HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae

Department of Biochemistry, Faculty of Medicine, Masaryk University, Komenského nám. 2, CZ - 662 43 Brno, Czech Republic.
Journal of Pharmaceutical and Biomedical Analysis (Impact Factor: 2.98). 06/2007; 44(1):283-7. DOI: 10.1016/j.jpba.2007.02.005
Source: PubMed


The content of the seven quaternary benzo[c]phenanthridine alkaloids (QBA) sanguinarine (SA), chelerythrine (CHE), chelirubine (CHR), chelilutine (CHL), sanguilutine (SL), sanguirubine (SR) and macarpine (MA) was determined in the underground part of six plant species of the family Papaveraceae (Sanguinaria canadensis L., Dicranostigma lactucoides THOMS, Chelidonium majus L., Macleaya cordata (Willd.), Macleaya microcarpa (Maxim) and Stylophorum lasiocarpum (Oliv.)). HPLC method with reversed phase column Synergi Max-RP C-12 Phenomenex was used, mobile phase consisted of heptanesulfonic acid (0.01 mol/l) with triethanolamine (0.1 mol/l) in redistilled water, pH 2.5, acetonitrile gradient 25-60% during 25 min. Detection was performed at 280 nm. The highest content of SA and CHE was found in the roots of D. lactucoides (1.99%, resp. 3.43% of the dried roots). In rhizomes of S. canadensis was their content more then two times lower.

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    • "First, the standard chloroform/SDS method [11] relying on the ion pairing of alkaloids with an anionic detergent (Method A) was used. Second, the dry plant was macerated for extended period of time in methanol solutions, solution pH was adjusted, and alkaloids were extracted into diethylether [12] (Method B). Alkaloids contained in different fractions were analysed using the diode-array spectrophotometer coupled to HPLC and with the electrospray-tandem MS/MS spectrometry (ESI-MS/MS). "
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    ABSTRACT: The California poppy (Eschscholzia californica Cham.) contains a variety of natural compounds including several alkaloids found exclusively in this plant. Because of the sedative, anxiolytic, and analgesic effects, this herb is currently sold in pharmacies in many countries. However, our understanding of these biological effects at the molecular level is still lacking. Alkaloids detected in E. californica could be hypothesized to act at GABAA receptors, which are widely expressed in the brain mainly at the inhibitory interneurons. Electrophysiological studies on a recombinant 𝛼 1 𝛽 2 𝛾 2 GABAA receptor showed no effect of N-methyllaurotetanine at concentrations lower than 30 𝜇M. However, (𝑆)-reticuline behaved as positive allosteric modulator at the 𝛼 3, 𝛼 5, and 𝛼 6 isoforms of GABAA receptors.The depressant properties of aerial parts of E. californica are assigned to chloride-current modulation by (𝑆)-reticuline at the 𝛼3𝛽2𝛾2 and 𝛼5𝛽2𝛾2 GABAA receptors. Interestingly, 𝛼1, 𝛼3, and 𝛼5 were not significantly affected by (𝑅)-reticuline, 1,2-tetrahydroreticuline,codeine, and morphine—suspected (𝑆)-reticuline metabolites in the rodent brain.
    Biochemistry Research International 09/2015; 2015(Article ID 617620). DOI:10.1155/2015/617620
    • "Pharmacological studies from Chelidonium majus L. has demonstrated the cytotoxic (Hu and Wang, 2009; Spiridonov et al., 2005), antimicrobial (Kokoska et al., 2002; Saglam and Arar, 2003), antibacterial (Zuo et al., 2008) and antifungal (Meng et al., 2009) activities, which support some of the traditional uses (Yang et al., 2011). Chelidonium majus displays a variety of biological properties due to the alkaloids (Gu et al., 2010; Suchomelová et al., 2007), acids and hydroxycinnamic acid derivates (Hahn and Nahrstedt, 1991, 1993), flavonoids (Kurkin and Artamonova, 2007; Stancic- Rotaru et al., 2002) components. "
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    ABSTRACT: This paper provides significant ethnopharmacological information on plant used in dermatological affections in Navarra. Information was collected using semi-structured ethnobotanical interviews with 667 informants (mean age 72; 55.47% women, 44.53% men) in 265 locations. In order to confirm the pharmacological validation of the uses reports, the European Scientific Cooperative on Phytotherapy (ESCOP), German Commission E, World Health Organization (WHO), European Medicines Agency (EMA), European Pharmacopoeia (Ph. Eur.) and Real Farmacopea Española (RFE) monographs have been revised. A literature review has been carried out with the plants without monograph and high frequency citations, using a new tool of the University of Navarra, UNIKA. A total of 982 pharmaceutical uses are reported from the informants, belonging to 91 plants and 42 families, mainly represented by Asteraceae, Lamiaceae, Euphorbiaceae and Crassulaceae. The most frequently used parts of the plants are aerial parts followed by leaves and inflorescences. Seventeen out of 91 plants (19%) and 148 of 982 popular uses (15%), have already been pharmacologically validated. The authors propose seven species for their validation (Allium cepa, Sambucus nigra, Hylotelephium maximum, Chelidonium majus, Ficus carica, Allium sativum and Anagallis arvensis).
    Journal of ethnopharmacology 07/2013; 149(2). DOI:10.1016/j.jep.2013.07.012 · 3.00 Impact Factor
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    • "Some methods have been reported for the determination of isoquinoline alkaloids in Chelidonium majus L., including high-performance liquid chromatography (HPLC), [12] [13] [14] [15] ultraperformance LC [16] and capillary electrophoresis. [17] [18] [19] [20] However, these methods suffer from long analysis time and/or low sensitivity and thus are not suitable for the determination of alkaloids in biological fluids after administration of Chelidonium majus L. extract. "
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    ABSTRACT: Chelidonium majus L. is one of the most important medicinal plants of the family Papaveraceae. Its pharmacological effects have been primarily attributed to the presence of a number of alkaloids. In the present study, a sensitive and selective liquid chromatography-tandem mass spectrometry method for simultaneous determination of five isoquinoline alkaloids from Chelidonium majus L. was developed and validated. The analytes (protopine, chelidonine, coptisine, sanguinarine and chelerythrine), together with the internal standard (palmatine), were extracted from acidified rat plasma with ethyl acetate-dichloromethane (4:1, v/v). Chromatographic separation was carried out on a Diamonsil C(18) column with an isocratic mobile phase consisting of acetonitrile and water (adjusted to pH 2.3 with formic acid) (30:70, v/v) at a flow rate of 0.4 ml/min. Mass spectrometric detection was performed by selected reaction monitoring mode via electrospray ionization source operating in positive ionization mode. The assay exhibited good linearity (r ≥ 0.9933) for all the analytes. The lower limits of quantification were 0.197-1.27 ng/ml using only 50 µl of plasma sample. The intra- and inter-day precisions were less than 11.9%, and the accuracy was between -6.3% and 9.3%. The method was successfully applied to the pharmacokinetic study of the five alkaloids in rats after intragastric administration of Chelidonium majus L. extract. Copyright © 2013 John Wiley & Sons, Ltd.
    Journal of Mass Spectrometry 01/2013; 48(1):111-8. DOI:10.1002/jms.3133 · 2.38 Impact Factor
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