Printer Friendly

Volatile chemical composition and bioactivities from Colombian Kyllinga pumila Michx (Cyperaceae) essential oil/Composicao quimica volatil e bioactividades do oleo essencial do colombiano Kyllinga pumila Michx (Cyperaceae).

Introduction

The genus Kyllinga belongs to Cyperaceae family, distributed in tropical, subtropical, and warm temperate regions around the world. Consists of about 40 species that are distributed worldwide. Kyllinga pumila Mixch, known in Colombia as 'estrellon', is a perennial plant, growing in North America, South America, Caribbean Islands and Africa (Simpson & Inglis, 2001). Except for reports on K erecta Schum. (Mahmout, Bessiere, & Dolmazon, 1993); K brevifolia (Guilhon, Vilhena, Zoghbi, Bastos, & Rocha, 2008) and K odorata (Tucker, Maciarello, & Bryso, 2006), no reports exist on the chemistry of the essential oils (EOs) from K pumila Mixch species. One objective of this paper was to determine the volatile chemical composition of the EOs from K pumila growing in the Department of Bolivar, Colombia. We believe that the data obtained from this study could contribute to the taxonomic investigation of the genus and explore possible uses of added value.

Natural products from several plants species, such as essential oils have demonstrated to act as repellents (De Lira et al., 2015; Jaramillo-Colorado, Martelo, & Duarte, 2012), toxicants (Harraz et al., 2015) and antifeedants (Julio et al., 2014) against insects that attack stored products (Erland, Rheault, & Mahmoud, 2015; Rajendran & Sriranjini, 2008). Furthermore, they are known for their antimicrobial and antioxidant properties, and their use in the food industry has been widely described (Duarte, Luis, Oleastro, & Domingues, 2016)

In previous studies, oils isolated from Triphasia trifolia (Jaramillo et al., 2012), Laurelia sempervirens, Origanum vulgare (Kim et al., 2010), Achillea (Nenaah, 2014), among others, showed repellent activity against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae). This is one of the stored-product pests most widespread and destructive, causing damage to storage grains directly by feeding (Rees, 2004) and indirectly by the secretion of quinones that are responsible for human allergies (Hodges, Robinson, & Hall, 1996). Also, the increasing public concern over pesticide safety and possible environmental damage has resulted in rising attention to natural products as alternatives for the control of stored pests (Rajendran & Sriranjini, 2008). Terpenoids present in essential oils have shown strong repellent or insecticide activity, including hydrogenated monoterpenoids, such as thymol, [alpha]-pinene, carvacrol, myrcene, and oxygenated sesquiterpenes as caryophyllene oxide (Kim et al., 2010). Additionally, many phenolic compounds such as eugenol, estragole, anethole, carvacrol, thymol, coniferyl alcohol, etc., are widely distributed in the plant kingdom and constitute one of the most important classes of natural antioxidants (Amorati, Foti, & Valgimigli, 2013). However, the main compounds found in essential oils are not always responsible for the biological activities, for this reason is necessary the identification and detection of all compounds (Jaramillo-Colorado et al., 2012).

As part of our ongoing search to improved botanical biopesticides, the volatile chemical composition of the K. pumila essential oil has been analyzed in this study using GC-MS along with their repellent and fumigant effects against T. castaneum, antioxidant activity, and its phytotoxicity against L. perenne.

Material and methods

Plant material

The fresh flowers and leaves from K. pumila were collected on a farm, next to Maria La Baja, Bolivar department, Colombia (9[degrees] 58' 52" N, 75[degrees] 17' 55" W) in April of 2014. The taxonomic characterization of the plant was carried out at the Institute of Biology, Faculty of Natural Sciences-University of Antioquia, Medellin, Antioquia, Colombia (Dr. F. J. Roldan Palacios, Herbarium University of Antioquia, HUA 185261).

Extraction of the essential oil

Extraction of essential oil from K. pumila was done according to European Pharmacopeia (European Pharmacopeia, 2008). Five hundred grams Five hundred grams of fresh leaves chopped and 900 mL of distilled water were placed in a flask. After hydrodistillation for three hours in a modified Clevenger apparatus, the essential oil was separated by decantation and added [Na.sub.2]S[O.sub.4] anhydrous (Panreac, USA). For GC analysis, 30 [micro]L of essential oil was added to 1.0 mL of dichloromethane (Merck, Germany) and 1 [micro]L of this solution was injected into the injection port.

