Preparation of human milk fat substitute and improvement of its oxidative stability

H.A.  Liu; J.Y.  Huang; T.M.  Olajide; T.  Liu; Z.M.  Liu; X.Y.  Liao; X.C.  Weng

doi:10.3989/gya.0444211

Authors

H.A. Liu State Key Laboratory of Dairy Biotechnology, Shanghai Engineering Research Center of Dairy Biotechnology, Dairy Research Institute - School of Life Sciences, Shanghai University https://orcid.org/0000-0002-0528-0860
J.Y. Huang School of Life Sciences, Shanghai University https://orcid.org/0000-0001-7410-0504
T.M. Olajide School of Environmental and Chemical Engineering, Shanghai University https://orcid.org/0000-0003-4751-8715
T. Liu School of Environmental and Chemical Engineering, Shanghai University https://orcid.org/0000-0002-8975-4989
Z.M. Liu State Key Laboratory of Dairy Biotechnology, Shanghai Engineering Research Center of Dairy Biotechnology, Dairy Research Institute https://orcid.org/0000-0003-3777-087X
X.Y. Liao School of Life Sciences, Shanghai University https://orcid.org/0000-0003-1394-1160
X.C. Weng School of Life Sciences, Shanghai University - School of Environmental and Chemical Engineering, Shanghai Universit https://orcid.org/0000-0003-2047-1654

DOI:

https://doi.org/10.3989/gya.0444211

Keywords:

1,3-dioleoyl-2-palmitoylglycerol, Enzymatic interesterification, Human milk fat substitutes, Oxidative stability, Physical blending

Abstract

1,3-Dioleoyl-2-palmitoylglycerol (OPO) was synthesized by enzymatic interesterification using palm stearin rich in tripalmitin (PPP) and ethyl oleate. Enzymatic interesterification parameters such as temperature, water content, enzyme load, and substrate molar ratio were optimized. High contents of C52 (primarily OPO and its isomeric compounds) production (46.7%) and sn-2 palmitic acid (PA) content of 75.3% were detected. In addition, OPO-human milk fat substitute (HMFS) was blended with coconut, soybean, algal and microbial oils at a weight ratio of 0.70:0.18:0.11:0.004:0.007 to simulate fatty acids in human milk fat (HMF) according to the mathematical model. The main and important fatty acids in the Final-HMFS were within the ranges of those present in HMF. The Final-HMFS could promote the absorption of fats and minerals and the development of retina tissues in infants. The mixture of L-ascorbyl palmitate (L-AP) and vitamin E (VE) resulted in a synergistic antioxidant effect both in OPO-HMFS and OPO-HMFS emulsions. This finding has great significance in improving the quality and extending shelf-life of HMFS.

Downloads

Download data is not yet available.

References

Ab Ed, S M, Zou X, Ali AH, Jin Q, Wang X. 2017. Synthesis of 1,3-dioleoyl-2-arachidonoylglycerol-rich structured lipids by lipase-catalyzed acidolysis of microbial oil from Mortierella alpina. Biores. Technol. 243, 448-456. https://doi.org/10.1016/j.biortech.2017.06.090 PMid:28688328

AOCS. 1997. Official methods and recommended practices of the American Oil Chemists' Society. 5th. edition, 383 Champaign, USA.

AOCS. 2009. Official methods and recommended practices of the American Oil Chemists' Society. 6th. edition, Cj1-94 Champaign, USA.

Chen QQ, Pasdar H, Weng XC. 2020. Butylated methyl caffeate: a novel antioxidant. Grasas Aceites, 71, 352. https://doi.org/10.3989/gya.0226191

Esteban L, Jimenez M J, Hita E, Gonzalez PA, Martin L, Robles A. 2011. Production of structured triacylglycerols rich in palmitic acid at sn-2 position and oleic acid at sn-1,3 positions as human milk fat substitutes by enzymatic acidolysis. Biochem. Eng. J. 54, 62-69. https://doi.org/10.1016/j.bej.2011.01.009

Ghide MK, Yan Y. 2021. 1,3-Dioleoyl-2-palmitoyl glycerol (OPO)-Enzymatic synthesis and use as an important supplement in infant formulas. J. Food Biochem. 45 (2), 13799. https://doi.org/10.1111/jfbc.13799 PMid:34080206

Haddad I, Mozzon M, Frega NG. 2012. Trends in fatty acids positional distribution in human colostrum, transitional, and mature milk. Eur. Food. Res. Technol. 235, 325-332. https://doi.org/10.1007/s00217-012-1759-y

Hoffman DR, Boettcher JA, Diersen-Schade DA. 2009. Toward optimizing vision and cognition in term infants by dietary docosahexaenoic and arachidonic acid supplementation: a review of randomized controlled trials. Plefa Medline 81,151-158. https://doi.org/10.1016/j.plefa.2009.05.003 PMid:19505812

Hu M, Mcclements DJ, Decker EA. 2003. Lipid Oxidation in Corn Oil-in-Water Emulsions Stabilized by Casein, Whey Protein Isolate, and Soy Protein Isolate. J. Agric. Food Chem. 51, 1696-1700. https://doi.org/10.1021/jf020952j PMid:12617607

Jimenez MJ, Esteban L, Robles A, Hita E, Gonzalez PA, Munio MM, Molina E. 2010. Production of triacylglycerols rich in palmitic acid at position 2 as intermediates for the synthesis of human milk fat substitutes by enzymatic acidolysis. Process Biochem. 45, 407-414. https://doi.org/10.1016/j.procbio.2009.10.018

