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Cyperaceae) Essential Oil Acta Scientiarum http://www.uem.br/acta ISSN printed: 1679-9283 ISSN on-line: 1807-863X Doi: 10.4025/actascibiolsci.v38i3.32386 Volatile chemical composition and bioactivities from Colombian Kyllinga pumila Michx (Cyperaceae) essential oil Beatriz Eugenia Jaramillo-Colorado*, Eduardo Luis Martínez-Cáceres and Edisson Duarte- Restrepo Chemistry Program, Agrochemical Research Group, University of Cartagena, Campus San Pablo, Zaragocilla Street, ZIP code 130015, Cartagena of Indias, Colombia. *Author for corrrespondence. E-mail: [email protected], [email protected] ABSTRACT. The essential oil from the fresh leaves of Kyllinga pumila (Michx) was obtained by hydrodistillation and characterized by gas chromatography-mass spectrometry (GC-MS). Twenty-eight volatile compounds were identified, major constituents of the oil were Methyl E,E-10,11-epoxyfarnesoate (43.8%), β-elemene (12.5%), Z-caryophyllene (11.3%), germacrene D (7.1%) and E-caryophyllene (5.6%). Repellent and fumigant activities of the oil against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae), were done using the area preference method. Additionally, we studied their antioxidant and phytotoxic effects. Essential oils exhibited a dose-dependent repellent activity, with values 90% at the applied concentration (0.01%), for both two and four hour’s exposure. Essential oil from K. pumila showed 92% -1 -1 mortality at 500 μL L air against T. castaneum on 24 hours of exposure. The value LC50 was 153.4 μL L . With moderate selective phytotoxic effects on L. perenne root growth (±70% inhibition). Kyllinga pumila shows high antioxidant potential (91.5%), an effect that is comparable with ascorbic acid (92.9%) used as a standard. The results indicated that K. pumila essential oil could be a promising alternative to new natural antioxidants, repellents, and biocides. Keywords: essential oils, repellent activity, fumigant, Tribolium castaneum, phytotoxic, DPPH. Composição química volátil e bioactividades do óleo essencial do colombiano Kyllinga pumila Michx (Cyperaceae) RESUMO. O óleo essencial das folhas frescas de Kyllinga pumila Michx., foi obtido por hidrodestilação e caracterizado por cromatografia gasosa acoplada a espectrometria de massas (CG-EM). O constituinte majoritário do óleo foi Metil E,E-10,11-epoxifarnesoato (43,8%), β-elemeno (12,5%), Z-caryophylleno (11,3%), germacreno D (7,1%), E-caryophylleno (5,6%). A atividade repelente e fumigante do óleo frente à Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) foi determinada pelo método da área de preferencia. Também, foi estudado os efeitos antiferrugens e fitotóxicos. Óleos essenciais exibiram uma atividade repelente dependente da dose, com valores de 90% na concentração aplicada (0,01%), tanto para duas e quatro horas de exposição. O óleo essencial de K. pumila mostrou mortalidade de 92% a 500 μL L-1 -1 ar frente à T. castananeum, em 24 horas de exposição. O valor LC50 foi 153,4 μL L . Com efeitos fitotóxicos seletivos moderado sobre o crescimento da raíz de L. perenne (± 70% de inibição). Kyllinga pumila mostra um elevado potencial antioxidante (92%), um efeito que é comparável com ácido ascórbico (95%) usado como padrão. Os resultados indicaram que o óleo essencial K. pumila poderia ser uma alternativa promissora para novos antioxidantes, repelentes e biocidas naturais. Palavras-chave: Plantas ciperáceas, óleos essenciais, actividade repelente, fumigante, Tribolium castaneum, DPPH. Introduction (Guilhon, Vilhena, Zoghbi, Bastos, & Rocha, 2008) The genus Kyllinga belongs to Cyperaceae family, and K. odorata (Tucker, Maciarello, & Bryso, 2006), no distributed in tropical, subtropical, and warm reports exist on the chemistry of the essential oils temperate regions around the world. Consists of about (EOs) from K. pumila Mixch species. One objective of 40 species that are distributed worldwide. Kyllinga this paper was to determine the volatile chemical pumila Mixch, known in Colombia as ‘estrellón’, is a composition of the EOs from K. pumila growing in the perennial plant, growing in North America, South Department of Bolivar, Colombia. We believe that the America, Caribbean Islands and Africa (Simpson & data obtained from this study could contribute to the Inglis, 2001). Except for reports on K. erecta Schum. taxonomic investigation of the genus and explore (Mahmout, Bessiere, & Dolmazon, 1993); K. brevifolia possible uses of added value. Acta Scientiarum. Biological Sciences Maringá, v. 38, n. 3, p. 273-282, July-Sept., 2016 274 Jaramillo-Colorado et al. Natural products from several plants species, department, Colombia (9° 58′ 52″ N, 75° 17′ 55″ W) such as essential oils have demonstrated to act as in April of 2014. The taxonomic characterization of repellents (De Lira