Chromatography analysis

The chromatographic analysis of the essential oils was carried out in a gas chromatograph Agilent Technologies 4890D, equipped with an injection port split/splitless (230[degrees]C, split ratio 30:1) and a flame ionization detector (FID) (250[degrees]C). For the separation of the mixtures were used a capillary columns: HP-5 (30 m X 0.32 mm i.d X 0.25 [micro]m df), stationary phase 5% diphenyl-95% polydimethylsiloxane (J & W Scientific, USA) and ZB-WAX (30 m x 0.53 mm i.d x 0.50 [micro]m df), stationary phase polyethylene glycol (Phenomenex Inc, USA). Oven temperature was 50[degrees]C for 2 min and then continued at the rate of 5[degrees]C [min.sup.-1] to 250[degrees]C (5 min). A carrier gas, helium, adjust to a rate of 1.160 mL [min.sup.-1] with inlet pressure head of the column of 87.3 kPa. The identity of the components was assigned by comparison of their linear retention indices (LRI), relative to C7-C30 n-alkanes (Supelco, Bellefonte, PA, USA) compared with the literature reported (Adams, 1995; Davies, 1990), and GC-MS spectra of each GC component with those of standard substances, Wiley library data of the GC. High-purity gases for chromatography (helium and hydrogen grade 5.0, and zero air) were obtained from Linde (Cartagena, Colombia).

GC-MS analyses were carried out using a gas chromatograph Agilent Technologies 7890A Network GC (Palo Alto, California, USA) coupled to a mass selective detector (MSD) Agilent Technologies 5975 inert GC-MS system, equipped with an automatic injector Agilent 4513A. For the separation of the essential oil was used a capillary column HP-5MS (30m x 0.25 mm id) coated with 5% diphenyl-95% polydimethylsiloxane (0.25 [micro]m phase thickness) (J & W Scientific, USA). The oven temperature programmed was 50[degrees]C (2 min), 50-250[degrees]C at 5[degrees]C [min.sup.-1], 250[degrees]C (5 min); the injector temperature was 230[degrees]C; the carrier gas was helium (quality grade 5.0, 99.99%) at 87 kPa (1.17 mL [min.sup.-1]); the injection mode was split (ratio of 1:20); the sample volume injected was 1 [micro]L. The mass spectra were obtained by electron-impact ionization (EI) and energy of 70eV. The temperatures of the ionization chamber and transfer line were 230 and 280[degrees]C, respectively, and the acquisition mass range was 30-400 m/z.

Insects and bioassays

Were used adults of T. castaneum 5-7 days post-eclosion. Bioassays were carried out in the dark incubators at 28-30[degrees]C and 70-80% relative humidity (r.h) at the laboratory of Agrochemical Research of the University of Cartagena. T. castaneum were reared with Oat (Avena sativa).

Repellent activity

Repellent activity was as described by Tapondjou, Adler, Fontem, Bouda, and Reichmuth (2005). The experimental method was measured using the area preference method. Filter papers (Whatman No. '1, diameter 9 cm) were cut in half. The essential oil of K. pumila was dissolved in acetone. The concentrations chosen to evaluate the repellent were 0.0001, 0.001, 0.01, 0.1 and 1%. A volume of 0.5 mL of each essential oil solution was applied slowly and uniformly to one-half of each filter paper, the other half of the filter paper was treated with acetone as a control. The treated and control half discs were dried at room temperature to allow evaporation of the solvent. Treated and untreated halves were attached to their opposites using adhesive tape and placed in Petri dishes. Twenty adults (5-7 day old) of T. castaneum were released separately at the center of each filter paper disc. The dishes were then covered and transferred to an incubator at room temperature. The treatments were replicated four times, and the numbers of insects presented on the control (Nc) and treated (Nt) areas of the disks were recorded after 2 and four hours of exposition (Jaramillo-Colorado et al., 2012). Percentage repellency (PR) values were calculated as follows:

PR (%)= [([N.sub.c]-[N.sub.t])/([N.sub.c]+[N.sub.t])]*100

The results obtained were transformed into percentage repellency and analyzed by ANOVA and Student t test. Mortality rates were calculated using statistical formulas Abbott and Probit to determine the [LC.sub.50]. A statistical software Version 2009 Biostat (AnalystSoft Robust Business Solutions, BioStat 2009) was used, with a level of the confidence interval of 5%. Four replicates for each analysis were performed.

Fumigant activity

The toxic effect of the essential oil from K. pumila was tested on T. castaneum adults. To determine the fumigant toxicity were used filter paper discs (Whatman No. 1, 2-cm diameter pieces), deposited at the bottom of petri dish covers (90 x 15 mm). These were impregnated with oil at doses calculated to give equivalent fumigant concentrations of 500, 350, 250, 150, 50 [micro]L of oil [L.sup.-1] air, respectively. Twenty adult insects (1 to 10-d-old) were introduced and tightly capped (replicated four times for each concentration). Was employed as a positive control, Pirilan 50EC, commercial pesticides, this contains as active ingredient methyl pirimiphos (organophosphorus pesticide). Mortality percentage was determined after 24 hours from the start of exposure (Negahban, Moharramipour, & Sefidkon, 2007).

