To reveal the influences of food matrix components on the formation of hydrophobic polysaccharide micelles, the effect of seven common amino acids (glutamic acid, lysine, isoleucine, phenylalanine, cysteine, alanine, and serine) on the formation of octenylsuccinated oat β-glucan (OSβG) micelles and their nature were investigated for widening the application scope of OSβG micelles in the food industry. Effects of seven hydrophobic amino acids on the critical micelle concentration (CMC) of OSβG, size, polydispersity index (PDI) and Zeta potential of OSβG micelles at different pH (3, 6 and 10) conditions were investigated. Moreover, the effects of five neutral amino acids (isoleucine, phenylalanine, cysteine, alanine, and serine) on curcumin-loaded OSβG micelles were also studied. The results showed that the CMC of OSβG, size, and absolute Zeta potential of OSβG micelles increased with pH value for each amino acid. This was mainly due to pH-induced dissociation of OSβG and amino acids, which further changed the stability of OSβG micelles via the electrostatic and hydrogen-bonding interactions between hydrophilic/hydrophobic chains of OSβG and the side chains of amino acids. The hydrophobicity of amino acids was not the only factor determining the micellar properties of loading curcumin by OSβG micelles. This study confirmed that the effects of amino acids and their environmental pH conditions on OSβG micelles and curcumin-loaded OSβG micelles were mainly due to the hydrogen-bonding and electrostatic interactions between OSβG and amino acid molecules in nature. It provides support for the stabilizing application of OSβG micelles and curcumin-loaded OSβG micelles in food systems.
[1] VALENCIA G A,ZARE E N,MAKVANDI P,et al.Self-assembled carbohydrate polymers for food applications:A review[J].Comprehensive Reviews in Food Science and Food Safety,2019,18(6):2 009-2 024.
[2] WANG Z,DENG X P,DING J S,et al.Mechanisms of drug release in pH-sensitive micelles for tumour targeted drug delivery system:A review[J].International Journal of Pharmaceutics,2018,535(1):253-260.
[3] WU Z,ZHAO C Y,HUANG Y X,et al.Molecular mechanism underlying the effects of temperature and pH on the size and surface charge of octenylsuccinated oat β-glucan aggregates[J].Carbohydrate Polymers,2020,237:116115.
[4] LU X,CHEN J H,GUO Z B,et al.Using polysaccharides for the enhancement of functionality of foods:A review[J].Trends in Food Science & Technology,2019,86:311-327.
[5] 向卓亚, 赵国华,叶发银,等.两亲性多糖壳-核胶束稳定性研究进展[J].食品与机械,2016,32(7):207-213.
XIANG Z Y,ZHAO G H,YE F Y,et al.Stability of "shell-core" micelles formed by amphiphilic polysaccharides[J].Food and Machinery,2016,32(7):207-213.
[6] 肖丽,叶发银,赵国华.两亲性多糖的制备及其自聚集胶束的特性研究进展[J].食品科学,2017,38(1):263-268.
XIAO L,YE F Y,ZHAO G H.Advances in synthesis of amphiphilic polysaccharides and properties of their self-aggregated micelles[J].Food Science,2017,38(1):263-268.
[7] OWEN S C,CHAN D P Y,SHOICHET M S.Polymeric micelle stability[J].Nano Today,2012,7(1):53-65.
[8] HE D G,WANG S,LEI L,et al.Core-shell particles for controllable release of drug[J].Chemical Engineering Science,2015,125:108-120.
[9] HAN X,ZHANG X X,ZHU H F,et al.Effect of composition of PDMAEMA-b-PAA block copolymers on their pH-and temperature-responsive behaviors[J].Langmuir,2013,29(4):1 024-1 034.
[10] ALTUNA L,HERRERA M L,FORESTI M L.Synthesis and characterization of octenyl succinic anhydride modified starches for food applications.A review of recent literature[J].Food Hydrocolloids,2018,80:97-110.
[11] SWEEDMAN M C,TIZZOTTI M J,SCHFER C,et al.Structure and physicochemical properties of octenyl succinic anhydride modified starches:A review[J].Carbohydrate Polymers,2013,92(1):905-920.
[12] ZHANG R Y,BELWAL T,LI L,et al.Recent advances in polysaccharides stabilized emulsions for encapsulation and delivery of bioactive food ingredients:A review[J].Carbohydrate Polymers,2020,242:116388.
