Abstract
The aim of this study was to prepare the inclusion complexes of citronella oil, citronellal or citronellol with β-cyclodextrin and evaluate their physicochemical properties using scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC). A kneading method was employed to prepare the inclusion complexes and weight ratios of each of the active substance to β-cyclodextrin were 1:1 (1:1 CPX) and 1:2 (1:2 CPX). For comparison purposes, physical mixtures of these active compounds and β-cyclodextrin were also prepared and investigated. Unlike the physical mixtures, the SEM technique revealed drastic changes in the shapes and morphologies of the particles for the inclusion complexes. Furthermore, the FTIR and DSC results seemed to reveal some interactions between the active substance and β-cyclodextrin. The o/w lotions, which contained 10% w/w citronella oil (normal citronella oil; 1:1 CPX or 1:2 CPX), were formulated using Cremophors as emulsifiers. With modified Franz diffusion cell and synthetic membrane, the release rates of citronella oil from the lotions containing the inclusion complexes were significantly lower than that from the prepared lotion containing normal citronella oil. The mosquito (Aedes aegypti) repellent efficacy of the lotions containing citronella oil, citronellal or citronellol (both normal and inclusion complexes) was further evaluated by human-bait technique. The highest mosquito repellent activity was observed in the formulation which contained citronella oil–β-cyclodextrin inclusion complex at weight ratio of 1:1.
Similar content being viewed by others
References
Katz, T.M., Miller, J.H., Hebert, A.A.: Insect repellents: historical perspectives and new developments. J. Am. Acad. Dermatol. 58, 865–871 (2008)
Karunamoorthi, K., Mulelam, A., Wassie, F.: Assessment of knowledge and usage custom of traditional insect/mosquito repellent plants in Addis Zemen Town, South Gonder, North Western Ethiopia. J. Ethnopharmacol. 121, 49–53 (2009)
Gillij, Y.G., Gleiser, R.M., Zygadlo, J.A.: Mosquito repellent activity of essential oils of aromatic plants growing in Argentina. Bioresour. Technol. 99, 2507–2515 (2008)
Choochote, W., Chaithong, U., Kamsuk, K., Jitpakdi, A., Tippawangkosol, P., Tuetun, B., Champakaew, D., Pitasawat, B.: Repellent activity of selected essential oils against Aedes aegypti. Fitoterapia 78, 359–364 (2007)
Nerio, L.S., Olivero-Verbel, J., Stashenko, E.: Repellent activity of essential oils: a review. Bioresour. Technol. 101, 372–378 (2010)
Lis-Balchin, M.: Aromatherapy Science: A Guide for Healthcare Professionals. Pharmaceutical Press, London (2006)
Keystone, J.S., Kozarsky, P.E., Freedman, D.O., Nothdurft, H.D., Connor, B.A.: Travel Medicine, 2nd edn. Elsevier Science, St. Louis (2004)
Hsieh, W., Chang, C., Gao, Y.: Controlled release properties of chitosan encapsulated volatile citronella oil microcapsules by thermal treatments. Colloid Surf. B 53, 209–214 (2006)
Chittiteeranon, P., Soontaros, S., Pongsawasdi, P.: Preparation and characterization of inclusion complexes containing fixolide, a synthetic musk fragrance and cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 57, 69–73 (2007)
Maji, T.K., Baruah, I., Dube, S., Hussain, M.R.: Microencapsulation of Zanthoxylum limonella oil (ZLO) in glutaraldehyde crosslinked gelatin for mosquito repellent application. Bioresour. Technol. 98, 840–844 (2007)
Sakulka, U., Nuchuchua, O., Uawongyart, N., Puttipipatkhachorn, S., Soottitantawat, A., Ruktanonchai, U.: Characterization and mosquito repellent activity of citronella oil nanoemulsion. Int. J. Pharm. 72, 105–111 (2009)
Numanoglu, U., Şen, T., Tarimci, N., Kartal, M., Koo, O.M.Y., Onyuksel, H.: Use of cyclodextrins as a cosmetic delivery system for fragrance materials: linalool and benzyl acetate. AAPS PharmSciTech. 8, 34–42 (2007)