Antioxidant activity

Was evaluated as a measure of the ability to scavenge radicals, by reacting DPPH (1,1-diphenyl-2-picrylhydrazyl) radical (Sigma, USA), with potential antioxidants (essential oil) and ascorbic acid (standard substance) (Merck, Germany). Two milliliters of a 3.6 X [10.sup.-5] M ethanolic solution of DPPH was added to 50 [micro]L of an ethanolic solution of the antioxidant. The decrease in absorbance at 517 nm was recorded in an UV-Vis spectrophotometer for 16 min. Antioxidant activity is expressed as percentage inhibition, which corresponds to the amount of radical DPPH. offset by essential oils, (inhibition percentage of DPPH. radical, % I DPPH), according to the following equation (Jaramillo-Colorado et al., 2012):

%I DPPH = [[[AbS.sub.0] - [Abs.sub.1]]/[Abs.sub.0]]x100

Where [Abs.sub.0] is the absorbance of control (without test sample), and [Abs.sub.1] is the absorbance of the test samples at different concentrations. The antioxidant activity was measured at 0,1, 0.5, 1.0, 1.5, 2.0, and 2.5 mg [mL.sup.-1] of K. pumila extracts.

Phytotoxic activity

The experiments were conducted with Lolium perenne seeds. 2.5 cm diameter filter paper with 20 [micro]L of the test compound (10 [micro]g [micro][L.sup.-1] for extracts and 5 [micro]g [micro][L.sup.-1] for pure compounds) were placed on 12-well plates (Falcon), according to Martin et al. (2011).

Germination was monitored for six days and the rootlet/leaf length measured at the end of the experiment (25 plantlets randomly selected for each test and digitalized with the application ImageJ 1.43, http://rsb.info.nih.gov./ij/). This was performed a non-parametric analysis of variance (ANOVA) on radical length data. The juglone (JU) (5 [micro]g [micro][L.sup.-1]) was used as a positive control.

Results and discussion

Volatile chemical analysis of Kyllinga pumita

The essential oil of K. pumila was isolated from its aerial parts using hydrodistillation method (yield 0.39%) and analyzed using GC-FID and GC/MS techniques, to determine its qualitative and quantitative composition. Twenty-eight components were identified by GC/MS representing about 97% of the composition of K. pumila essential oil. Figure 1 shows the chromatographic profile of the volatile compounds.

Peak identification for the chromatogram appears in Table 1 and the structures of compounds can be seen in Figure 2. The detected analytes were listed according to their elution order on the HP-5 column. The majority components found in the essential oil were Methyl E,E-10,11-epoxyfarnesoate (2,6-nonadienoic acid, 9-(3,3-dimethyloxiranyl)-3,7-dimethyl, methyl ester, E,E) (43.8%), [beta]-Elemene (12.5%), Z-caryophyllene (11.3%), germacrene D (7.1%) and E- caryophyllene (5.6%), 2-Z-6-E-farnesol (2.7%).

The composition of K. pumila essential oil obtained from plants collected in Maria la Baja, Colombia, reveals the predominance of sesquiterpenoids compounds, principally, E-E-10,11-Epoxy farnesenic acid methyl ester (juvenile hormone III, JH III). This is an insect juvenile hormone, is structurally-related sesquiterpenoids that regulate developmental processes such as metamorphosis and reproduction. Methyl farnesoate, the immediate biosynthetic precursor to JH III in insects, has been identified in Cyperus iria and Cyperus aromaticus (Toong, Schooley, & Baker, 1988; Bede, Goodman, & Tobea, 1999; Bede, Teal, Goodman, & Tobea 2001), species belongs to Cyperaceae family too.

There are not reports about the chemistry of the essential oils of K. pumila Mixch species. But exist publications related to K. erecta Schum., (Mahmout et al., 1993), K. brevifolia (Guilhon et al., 2008) and K. odorata (Tucker et al., 2006). The results obtained in those works were differents compared with our study. The main components present in K. brevifolia were the manoyl oxide (6.8%-31.1%), 13-epimanoyl oxide (5.7%-26.1%), 11[alpha]-hydroxymanoyl oxide (5.9%-16.2%) and 1[beta]-hydroxymanoyl oxide (4.6%-22.1%). In K. odorata were dihydrokaranone (53.1 [+ or -] 16.6%) and aristolochene (11.3 [+ or -] 2.4%) (Tucker et al., 2006). And for K. erecta, Mahmout et al. (1993) reported manoyl oxide, cyperene, sativene, and spathulenol). While Oyedeji, Mdlolo, Adeniyi, & Akinde (2010) described 1,8-cineole (10.5%), a-humulene (21.7%), farnesyl acetate (11.2%).

Repellent activity

Kyllinga pumila oil showed significant pest repellent activity. The oil was repellent to T. castaneum adults at all concentrations (Table 2). K. pumila oil had a strong repellent activity to adults at a 0.01 [micro]L [cm.sup.-2] and exposure period of two and four hours, repellency reached 90% for both. Thus, K. pumila oil has the potential for use with at least some stored-product insects as a repellent.

