Preparation and structural characterization of different amylose–flavor molecular inclusion complexes
Corresponding Author
Tao Feng
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Correspondence: Dr. Tao Feng, School of Perfume and Aroma Technology, Shanghai Institute of Technology, No.100 Hai Quan Road, Shanghai 201418, P. R. China
E-mail:[email protected]
Fax: +86-21-60873210
Search for more papers by this authorHui Wang
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorKe Wang
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorYi Liu
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorZhiwei Rong
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorHaining Zhuang
Institute of Edible Fungi, Shanghai Academy of Agricultural Sciences, National Engineering Research Center of Edible Fungi, Shanghai, P. R. China
Search for more papers by this authorZhimin Xu
School of Nutrition and Food Sciences, Louisiana State University Agricultural Center, Baton Rouge, LA, USA
Search for more papers by this authorMin Sun
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorCorresponding Author
Tao Feng
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Correspondence: Dr. Tao Feng, School of Perfume and Aroma Technology, Shanghai Institute of Technology, No.100 Hai Quan Road, Shanghai 201418, P. R. China
E-mail:[email protected]
Fax: +86-21-60873210
Search for more papers by this authorHui Wang
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorKe Wang
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorYi Liu
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorZhiwei Rong
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorHaining Zhuang
Institute of Edible Fungi, Shanghai Academy of Agricultural Sciences, National Engineering Research Center of Edible Fungi, Shanghai, P. R. China
Search for more papers by this authorZhimin Xu
School of Nutrition and Food Sciences, Louisiana State University Agricultural Center, Baton Rouge, LA, USA
Search for more papers by this authorMin Sun
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P. R. China
Search for more papers by this authorAbstract
Flavor microencapsulation has been widely used in foods, medicines, cosmetics, and other fields. The use of amylose-based complexes is receiving increasing attention because they are biodegradable, non-toxic, and biocompatible, and these complexes provide a new way to develop and impart flavors. In this study, with the aim of investigating the properties of amylose–flavor complexes, linear aliphatic alcohols (C6–C9) and the aromatic alcohol naphthol were used to prepare inclusion complexes by the sealed heating method in yields ranging from 45 to 50%. In addition, scanning electron microscopy (SEM), X-ray diffraction (XRD), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) were utilized to investigate the structural characteristics of these inclusion complexes, and it was found that the amylose-n-heptanol inclusion complex was most stable. Furthermore, nuclear magnetic resonance (NMR) spectroscopy revealed that V-type crystals existed in the amylose–flavor complexes. Moreover, TGA showed that all amylose–flavor inclusion complexes have excellent thermal stability. The encapsulation efficiency of the complexes increased with decreasing chain length, but the encapsulation efficiency of the complexes with the aromatic alcohol naphthol was lower than that of the complexes with some linear alcohols. This indicated that the stereoscopic confirmation of α-naphthol may influence the complexes being formed.
References
- 1 Andreu-Sevilla, A. J., López-Nicolás, J. M., Carbonell-Barrachina, A. A., García-Carmona, F., Comparative effect of the addition of α-, β-, or γ-cyclodextrin on main sensory and physico-chemical parameters. J. Food Sci. 2011, 76, S347–S353.
- 2 Desai, K. G. H., Jin Park, H., Recent developments in microencapsulation of food ingredients. Drying Technol. 2005, 23, 1361–1394.
- 3 Bluhm, T. L., Zugenmaier, P., Detailed structure of the Vh-amylose-iodine complex: A linear polyiodine chain. Carbohydr. Res. 1981, 89, 1–10.
- 4 Tufvesson, F., Eliasson, A. C., Formation and crystallization of amylose-monoglyceride complex in a starch matrix. Carbohydr. Polym. 2000, 43, 359–365.
- 5 Cao, Z., Woortman, A. J., Rudolf, P., Loos, K., Facile synthesis and structural characterization of amylose-fatty acid inclusion complexes. Macromol. Biosci. 2015, 15, 691.
- 6 Lay Ma, U. V., Floros, J. D., Ziegler, G. R., Formation of inclusion complexes of starch with fatty acid esters of bioactive compounds. Carbohydr. Polym. 2011, 83, 1869–1878.
