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Phellopterin

$672

  • Brand : BIOFRON

  • Catalogue Number : BD-P0744

  • Specification : 99.0%(HPLC&TLC)

  • CAS number : 2543-94-4

  • Formula : C17H16O5

  • Molecular Weight : 300.3

  • PUBCHEM ID : 98608

  • Volume : 25mg

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Catalogue Number

BD-P0744

Analysis Method

HPLC,NMR,MS

Specification

99.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

300.3

Appearance

Powder

Botanical Source

Amyris pinnata, Phellopterus littoralis, Ferula alliacea, Angelica dahurica, Angelica glabra, Heracleum mantegazzianum and other plants

Structure Type

Coumarins

Category

SMILES

CC(=CCOC1=C2C(=C(C3=C1OC(=O)C=C3)OC)C=CO2)C

Synonyms

4-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one

IUPAC Name

4-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one

Applications

Hesperidin, hesperidin methyl chalone and phellopterin from Poncirus trifoliata (Rutaceae) differentially regulate the expression of adhesion molecules in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells PUMID/DOI:18387509 Int Immunopharmacol. 2008 May;8(5):670-8. Recently, several active compounds including hesperidin, hesperidin methyl chalone and Phellopterin from P. trifoliata (Rutaceae) were isolated and characterized. Interestingly, the inhibitory effect of hesperidin, hesperidin methyl chalone and Phellopterin on monocyte adhesion to HUVECs was recapitulated by transfecting cells with VCAM-1 siRNA. Taken together, hesperidin, hesperidin methyl chalone and Phellopterin reduce TNF-alpha-induced VCAM-1 expression through regulation of the Akt and PKC pathway, which contributes to inhibit the adhesion of monocytes to endothelium.

Density

1.2±0.1 g/cm3

Solubility

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

Flash Point

244.4±28.7 °C

Boiling Point

480.4±45.0 °C at 760 mmHg

Melting Point

102-103ºC

InChl

InChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3

InChl Key

BMLZFLQMBMYVHG-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#:2543-94-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29516524

Abstract

Isoimperatorin (IP) and phellopterin (PP) are two furocoumarins existing in Angelicae Dahuricae Radix. There is an isopentenyloxyl substituted at C-5 in IP, and an isopentenyloxyl and a methoxyl substituted at C-8 and C-5, respectively, in PP. To elucidate the in vivo metabolic characteristics of PP and IP, HPLC coupled with diode array detector and electrospray ionization ion trap time-of-flight mass spectrometry technique was used. In total, 111 metabolites, including 53 new ones, were identified from the urine and plasma samples of rats after oral administration of IP and PP, respectively. The metabolites were formed through eight reactions on IP and PP: oxidation, hydroxylation-hydrogenation, carboxylation on the isopentenyloxyl, O-dealkylation, hydroxylation on the furocoumarin nucleus, ring-opening reaction on the furan ring and reduction or ring-opening reaction on the lactone ring. Among these, hydroxylation on the furocoumarin nucleus was found for the first time for in vivo metabolites of PP and IP, and the ring-opening reaction on the furan ring or lactone ring was found for the first time for in vivo metabolites of isopentenyloxyl furocoumarins. The research gave us a new insight into the in vivo metabolic profiles of IP and PP, which could help us better understand their important roles as two active constituents of Angelicae Dahuricae Radix.

KEYWORDS

HPLC-DAD-ESI-IT-TOF-MS; furocoumarin; in vivo metabolites; isoimperatorin; phellopterin.

Title

In vivo metabolite profiles of isoimperatorin and phellopterin in rats analyzed using HPLC coupled with diode array detector and electrospray ionization ion trap time-of-flight mass spectrometry technique

Author

Lili Li 1, Jiaxing Chen 1, Xiaoyan Yang 1, Yingtao Zhang 1, Donghui Yang 1

Publish date

2018 Aug

PMID

27912884

Abstract

Background: Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious therapeutic challenge in current clinic and new drug development. Natural coumarins have diverse bioactivities and the potential of resistance modifying effects.

Purpose: This study is to present in-depth evaluations of in vitro antimicrobial activities of four natural coumarins 5-geranyloxy-7-methoxycoumarin (Gm, 1), (5,7-dimethoxy-8-prenyloxycoumarin (artanin, Ar, 2)), isopimpinellin (Is, 3) and phellopterin (Ph, 4) from Zanthoxylum nitidum (Roxb.) DC. (Rutaceae) extracts, focusing on their potential restoration the activity of conventional antibacterial agents against clinical MRSA strains.

