Characterization of Clove Oil Nanoparticles and Their Insecticidal Activity against Cryptolestes ferrugineus (Stephens) (Coleoptera: Laemophloeidae)

Silvi Ikawati, Toto Himawan, Abdul Latief Abadi, Hagus Tarno

Abstract


The application of essential oils to storage pest control requires an appropriate formulation formed by biodegradable compounds. This formulation should protect essential oils from degradation and evaporation while simultaneously allowing sustained release. This study aims to characterize nanoparticles loaded by clove essential oil-based polymer polyethylene glycol (PEG) and to investigate their insecticidal activity. In this study, clove oil solid dispersion was prepared using the fusion or melting-dispersion method with polyethylene glycol 6000 (PEG 6000) to form a binary solid dispersion system. The ratio of 10% of clove oil to PEG was optimal and had low PDI, small size, and the highest clove oil loading efficiency. Their size changed from 179 to 197 nm after 24 weeks of storage and the loading efficiency decreased for about 36%. Clove oil formulation in nanoparticles could not enhance the toxicity of clove oil but yet still showed high contact toxicity to C. ferrugineus. These formulations also have the slow and persistent release of the bioactive.


Keywords


Clove oil; Contact toxicity; Nanoparticles; Polyethylene glycol (PEG); Sustained release

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References


Anjali, C. H., Sudheer Khan, S., Margulis-Goshen, K., Magdassi, S., Mukherjee, A., & Chandrasekaran, N. (2010). Formulation of water-dispersible nanopermethrin for larvicidal applications. Ecotoxicology and Environmental Safety, 73(8), 1932–1936. crossref

Caliceti, P., Monfardini, C., Sartore, L., Schiavon, O., Baccichetti, F., Carlassare, F., & Veronese, F. M. (1993). Preparation and properties of monomethoxy poly(ethylene glycol) doxorubicin conjugates linked by an amino acid or a peptide as spacer. Farmaco, 48(7), 919–932. Retrieved from website

Chaieb, K., Hajlaoui, H., Zmantar, T., Kahla-Nakbi, A. Ben, Rouabhia, M., Mahdouani, K., & Bakhrouf, A. (2007). The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): a short review. Phytotherapy Research, 21(6), 501–506. crossref

Chidavaenzi, O. C., Buckton, G., & Koosha, F. (2001). The effect of co-spray drying with polyethylene glycol 4000 on the crystallinity and physical form of lactose. International Journal of Pharmaceutics, 216(1–2), 43–49. crossref

Chiou, W. L., & Riegelman, S. (1971). Pharmaceutical applications of solid dispersion systems. Journal of Pharmaceutical Sciences, 60(9), 1281–1302. crossref

Cosimi, S., Rossi, E., Cioni, P. L., & Canale, A. (2009). Bioactivity and qualitative analysis of some essential oils from Mediterranean plants against stored-product pests: Evaluation of repellency against Sitophilus zeamais Motschulsky, Cryptolestes ferrugineus (Stephens) and Tenebrio molitor. Journal of Stored Products Research, 45(2), 125–132. crossref

Craig, D. Q. M. (1995). A review of thermal methods used for the analysis of the crystal form, solution thermodynamics and glass transition behaviour of polyethylene glycols. Thermochimica Acta, 248, 189–203. crossref

da Costa, J. T., Forim, M. R., Costa, E. S., De Souza, J. R., Mondego, J. M., & Boiça Junior, A. L. (2014). Effects of different formulations of neem oil-based products on control Zabrotes subfasciatus (Boheman, 1833) (Coleoptera: Bruchidae) on beans. Journal of Stored Products Research, 56, 49–53. crossref

Dayan, F. E., Cantrell, C. L., & Duke, S. O. (2009). Natural products in crop protection. Bioorganic and Medicinal Chemistry, 17(12), 4022–4034. crossref

Dittmann, E. C. (1973). Structure activity relations in homologous alkyl polyglycol ethers. NaunynSchmiedeberg’s Archives of Pharmacology, 276, 199–210. crossref

Flinn, P. W., & Hagstrum, W. D. (1998). Distribution of Cryptolestes ferrugineus (Coleoptera: Cucujidae) in response to temperature gradients in stored wheat. Journal of Stored Products Research, 34(2–3), 107–112. crossref

Gasch, T. (2014). The use of semiochemicals for stored product protection. Paper presented at Conference of the Young Scientists Meeting 2014 (p. 177), Quedlinburg, Germany: Berichte aus dem Julius Kühn-Institu. Retrieved from website

Gupta, A. K., & Curtis, A. S. G. (2004). Surface modified superparamagnetic nanoparticles for drug delivery: Interaction studies with human fibroblasts in culture. Journal of Materials Science: Materials in Medicine, 15, 493–496. crossref

Hancock, B. C., & Zografi, G. (1997). Characteristics and significance of the amorphous state in pharmaceutical systems. Journal of Pharmaceutical Sciences, 86(1), 1–12. crossref

