Cmax were significantly increased, indicating that coumarin constituents in Angelica dahurica could promote the oral bioavailability of docetaxel, and their effects were in the following order: oxypeucedanin> isoimperatorin> imperatorin.

Copyright© by the Chinese Pharmaceutical Association.

KEYWORDS

docetaxel ; imperatorin ; isoimperatorin ; oxypeucedanin ; phamacokinetic

Title

[Effect investigation of coumarin constituents in Angelica dahurica on pharmacokinetics of docetaxel by LC-MS].

Author

Guan YM1, Zhu WF1, Guan XJ1, Liao ZG1, Zhao GW1, Dong W1, Liang XL1.

Publish date

2017 Dec

PMID

28954543

Abstract

Phytochemical analysis of the Ferulago trifida Boiss. from Apiaceae family led to the isolation and identification of suberosin (1), isoimperatorin (2), prantschimgin (3), oxypeucedanin (4), oxypeucedanin methanolate (5), suberenol (6), 6-hydroxymethylherniarin (7), oxypeucedanin hydrate (8), ulopterol (9), bergapten (10), xanthotoxin (11), imperatorin (12) and grandivittin (13) from chloroform extracts of the roots (1-9) and fruits (1, 2, 8, 10-13) of this species. Oxypeucedanin methanolate and suberenol demonstrated a potent antioxidant power with 268.2 ± 5.4 and 251.2 ± 6.2 mmol FSE/100 g, respectively, compared by BHT (267.2 ± 4.2 mmol FSE/100 g) in FRAP method. The potent antibacterial effects were found for oxypeucedanin methanolate on S. epidermidis (IZ; 26 mm, MIC; 250 μg mL-1) an oxypeucedanin hydrate on K. pneumoniae (IZ: 21 mm, MIC: 250 μg mL-1). Moreover, suberosin showed higher preferential toxicity against MDA-MB-23 cells (IC50: 0.21 mM, SI: 5.0), in comparison with tamoxifen (IC50: 0.012 mM, SI: 2.45) in MTT assay.

KEYWORDS

Boiss; Apiaceae; MTT assay; antibacterial; antioxidant; coumarin

Title

Bioactive coumarins from the roots and fruits of Ferulago trifida Boiss., an endemic species to Iran.

Author

Tavakoli S1,2, Delnavazi MR1, Hadjiaghaee R2, Jafari-Nodooshan S3, Khalighi-Sigaroodi F2, Akhbari M4, Hadjiakhoondi A1, Yassa N1.

Publish date

2018 Nov


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