Abstract
A series of methyl salicylate (MeSA)/β-cyclodextrin (β-CD) inclusion complexes (ICs) were prepared at different MeSA concentrations by the co-precipitation method using methyl salicylate for maintaining the quality of fresh produce. The formation of IC was confirmed through FTIR, 1H NMR, TGA, and SEM measurements. Among the grades applied, IC with 1:1 grade showed the highest MeSA entrapment efficiency (59%). The release rate of MeSA from an IC was greater at higher temperature and higher relative humidity. In addition, the MeSA release from ICs of all grades followed a diffusive nature and first-order kinetics at 25 °C under all RH conditions, except at 7 °C. These results indicate that the use of a MeSA/β-CD IC in active packaging applications can effective maintain the quality of fresh produce.
Similar content being viewed by others
References
Abarca RL, Rodriguez FJ, Guarda A, Galotto MJ, Bruna JE. Characterization of beta-cyclodextrin inclusion complexes containing an essential oil component. Food Chem. 196: 968-975 (2016)
Almenar E, Del Valle V, Catala R, Gavara R. Active package for wild strawberry fruit (Fragaria vesca L.). J. Agric. Food Chem. 55: 2240-2245 (2007)
Assaf KI, Gabel D, Zimmermann W, Nau WM. High-affinity host–guest chemistry of large-ring cyclodextrins. Org. Biomol. Chem. 14: 7702-7706 (2016)
Aytac Z, Yildiz ZI, Kayaci-Senirmak F, Keskin NOS, Kusku SI, Durgun E, Tekinay T, Uyar T. Fast-dissolving, prolonged release, and antibacterial cyclodextrin/limonene-inclusion complex nanofibrous webs via polymer-free electrospinning. J. Agric. Food Chem. 64: 7325-7334 (2016)
Bouchemela H, Madi F, Nouar L. DFT investigation of host–guest interactions between α-Terpineol and β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 95: 247-258 (2019)
Cheng M, Wang J, Zhang R, Kong R, Lu W, Wang X. Characterization and application of the microencapsulated carvacrol/sodium alginate films as food packaging materials. Int. J. Biol. Macromol. 141: 259-267 (2019)
Crini G. A history of cyclodextrins. Chem. Rev. 114: 10940-10975 (2014)
Devi NKD, Rani AP, Aved MM, SaiKumar K, Kaushik J, Sowjanya V. Cyclodextrins in pharmacy—an overview. Pharmacophore 1: 155-165 (2010)
Duran M, Aday MS, Zorba NND, Temizkan R, Büyükcan MB, Caner C. Potential of antimicrobial active packaging ‘containing natamycin, nisin, pomegranate and grape seed extract in chitosan coating’ to extend shelf life of fresh strawberry. Food Bioprod. Process. 98: 354-363 (2016)
Habibi F, Ramezanian A, Rahemi M, Eshghi S, Guillén F, Serrano M, Valero D. Postharvest treatments with γ-aminobutyric acid, methyl jasmonate or methyl salicylate enhance chilling tolerance of blood orange fruit at prolonged cold storage. J. Sci. Food Agric. 99: 6408-6417 (2019)
Hill LE, Gomes C, Taylor TM. Characterization of beta-cyclodextrin inclusion complexes containing essential oils (trans-cinnamaldehyde, eugenol, cinnamon bark, and clove bud extracts) for antimicrobial delivery applications. LWT Food Sci. Technol. 51:86-93 (2013)
Hu QD, Tang GP, Chu PK. Cyclodextrin-based host–guest supramolecular nanoparticles for delivery: from design to applications. Acc. Chem. Res. 47: 2017-2025 (2014)
Jeon SS, Lee SJ, Ganesan P, Kwak HS. Comparative study of flavor, texture, and sensory in cream cheese and cholesterol-removed cream cheese. Food Sci. Biotechnol. 21: 159-165 (2012)
Jin H, Yang L, Ahonen MJR, Schoenfisch MH. Nitric oxide-releasing cyclodextrins. J. Am. Chem. Soc. 140: 14178-14184 (2018)
Kant A, Linforth RS, Hort J, Taylor AJ. Effect of β-cyclodextrin on aroma release and flavor perception. J. Agric. Food Chem. 52: 2028-2035 (2004)
Li S, Purdy WC. Cyclodextrins and their applications in analytical chemistry. Chem. Rev. 92: 1457-1470 (1992)
