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Redalyc.Circadian Variation of Essential Oil from Piper Marginatum Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas ISSN: 0717-7917 [email protected] Universidad de Santiago de Chile Chile MORAES, Marcilio M.; da SILVA, Telma M. G.; da SILVA, Rodolfo R.; RAMOS, Clecio S.; da CÂMARA, Claúdio A. G. Circadian variation of essential oil from Piper marginatum Jacq Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, vol. 13, núm. 3, mayo-, 2014, pp. 270-277 Universidad de Santiago de Chile Santiago, Chile Available in: http://www.redalyc.org/articulo.oa?id=85631010006 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 (3): 270 - 277 ISSN 0717 7917 www.blacpma.usach.cl Artículo Original | Original Article Circadian variation of essential oil from Piper marginatum Jacq [Variaciones circadiana de aceite esencial de Piper marginatum Jacq] Marcilio M. MORAES, Telma M. G. da SILVA, Rodolfo R. da SILVA, Clecio S. RAMOS & Claúdio A. G. da CÂMARA. Department of Molecular Sciences, Rural Federal University of Pernambuco, Street Dom Manoel de Medeiros s/n, 52.171-030 Recife, PE, Brazil Contactos | Contacts: Clecio S. RAMOS - E-mail address: [email protected] Abstract: The composition of the essential oil from the leaves of Piper marginatum (Piperaceae) shows circadian variation and a higher yield during high solar incidence. The essential oils samples were investigated by GC-FID and GC-MS, which allowed identification of 29 compounds. Principal component analysis (PCA) and cluster analysis (CA) showed a significant quantitative variability in the chemical composition of the studied samples as well as a correlation between the oil profiles and the collection time. Two main groups were observed, with predominance of phenylpropanoids or sesquiterpenes. The predominant chemical compounds were phenylpropanoids, having as main representative (Z)-asarone and (E)-asarone. Keywords: Piper marginatum, essential oil, Piperaceae, Circadian variation Resumen: La composición del aceite esencial de hojas de Piper marginatum (Piperaceae) muestra una variación circadiana y un mayor rendimiento durante la mayor incidencia solar. Las muestras de aceites esenciales se investigaron por GC-FID y GC-MS, lo que permitió la identificación de 29 compuestos. El análisis de componentes principales y el análisis de conglomerados mostraron una variación cuantitativa significativa en la composición química de las muestras estudiadas, así como una correlación entre los perfiles del aceite esencial y el tiempo de recolección. Se observaron dos grupos principales, con predominio de fenilpropanoides o sesquiterpenos. Los compuestos predominantes fueron los fenilpropanoides, (Z)-asarona y (E)-asarona. Palabras clave: Piper marginatum, aceite esencial, Piperaceae, Variación circadiana Recibido | Received: May 16, 2013 Aceptado en versión corregida | Accepted in revised form: October 20, 2013 Publicado en línea | Published online: May 30, 2014 Declaración de intereses | Declaration of interests: This work was funded by grants provided by FACEPE. The authors are indebted to the Centro de Apoio a Pesquisa (CENAPESQ). Este artículo puede ser citado como / This article must be cited as: MM Moraes, TMG da Silva, RR da Silva, CS Ramos, CAG da Camara. 2014. Cicardian variation of essential oil from Piper marginatum Jacq. Bol Latinoam Caribe Plant Med Aromat 13(3): 270 – 277. 270 Moraes et al. Circadian variation of essential oil from Piper marginatum Jacq INTRODUCTION 2009). However, no previous studies have The Piperaceae family comprises 14 genera (Lopes et investigated the chemical variation of the essential oil al., 1997), the most abundant being the Piper genus, of P. marginatum associated with the time of day of with approximately 700 species, distributed in collecting plant parts. Therefore, the objective of this tropical and temperate regions in both hemispheres work was to assess the effect of collection time on the (Barroso, 1986). In Brazil, there are approximately yield and chemical components of the essential oil 266 species, many of them occurring in remaining obtained from the leaves of P. marginatum. Atlantic Forest areas, where they are present in great abundance and diversity (Di Stasi et al., 2002). Some MATERIAL AND METHODS species of this genus, such as P. nigrum and P. Plant hispidinervium, have great economic and medicinal Fresh P. marginatum Jacq. leaves were collected importance (Barbosa et al., 2012; Parmar et al., from a fragment of Atlantic Forest located on the 1997). campus of Federal Rural University of Pernambuco The bushy aromatic shrub Piper marginatum (UFRPE) in Recife, Pernambuco, Brazil. The leaves Jacq. abundantly grows in Central America, the were collected in July 2009 at each two hours from Antilles and South America. In Brazil, it is 10:30 a.m. to 8:30 p.m. of next day. The plant was particularly found around the borders of Atlantic identified by Dr. Margareth F. de Sales