Methods: Bioactivity-guided fractionation and spectral analyses were used to isolate the coumarins and identify the structures, respectively. The double broth microdilution method was used to assay the coumarins’ alone activity. The classic checkerboard microdilution and dynamic time-killing methods were used to evaluate combinatory effects.

Results: The four plant coumarins Gm (1), Ar (2), Is (3) and Ph (4) were isolated and identified from Z. nitidum extracts. Coumarins 1-4 displayed promising inhibition against both MSSA and MRSA with minimal inhibitory concentrations (MICs) of 8-64µg/ml, but very weak against Gram-negative pathogen and yeast with MICs of 256 to ≥1024µg/ml. The geranyloxy and prenyloxy substitutions showed to be more active than the methoxy substitution on the coumarin skeletons. 1-4 also showing different extent of synergism with a total of eight conventional antibacterial agents, i.e. chloramphenicol (CL), gentamicin (CN), fosfomycin (FF), levofloxacin (LE), minocycline (MI), piperacillin/tazobactam (P/T), teicoplanin (TE) and vancomycin (VA) against ten clinical MRSA strains. Four to ten of the tested MRSA strains showed bacteriostatic synergy in the eleven combinations. The anti-MRSA modifying effects were related to different arrangement in the combinations with fractional inhibitory concentration indices (FICIs) from 0.187 to 1.125 and the three combinations CN (Is), CL (Ph) and MI (Gm) were the best ones. The enhancement of activity was also shown by 2-64 of dose reduction indices (DRIs) of the combined MICs, with VA (Ph) combination resulted the biggest DRI. The resistance of MRSA to antibacterial agents could be reversed in the combinations of CL (Gm or Ph), LE (Ph) and MI (Is) following the Clinical and Laboratory Standards Institute (CLSI) criteria. Six combinations P/T (Gm), TE (Ar), CN (Is), VA (Ph) and CL (Gm or Ph) also showed bactericidal synergy with Δlog10CFU/ml >2 at 24h incubation.

Conclusions: The coumarins showed high potentiating effects of the antibacterial agents against multi-drug resistant SA. The resistance reversal effect of CL, LE and MI warrants further pharmacological investigation on combinatory therapy for the sake of fighting against MRSA infections.

KEYWORDS

Antibacterial agents; Antimicrobial activity; Coumarin; MRSA; Synergy.

Title

Synergism of coumarins from the Chinese drug Zanthoxylum nitidum with antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA)

Author

Guo-Ying Zuo 1, Chun-Juan Wang 2, Jun Han 3, Yu-Qing Li 4, Gen-Chun Wang 5

Publish date

2016 Dec 15

PMID

25976802

Abstract

An efficient strategy, based on bioassay-guided fractionation, high-performance liquid chromatography (HPLC), and high-performance counter-current chromatography (HPCCC), was established to purify and evaluate the bioactive compounds from the dichloromethane extract of the fruits of Heracleum mantegazzianum Sommier & Levier (Apiaceae). The quaternary solvent system n-heptane-ethyl acetate-methanol-water (6:5:6:5 v/v) was used in the reversed phase mode. Using this method, in a single run, seven fractions were isolated, among them three were the pure furanocoumarins: pimpinellin, imperatorin, and phellopterin. In order to purify xanthotoxin a more polar system (1:1:1:1 v/v) was further applied. The antimicrobial activity of extract, chromatographic fractions, and single compounds were in the range of MIC = 0.03-1 mg mL(-1). Xanthotoxin may have priority as a compound of further interest based on its antimicrobial activity. For the first time, an extensive antimicrobial study was performed for pimpinellin and phellopterin.

KEYWORDS

Antimicrobial activity; Furanocoumarins; Heracleum mantegazzianum; High-performance counter-current chromatography.

Title

Bioactivity-guided isolation of antimicrobial coumarins from Heracleum mantegazzianum Sommier & Levier (Apiaceae) fruits by high-performance counter-current chromatography

Author

Magdalena Walasek 1, Agnieszka Grzegorczyk 2, Anna Malm 2, Krystyna Skalicka-Woźniak 3

Publish date

2015 Nov 1;