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Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas ISSN: 0717-7917 [email protected] Universidad de Santiago de Chile Chile MANOSALVA, Loreto; MUTIS, Ana; DÍAZ, Juan; URZÚA, Alejandro; FAJARDO, Víctor; QUIROZ, Andrés Identification of isoquinoline alkaloids from Berberis microphylla by HPLC ESI-MS/MS Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, vol. 13, núm. 4, 2014, pp. 324-335 Universidad de Santiago de Chile Santiago, Chile Available in: http://www.redalyc.org/articulo.oa?id=85631435002 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative © 2014 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 13 (4): 324 - 335 ISSN 0717 7917 www.blacpma.usach.cl Artículo Original | Original Article In memorian Professor Luis Astudillo, Universidad de Talca, Chile Identification of isoquinoline alkaloids from Berberis microphylla by HPLC ESI-MS/MS [Identificación de alcaloides isoquinolínicos en Berberis microphylla G. Forst mediante CLAE IES-MS/MS] Loreto MANOSALVA1, Ana MUTIS2, Juan DÍAZ3, Alejandro URZÚA4, Víctor FAJARDO5 & Andrés QUIROZ2 1Doctorado en Ciencias de Recursos Naturales; 2Laboratorio de Ecología Química, Departamento de Ciencias Químicas y Recursos Naturales; 3Laboratory of Mass Spectrometry, Scientific and Technological Bioresource Nucleus (Bioren), Universidad de La Frontera, Temuco, Chile 4Laboratory of Chemical Ecology, Department of Environmental Sciences, Faculty of Chemistry and Biology, Universidad de Santiago de Chile 5Chile Laboratorio de Productos Naturales, Universidad de Magallanes, Punta Arenas, Chile Contactos | Contacts: Andrés QUIROZ - E-mail address: [email protected] Abstract: Berberis microphylla (G. Forst) is a native plant growing in Patagonia. In recent years Patagonia Berberis are becoming important due to their interesting biological properties related to their alkaloids content. The aim of this study was determine the distribution and proportion of isoquinoline alkaloids in leaves, stems and roots of B. microphylla collected in two different climatic zones from Chilean Patagonia. Using by HPLC ESI-MS/MS isocorydine, jatrorrhizine, palmatine, reticuline, scoulerine, tetrahydroberberine and thalifendine were detected for the first time in this specie, and the presence of allocryptopine, berberine, calafatine and protopine, previously isolated in B. microphylla was corroborated. The alkaloids profile showed differences of compounds in samples collected in two climatic zones, where more compounds were detected in plants from Lago Deseado than Cerro Sombrero. Furthermore, a greater number of alkaloids were found in stem and root extracts and berberine and thalifendine were detected in higher proportion in these structures. Keywords: Berberis microphylla, Patagonia, isoquinoline alkaloids, HPLC ESI-MS/MS Resumen: Berberis microphylla (G. Forst) es un arbusto nativo que crece en la Patagonia. Actualmente, esta planta ha sido foco de estudio dada las propiedades biológicas que presenta, atribuidas principalmente al contenido de alcaloides. El objetivo de este estudio fue determinar la distribución y proporción de alcaloides isoquinolínicos en hojas, tallos y raíces de B. microphylla colectadas en dos zonas climáticas de la Patagonia chilena. Mediante CLAE IES-MS/MS se informa por primera vez la presencia de isocoridina jatrorrizina, palmatina, reticulina, escoulerina, tetrahidroberberina y talifendina en esta especie y se confirma la presencia de allocriptopina, berberina, calafatina y protopina, identificados previamente en B. microphylla. El perfil de alcaloides mostró diferencias en la presencia de compuestos en las muestras colectas en las dos zonas climáticas, observándose un mayor número de compuestos en plantas provenientes de Lago