Scalia, S., Tursilli, R., Bianchi, A., Nostro, P.L., Bocci, E., Ridi, F., Baglioni, P.: Incorporation of the sunscreen agent, octyl methoxycinnamate in a cellulosic fabric grafted with β-cyclodextrin. Int. J. Pharm. 308, 155–159 (2006)
Cal, K., Centkowska, L.: Use of cyclodextrins in topical formulations: practical aspects. Eur. J. Pharm. Biopharm. 68, 467–478 (2008)
Del Valee, E.M.M.: Cyclodextrin and their uses: a review. Process Biochem. 39, 1033–1046 (2004)
Astray, G., Gonzalez-Barreiro, C., Mejuto, J.C., Rial-Otero, R., Simal-Gandara, J.: A review on the use of cyclodextrins in foods. Food Hydrocolloids 23, 1631–1640 (2009)
Tawatsin, A., Asavadachanukorn, P., Thavara, U., Wongsinkongman, P., Bansidhi, J., Boonruad, T., Chavalittumrong, P., Soonthornchareonnon, N., Komalamisra, N., Mulla, M.S.: Repellency of essential oils extracted from plants in Thailand against four mosquito vectors (Diptera: Culicidae) and oviposition deterrent effects against Aedes aegypti (Diptera: Culicidae). Southeast Asian J. Trop. Med. Public Health 37, 915–931 (2006)
Tisserand, R., Balacs, T.: Essential Oil Safety: A Guide for Health Care Professionals. Churchill Livingstone, London (1995)
Baranska, M., Schulz, H., Walter, A., Rosch, P., Quilitzsch, R., Losing, G., Popp, J.: Investigation of eucalyptus essential oil by using vibrational spectroscopy methods. Vib. Spectrosc. 42, 341–345 (2006)
O’Neil, M.J.: The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14th edn. Merck & Co., Inc., UK (2006)
Strazisar, M., Andrensek, S., Smidovnik, A.: Effect of β-cyclodextrin on antioxidant activity of coumaric acid. Food Chem. 110, 636–642 (2008)
Bratu, I., Astilean, S., Ionesc, C., Indrea, E., Huvenne, J.P., Legrand, P.: FT-IR and X-ray spectroscopic investigations of Na-diclofenac–cyclodextrins interactions. Spectrochim. Acta A 45, 191–196 (1998)
Brandao, T.A.S., Malheiros, A., Magro, J.D., Filho, V.C., Yunes, R.A.: Characterization of sesquiterpene polygodial–beta cyclodextrin inclusion complex. J. Incl. Phenom. Macrocycl. Chem. 46, 77–81 (2003)
Bertacche, V., Lorenzi, N., Nava, D., Pini, E., Sinico, C.: Host–guest interaction study of resveratrol with natural and modified cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 55, 279–287 (2006)
Ficarra, R., Ficarra, P., Di Bella, M.R., Raneri, D., Tommasini, S., Calabro, M.L., Gamberini, M.C., Rustichelli, C.: Study of β-blockers: β-cyclodextrins inclusion complex by NMR, DSC, X-ray and SEM investigation. J. Pharm. Biomed. Anal. 23, 33–40 (2000)
Pralhad, T., Rajendrakumar, K.: Study of freeze-dried quercetin–cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J. Pharm. Biomed. 34, 333–339 (2004)
Wang, J.H., Cai, Z.: Investigation of inclusion complex of miconazole nitrate with β-cyclodextrin. Carbohydr. Polym. 72, 255–260 (2008)
Santoyo, S., Arellano, A., Ygartua, P., Martin, C.: In vitro percutaneous absorption of piroxicam through synthetic membranes and abdominal skin. Pharm. Acta Helv. 71, 141–146 (1996)
Acknowledgments
The authors are indebted to the Faculty of Pharmaceutical Sciences, Prince of Songkla University, Thailand, for financial support, facilities and contributions. For the mosquito repellency testing, the authors wish to thank Dr. Usavadee Thavara from the National Institute of Health, Department of Medical Sciences, Ministry of Public Health, Thailand.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Songkro, S., Hayook, N., Jaisawang, J. et al. Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent. J Incl Phenom Macrocycl Chem 72, 339–355 (2012). https://doi.org/10.1007/s10847-011-9985-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-011-9985-7