- 7 Ades, H., Kesselman, E., Ungar, Y., Shimoni, E., Complexation with starch for encapsulation and controlled release of menthone and menthol. LWT − Food Sci. Technol. 2012, 45, 277–288.
- 8 Gunning, Y. M., Gunning, P. A., Kemsley, E. K., Parker, R., et al., Factors affecting the release of flavour encapsulated in carbohydrate matrixes. J. Agric. Food Chem. 1999, 47, 5198–5205.
- 9 Biais, B., Le Bail, P., Robert, P., Pontoire, B., Buléon, A., Structural and stoichiometric studies of complexes between aroma compounds and amylose. Polymorphic transitions and quantification in amorphous and crystalline areas. Carbohydr. Polym. 2006, 66, 306–315.
- 10 Fanta, G. F., Felker, F. C., Shogren, R. L., Salch, J. H., Preparation of spherulites from jet cooked mixtures of high amylose starch and fatty acids. Effect of preparative conditions on spherulite morphology and yield. Carbohydr. Polym. 2008, 71, 253–262.
- 11 Shogren, R. L., Fanta, G. F., Felker, F. C., X-ray diffraction study of crystal transformations in spherulitic amylose/lipid complexes from jet-cooked starch. Carbohydr. Polym. 2006, 64, 444–451.
- 12
Keatkrai, J.,
Lumdubwong, N.,
Chaiseri, S.,
Jirapakkul, W., Characteristics of menthone encapsulated complex by mungbean, tapioca and rice starches.
Int. J. Food Prop.
2017,
20, 810–820.
10.1080/10942912.2016.1183129 Google Scholar
- 13 Putaux, J.-L., Montesanti, N., Véronèse, G., Buléon, A., Morphology and structure of A-amylose single crystals. Polymer 2011, 52, 2198–2205.
- 14 Nuessli, J., Putaux, J. L., Bail, P. L., Buléon, A., Crystal structure of amylose complexes with small ligands. Int. J. Biol. Macromol. 2003, 33, 227–234.
- 15
Kenar, J. A.,
Compton, D. L.,
Little, J. A.,
Peterson, S. C., Formation of inclusion complexes between high amylose starch and octadecyl ferulate via steam jet cooking.
Carbohydr. Polym.
2016,
140, 246–252.
10.1016/j.carbpol.2015.12.048 Google Scholar
- 16 Seo, T. R., Kim, J. Y., Lim, S. T., Preparation and characterization of crystalline complexes between amylose and C18 fatty acids. LWT − Food Sci. Technol. 2015, 64, 889–897.
- 17 Yeo, L., Thompson, D. B., Peterson, D. G., Inclusion complexation of flavour compounds by dispersed high-amylose maize starch (HAMS) in an aqueous model system. Food Chem. 2016, 199, 393.
- 18 Zhang, S., Preparation and structural characterization of corn starch-aroma compound inclusion complexes. J. Sci. Food Agric. 2016, 97, 182–190.
- 19 Le Bail, P., Rondeau, C., Buléon, A., Structural investigation of amylose complexes with small ligands: helical conformation, crystalline structure and thermostability. Int. J. Biol. Macromol. 2005, 35, 1–7.
- 20 Ozturk, S., Koksel, H., Kahraman, K., Ng, P., Effect of debranching and heat treatments on formation and functional properties of resistant starch from high-amylose corn starches. Eur. Food Res. Technol. 2009, 229, 115–125.
- 21 Wulff, G., Avgenaki, G., Guzmann, M. S. P., Molecular encapsulation of flavours as helical inclusion complexes of amylose. J. Cereal Sci. 2005, 41, 239–249.
- 22 Liu Zhi, Y., Xin Xin, X., Miao Miao, Z., Yin Long, X., Yan Qi, L., Preparation and characterization of v-type amylose-hexanol complex. Adv. Mater. Res. 2011, 422, 641–645.
- 23 Misharina, T., Samusenko, A., Kalinchenko, M., Dependence of alcohol binding from aqueous dispersions on physicochemical properties of starch. Appl. Biochem. Microbiol. 2006, 42, 224–227.
- 24 Misharina, T. A., Samusenko, A. L., Kalinchenko, M. A., Effect of the composition of polysaccharides in gelatinized cornstarch on alcohol absorption. Appl. Biochem. Microbiol. 2003, 39, 703–707.