Deseado. Además, un mayor número de compuestos se identificó en extractos de tallos y raíces donde berberina y talifendina fueron detectados en mayor proporción. Palabras clave: Berberis microphylla, Patagonia, alcaloides isoquinolínicos, CLAE IES-MS/MS Recibido | Received: April 4, 2014. Aceptado en versión corregida | Accepted in revised form: July 12, 2014. Publicado en línea | Published online: July 30, 2014. Declaración de intereses | Declaration of interests: Authors thanks Conicyt scholarship 21100561 and Conicyt project AT24121407, which provided support for this research. Este artículo puede ser citado como / This article must be cited as: L Manosalva, A Mutis, J Díaz, A Urzúa, V Fajardo, A Quiroz. 2014. Identification of isoquinoline alkaloids from Berberis microphylla by HPLC ESI-MS/MS Bol Latinoam Caribe Plant Med Aromat 13(4): 323 – 334. 324 Manosalva et al. Isoquinoline alkaloids from B. microphylla INTRODUCTION to have an advantage over other methods for the high Berberis microphylla G. Forst, (Berberidaceae) sensitivity, specific and rapid analysis for the locally called “calafate” or “michay” is a native shrub identification of components in complex alkaloid that grows wildly in southern cone of South America mixtures (Chen et al., 2000; Fabre et al., 2000; Luo et (Chilean and Argentinean Patagonia) (Moore, 1983; al., 2005; Ding et al., 2007). Orsi, 1984). The plants had been used in traditional This work reported a qualitative and semi- medicine as a treatment of different diseases such as, quantitative study of the isoquinoline alkaloids found fevers, inflammations and diarrhea (Muñoz et al., in leaves, stems and roots of B. microphylla collected 2004). In recent years, Patagonia Berberis has also in two different climatic zones from the Patagonia gained prominence importance due to their determined by HPLC ESI-MS/MS. Furthermore, the interesting pharmacological (Morales et al., 1993; results have been discussed with the purpose to find Martinez et al., 1997; Alarcon et al., 2014), some relation between the variation of alkaloids in antifungal (Enriz & Freile, 2006; Freile et al., 2006; the plant and the habitat that they grow. Pitta-Alvarez et al., 2008) and antibacterial properties (Freile et al., 2003) based on the presence of MATERIALS AND METHODS alkaloids. Plant material To date, few chemical studies in B. Representative samples of leaves, stems and roots of microphylla (known also B. buxifolia) in relation to B. microphylla were collected during flowering the presence of isoquinolinoline alkaloids have been season at Cerro Sombrero (52°48’26.7’’S; reported (Fajardo et al., 1979; Leet et al., 1983). 68°52’50.1”W) and Lago Deseado (54°22’12.4”S; Alkaloids are naturally secondary metabolites and its 68°45’45.0”W) in November and December 2011. biosynthesis in some plants family is influenced for Sample collections were performed in the Province of abiotic factors in order to tolerate and survive under Tierra del Fuego in two climatic zones corresponding harsh weather conditions (Bustamante et al., 2006; to cold steppe (Cerro Sombrero) and submontane Cuadra and Fajardo, 2008). B. microphylla grown in (Lago Deseado). In cold steppe the climatic data Patagonia is exposed to stressful habitats such as indicate that the rainfall gradient is low (250-350 strong wind, cloudy and cold days and arid soils mm), mean annual temperature is 6.8 °C, soils (Garredau et al., 2013). Moreover, the altitude, soil present a pH 6-7 and erode readily for strong winds. nutrients and phenological stage of the plant affects Further south, submontane zone is characterized by the alkaloids content in Berberis species (Chandra & more acid soil (pH 4 - 5.2), rainfall increases (338- Purohit, 1980; Andola et al., 2010a; Echeverria & 852 mm) and the