Li S, Tang Y, Zhang X, Dou Y, Shen X. Preparation and characterization of diclofenac sodium β-cyclodextrin inclusion complex eye drops. J. Incl. Phenom. Macrocycl. Chem. 94: 85-94 (2019)
Li X, Jin Z, Wang J. Complexation of allyl isothiocyanate by α-and β-cyclodextrin and its controlled release characteristics. Food Chem. 103: 461-466 (2007)
Liu L, Song K-S, Li X-S, Guo Q-X. Charge-transfer interaction: a driving force for cyclodextrin inclusion complexation. J. Incl. Phenom. Macrocycl. Chem. 40: 35-39 (2001)
Min D, Li F, Zhang X, Shu P, Cui X, Dong L, Ren C, Meng D, Li J. Effect of methyl salicylate in combination with 1-methylcyclopropene on postharvest quality and decay caused by Botrytis cinerea in tomato fruit. J. Sci. Food Agric. 98: 3815-3822 (2018)
Nguyen TVA, Yoshii H. Release behavior of allyl sulfide from cyclodextrin inclusion complex of allyl sulfide under different storage conditions. Biosci. Biotechnol. Biochem. 82: 848-855 (2018)
Polyakov NE, Leshina TV, Konovalova TA, Hand EO, Kispert LD. Inclusion complexes of carotenoids with cyclodextrins: 1HNMR, EPR, and optical studies. Free Radical Biol. Med. 36: 872-880 (2004)
Rehmann L, Yoshii H, Furuta T. Characteristics of modified β-cyclodextrin bound to cellulose powder. Starch-Stärke 55: 313-318 (2003)
Ryals JA, Neuenschwander UH, Willits MG, Molina A, Steiner H-Y, Hunt MD. Systemic acquired resistance. Plant Cell 8: 1809-1819 (1996)
Shiga H, Yoshii H, Nishiyama T, Furuta T, Forssele P, Poutanen K, Linko P. Flavor encapsulation and release characteristics of spray-dried powder by the blended encapsulant of cyclodextrin and gum arabic. Drying Technol. 19: 1385-1395 (2001)
Shulaev V, Silverman P, Raskin I. Airborne signalling by methyl salicylate in plant pathogen resistance. Nature 385: 718-721 (1997)
Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98: 1743-1754 (1998)
Szente L, Fenyvesi É, Szejtli J. Entrapment of iodine with cyclodextrins: potential application of cyclodextrins in nuclear waste management. Environ. Sci. Technol. 33: 4495-4498 (1999)
Szente L, Szemán J. Cyclodextrins in analytical chemistry: host–guest type molecular recognition. Anal. Chem. 85: 8024-8030 (2013)
Tanwar S, Barbey C, Dupont N. Experimental and theoretical studies of the inclusion complex of different linear aliphatic alcohols with cyclodextrins. Carbohydr. Polym. 217: 26-34 (2019)
Wang J, Cao Y, Sun B, Wang C. Physicochemical and release characterisation of garlic oil-β-cyclodextrin inclusion complexes. Food Chem. 127: 1680-1685 (2011)
Yoshii H, Furuta T, Yasunishi A, Hirano H. Minimum number of water molecules required for inclusion of d-limonene in the cyclodextrin cavity. J. Biochem. 115: 1035-1037 (1994)
Yuan C, Jin Z, Xu X. Inclusion complex of astaxanthin with hydroxypropyl-β-cyclodextrin: UV, FTIR, 1H NMR and molecular modeling studies. Carbohydr. Polym. 89: 492-496 (2012)
Zhang W, Li X, Yu T, Yuan L, Rao G, Li D, Mu C. Preparation, physicochemical characterization and release behavior of the inclusion complex of trans-anethole and β-cyclodextrin. Food Res. Int. 74: 55-62 (2015)
Acknowledgements
This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (IPET) through the Agricultural Export Business Model Development Program, funded by the Ministry of Agriculture, Food and Rural Affairs (MAFRA, 319091-03).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Lee, M., Dey, K.P. & Lee, Y.S. Complexation of methyl salicylate with β-cyclodextrin and its release characteristics for active food packaging. Food Sci Biotechnol 29, 917–925 (2020). https://doi.org/10.1007/s10068-020-00749-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10068-020-00749-z