Synthesis of maltodextrin-grafted-cinnamic acid and evaluation on its ability to stabilize anthocyanins via microencapsulation

References

• Abers JE, Wrolstad RE. Causative factors of colour deterioration in strawberry perserves during processing and storage. J Food Sci, 1979;44(1):76–81.
   Web of Science ®Google Scholar
• Amr A, Al-Tamimi E. Stability of the crude extracts of ranunculus asiaticus anthocyanins and their use as food colourants. Int J Food Sci Technol, 2007;42(8):985–91.
   Web of Science ®Google Scholar
• Augustin MA, Hemar Y. Nano- and micro-structured assemblies for encapsulation of food ingredients. Chem Soc Rev, 2009;38(4):902–12.
   PubMed Web of Science ®Google Scholar
• Boranbayeva T, Karadeniz F, Yılmaz E. Effect of storage on anthocyanin degradation in black mulberry juice and concentrates. Food Bioprocess Technol, 2014;7(7):1894–902.
   Web of Science ®Google Scholar
• Brouillard RDB. Chemistry of anthocyanin pigments. 2. Kinetic and thermodynamic study of proton transfer, hydration, and tautomeric reactions of malvidin 3-glucoside. J Am Chem Soc, 1977;99(26):8461–8.
   Web of Science ®Google Scholar
• Chen Q, Yu H, Wang L, Abdin Z, Chen YS, Wang JH, Zhou WD, Yang XP, Khan RU Zhang HT, et al. Recent progress in chemical modification of starch. RSC Advance, 2015;5:67459–74.
   Web of Science ®Google Scholar
• Davidov-Pardo G, Arozarena I, Marín-Arroyo MR. Optimisation of a wall material formulation to microencapsulate a grape seed extract using a mixture design of experiments. Food Bioprocess Technol, 2012;6(4):941–51.
   Web of Science ®Google Scholar
• Diaconeasa Z, Leopold L, Rugina D, Ayvaz H, Socaciu C. Antiproliferative and antioxidant properties of anthocyanin rich extracts from blueberry and blackcurrant juice. Int J Mol Sci, 2015;16(2):2352–65.
   PubMed Web of Science ®Google Scholar
• Diaz DI, Beristain CI, Azuara E, Luna G, Jimenez M. Effect of wall material on the antioxidant activity and physicochemical properties of rubus fruticosus juice microcapsules. J Microencapsul, 2015;32(3):247–54.
   PubMed Web of Science ®Google Scholar
• Ersus S, Yurdagel U. Microencapsulation of anthocyanin pigments of black carrot (Daucus carota L.) by spray drier. J Food Eng, 2007;80(3):805–12.
   Web of Science ®Google Scholar
• Ezhilarasi PN, Karthik P, Chhanwal N, Anandharamakrishnan C. Nanoencapsulation techniques for food bioactive components: A review. Food Bioprocess Technol, 2012;6(3):628–47.
   Web of Science ®Google Scholar
• Faria A, O J, Neves P, Gameiro P, Buelga CS, Freitas VD, Mateus N. Antioxidant properties of prepared blueberry. J Agric Food Chem, 2005;53:6896–902.
   PubMed Web of Science ®Google Scholar
• García-Tejeda YV, Salinas-Moreno Y, Martínez-Bustos F. Acetylation of normal and waxy maize starches as encapsulating agents for maize anthocyanins microencapsulation. Food Bioproducts Processing, 2015;94:717–26.
   Web of Science ®Google Scholar
• Ghidouche S, Rey B, Michel M, Galaffu N. A rapid tool for the stability assessment of natural food colours. Food Chem, 2013;139:978–85.
   PubMed Web of Science ®Google Scholar
• Golachowski A, Zieba T, Kapelko-Zeberska M, Drozdz W, Gryszkin A, Grzechac M. Current research addressing starch acetylation. Food Chem, 2015;176:350–6.
   PubMed Web of Science ®Google Scholar
• Gomes R, Parola AJ, Lima JC, Pina F. Solvent effects on the thermal and photochemical reactions of 4′-iodo-8-methoxyflavylium and their consequences on the coloring phenomena caused by anthocyanins in plants. Chemistry, 2006;12(30):7906–12.