Ho, S. H., Cheng, L. P. L., Sim, K. Y., & Tan, H. T. W. (1994). Potential of cloves (Syzygium aromaticum (L.) Merr. and Perry as a grain protectant against Tribolium castaneum (Herbst) and Sitophilus zeamais Motsch. Postharvest Biology and Technology, 4(1–2), 179–183. crossref

Hu, Y., Xie, J., Tong, Y. W., & Wang, C. H. (2007). Effect of PEG conformation and particle size on the cellular uptake efficiency of nanoparticles with the HepG2 cells. Journal of Controlled Release, 118(1), 7–17. crossref

Hummelbrunner, L. A., & Isman, M. B. (2001). Acute, sublethal, antifeedant, and synergistic effects of monoterpenoid essential oil compounds on the tobacco cutworm, Spodoptera litura (Lep., Noctuidae). Journal of Agricultural and Food Chemistry, 49(2), 715–720. crossref

Hyari, S., Kadoum, A. M., & Lahue, D. W. (1977). Laboratory evaluations of emulsifiable and encapsulated formulations of malathion and fenitrothion on soft red winter wheat against attack by adults of four species of stored-product insects. Journal of Economic Entomology, 70(4), 480–482. crossref

Ikawati, S., Himawan, T., Abadi, A. L., & Tarno, H. (2020). Toxicity nanoinsecticide based on clove essential oil against Tribolium castaneum (Herbst). Journal of Pesticide Science, 20(59), 1-7. crossref

Isman, M. B. (2006). Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annual Review of Entomology, 51, 45–66. crossref

Isman, M. B. (2016). Pesticides based on plant essential oils: Phytochemical and practical considerations. In ACS Symposium Series Vol. 1218 (pp. 13–26). American Chemical Society. crossref

Jiang, Z., Akhtar, Y., Bradbury, R., Zhang, X., & Isman, M. B. (2009). Comparative toxicity of essential oils of Litsea pungens and Litsea cubeba and blends of their major constituents against the cabbage looper, Trichoplusia ni. Journal of Agricultural and Food Chemistry, 57(11), 4833–4837. crossref

Jirovetz, L., Buchbauer, G., Stoilova, I., Stoyanova, A., Krastanov, A., & Schmidt, E. (2006). Chemical composition and antioxidant properties of clove leaf essential oil. Journal of Agricultural and Food Chemistry, 54(17), 6303–6307. crossref

Koh, P., Chuah, J., Talekar, M., Gorajana, A., & Garg, S. (2013). Formulation development and dissolution rate enhancement of efavirenz by solid dispersion systems. Indian Journal of Pharmaceutical Sciences, 75(3), 291–301. crossref

Koul, O., Walia, S., & Dhaliwal, G. (2008). Essential oils as green pesticides: Potential and Constraints. Biopesticides International, 4(1), 63–84. Retrieved from website

Kubeczka, K.-H., & Formácek, V. (2002). Essential oils analysis by capillary gas chromatography and carbon-13 NMR spectroscopy (2nd ed.). Chichester, UK: John Wiley & Sons Ltd. Retrieved from website

Lai, F., Wissing, S. A., Müller, R. H., & Fadda, A. M. (2006). Artemisia arborescens L. essential oil-loaded solid lipid nanoparticles for potential agricultural application: Preparation and characterization. AAPS PharmSciTech, 7(1), E10. crossref

Lo, P. K. (1986). Recognition and control of insect pests in stored grains. Taiwan. Retrieved from website

Majumdar, R., Alexander, K. S., & Riga, A. T. (2010). Physical characterization of polyethylene glycols by thermal analytical technique and the effect of humidity and molecular weight. Pharmazie, 65(5), 343–347. crossref

Martín, Á., Varona, S., Navarrete, A., & Cocero, M. J. (2014). Encapsulation and co-precipitation processes with supercritical fluids: Applications with essential oils. The Open Chemical Engineering Journal, 4, 31–41. crossref

Moretti, M. D. L., Sanna-Passino, G., Demontis, S., & Bazzoni, E. (2002). Essential oil formulations useful as a new tool for insect pest control. AAPS PharmSciTech, 3(2), 64–74. crossref

Nel, A. E., Mädler, L., Velegol, D., Xia, T., Hoek, E. M. V., Somasundaran, P., … Thompson, M. (2009). Understanding biophysicochemical interactions at the nano-bio interface. Nature Materials, 8, 543–557. crossref

Nobbmann, U. (2017). Polydispersity – what does it mean for DLS and chromatography? Malvern Instruments. Retrieved from website

Oehlschlager, A. C., Wong, J. W., Verigin, V. G., & Pierce Jr, H. D. (1983). Synthesis of two macrolide pheromones of the rusty grain beetle, Cryptolestes ferrugineus (Stephens). Journal of Organic Chemistry, 48(25), 5009–5017. crossref

