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Roemerine

$1,344

  • Brand : BIOFRON

  • Catalogue Number : BD-P0824

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 548-08-3

  • Formula : C18H17NO2

  • Molecular Weight : 279.337

  • PUBCHEM ID : 119204

  • Volume : 25mg

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Catalogue Number

BD-P0824

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

279.337

Appearance

Powder

Botanical Source

Alkaloid from Roemeria refracta, Annona senegalensis and Nelumbo nucifera (Nelumbonaceae). Present in the Annonaceae, Magnoliaceae, Menispermaceae and Rhamnaceae

Structure Type

Alkaloids

Category

SMILES

CN1CCC2=CC3=C(C4=C2C1CC5=CC=CC=C54)OCO3

Synonyms

IUPAC Name

(12R)-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene

Applications

Density

1.269±0.06 g/cm3 (20 ºC 760 Torr)

Solubility

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

Flash Point

Boiling Point

Melting Point

102-103 ºC

InChl

InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3/t14-/m1/s1

InChl Key

JCTYWRARKVGOBK-CQSZACIVSA-N

WGK Germany

RID/ADR

HS Code Reference

2942000000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:548-08-3) 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

31629051

Abstract

Extrusion of drugs or drug-like compounds through bacterial efflux pumps is a serious health issue that leads to loss in drug efficacy. Combinatorial therapies of low-efficacy drugs with efflux pump inhibitors may help to restore the activities of such drugs. In this quest, natural products are attractive molecules, since in addition to their wide range of bioactivities they may inhibit efflux pumps. The current work repurposed the bioactive alkaloid roemerine as a potential efflux pump inhibitor. In Bacillus subtilis, both Bmr and BmrA, belonging to the major facilitator and the ATP-binding cassette superfamilies, respectively, were found to be inhibited by roemerine. Scanning electron microscopy and RNA-Seq analyses showed that it potentiated the effect of berberine. Growth rates and checkerboard assays confirmed the synergy of roemerine and berberine and that roemerine prevented berberine efflux by inhibiting Bmr. Transport assays with inverted membrane vesicles prepared from Escherichia coli overexpressing BmrA showed that increasing roemerine concentration decreased the transport of doxorubicin, the BmrA substrate, confirming that roemerine may also be considered as an inhibitor of BmrA. Thus, these findings suggest that conjugation of roemerine to substrates of efflux pumps, Bmr and BmrA, may help to potentiate the activity of their drug substrates.

KEYWORDS

Alkaloid; Berberine; Bmr; BmrA; Efflux pump inhibition; Roemerine.

Title

Repurposing bioactive aporphine alkaloids as efflux pump inhibitors

Author

Fatma Gizem Avci 1, Basak Atas 2, Cemile Selin Aksoy 3, Eldin Kurpejovic 3, Gizem Gulsoy Toplan 4, Caglayan Gurer 5, Maxime Guillerminet 6, Cedric Orelle 7, Jean-Michel Jault 8, Berna Sariyar Akbulut 9

Publish date

2019 Nov;

PMID

30189375

Abstract

Papaver species, well known for their alkaloids, have been used for the treatment of several diseases, such as inflammation, diarrhea, depression, and sleep disorders in certain parts of Anatolia. In this study, four Papaver species (P. lacerum, P. syriacum, P. glaucum and P. rhoeas) were collected from different localities of Turkey. Methanolic extracts were prepared from the aerial parts of the plants. A rapid analytical method was developed for the simultaneously quantitative analysis of two alkaloids, pronuciferine and roemerine, using liquid chromatography tandem mass spectrometry. Multiple reaction monitoring in the positive ionization mode was used for detection. Pronuciferine and roemerine were analyzed on a C18 column (2.1 × 50 mm, 3 μm) with the mobile phase run in the gradient mode with 0.1% formic acid in water (A) and 0.1% formic acid in acetonitrile at a flow rate of 0.3 mL/min. The transitions 312.1→283.1 m/z and 280.0→249.0 m/z were used to monitor pronuciferine and roemerine, respectively. The assay was linear in the concentration range of 0.01 μg/mL to 1 μg/mL (r = 0.996 for roemerine, r = 0.998 for pronuciferine). The validation studies revealed that the method was linear, sensitive, accurate, precise, selective, repeatable, robust, and rugged. Finally, the developed method was applied to quantify pronuciferine and roemerine in the selected species. The amounts of pronuciferine and roemerine were respectively found as 8.5 to 48 μg/g and 4.4 to 43,000 μg/g.

KEYWORDS

LC-ESI-MS/MS; Papaver species; Pronuciferine; Roemerine; Validation.

Title

An LC-ESI-MS/MS method for the simultaneous determination of pronuciferine and roemerine in some Papaver species

Author

Omer Bayazeid 1, Cemil Can Eylem 2, Tuba Recber 2, Funda Nuray Yalcın 1, Sedef Kır 2, Emirhan Nemutlu 3

Publish date

2018 Oct 1;

PMID

29494814

Abstract

Plant-derived substances have regained interest in the fight against antibiotic resistance owing to their distinct antimicrobial mechanisms and multi-target properties. With the recent advances in instrumentation and analysis techniques, OMIC approaches are extensively used for target identification and elucidation of the mechanism of phytochemicals in drug discovery. In the current study, RNA sequencing based transcriptional profiling together with global differential protein expression analysis was used to comparatively elaborate the activities and the effects of the plant alkaloids boldine, bulbocapnine, and roemerine along with the well-known antimicrobial alkaloid berberine in Bacillus subtilis cells. The transcriptomic findings were validated by qPCR. Images from scanning electron microscope were obtained to visualize the effects on the whole-cells. The results showed that among the three selected alkaloids, only roemerine possessed antibacterial activity. Unlike berberine, which is susceptible to efflux through multidrug resistance pumps, roemerine accumulated in the cells. This in turn resulted in oxidative stress and building up of reactive oxygen species, which eventually deregulated various pathways such as iron uptake. Treatment with boldine or bulbocapnine slightly affected various metabolic pathways but has not changed the growth patterns at all.

KEYWORDS

Antibacterial; Aporphine alkaloid; Bacillus subtilis; Proteomics; RNA-Seq; Roemerine.

Title

An OMIC approach to elaborate the antibacterial mechanisms of different alkaloids

Author

Fatma Gizem Avci 1, Nihat Alpagu Sayar 2, Berna Sariyar Akbulut 3

Publish date

2018 May