   PubMed Web of Science ®Google Scholar
• Goula AM, Adamopoulos KG. A new technique for spray drying orange juice concentrate. Innov Food Sci Emerg, 2010;11(2):342–51.
   Web of Science ®Google Scholar
• Giusti MM, Wrolstad RE. 2001. Anthocyanins. Characterisation and measurement with UV-visible spectroscopy. In: Wrolstad RE, ed. Current protocols in food analytical chemistry. New York: Wiley, pp. 24–7.
   Google Scholar
• He W, Zeng M, Chen J, Jiao Y, Niu F, Tao G, Zhang S, Qin F, He Z. Identification and Quantitation of Anthocyanins in Purple-Fleshed Sweet Potatoes Cultivated in China by UPLC-PDA and UPLC-QTOF-MS/MS. J Agric Food Chem, 2016;64(1):171–7.
   PubMed Web of Science ®Google Scholar
• Hu X, Wei B, Zhang B, Xu X, Jin Z, Tian Y. Synthesis and characterization of dextrin monosuccinate. Carbohydr Polym, 2013;97(1):111–15.
   PubMed Web of Science ®Google Scholar
• Jing P, Qian B, Zhao S, Qi X, Ye L, Monica Giusti M, Wang X. Effect of glycosylation patterns of Chinese eggplant anthocyanins and other derivatives on antioxidant effectiveness in human colon cell lines. Food Chem, 2015;172:183–9.
   PubMed Web of Science ®Google Scholar
• Jyothi NV, Prasanna PM, Sakarkar SN, Prabha KS, Ramaiah PS, Srawan GY. Microencapsulation techniques, factors influencing encapsulation efficiency. J Microencapsul, 2010;27(3):187–97.
   PubMed Web of Science ®Google Scholar
• Kahkonen MP, Heinonen M. Antioxidant activity of anthocyanins and their aglycons. J Agric Food Chem, 2003;51(3):628–33.
   PubMed Web of Science ®Google Scholar
• Klein M, Aserin A, Ben Ishai P, Garti N. Interactions between whey protein isolate and gum arabic. Colloids Surf B Biointerfaces, 2010;79(2):377–83.
   PubMed Web of Science ®Google Scholar
• Kitchin C. 2003. Spectroscopy. In: Kitchin C, ed. Telescopes and techniques: An introduction to practical astronomy. London York: Springer, pp. 219–27.
   Google Scholar
• Laokuldilok T, Kanha N. Effects of processing conditions on powder properties of black glutinous rice (Oryza sativa L.) bran anthocyanins produced by spray drying and freeze drying. LWT – Food Sci Technol, 2015;64(1):405–11.
   Web of Science ®Google Scholar
• Lee MJ, Park JS, Choi DS, Jung MY. Characterization and quantitation of anthocyanins in purple-fleshed sweet potatoes cultivated in Korea by HPLC-DAD and HPLC-ESI-QTOF-MS/MS. J Agric Food Chem, 2013;61(12):3148–58.
   PubMed Web of Science ®Google Scholar
• Lee S, Han JM, Kim H, Kim E, Jeong TS, Lee WS, Cho KH. Synthesis of cinnamic acid derivatives and their inhibitory effects on LDL-oxidation, acyl-CoA:cholesterol acyltransferase-1 and -2 activity, and decrease of HDL-particle size. Bioorg Med Chem Lett, 2004;14(18):4677–81.
   PubMed Web of Science ®Google Scholar
• Li JJ, Song CX, Hou CJ, Huo DQ, Shen CH, Luo XG, Yang M, Fa HB. Development of a colorimetric sensor array for the discrimination of Chinese liquors based on selected volatile markers determined by GC-MS. J Agric Food Chem, 2014;62(43):10422–30.
   PubMed Web of Science ®Google Scholar
• Li NG, Shi ZH, Tang YP, Li BQ, Duan JA. Highly efficient esterification of ferulic acid under microwave irradiation. Molecules, 2009;14(6):2118–26.
