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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: 2.83). 06/2007; 44(1):283-7. DOI: 10.1016/j.jpba.2007.02.005
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ABSTRACT 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 HOOK.f.et 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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    • "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 · 2.94 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 · 2.71 Impact Factor
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    • "Fig. 6 shows a typical HPLC chromatogram of a PLE extract of Macleaya microcarpa roots with seven resolved peaks. According to our previous study, the first two unlabelled peaks belong to protopine and allocryptopine (Suchomelová et al., 2007). The chromatograms of the extracts obtained by the other two methods were similar in the shape and retention time of the peaks but different in the peak areas. "
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    ABSTRACT: Macleaya microcarpa (Papaveraceae family) has been of considerable interest in recent years as a prospective source of quaternary benzo[c]phenanthridine alkaloids (QBAs) related to many pharmaceutical beneficial effects. For this purpose, a quantitative, efficient and fast method to isolate the QBAs from the plant material is required. To optimise and compare pressurised liquid extraction (PLE) with Soxhlet extraction and maceration in order to estimate extraction conditions for fast and efficient isolation of QBAs contained in the roots of Macleaya microcarpa. The QBAs were extracted by PLE, Soxhlet extraction and maceration at different conditions (solvent, time, etc.). Reversed phase HPLC with diode-array detector was utilised for their determination and quantification. To optimise the PLE procedure, the variable parameters, including temperature (40-150 °C), sample-to-inert material ratio, extraction time (5-30 min) and number of extraction cycles (1-4), were also tested. Quantitative determination of QBAs resulted in 0.2-2.8 mg/g, 0.3-2.5 mg/g and 0.3-3.1 mg/g for PLE, Soxhlet extraction and maceration. To produce the yields mentioned above, PLE required only up to 30 min compared with 21 h for Soxhlet extraction and 49 days for maceration. PLE provided an effective and fast extraction of QBAs from M. microcarpa roots and can be recommended as an alternative isolation method to conventional techniques for QBAs from the plant sources.
    Phytochemical Analysis 09/2012; 23(5):477-82. DOI:10.1002/pca.2344 · 2.45 Impact Factor
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