[13] PUNIA S.Barley starch modifications:Physical,chemical and enzymatic-A review[J].International Journal of Biological Macromolecules,2020,144:578-585.
[14] MA Y Q,LIU J,YE F Y,et al.Solubilization of β-carotene with oat β-glucan octenylsuccinate micelles and their freeze-thaw,thermal and storage stability[J].LWT-Food Science and Technology,2016,65:845-851.
[15] LIU J,LI J,MA Y Q,et al.Synthesis,Characterization,and aqueous self-assembly of octenylsuccinate oat β-glucan[J].Journal of Agricultural and Food Chemistry,2013,61(51):12 683-12 691.
[16] PATIDAR P,BAHADUR A.Modulating effect of different biomolecules and other additives on cloud point and aggregation of amphiphilic linear and starblock copolymer[J].Journal of Molecular Liquids,2018,249:219-226.
[17] WU S Y,YAN Z N,WEN X L,et al.Conductometric and fluorescence probe investigations of molecular interactions between dodecyltrimethylammonium bromide and dipeptides[J].Colloid and Polymer Science,2014,292(11):2 775-2 783.
[18] GELAMO E L,SILVA C H T P,IMASATO H,et al.Interaction of bovine(BSA) and human(HSA) serum albumins with ionic surfactants:Spectroscopy and modelling[J].Biochimica et Biophysica Acta(BBA)-Protein Structure and Molecular Enzymology,2002,1 594(1):84-99.
[19] BONNAUD M,WEISS J,MCCLEMENTS D J.Interaction of a food-grade cationic surfactant(Lauric Arginate) with good-grade biopolymers(pectin,carrageenan,xanthan,alginate,dextran,and chitosan)[J].Journal of Agricultural and Food Chemistry,2010,58(17):9 770-9 777.
[20] KHRUSTALEV V V,BARKOVSKY E V.Stabilization of secondary structure elements by specific combinations of hydrophilic and hydrophobic amino acid residues is more important for proteins encoded by GC-poor genes[J].Biochimie,2012,94(12):2 706-2 715.
[21] 王传怀,袁玉荪.等电状态两性化合物的电化学性质[J].南京大学学报(自然科学版),1985,21(1):192-201.
WANG C H,YUAN Y S.The electrochemical properties of the ampholytes in isoelectrical states[J].Journal of Nanjing University(Natural Sciences Edition),1985,21(1):192-201.
[22] LIU Y,GUO R.pH-dependent structures and properties of casein micelles[J].Biophysical Chemistry,2008,136(2):67-73.
[23] HE F,XU G Y,PANG J Y,et al.Effect of amino acids on aggregation behaviors of sodium deoxycholate at air/water surface:Surface tension and oscillating bubble studies[J].Langmuir,2011,27(2):538-545.
[24] XUE Y N,HUANG Z Z,ZHANG J T,et al.Synthesis and self-assembly of amphiphilic poly(acrylic acid-b-DL-lactide) to form micelles for pH-responsive drug delivery[J].Polymer,2009,50(15):3 706-3 713.
[25] LE-VINH B,LE N-M N,NAZIR I,et al.Chitosan based micelle with zeta potential changing property for effective mucosal drug delivery[J].International Journal of Biological Macromolecules,2019,133:647-655.
[26] JIANG X Y,LU G L,FENG C,et al.Poly(acrylic acid)-graft-poly(N-vinylcaprolactam):A novel pH and thermo dual-stimuli responsive system[J].Polymer Chemistry,2013,4(13):3 876-3 884.
[27] HE F,XU G Y,PANG J Y,et al.Effect of amino acids on aggregation behaviour of sodium deoxycholate in solution:A fluorescence study[J].Luminescence,2012,27(1):4-10.
[28] YANG Y,DONG J,LI X F.Micelle to vesicle transitions of N-dodecyl-1,ω-diaminoalkanes:Effects of pH,temperature and salt[J].Journal of Colloid and Interface Science,2012,380(1):83-89.
[29] LIU J,CHEN F,TIAN W N,et al.Optimization and characterization of curcumin loaded in octenylsuccinate oat β-Glucan micelles with an emphasis on degree of substitution and molecular weight[J].Journal of Agricultural and Food Chemistry,2014,62(30):7 532-7 540.
[30] WU Z,ZHAO C Y,LI R H,et al.Insights into micellization of octenylsuccinated oat β-glucan and uptake and controlled release of β-carotene by the resultant micelles[J].Journal of Agricultural and Food Chemistry,2019,67(26):7 416-7 427.