   PubMed Web of Science ®Google Scholar
• Mahdavi SA, Jafari SM, Ghorbani M, Assadpoor E. Spray-drying microencapsulation of anthocyanins by natural biopolymers: A review. Drying Technol, 2014;32(5):509–18.
   Web of Science ®Google Scholar
• Mazza G. Recent developments in the stabilisation of anthocyaninsin food products. Food Chem, 1987;25:207–25.
   Web of Science ®Google Scholar
• Namazi H, Dadkhah A. Convenient method for preparation of hydrophobically modified starch nanocrystals with using fatty acids. Carbohydr Polym, 2010;79(3):731–7.
   Web of Science ®Google Scholar
• Netzel M, Netzel G, Kammerer DR, Schieber A, Carle R, Simons L, Bitsch I, Bitsch R, Konczak I. Cancer cell antiproliferation activity and metabolism of black carrot anthocyanins. Innov Food Sci Emerg, 2007;8(3):365–72.
   Web of Science ®Google Scholar
• Ngo T, Wrolstad RE, Zhao Y. Colour quality of Oregon strawberries–impact of genotype, composition and processing. J Food Sci, 2007;72(1):25–32.
   Web of Science ®Google Scholar
• Nicks F, Richel A, Richard G, Laurent P, Wathelet B, Wathelet J-P, Paquot M. Green synthesis and antioxidant activity of new PEGylated ferulic acids. Tetrahedron Lett, 2012;53(19):2402–5.
   Web of Science ®Google Scholar
• Osorio C, Acevedo B, Hillebrand S, Carriazo J, Winterhalter P, Morales AL. Microencapsulation by spray-drying of anthocyanin pigments from Corozo (Bactris guineensis) fruit. J Agric Food Chem, 2010;58(11):6977–85.
   PubMed Web of Science ®Google Scholar
• Ou J, Sun Z. Feruloylated oligosaccharides: Structure, metabolism and function. J Funct Foods, 2014;7:90–100.
   Web of Science ®Google Scholar
• Park HJ, Lee GH, Jun JH, Son M, Choi YS, Choi MK, Kang MJ. Formulation and in vivo evaluation of probiotics-encapsulated pellets with hydroxypropyl methylcellulose acetate succinate (HPMCAS). Carbohydr Polym, 2016;136:692–9.
   PubMed Web of Science ®Google Scholar
• Pavón-García LMA, Pérez-Alonso C, Orozco-Villafuerte J, Pimentel-González DJ, Rodríguez-Huezo ME, Vernon-Carter EJ. Storage stability of the natural colourant from Justicia spicigera microencapsulated in protective colloids blends by spray-drying. Int J Food Sci Technol, 2011;46(7):1428–37.
   Web of Science ®Google Scholar
• Robert P, Gorena T, Romero N, Sepulveda E, Chavez J, Saenz C. Encapsulation of polyphenols and anthocyanins from pomegranate (Punica granatum) by spray drying. Int J Food Sci Technol, 2010;45(7):1386–94.
   Web of Science ®Google Scholar
• Romero C, Bakker J. Effect of storage temperature and pyruvate on kinetics of anthocyanin degradation, vitisin A derivative formation, and color characteristics of model solutions. J Agric Food Chem, 2000;48:2135–41.
   PubMed Web of Science ®Google Scholar
• Santiago-Adame R, Medina-Torres L, Gallegos-Infante JA, Calderas F, González-Laredo RF, Rocha-Guzmán NE, Ochoa-Martínez LA, Bernad-Bernad MJ. Spray drying-microencapsulation of cinnamon infusions (Cinnamomum zeylanicum) with maltodextrin. LWT – Food Sci Technol, 2015;64(2):571–7.
   Web of Science ®Google Scholar
• Santos-Buelga C, Mateus N, De Freitas V. Anthocyanins. Plant pigments and beyond. J Agric Food Chem, 2014;62(29):6879–84.
   PubMed Web of Science ®Google Scholar
• Shi Z-H, Li N-G, Shi Q-P, Hao T, Tang Y-P. Design, synthesis, and preliminary evaluation of substituted cinnamic acid esters as selective matrix metalloproteinase inhibitors. Drug Develop Res, 2012;73(6):317–24.