The insect known as weevil flour (Tribotium castaneum), is one of the most damaging for the food industry due to its high economic effect on flour, cereals, pasta, crackers, nuts, etc. (Nenaah, 2014). The essential oil of K. pumita had a high repellent activity (90,0%) against T. castaneum, this effect can be related to the primary compound found in the essential oil, JH III, as previously mentioned, play critical roles in physiological processes, such as metamorphosis and reproduction of the insects (Yang et al., 2013). Chaitanya, Sridevi, Senthilkumaran, & Dutta Gupta (2012) show that the insecticidal activity of JH III analogs may form part of a defensive strategy of plants against insect herbivores by preventing the development from insect larvae to insect adults. Furthermore, is well known that repellent properties of EOs are associated with the presence of specific compounds, specifically monoterpenoids and sesquiterpenes (Ukeh & Umoetok, 2011; Zhang et al., 2011; Tabanca et al., 2013). Zhang et al. (2011) showed that the essential oil of Cymbopogon distans aerial parts possessed strong repellency against the booklouse, Liposcelis bostrychophila, and the red flour beetle, Tribotium castaneum. Kim et al. (2010) evaluated the repellency activity against T. castaneum using nine constituents of origanum oil. Caryophyllene oxide and [alpha]-pinene produced the strongest repellency. These compounds were identified in the EO from Colombian K. pumita.

Fumigant activity

Results related to fumigant toxicity bioassays were shown in Figure 3. The values [LC.sub.50] and [LC.sub.95] for K. pumiUa on T. castaneum were respectively 153.4 and 535.0 [micro]L [L.sup.-1]. Such activity seems to be moderate compared to Pirilan, methyl pirimiphos (commercial insecticide) with [LC.sub.50] and [LC.sub.95] values of 50.1 and 359.5 [micro]L [L.sup.-1] air, respectively, as shown Table 3. The highest value of fumigant activity was 92.0 % at 500 [micro]L EO [L.sup.-1] air (see Figure 3).

Essential oils of many plant species are insecticidal to stored-product insects (Rajendran & Sriranjini, 2008). The insecticidal propriety of many essentials oils is mainly attributed to monoterpenoids which are typically volatile and rather lipophilic compounds that can penetrate into insects rapidly and interfere with their physiological functions (Suthisut, Fields, & Chandrapatya, 2011; Bakkali, Averbeck, Averbeck, & Idaomar, 2008). Due to their high volatility, they have fumigant and gaseous action which are very crucial in controlling the stored-product insects (Bachrouch, Ferjani, Haouel, & Ben Jemaa, 2015).

Suthisut et al. (2011) found significative fumigant activity in individual monoterpenoids proved against T. castaneum. They were terpinen-4-ol, Camphor, isoborneol, 1,8-cineole, and [beta]-pinene. These last has been known as possessing strong acetylcholinesterase inhibition activity from T. castaneum and S. oryzae (Zarrad, Ben Hamouda, Chaieb, Laarif, & Jemaa, 2015; Kim, Kang, & Park, 2013).

Antioxidant activity

Figure 4 shows that radical DPPH. was neutralized by the essential oil from K. pumita, with a maximum percentage of inhibition of 91.5% (2.5 mg [mL.sub.-1]); a comparison was made with ascorbic acid (a substance used as a reference antioxidant), where the percentage of inhibition against DPPH. radical was 92.9%.

The DPPH radical is scavenged by antioxidants through the donation of hydrogen, which forms the reduced compound, DPPH-H. The color changes from purple to yellow after reduction (product known as diphenyl-picryl hydrazine), which can be quantified by a decrease in the absorbance at 517 nm. The presence of an antioxidant leads to the disappearance of these radical chromogens (Jaramillo-Colorado et al., 2012). This resulting decolorization depends on the number of electrons that are captured. This scavenging occurs due to the donation of hydrogen ions as a result of the progression of the reaction between free radicals and antioxidants. Various works reported high scavenging activity of terpenes found in citrus peel essential oils as [alpha]-pinene, linalool, citronelol, myrcene, [gamma]-terpinene, and limonene, among others (Behrendorff, Vickers, Chrysanthopoulos, & Nielsen, 2013; Sawamura, 2013). As antioxidant compounds donate a proton to the DPPH radical, greater weighting may be given to double bond positions that increase the availability of allylic protons (due to the weaker C-H bond at allyl groups) (Behrendorff et al., 2013).

Phytotoxic activity

The effect of essential oil from K. pumila (100 [micro]g [cm.sup.-2]) was moderate and selective against the monocotyledonous weed L. perenne, and affected both root (70%) and leaf (78.2%) growth. The results can be checked in Table 4.