- 25 Misharina, T. A., Samusenko, A. L., Kalinchenko, M. A., Binding by cornstarch of components of a mixture of volatile organic substances from aqueous solutions. Appl. Biochem. Microbiol. 2004, 40, 609–612.
- 26 Liu, Y. Q., Xiao, X. X., Li, H., Li, X. H., Yang, L. Z., Analysis of preparation of V-type amylose-hexanol complex. Food Sci. Technol. 2011, 361–363, 1827–1831.
- 27 Yang, L. Z., Xiao, X. X., Zheng, M. M., Xu, Y. L., Liu, Y. Q., Preparation and characterization of v-type amylose-hexanol complex. Adv. Mater. Res. 2011, 422, 641–645.
- 28 Arvisenet, G., Voilley, A., Cayot, N., Retention of aroma compounds in starch matrices: Competitions between aroma compounds toward amylose and amylopectin. J. Agric. Food Chem. 2002, 50, 7345–7349.
- 29 Jouquand, C., Ducruet, V., Le Bail, P., Formation of amylose complexes with C6-aroma compounds in starch dispersions and its impact on retention. Food Chem. 2006, 96, 461–470.
- 30 Qunjie, X., Honghua, G., Junxi, Z., Analysis of preparation of V-type amylose-hexanol complex. Nat. Resour. Sustainable Dev. 2011, 361–363, 1827–1831.
- 31 Nuessli, J., Sigg, B., Condepetit, B., Escher, F., Characterization of amylose-flavour complexes by DSC and X-ray diffraction. Food Hydrocolloids 1997, 11, 27–34.
- 32 Itthisoponkul, T., Mitchell, J. R., Taylor, A. J., Farhat, I. A., Inclusion complexes of tapioca starch with flavour compounds. Carbohydr. Polym. 2007, 69, 106–115.
- 33 Duta, D., Brownsey, G. J., Noel, T. R., Ring, S. G., Formation of crystalline complexes of amylose with some selected flavour compounds. Pol. J. Food Nutr. 2009, 59, 29–33.
- 34 Heinemann, C., Conde-Petit, B., Nuessli, J., Escher, F., Evidence of starch inclusion complexation with lactones. J. Agric. Food Chem. 2001, 49, 1370.
- 35 Cardoso, M. B., Putaux, J.-L., Nishiyama, Y., Helbert, W., et al., Single crystals of v-amylose complexed with α-naphthol. Biomacromolecules 2007, 8, 1319–1326.
- 36 Falk, H., Stanek, M., Two-dimensional 1 H and 13C NMR spectroscopy and the structural aspects of amylose and amylopectin. Monatsh. Chem. 1997, 128, 777–784.
- 37 Cao, Z., Woortman, A. J. J., Rudolf, P., Loos, K., Facile synthesis and structural characterization of amylose-fatty acid inclusion complexes. Macromol. Biosci. 2015, 15, 691.
- 38 Le Bail, P., Bizot, H., Ollivon, M., Keller, G., et al., Monitoring the crystallization of amylose–lipid complexes during maize starch melting by synchrotron X-ray diffraction. Biopolymers 1999, 50, 99–110.
- 39 Liu, X., Yu, L., Xie, F., Li, M., et al., Kinetics and mechanism of thermal decomposition of cornstarches with different amylose/amylopectin ratios. Starch/Stärke 2010, 62, 139–146.
- 40 O'Connell, C., The effects of methylparaben on the gelatinization and thermal decomposition of corn starch. Thermochim. Acta 1999, 340, 183–194.
- 41 Yang, Y., Gu, Z., Xu, H., Li, F., Zhang, G., Interaction between amylose and β-cyclodextrin investigated by complexing with conjugated linoleic acid. J. Agric. Food Chem. 2010, 58, 5620–5624.
- 42 Zhang, S., Zhou, Y., Jin, S., Meng, X., et al., Preparation and structural characterization of corn starch-aroma compound inclusion complexes. J. Sci. Food Agric. 2016, 97, 182–190.
- 43 Heinemann, C., Escher, F., Conde-Petit, B., Structural features of starch-lactone inclusion complexes in aqueous potato starch dispersions: The role of amylose and amylopectin. Carbohydr. Polym. 2003, 51, 159–168.