   Web of Science ®Google Scholar
• Shimotori Y, Hoshi M, Soga K, Osawa Y, Miyakoshi T. Synthesis of hydroxycinnamoyl β-D-xylopyranosides and evaluation of their antioxidant properties. Carbohydr Res, 2014;388:138–46.
   PubMed Web of Science ®Google Scholar
• Sui X, Dong X, Zhou W. Combined effect of pH and high temperature on the stability and antioxidant capacity of two anthocyanins in aqueous solution. Food Chem, 2014;163:163–70.
   PubMed Web of Science ®Google Scholar
• Tan LH, Chan LW, Heng PWS. Alginate/starch composites as wall material to achieve microencapsulation with high oil loading. J Microencapsul, 2008;26(3):263–71.
   PubMed Web of Science ®Google Scholar
• Tan W, Li Q, Li W, Dong F, Guo Z. Synthesis and antioxidant property of novel 1,2,3-triazole-linked starch derivatives via ‘click chemistry’. Int J Biol Macromol, 2016;82:404–10.
   PubMed Web of Science ®Google Scholar
• Thirathumthavorn D, Charoenrein S. Thermal and pasting properties of native and acid-treated starches derivatized by 1-octenyl succinic anhydride. Carbohydr Polym, 2006;66(2):258–65.
   Web of Science ®Google Scholar
• Tonon RV, Alexandre D, Hubinger MD, Cunha RL. Steady and dynamic shear rheological properties of açai pulp (Euterpe oleraceae Mart.). J Food Eng, 2009;92(4):425–31.
   Web of Science ®Google Scholar
• Vrignaud S, Benoit JP, Saulnier P. Strategies for the nanoencapsulation of hydrophilic molecules in polymer-based nanoparticles. Biomaterials, 2011;32(33):8593–604.
   PubMed Web of Science ®Google Scholar
• Wang M, Kim J-C. Tween 20-cinnamic acid conjugate as a UV-absorbing emulsifier. Colloid Surface a, 2014;453:62–7.
   Web of Science ®Google Scholar
• Wrigstedt P, Kylli P, Pitkanen L, Nousiainen P, Tenkanen M, Sipila J. Synthesis and antioxidant activity of hydroxycinnamic acid xylan esters. J Agric Food Chem, 2010;58(11):6937–43.
   PubMed Web of Science ®Google Scholar
• Wrolstad RE, Durst RW, Lee J. Tracking colour and pigment changes in anthocyanin products. Trends Food Sci Tech, 2005;16:423–8.
   Web of Science ®Google Scholar
• Wu W, Lu L, Long Y, Wang T, Liu L, Chen Q, Wang R. Free radical scavenging and antioxidative activities of caffeic acid phenethyl ester (CAPE) and its related compounds in solution and membranes: A structure–activity insight. Food Chem, 2007;105(1):107–15.
   Web of Science ®Google Scholar
• Yen GC, Chen YL, Sun FM, Chiang YL, Lu SH, Weng CJ. A comparative study on the effectiveness of cis- and trans-form of cinnamic acid treatments for inhibiting invasive activity of human lung adenocarcinoma cells. Eur J Pharm Sci, 2011;44(3):281–7.
   PubMed Web of Science ®Google Scholar
• Zhang L, Mou D, Du Y. Procyanidins: Extraction and micro-encapsulation. J Sci Food Agric, 2007;87(12):2192–7.
   Web of Science ®Google Scholar
• Zhang Y, Liao X, Ni Y, Wu J, Hu X, Wang Z, Chen F. Kinetic analysis of the degradation and its colour change of cyanidin-3-glucoside exposed to pulsed electric field. Eur Food Res Technol, 2006;224(5):597–603.
   Web of Science ®Google Scholar
• Zuidam NJ. 2009. Overview of microencapsulates for use in food products or processes and methods to make them. In: Zuidam NJ, Nedovic VA, eds. Encapsulation technologies for active food ingredients and food. New York: Springer, pp. 57–68.
   Google Scholar