Allelopathy is a process for which products of the secondary metabolism, as terpenes phenolic, of a certain vegetal intervene significantly, generally of antagonistic form, in the development of other species of plants. The volatile terpenes, components of essential oils, show important allelopathic action, as caryophyllene oxide, carvacrol, thymol, 1,8-cineole, among others (Pinheiro et al., 2015; Oliveira, Moreira, & Mendes, 2013; Dias, Gomes, & Dallarmi, 2009).

Conclusion

This study demonstrated repellent and fumigant activities of K. pumila essential oils. This oil is promising and could be considered for practical applications for stored food pest control. This finding suggests that the EO of K. pumila or single active compound can be a source of potential candidates and precursors for the development of natural repellent or biocides and antioxidant products.

Acknowledgements

The authors acknowledge support from the University of Cartagena, Program to Support Research Groups, sponsored by the Vice-Presidency for Research at the University of Cartagena, (2012-2014).

Thanks to Dr. Azucena Gonzalez-Coloma for her valuable cooperation.

The authors have declared no conflict of interest.

References

Adams, R. P. (1995). Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy. Carol Stream, 111: Allured.

Amorati, R., Foti, M. C., & Valgimigli, L. (2013). Antioxidant activity of essential oils: review. Journal Agricultural and Food Chemistry, 61(46), 10835-10847.

Bachrouch, O., Ferjani, N., Haouel, S., & Ben Jemaa, J. M. (2015). Major compounds and insecticidal activities of two Tunisian Artemisia essential oils toward two major coleopteran pests. Industrial Crops Products, 65, 127-133.

Bakkali, F., Averbeck, S., Averbeck, D., & Idaomar, M. (2008). Biological effects of essential oils: a review. Food and Chemical Toxicology, 46(2), 446-475.

Bede, J. C., Goodman, W. G., & Tobea, S. S. (1999). Developmental distribution of insect juvenile hormone III in the sedge, Cyperus iria L. Phytochemistry, 52(7), 1269-1274.

Bede, J. C., Teal, P. E., Goodman, W. G., & Tobea, S. S. (2001). Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria. Plant Physiology, 127(2), 584-593.

Behrendorff, J. B., Vickers, C. E., Chrysanthopoulos, P., & Nielsen, L. K. (2013). 2,2-Diphenyl-1-picrylhydrazyl as a screening tool for recombinant monoterpene biosynthesis. Microbial Cell Factories, 12(1), 76-86.

Chaitanya, R. K., Sridevi, P., Senthilkumaran, B., & Dutta Gupta, A. (2012). Effect of juvenile hormone analog, methoprene on H-fibroin regulation during the last instar larval development of Corcyra cephalonica. General and Comparative Endocrinology Journal, 181, 10-17.

Davies, N. W. (1990). Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicon and Carbowax 20M phases. Journal Chromatography A, 503, 1-24.

De Lira, C. S., Pontual, E. V., De Albuquerque, L. P., Mesquita, L., Guedes, M. P., Vargas De Oliveira, J., ... Ferraz Navarro, D.M.A. (2015). Evaluation of the toxicity of essential oil from Alpinia purpurata inflorescences to Sitophilus zeamais (maize weevil). Crop Protection, 71, 95-100.

Dias, J. F. G., Gomes, M. O., & Dallarmi, M. O. (2009). Composition of essential oil and allelopathic activity of aromatic water of Aster lanceolatus Willd. (Asteraceae). Brazilian Journal Pharmaceutical Sciences, 45(3), 469-474.

Duarte, A., Luis, A., Oleastro, M., & Domingues, F. C. (2016). Antioxidant properties of coriander essential oil and linalool and their potential to control Campylobacter spp. Food Control, 61, 115-122.

Erland, L. A. E., Rheault, M. R., & Mahmoud, S. S. (2015). Insecticidal and oviposition deterrent effects of essential oils and their constituents against the invasive pest Drosophila suzukii (Matsumura) (Diptera: Drosophilidae). Crop Protection, 78, 20-26.

European Pharmacopeia. (2008). The Council of Europe (6th ed.). Vienna, IT: Verlag Osterreich.

Guilhon, G. M. S. P., Vilhena, K. S. S., Zoghbi, M. G. B., Bastos, M. N. C., & Rocha, A. E. S. (2008). Volatiles from aerial parts and rhizomes of Kyllinga brevifolia Rottb. Growing in Amazon. Journal Essential Oil Research, 20(6), 545-548.

Harraz, F. M., Hammoda, H. M., El Ghazouly, M. G., Farag, M. A., El-Aswad, A. F., & Bassam, S. M. (2015). Chemical composition, antimicrobial and insecticidal activities of the essential oils of Conyza linifolia and Chenopodium ambrosioides. Natural Products Research, 29(9), 879-882.