of the Forest stands. It is popularly known as “malvaísco” Department of Biology of UFRPE and a voucher in northeastern Brazil (states of Pernambuco, Paraíba specimen was deposited in the Vasconcelos Sobrinho and Rio Grande do Norte) and as “caapeba cheirosa” Herbarium of UFRPE with number 48210. or “pimenta do mato” in the northern region, especially in the Amazon. It is generally encountered Chemicals at forest edges, reaching heights up to five meters The monoterpenes (β-Pinene, linalool, α-terpineol, α- (Pio-correia, 1984; Guimarães and Giordano, 2004). copaene and β-elemene), sesquiterpenes (β- The extract of P. marginatum leaves has been Caryophyllene, α-cadinene, γ-cadinene, elemol, α- used in popular medicine to treat inflammation, snake humulene) and phenylpropanoids (E-methyl bites and diseases of the liver and vesicles (Van Den isoeugenol, Z-asarone, E-asarone) used to identify the Berg, 1982; D’Angelo et al., 1997; Maxwell and volatile components were purchased from Sigma– Rampersad, 1988). Aldrich, Brazil. Phytochemical and biological studies of P. marginatum have been extensively conducted, Isolation of the Essential Oil describing the presence of phenyloctanoids, The essential oils from fresh leaves (100 g) were flavonoids, aristolactams, prenylated 4- obtained by hydrodistillation using a modified hydroxybenzoic acid derivatives, terpenes and Clevenger apparatus for 2 h. The oil layers were phenylpropanoids (Lago, et al., 2004, Ramos and separated and dried over anhydrous sodium sulfate, Kato, 2009, Foungbe et al., 1976, Hussain et al., stored in hermetically sealed glass containers, and 1990, Ramos et al., 1986, Tillequin et al., 1978). kept under refrigeration at 0º C until analysis. Total Variations have been found in the chemical oil yields were expressed as percentages (g/100 g of composition of the essential oil from P. marginatum fresh plant material). All experiments were carried leaves. Among the predominant chemical classes out in triplicate. mentioned are both sesquiterpenes and phenilpropanoids (Autran et al., 2009; Andrade et al., GC Analysis 2008). This variation is attributed to the environment Oil samples were analyzed using a Hewlett–Packard and climate conditions (Gobbo-Neto and Lopes, 5890 Series II GC apparatus equipped with a flame 2007). ionization detector and a J & W Scientific DB-5 The essential oil of P. marginatum has been fused silica capillary column (30 m × 0.25 mm i.d.), extensively examined for its biological activities, with a programmed temperature of 60 to 246º C at 3º such as insecticidal (Mesa et al., 2012; Coitinho et C/min,. The injector and detector temperatures were al., 2010; Coitinho et al., 2011), acaricidal (Assis et 260 and 280º C, respectively. Hydrogen was used as al., 2011) and antifungal (Reigada et al., 2007), as carrier gas at a flow rate of 1.0 mL/min; injection was well as for its cytotoxic effects (Olivero-Verbel et al., in split mode (1:30) and the injection volume was 1.0 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/271 Moraes et al. Circadian variation of essential oil from Piper marginatum Jacq μL of a solution containing 10 mg/mL of oil in hexane. RESULTS AND DISCUSSION The amount of each compound was The essential oils of P. marginatum leaves obtained calculated from GC peak areas in the order of DB-5 by hydrodistillation showed yellowish coloration. column elution and expressed as a relative percentage The chemical constituents identified in these oils are of the total area of the chromatograms. Analyses listed in Table 1 in the order of elution in the DB-5 were carried out in triplicate and results were column. The range of oil yields varied according to submitted to descriptive statistical analysis. the time of collection. The highest yield was observed during the hottest period (26.6 - 27.3º C), GC/MS Analysis from the sample collected at 10:30 a.m. (yield of 0.31 Qualitative GC/MS analysis was carried out using a ± 0.4%). This was twice the yield of the sample Varian GC/MS (GC: Varian 431/GC-MS: Varian collected during the period of lowest temperature. 220-MS) system operating in the EI mode at 70 eV, Also, the yield varied according to the relative air fitted with the same column and using the same humidity (Table Nº 1), with the highest yield found temperature program as for the GC experiments. The from the leaves gathered during the period of lowest carrier gas was helium, 1 mL/min flow rate, split humidity. These results were consistent with other mode (1:30), with an injected volume of 1.0 µL of a findings in the literature regarding variations in yield solution containing 10 mg/mL of oil in hexane. depending on temperature and humidity (Evans, 1996). Statistical Analysis The chemical composition analysis of The clustering method based on linkage distances essential oil samples allowed the identification of 29 was used to determine similarities between the compounds.
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