Abstract
Cinnamon leaf (CLO) and garlic oils (GO) are good antimicrobials, however, their volatility complicates their application as food preservatives. Hence, microencapsulation of CLO and GO with β-cyclodextrin (β-CD) was studied at 4:96, 8:92, 12:88, and 16:84 (oil:β-CD) percent weight ratios. Microcapsule characterization included gas chromatography analysis, moisture sorption–desorption isotherms, infrared spectroscopy (IR), and antifungal activity against Alternaria alternata. Major oil constituents were eugenol for CLO and allyl disulfide for GO. The 16:84 ratio (CLO:β-CD) showed the highest eugenol content; the allyl disulfide content was higher, but not significantly different (P > 0.05) for the 12:88 and 16:84 ratios. Microcapsules showed lower moisture sorption than β-CD, although during water desorption there were no difference between them. Hydrogen bonds were detected between oil constituents and β-CD by IR spectroscopy. CLO:β-CD and GO:β-CD microcapsules displayed good antifungal activity against Alternaria alternata. Therefore, CLO and GO microcapsules can have important applications in the food industry as stable natural antimicrobial compound systems.
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Abbreviations
- β-CD:
-
β-cyclodextrin
- CLO:
-
Cinnamon leaf oil
- GO:
-
Garlic oil
- GRAS:
-
Generally recognized as safe
- FDA:
-
Food and Drug Administration
- GC-MS:
-
Gas chromatography-mass spectrometry
- GC-FID:
-
Gas chromatography-flame ionization detector
- RH:
-
Relative humidity
- IR:
-
Infrared
- PDA:
-
Potato dextrose agar
- NCSS:
-
Number Cruncher Statistical System
- LSD:
-
Least significant difference
References
Szente, L., Szejtli, J.: Cyclodextrins as food ingredients. Trends Food Sci. Technol. 15, 137–142 (2004)
Hedges, A.R., Shiech, W.J., Sikorski, C.T.: Use of cyclodextrins for encapsulation in the use and treatment of food products. In: Risch, S.J., Reineccius, G.A. (eds.) Encapsulation and Controlled Release of Food Ingredients, pp. 61–71. American Chemical Society, Washington D.C. (1995)
Conner, D.E.: Naturally occurring compounds. In: Davidson, P.M., Branen, A.L. (eds.) Antimicrobials in Foods, 2nd edn. Marcel Dekker, New York (1993)
Maruzzella, J.C., Sicurella, N.A.: Antibacterial activity of essential oil vapors. J. Amer. Pharm. Assoc. 49, 692–694 (1960)
Vitranen, A.I.: Some organic sulfur compounds in vegetables and fodder plants and their significance in human nutrition. Angew. Chem. Int. Ed. 1, 299–306 (1962)
Senanayake, V.M., Lee, T.H., Wills, B.H.: Volatile constituents of cinnamon (Cinnamomun zeylanicum) oils. J. Agric. Food Chem. 26, 822–827 (1978)
Mallavarapu, G.R., Ramesh, S., Chandrasekhara, R.S., Rao, B.R.P., Kaul, P.N., Bhattacharya, A.K.: Investigation of the essential oil of cinnamon leaf growth at Bangalore and Hyderabad. Flav. Fragr. J. 10, 239–242 (1995)
Kimbaris, A.C., Siatis, N.G., Pappas, C.S., Tarantilis, P.A., Daferera, D.J., Polissiou, M.G.: Quantitative analysis of garlic (Allium sativum) oil unsaturated acyclic components using FT-Raman spectroscopy. Food Chem. 94, 287–295 (2006)
Bhandari, B.R., D’Arcy, B.R., Thi-Bich, L.L.: Lemon oil to β-cyclodextrin ratio effect on the inclusion efficiency of β-cyclodextrin and the retention of oil volatiles in the complex. J. Agric. Food Chem. 46, 1494–1499 (1998)
AOAC: Official method 925.45. Moisture in sugars––vacuum drying. Sugars and sugar products. In: Bernetti R. (Chapter ed.) Association of Official Analytical Chemist, Arlington, VA (2000)
Pouchert, C.J.: The Aldrich Library of Infrared Spectra, 3rd edn. Aldrich Chemical Co., Milwaukee, WI (1981)
Simmons, E.G.: Alternaria taxonomy: current status, view point, challenge. In: Chelkowski, J., Visconti, A. (eds.) Alternaria Biology, Plant Diseases and Metabolites, pp. 1–35. Elsevier Science Publishers, Amsterdam, Holland (1992)
Sodini, G., Canella, M.: Acidic butanol removal of color-forming phenols from sunflower meal. J. Agric. Food Chem. 25, 822–825 (1977)