Hodges, R. J., Robinson, R., & Hall, D. R. (1996). Quinone contamination of dehusked rice by Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Journal Stored Products Research, 32(1), 31-37.

Jaramillo-Colorado, B. E., Martelo, I. P., & Duarte, E. (2012). Antioxidant and repellent activities of the essential oil from Colombian Triphasia trifolia (Burm. f.) P. Wilson. Journal Agricutural Food Chemistry, 60(25), 6364-6368.

Julio, L. F., Martin, L., Munoz, R., Mainar, A. M., Urieta, J. S., Sanz, J., ... Gonzalez-Coloma, A. (2014). Comparative chemistry and insect antifeedant effects of conventional (Clevenger and Soxhlet) and supercritical extracts (CO2) of two Lavandula luisieri populations. Industrial Crops Products, 58, 25-30.

Kim, S. I., Yoon, J. S., Jung, J. W., Hong, K. B., Ahn, Y. J., & Kwon, H. W. (2010). Toxicity and repellency of origanum essential oil and its components against Tribolium castaneum (Coleoptera: Tenebrionidae) adults. Journal of Asia-Pacific Entomology, 13(4), 369-373.

Kim, S. W., Kang, J., & Park, I. K. (2013). Fumigant toxicity of Apiaceae essential oils and their constituents against Sitophilus oryzae and their acetylcholinesterase inhibitory activity. Journal of Asia-Pacific Entomology, 16(4), 443-448.

Mahmout, Y., Bessiere, J. M., & Dolmazon, R. (1993). Composition of the essential oil from Kyllinga erecta S. Journal Agricultural and Food, 41 (2), 277-279.

Martin, L., Julio, L. F., Burillo, J., Sanz, J., Mainar, A. M., Gonzalez-Coloma, A. (2011). Comparative chemistry and insect antifeedant action of traditional (Clevenger and Soxhlet) and supercritical extracts (CO2) of two cultivated wormwood (Artemisia absinthium L.) populations. Industrial Crops Products, 34(3), 1615-1621.

Negahban, M., Moharramipour, S., & Sefidkon, F. (2007). Fumigant toxicity of essential oil from Artemisia sieberi Besser against three stored-product insects. Journal Stored Products Research, 43(2), 123-128.

Nenaah, G. E. (2014). Chemical composition, toxicity and growth inhibitory activities of essential oils of three Achillea species and their nano-emulsions against Tribolium castaneum (Herbst). Industrial Crops Products, 53, 252-260.

Oliveira, G. L., Moreira, D. L., & Mendes, A. D. R. (2013). Growth study and essential oil analysis of Piper aduncum from two sites of Cerrado biome of Minas Gerais State, Brazil. Revista Brasileira de Farmacognosia, 23(5), 3743-3753.

Oyedeji, A. O., Mdlolo, C. M., Adeniyi, B., & Akinde, T. (2010). 1, 8-Cineole chemotype of the essential oils of Kyllinga erecta schum et thonn and its antimicrobial activities. Journal Essential Oil Research, 22(2), 189-192.

Pinheiro, P. F., Costa A. V., Alves, T., Galter, I. N., Pinheiro, C. A., Pereira, A. F., ... Fontes, M. M. (2015). Phytotoxicity and cytotoxicity of essential oil from leaves of Plectranthus amboinicus, carvacrol, and thymol in plant bioassays. Journal Agricultural and Food Chemistry, 63(41), 8981-8990.

Rajendran, S., & Sriranjini, V. (2008). Plant products as fumigants for stored-product insect control-Review. Journal Stored Products Research, 44(2), 126-135.

Rees, D. P. (2004). Insects of stored products. Collingwood, Vic: CSIRO Publishing.

Sawamura, M. (2010). Citrus essential oils: flavor and fragrance. Hoboken, NJ: John Wiley and Sons.

Simpson, D. A., & Inglis, C. A. (2001). Cyperaceae of economic, ethnobotanical and horticultural importance: a checklist. Kew Bulletin, 56(2), 257-360.

Suthisut D., Fields, P. G., & Chandrapatya, A. (2011). Fumigant toxicity of essential oils from three Thai plants (Zingiberaceae) and their major compounds against Sitophilus zeamais, Tribolium castaneum and two parasitoids. Journal Stored Products Research, 47(3), 222-230.

Tabanca, N., Wang, M., Avonto, C., Chittiboyina, A. G., Parcher, J. F., Carroll, J. F., ... Khan, I. A. (2013). Bioactivity-guided investigation of geranium essential oils as natural tick repellents. Journal Agricultural and Food Chemistry, 61(17), 4101-4107.

Tapondjou, A., Adler, C., Fontem, D., Bouda, H., & Reichmuth, C. (2005). Bioactivities of cymol and essential oils of Cupressus sempervirens and Eucalyptus saligna against Sitophilus zeamais Motschulsky and Tribolium confusum du Val. Journal Stored Products Research, 41(1), 91-102.