Lee JH, Chang HJ. 2021. Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties. Molecules 26 (13), 4015-4015. https://doi.org/10.3390/molecules26134015 PMid:34209258 PMCid:PMC8271560

Lee JH, Son JM, Akoh CC, Kim MR, Lee KT. 2010. Optimized synthesis of 1,3-dioleoyl-2-palmitoylglycerol-rich triacylglycerol via interesterification catalyzed by a lipase from thermomyces lanuginosus. New Biotechnol. 27, 38-45. https://doi.org/10.1016/j.nbt.2009.10.006 PMid:19879984

Li W, Du W, Li Q, Li RW, Liu DH. 2010. Dependence on the properties of organic solvent: study on acyl migration kinetics of partial glycerides. Bioresource Technol. 101, 5737-5742. https://doi.org/10.1016/j.biortech.2010.03.018 PMid:20307973

Liu CS, Tian JJ, Zhang RW, Xu JT, Nie K, Deng L, Wang F. 2020. Solvent-Free Alcoholysis of Tripalmitin to Produce 2-Monoglyceride as Precursor for 1, 3-Oleoyl-2-Palmitoyl-glycerol. Appl. Biochem. Biotechnol. 190, 867-879. https://doi.org/10.1007/s12010-019-03136-5 PMid:31506906

Nielsen NS, Yang TK, Xu XB, Jacobsen C. 2006. Production and oxidative stability of a human milk fat substitute produced from lard by enzyme technology in a pilot packed-bed reactor. Food. Chem. 94, 53-60. https://doi.org/10.1016/j.foodchem.2004.10.049

Olajide TM, Liu T, Liu HA, Weng XC. 2020. Antioxidant properties of two novel lipophilic derivatives of hydroxytyrosol. Food Chem. 315, 126-197. https://doi.org/10.1016/j.foodchem.2020.126197 PMid:32018079

Qin XL, Zhong JF, Wang YH, Yang B, Lan DM, Wang FH. 2014. 1,3-dioleoyl-2-palmitoylglycerol-rich human milk fat substitutes: production, purification, characterization and modeling of the formulation. Eur. J. Lipid Sci. Technol. 116, 282-290. https://doi.org/10.1002/ejlt.201300343

Sakai T, Kuwazuru S, Yamauchi, K, Uchida K. 1995. A lipid peroxidation-derived aldehyde, 4-hydroxy-2-nonenal and omega 6 fatty acids contents in meats. Biosci Biotech Bioch. 59, 1379-1380. https://doi.org/10.1271/bbb.59.1379 PMid:7670203

Sala-Vila A, Castellote AI, Rodriguez-Palmero M, Campoy C, Lopez-Sabater MC. 2005. Lipid composition in human breast milk from Granada (Spain): changes during lactation. Nutrition. 21, 467-473. https://doi.org/10.1016/j.nut.2004.08.020 PMid:15811767

Shi G, Liao X, Olajide TM, Liu J, Jiang X, Weng XC. 2017. Butylated caffeic acid: An efficient novel antioxidant. Grasas Aceites, 68, e201. https://doi.org/10.3989/gya.1278162

Srivastava A, Akoh CC, Chang SW, Lee GC, Shaw JF. 2006. Candida rugosa lipase lip1-catalyzed interesterification to produce human milk fat substitute. J. Agric. Food Chem. 54, 5175. https://doi.org/10.1021/jf060623h PMid:16819932

Victoria CG, Horta BL, de Mola CL, Quevedo L, Pinheiro RT, Gigante DP, Goncalves H, Barros FC. 2015. Association between breastfeeding and intelligence, educational attainment, and income at 30 years of age: a prospective birth cohort study from Brazil. Lancet. Glob. Health. 3, E199-E205. https://doi.org/10.1016/S2214-109X(15)70002-1 PMid:25794674

Wang X, Jiang C, Xu W, Miu Z. 2019. Enzymatic synthesis of structured triacylglycerols rich in 1,3-dioleoyl-2-palmitoylglycerol and 1-oleoyl-2-palmitoyl-3-linoleoylglycerol in a solvent-free system. Lwt-Food Sci. Technol. 118(C), 108798-108798. https://doi.org/10.1016/j.lwt.2019.108798

Wei W, Feng YF, Zhang X, Ca X, Feng FQ. 2015. Synthesis of structured lipid 1,3-dioleoyl-2-palmitoylglycerol in both solvent and solvent-free system. Lwt-Food Sci. Technol. 60, 1187-1194. https://doi.org/10.1016/j.lwt.2014.09.013

Xu X, Skands ARH, Hoy CE, Mu H, Balchen S, Adler-Nissen, J. 1998. Production of specific-structured lipids by enzymatic interesterification: elucidation of acyl migration by response surface design. J. Am. Oil. Chem. Soc. 75, 1179-1186. https://doi.org/10.1007/s11746-998-0309-z

Zou XQ, Guo Z, Huang JH, Jin QZ, Cheong LZ, Wang XG, Xu XB. 2012a. Human milk fat globules from different stages of lactation: a lipid composition analysis and microstructure characterization. J. Agric. Food Chem. 60, 7158-67. https://doi.org/10.1021/jf3013597 PMid:22747344

Zou XQ, Huang JH, Jin QZ, Liu YF, Tao GJ, Cheong LZ, Wang XG. 2012b. Preparation of human milk fat substitutes from palm stearin with arachidonic and docosahexaenoic acid: combination of enzymatic and physical methods. J. Agric. Food Chem. 60, 9415-9423. https://doi.org/10.1021/jf3017354 PMid:22920386