Lezcano-Brito, M.: Complejación de biocinas por ciclodextrinas. PhD dissertation. Universidad de Santiago de Compostela, Spain (2002)
Fricke, C., Rieck, A., Hardt, I.H., König, WA., Muhle, H.: Identification of (+)-β-caryophyllene in essential oils of liverworts by enantioselective gas chromatography. Phytochemistry 39, 1119–1121 (1995)
Vermin, G., Metzger, J.: GC-MS (EI, PCI, NCI, SIM) SPECMA bank analysis of volatile sulfur compounds in garlic essential oils. In: Linskens, H.F., Jackson, J.F. (eds.) Essential Oils and Waxes, pp. 99–130. Springer-Verlag, Berlin Germany (1991)
Tsao, S.M., Yin, M.C.: In vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils. J. Med. Microbiol. 50, 646–649 (2001)
Angelova, A., Lefebvre, C.R., Baszikin, A.: Drug-cyclodextrin association constants determined by surface tension and surface pressure measurements. J. Colloidal Interface Sci. 212, 280–285 (1999)
Zhang, J., Zografi, G.: The relationship between BET and free volume-derived parameters for water vapor absorption into amorphous solids. J. Pharm. Sci. 89, 1063–1072 (2000)
Suihko, E., Korhonen, O., Järvinen, T., Ketolainen, J., Jarho, P., Laine, E., Paronen, P.: Complexation with tolbutamide modifies the physicochemical and tableting properties of hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 215, 137–145 (2001)
Shen, Y.L., Yang, S.H., Wu, L.M., Ma, X.Y.: Study on structure and characterization of inclusion complex of gossypol/beta cyclodextrin. Spectrochim. Acta A 61, 1025–1028 (2005)
Cunha-Silva, L., Texeira-Dias, J.J.C.: How humidity affects the solid-state inclusion of 2-phenoxyethanol in β-cyclodextrin: a comparison with β-cyclodextrin. New J. Chem. 28, 200–206 (2004)
Fernandez, C.M., Vierea, M.T., Veiga, F.J.B.: Physicochemical characterisation and in vitro dissolution behaviour of nicardipine-cyclodextrins inclusion compounds. Eur. J. Pharm. Sci. 15, 79–88 (2002)
Redenti, E., Peveri, T., Zanol, M., Ventura, P., Gnappi, G., Montenero, A.: A study on the differentiation between amorphous piroxicam:β-cyclodextrin complex and a moisture of the two amorphous components. Int. J. Pharm. Sci. 129, 289–294 (1996)
Baranska H., Labudzinska A., Terpinski J.: Laser Raman Spectroscopy. In: Analytical Applications. Wiley, New York (1987)
Dean J.A.: Lange’s Book of Chemistry, 15th edn, pp. 441–468. McGraw Hill, New York (1999)
Singh, H.B., Srivastava, M., Singh, A.B., Srivastava, A.K.: Cinnamon bark oil, a potent fungitoxicant against fungi causing respiratory tract mycoses. Allergy 50, 995–999 (1995)
Huang, Y., Ho, S.H.: Toxicity and antifeedant activities of cinnamaldehyde against the grain storage insects, Tribolium castaneum (Herbst) and Sitophilus zeamais Motsch. J. Stored Prod. Res. 34, 11–17 (1998)
Valverde, J.M., Guillén, F., Martínez-Romero, D., Castillo, S., Serrano, M., Valero, D.: Improvement of table grapes quality and safety by the combination of Modified Atmosphere Packaging (MAP) and eugenol, menthol, or thymol. J. Agric. Food Chem. 53, 7458–7464 (2005)
Park, I., Shin, S.: 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). J. Agric. Food Chem. 53, 4388–4392 (2005)
Costa-E-Silva, M., Galhano, C.I.C.A., Moreira Da Silva, M.G.: A new sprout inhibitor of potato tuber based on carvone/β-cyclodextrin inclusion compound. J. Incl. Phenom. Macrocycl. Chem. 57:121–124 (2007)
Acknowledgments
We thank Monica A. Villegas-Ochoa for technical assistance and give special acknowledgement to CIAD A.C., CONACYT and CYTED (Project XI.22) for financial support.
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Ayala-Zavala, J.F., Soto-Valdez, H., González-León, A. et al. Microencapsulation of cinnamon leaf (Cinnamomum zeylanicum) and garlic (Allium sativum) oils in β-cyclodextrin. J Incl Phenom Macrocycl Chem 60, 359–368 (2008). https://doi.org/10.1007/s10847-007-9385-1
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DOI: https://doi.org/10.1007/s10847-007-9385-1