et al., 2015; Jaramillo-Colorado, the plant was carried out at the Institute of Biology, Martelo, & Duarte, 2012), toxicants (Harraz et al., Faculty of Natural Sciences-University of 2015) and antifeedants (Julio et al., 2014) against Antioquia, Medellin, Antioquia, Colombia (Dr. F. J. insects that attack stored products (Erland, Rheault, Roldan Palacios, Herbarium University of & Mahmoud, 2015; Rajendran & Sriranjini, 2008). Antioquia, HUA 185261). Furthermore, they are known for their antimicrobial and antioxidant properties, and their use in the food Extraction of the essential oil industry has been widely described (Duarte, Luis, Extraction of essential oil from K. pumila was Oleastro, & Domingues, 2016) done according to European Pharmacopeia In previous studies, oils isolated from Triphasia (European Pharmacopeia, 2008). Five hundred trifolia (Jaramillo et al., 2012), Laurelia sempervirens, grams Five hundred grams of fresh leaves chopped Origanum vulgare (Kim et al., 2010), Achillea (Nenaah, and 900 mL of distilled water were placed in a flask. 2014), among others, showed repellent activity After hydrodistillation for three hours in a modified against Tribolium castaneum Herbst (Coleoptera: Clevenger apparatus, the essential oil was separated Tenebrionidae). This is one of the stored-product by decantation and added Na2SO4 anhydrous pests most widespread and destructive, causing (Panreac, USA). For GC analysis, 30 μL of essential damage to storage grains directly by feeding (Rees, oil was added to 1.0 mL of dichloromethane (Merck, 2004) and indirectly by the secretion of quinones Germany) and 1 μL of this solution was injected that are responsible for human allergies (Hodges, into the injection port. Robinson, & Hall, 1996). Also, the increasing public concern over pesticide safety and possible Chromatography analysis environmental damage has resulted in rising attention to natural products as alternatives for the The chromatographic analysis of the essential control of stored pests (Rajendran & Sriranjini, oils was carried out in a gas chromatograph Agilent 2008). Terpenoids present in essential oils have Technologies 4890D, equipped with an injection shown strong repellent or insecticide activity, port split/splitless (230°C, split ratio 30:1) and a including hydrogenated monoterpenoids, such as flame ionization detector (FID) (250°C). For the thymol, α-pinene, carvacrol, myrcene, and separation of the mixtures were used a capillary oxygenated sesquiterpenes as caryophyllene oxide columns: HP-5 (30 m × 0.32 mm i.d × 0.25 μm (Kim et al., 2010). Additionally, many phenolic df), stationary phase 5% diphenyl-95% compounds such as eugenol, estragole, anethole, polydimethylsiloxane (J & W Scientific, USA) and carvacrol, thymol, coniferyl alcohol, etc., are widely ZB-WAX (30 m x 0.53 mm i.d x 0.50 μm df), distributed in the plant kingdom and constitute one stationary phase polyethylene glycol (Phenomenex of the most important classes of natural antioxidants Inc, USA). Oven temperature was 50°C for 2 min (Amorati, Foti, & Valgimigli, 2013). However, the and then continued at the rate of 5°C min−1 to main compounds found in essential oils are not 250°C (5 min). A carrier gas, helium, adjust to a rate always responsible for the biological activities, for of 1.160 mL min-1 with inlet pressure head of the this reason is necessary the identification and column of 87.3 kPa. The identity of the components detection of all compounds (Jaramillo-Colorado et was assigned by comparison of their linear retention al., 2012). indices (LRI), relative to C7-C30 n-alkanes As part of our ongoing search to improved (Supelco, Bellefonte, PA, USA) compared with the botanical biopesticides, the volatile chemical literature reported (Adams, 1995; Davies, 1990), and composition of the K. pumila essential oil has been GC-MS spectra of each GC component with those analyzed in this study using GC–MS along with of standard substances, Wiley library data of the GC. their repellent and fumigant effects against T. High-purity gases for chromatography (helium and castaneum, antioxidant activity, and its phytotoxicity hydrogen grade 5.0, and zero air) were obtained against L. perenne. from Linde (Cartagena, Colombia). GC-MS analyses were carried out using a gas Material and methods chromatograph Agilent Technologies 7890A Network Plant material GC (Palo Alto, California, USA) coupled to a mass The fresh flowers and leaves from K. pumila were selective detector (MSD) Agilent Technologies 5975 collected on a farm, next to Maria La Baja, Bolivar inert GC-MS system, equipped with an automatic Acta Scientiarum. Biological Sciences Maringá, v. 38, n. 3, p. 273-282, July-Sept., 2016 Volatile chemical composition and bioactivities 275 injector Agilent
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