Toong, Y. C., Schooley, D. A., & Baker, F. C. (1988). Isolation of insect juvenile hormone III from a plant. Nature, 333(6169), 170-171.

Tucker, A. O., Maciarello, M. J., & Bryso, C. T. (2006). The essential oil of Kyllinga odorata Vahl (Cyperaceae) from Mississippi. Journal Essential Oil Research, 18(4), 381-382.

Ukeh, D. A., & Umoetok, S. B. A. (2011). Repellent effects of five monoterpenoid odours against Tribolium castaneum (Herbst) and Rhyzopertha dominica (F.) in Calabar, Nigeria. Crop Protection, 30(10), 1351-1355.

Yang, H., Kim, H. S., Jeong, E. J., Khiev, P., Chin, Y. W., & Sung, S. H. (2013). Plant-derived juvenile hormone III analogues and other sesquiterpenes from the stem bark of Cananga latifolia. Phytochemistry, 94, 277-283.

Zarrad, K., Ben Hamouda, A., Chaieb, I., Laarif, A., & Jemaa, J. M. B. (2015). Chemical composition, fumigant and anti-acetylcholinesterase activity of the Tunisian Citrus aurantium L. essential oils. Industrial Crops Products, 76, 121-127.

Zhang, J. S., Zhao, N. N., Liu, Q. Z., Liu, Z. L., Du, S. S., Zhou, L., & Deng, Z. W. (2011). Repellent constituents of essential oil of Cymbopogon distans aerial parts against two stored-product insects. Journal Agricultural and Food Chemistry, 59(18), 9910-9915.

Received on June 22, 2016.

Accepted on August 30, 2016.

Doi: 10.4025/actascibiolsci.v38i3.32386

Beatriz Eugenia Jaramillo-Colorado *, Eduardo Luis Martinez-Caceres 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: beatrizjaramilloc@yahoo.com, bjaramilloc@unicartagena.edu.co

Caption: Figure 1. Typical chromatographic profile of the essential oil from Colombian Kyllinga pumila Michx. HP-5 column (30 m X 0.32 mm i.d. X 0.25 [micro]m [d.sub.f]), GC-FID. (See identification of number peak in Table 1).

Caption: Figure 2. Structures of principal compounds found in the essential oil from Colombian Kyttinga pumua. (See Table 1.). Structures of principal compounds found in the essential oil from Colombian Kyttinga pumlla. (See Table 1.)

Caption: Figure 4. Measure of the ability to scavenge radicals, by reacting DPPH' (1,1-diphenyl-2-picryl hydrazyl) radicals with essential oil of Kyllinga pumila and ascorbic acid (standard).
Table 1. Volatile chemical composition of the essential oil from
Kyttinga pumiia, obtained by hydrodistillation.

Peak No (a)   Compound

1             [alpha]-Pinene (b) *
2             [beta]-Pinene (b) *
3             [rho]-Methyl-anisol (b) *
4             Limonene *
5             Z-[beta]-Ocimeneb *
6             E-[beta]-Ocimene *
7             [gamma]-Terpinene (b) *
8             E-atto-Ocimene *
9             Estragol (methyl chavicol) (b) *
10            Chavicol (b) *
11            [alpha]-Cubebene (b) *
12            [beta]-Bourbonene (b) *
13            [beta]-Elemene (b) **
14            Z-Caryophyllene (b) *
15            [alpha]-Cedrene *
16            E-Caryophyllene (b) *
17            [beta]-Cedrene *
18            E-[beta]-Farnesene (b) *
19            Alio--Aromadendrene *
20            Germacrene D (b) *
21            [alpha]-Selineneb *
22            (+) epi-Byciclosesquiphellandrene *
23            [alpha]-Elemol *
24            Caryophyllene Oxideb
25            2-Z, 6-E-Farnesol *
26            2-E, 6-E-Farnesol (b) *
27            Methyl Farnesoate (b)
              Methyl E,E-10,11-epoxytarnesoate
                (2,6-nonadienoic
28            acid, 9-(3,3-dimethyloxiranyl)-3,7-dimethyl-,
                methyl ester, (E,E) b

Peak No (a)   LRI (c) HP-5   LRI ZB-WAX        Relative
                                              Area (d), %