temperature decreases to 2.7 °C Niemeyer, 2012; Niemeyer, 2014). The literature (annual mean) (Moore, 1983). Voucher specimens indicate that the presence of berberine (major (178056-Cerro Sombrero; 178057-Lago Deseado) alkaloid in Berberis plant) could be restricted to a were deposited in the Herbarium of the Universidad specific organ or distributed in different organs of de Concepción, Concepción, Chile. plants; including leaves, stem and roots (Khamidov et al., 2003; Končić et al., 2010). However, in B. Alkaloids extraction microphylla only has been studied the presence of Extraction was carried out according to the alkaloids but its distribution in the plant is unknown. methodology described by Cabezas et al. (2009) with In the last decades, several methods have some modifications. Oven dried and powdered leaves been report for the determination of alkaloids in (100 g), stems (300 g) and roots (300 g) of B. plant, included colorimetry (Shamsa et al., 2008), microphylla were sequentially extracted (24, 48 and thin layer chromatography (TLC) (Patel et al., 2012), 72 h) with methanol at room temperature. Methanolic capillary zone electrophoresis (CZE) (Gong et al., extracts were evaporated in vacuo at 40 °C, and the 2003) and nuclear magnetic resonance (H-NMR, C- residue was reconstituted with 200 mL 10% HCl for NMR) (Quevedo et al., 2008; Fajardo et al., 2009). In 1 h under agitation (orbital shaker, MS-NOR, some cases, the traditional methods mentioned above Taiwan), and allowed to stand for 12 h at 10° C and require sample extractions and long time for then filtered. The filtrate was washed with CHCl3 (5 x completing the whole analysis (Chan et al., 2007). In 100 mL). The aqueous phase was adjusted to pH 10
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  • Structure of a Berberine Bridge Enzyme-Like Enzyme with an Active Site Specific to the Plant Family Brassicaceae

    Structure of a Berberine Bridge Enzyme-Like Enzyme with an Active Site Specific to the Plant Family Brassicaceae

    Structure of a Berberine Bridge Enzyme-Like Enzyme with an Active Site Specific to the Plant Family Brassicaceae Daniel, Bastian; Wallner, Silvia; Steiner, Barbara; Oberdorfer, Gustav; Kumar, Prashant; van der Graaff, Eric; Roitsch, Thomas; Sensen, Christoph W; Gruber, Karl; Macheroux, Peter Published in: PLOS ONE DOI: 10.1371/journal.pone.0156892 Publication date: 2016 Document version Publisher's PDF, also known as Version of record Citation for published version (APA): Daniel, B., Wallner, S., Steiner, B., Oberdorfer, G., Kumar, P., van der Graaff, E., ... Macheroux, P. (2016). Structure of a Berberine Bridge Enzyme-Like Enzyme with an Active Site Specific to the Plant Family Brassicaceae. PLOS ONE, 11(6), e0156892. https://doi.org/10.1371/journal.pone.0156892 Download date: 08. Apr. 2020 RESEARCH ARTICLE Structure of a Berberine Bridge Enzyme-Like Enzyme with an Active Site Specific to the Plant Family Brassicaceae Bastian Daniel1, Silvia Wallner1, Barbara Steiner1, Gustav Oberdorfer2, Prashant Kumar2, Eric van der Graaff3, Thomas Roitsch3,4, Christoph W. Sensen5, Karl Gruber2, Peter Macheroux1* 1 Institute of Biochemistry, Graz University of Technology, Graz, Austria, 2 Institute of Molecular Biosciences, University of Graz, Graz, Austria, 3 Department of Plant and Environmental Sciences, a11111 University of Copenhagen, Copenhagen, Denmark, 4 Global Change Research Centre, Czech Globe AS CR, v.v.i., Drásov 470, Cz-664 24 Drásov, Czech Republic, 5 Institute of Molecular Biotechnology, Graz University of Technology, Graz, Austria * [email protected] OPEN ACCESS Abstract Citation: Daniel B, Wallner S, Steiner B, Oberdorfer Berberine bridge enzyme-like (BBE-like) proteins form a multigene family (pfam 08031), G, Kumar P, van der Graaff E, et al.