Paranagama, P., Abeysekera, T., Nugaliyadde, L., & Abeywickrama, K. (2003). Effect of the essential oils of Cymbopogon citratus, C. nardus and Cinnamomum zeylanicum on pest incidence and grain quality of rough rice (paddy) stored in an enclosed seed box. Journal of Food, Agriculture & Environment, 1(2), 134–137. Retrieved from website

Park, I. K., & Shin, S. C. (2005). Fumigant activity of plant essential oils and components from garlic (Allium sativum) and clove bud (Eugenia caryophyllata) oils against the Japanese termite (Reticulitermes speratus Kolbe). Journal of Agricultural and Food Chemistry, 53(11), 4388–4392. crossref

Plata-Rueda, A., Campos, J. M., da Silva Rolim, G., Martínez, L. C., Dos Santos, M. H., Fernandes, F. L., … Zanuncio, J. C. (2018). Terpenoid constituents of cinnamon and clove essential oils cause toxic effects and behavior repellency response on granary weevil, Sitophilus granarius. Ecotoxicology and Environmental Safety, 156, 263–270. crossref

Prego, C., Torres, D., Fernandez-Megia, E., NovoaCarballal, R., Quiñoá, E., & Alonso, M. J. (2006). Chitosan-PEG nanocapsules as new carriers for oral peptide delivery: Effect of chitosan pegylation degree. Journal of Controlled Release, 111(3), 299–308. crossref

Price, D. N., & Berry, M. S. (2006). Comparison of effects of octopamine and insecticidal essential oils on activity in the nerve cord, foregut, and dorsal unpaired median neurons of cockroaches. Journal of Insect Physiology, 52(3), 309–319. crossref

Rajendran, S., & Sriranjini, V. (2008). Plant products as fumigants for stored-product insect control. Journal of Stored Products Research, 44(2), 126–135. https://doi.org/10.1016/j.jspr.2007.08.003 Regnault-Roger, C., & Hamraoui, A. (1994). Inhibition of reproduction of Acanthoscelides obtectus Say (Coleoptera), a kidney bean (Phaseolus vulgaris) bruchid, by aromatic essential oils. Crop Protection, 13(8), 624–628. crossref

Tobío, M., Sánchez, A., Vila, A., Soriano, I., Evora, C., Vila-Jato, J. L., & Alonso, M. J. (2000). The role of PEG on the stability in digestive fluids and in vivo fate of PEG-PLA nanoparticles following oral administration. Colloids and Surfaces B: Biointerfaces, 18(3–4), 315–323. crossref

Vasconcelos, T., Sarmento, B., & Costa, P. (2007). Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discovery Today, 12(23–24), 1068–1075. crossref

Vila, A., Sánchez, A., Tobío, M., Calvo, P., & Alonso, M. J. (2002). Design of biodegradable particles for protein delivery. Journal of Controlled Release, 78(1–3), 15–24. crossref

Vippagunta, S. R., Brittain, H. G., & Grant, D. J. W. (2001). Crystalline solids. Advanced Drug Delivery Reviews, 48(1), 3–26. crossref

Viteri Jumbo, L. O., Faroni, L. R. A., Oliveira, E. E., Pimentel, M. A., & Silva, G. N. (2014). Potential use of clove and cinnamon essential oils to control the bean weevil, Acanthoscelides obtectus Say, in small storage units. Industrial Crops and Products, 56, 27–34. crossref

Werdin González, J. O., Gutiérrez, M. M., Ferrero, A. A., & Fernández Band, B. (2014). Essential oils nanoformulations for stored-product pest control - Characterization and biological properties. Chemosphere, 100, 130–138. crossref

Werdin González, J. O., Stefanazzi, N., Murray, A. P., Ferrero, A. A., & Fernández Band, B. (2015). Novel nanoinsecticides based on essential oils to control the German cockroach. Journal of Pest Science, 88, 393–404. crossref

Yang, F. L., Li, X. G., Zhu, F., & Lei, C. L. (2009). Structural characterization of nanoparticles loaded with garlic essential oil and their insecticidal activity against Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Journal of Agricultural and Food Chemistry, 57(21), 10156–10162. crossref

Yu, L. (2001). Amorphous pharmaceutical solids: Preparation, characterization and stabilization. Advanced Drug Delivery Reviews, 48(1), 27–42. crossref

Zalipsky, S. (1995). Chemistry of polyethylene glycol conjugates with biologically active molecules. Advanced Drug Delivery Reviews, 16(2–3), 157–182. crossref

Zheng, G.-Q., Kenney, P. M., & Lam, L. K. T. (1992). Sesquiterpenes from clove (Eugenia caryophyllata) as potential anticarcinogenic agents. Journal of Natural Products, 55(7), 999–1003. crossref




DOI: http://doi.org/10.17503/agrivita.v1i1.2532

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