1                 941           1020       0.1 [+ or -] 0.02
2                 985           1118       0.1 [+ or -] 0.03
3                 1017          1430       0.2 [+ or -] 0.07
4                 1032          1216       0.5 [+ or -] 0.04
5                 1038          1243       2.5 [+ or -] 0.39
6                 1046          1230       2.9 [+ or -] 0.95
7                 1060          1236       0.2 [+ or -] 0.03
8                 1130          1412       0.1 [+ or -] 0.02
9                 1189          1626       0.1 [+ or -] 0.03
10                1250          2314       0.1 [+ or -] 0.05
11                1351          1464       0.3 [+ or -] 0.09
12                1388          1518       1.3 [+ or -] 0.18
13                1391          1566      12.5 [+ or -] 1.48
14                1408          1577      11.3 [+ or -] 0.89
15                1409          1589       0.2 [+ or -] 0.03
16                1420          1603       5.6 [+ or -] 0.36
17                1422          1615       0.4 [+ or -] 0.09
18                1460          1659       1.5 [+ or -] 0.45
19                1462          1660       0.2 [+ or -] 0.03
20                1478          1667       7.1 [+ or -] 0.85
21                1485          1692       0.4 [+ or -] 0.10
22                1486          1712       1.3 [+ or -] 0.63
23                1550          2025       0.5 [+ or -] 0.09
24                1579          1988       0.9 [+ or -] 0.16
25                1684          2330       2.7 [+ or -] 0.23
26                1706          2349       0.3 [+ or -] 0.02
27                1758          2210       2.9 [+ or -] 0.59

28                1806          2346      43.8 [+ or -] 2.82

a) Peak number in Figure 1; b) Identification made by mass spectrum
(EI: electron impact ionization, 70 eV; peak matching >90%) and LRIs.
Spectral databases wiley8, NIST08; c) Experimentally LRI on the HP-5
and ZB-Wax column; d) Averages of three independent extractions;
*Tentative identification based in LRIs on HP-5 column. LRI -Linear
retention indices relative to [C.sub.7]-[C.sub.30] n-alkanes.

Table 2. Repellent activity of the essential oil from Kyttinga
pumita against Tribotium castaneum.

             Concentration      % Repellency as exposure time
            (%v [v.sup.-1])       2 hour            4 hours

Kyttinga      [10.sup.-4]      45 [+ or -] 2     50 [+ or -] 5
pumita M.     [10.sup.-3]      80 [+ or -] 2 *   75 [+ or -] 5 *
              [10.sup.-2]      90 [+ or -] 2 *   90 [+ or -] 3 *
              [10.sup.-1]      75 [+ or -] 5     75 [+ or -] 2
                   1           50 [+ or -] 1     90 [+ or -] 5

* Statistically significant difference between the number of organism
in treated and untreated areas, using the paired t test (p < 0.001).

Table 3. Toxicity of essential oil from Kyttinga pumita and
synthetic pesticide (Pirilan) against Tribotium castaneum.

                                  Level
Sample                          Confidence     [LC.sub.50] *
                                 Interval

Kyttinga pumita                    0.05      153.4 [+ or -] 13
Piritan, (methyl pirimiphos)       0.05       50.1 [+ or -] 8.3

Sample                            [LC.sub.90] *

Kyttinga pumita                 386.4 [+ or -] 39
Piritan, (methyl pirimiphos)    232.6 [+ or -] 8.6

Sample                            [LC.sub.95] *

Kyttinga pumita                 535.0 [+ or -] 67
Piritan, (methyl pirimiphos)    359.5 [+ or -] 8.1

* [LC.sub.50], [LC.sub.90], [LC.sub.95] they are expressed in
[micro]L EO [L.sup.-1] of air.

Table 4. Phytotoxic effects of Kyllinga pumila on Lolium perenne

Lolium perenne
                                           Growth (%C)

Kyllinga pumila essential        Radicular             Leaf

oil (100 [micro]g            70.0 [+ or -] 0.8   78.2 [+ or -] 2.2
  [cm.sup.-2])

%C: percentage of control. p < 0.05, Mann Whitney test.

Figure 3. Fumigant activity of essential oil
(EO) from Kyttinga pumita against Tribotium castaneum.

[micro]L        EO     Methy
EO [L.sup.-1]        pirimiphos
Of air

500             92       98

350             89       93

250             74       88

150             55       83

Note: Table made from line graph.
COPYRIGHT 2016 Universidade Estadual de Maringa
No portion of this article can be reproduced without the express written permission from the copyright holder.
Copyright 2016 Gale, Cengage Learning. All rights reserved.

Article Details
Printer friendly Cite/link Email Feedback
Author:Jaramillo-Colorado, Beatriz Eugenia; Martinez-Caceres, Eduardo Luis; Duarte-Restrepo, Edisson
Publication:Acta Scientiarum. Biological Sciences (UEM)
Article Type:Ensayo
Date:Jul 1, 2016
Words:5314
Previous Article:Impact of Brazilian fish species at early developmental stages on plankton communities and water chemical parameters/Impacto de especies de peixes...
Next Article:Use of human cadavers in teaching of human anatomy in brazilian medical faculties/Utilizacao de cadaveres humanos no ensino da anatomia humana nas...
Topics:

Terms of use | Privacy policy | Copyright © 2020 Farlex, Inc. | Feedback | For webmasters