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Xingguo Wang - One of the best experts on this subject based on the ideXlab platform.
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preparation of Human Milk Fat substitutes similar to Human Milk Fat by enzymatic acidolysis and physical blending
Lwt - Food Science and Technology, 2021Co-Authors: Xiaosan Wang, Zhuoneng Huang, Lei Hua, Feng Zou, Xinyi Cheng, Xingguo WangAbstract:Abstract In this study, a Human Milk Fat substitute (HMFS) rich in 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) was prepared by physical blending. First, OPL was enzymatically synthesized by the acidolysis of fractionated palm stearin with oleic and linoleic acids. The reaction parameters were assessed until an optimum process was achieved. Under optimum conditions, contents of OPL and sn-2 palmitic acid in the synthesized OPL product were 47.93% and 87.90%, respectively. Subsequently, a physical blending model was established for the first time to prepare the HMFS similar to Human Milk Fat (HMF). The optimum ratio of soybean oil, rapeseed oil, coconut oil, basa catfish oil and OPL product was determined to be 11.06%:2.91%:14.41%:35.02%:36.59%. The similarity between HMFS and HMF was evaluated by “deducting score” principle and the overall score of the HMFS was 84.98. The prepared HMFS have higher similarity than commercial HMFS products and thus are potential to be used in infant formulas.
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biosynthesis of structured lipids enriched with medium and long chain triacylglycerols for Human Milk Fat substitute
Lwt - Food Science and Technology, 2020Co-Authors: Tinglan Yuan, Wei Wei, Xingguo Wang, Qingzhe JinAbstract:Abstract Human Milk Fat is rich in medium and long-chain triacylglycerol (MLCT), especially the triacylglycerol with one medium-chain Fatty acid and two long-chain Fatty acids (MLL type). To obtain Human Milk Fat substitutes having similarity in medium and long-chain triacylglycerol (MLCT) composition to Human Milk, structured lipids (SLs) enriched with medium-chain Fatty acid and high content of 16:0 at sn-2 position of glycerol backbone were synthesized from catfish oil and coconut oil through enzymatic interesterification. The different immobilized lipases and the reaction conditions (substrate ratio, temperature, enzyme load and reaction time) were investigated. Under the optimal conditions, the content of MLCT and MLL reached 62.14% and 39.85%, respectively. Moreover, the relative content of 16:0 at the sn-2 position was 46.14%, and the most abundant TAGs in the final SL were 12:0/16:0/18:1, 12:0/18:1/18:1, 12:0/14:0/18:1, 12:0/12:0/18:1. The novel SLs as Human Milk Fat substitutes enriched with MLCTs was produced and have potential application in infant formulas.
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Human Milk Fat substitutes past achievements and current trends
Progress in Lipid Research, 2019Co-Authors: Wei Wei, Qingzhe Jin, Xingguo WangAbstract:The first commercial infant formula, invented in 1867, contained lipids mainly from cow's Milk. We now know that Human Milk Fat differs from the Milk Fat of other mammals and even more from vegetable oils. Human Milk Fat is one of the most complex natural lipid mixtures with a unique Fatty acid composition, distribution, and numerous complex lipids. Therefore, to mimic Human Milk Fat, Human Milk Fat substitutes (HMFSs) have been produced through the enzymatic/chemical modification of natural lipids. Researchers have become increasingly interested in use of HMFSs as functional lipids due to their nutritional effects on the growth and development of formula-fed infants. This paper discusses the history and recent advances in HMFSs. A comprehensive summary of the composition of Human Milk Fat (Fatty acids, sn-2 Fatty acids, triacylglycerols, and complex lipids) and its structure (Human Milk Fat globules), as well as the changes during the lactation period. Nutritional bases, preparation methods, and applications of HMFSs (long-chain polyunsaturated Fatty acids, sn-2 palmitate, medium-chain triacylglycerols, and Milk Fat globule membrane supplements) have been reviewed. Legislation relating to the Fat fraction of infant formulae are also presented in this paper.
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Branched chain Fatty acids positional distribution in Human Milk Fat and common Human food Fats and uptake in Human intestinal cells
Journal of Functional Foods, 2017Co-Authors: Yuanyuan Yan, Xingguo Wang, Zhen Wang, Yue Wang, Jingying Xiang, Kumar S.d. Kothapalli, J. Thomas BrennaAbstract:Abstract Branched chain Fatty acids (BCFA) are components of common food Fats but little is known about their positional distribution on triacylglycerols (TAG). Human Milk Fat, mature Milk of cows and goats, and several fish oil products available in China were evaluated for BCFA content in the sn-2 position. Compared to the sn-1/sn-3 (α) positions, BCFA are enriched in sn-2 (β) position of Human Milk (68% of BCFA), but randomly distributed among the sn-2 and sn-1/sn-3 positions of cow and goat Milk. Fish oil TAG sn-2 BCFA were consistently depleted compared to the sn-1/sn-3 positions (5.2–11.9% of BCFA). Human intestinal epithelial cells were incubated with Human Milk sn-2 MAG, or Fatty acids liberated from Human Milk sn-2 MAG. Cells incorporated more BCFA as sn-2 MAG than as FFA. The stereochemical positioning of BCFA in Human Milk Fat may be unique compared to other BCFA sources, and mediate selective absorption of BCFA.
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preparation of Human Milk Fat substitutes from basa catfish oil combination of enzymatic acidolysis and modeled blending
European Journal of Lipid Science and Technology, 2016Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Zheng Guo, Xingguo WangAbstract:Human Milk Fat substitutes (HMFSs) were prepared from basa catfish oil by combination of Lipozyme RM IM‐catalyzed acidolysis and physical blending. In acidolysis step, sesame oil Fatty acids were used as acyl donors to replace palmitic acid (PA) at sn‐1, 3 positions of basa catfish oil, and the enzymatic product had 23.8% PA, 48.3% PA at sn‐2 position (sn‐2 PA), and 67.7% distribution probability of sn‐2 PA among total PA (%sn‐2 PA) under the selected conditions: Enzyme load, 8 wt%; temperature, 40°C; substrate molar ratio, 1:3; water content, 3.5 wt%; and reaction time, 2 h. In blending step, with Fatty acid profiles of Human Milk Fat (HMF) as a preferable goal, selected oils were added to the enzymatic product, and the desirable formula predicted by the blending model which guaranteed the maximum addition constituted enzymatic product/flaxseed oil/sunflower oil/palm kernel oil/palm stearin/algal oil/microbial oil at a mole ratio of 1: 0.1319: 0.0353: 0.1775: 0.0674: 0.0078: 0.0128. The blending product had 21.5% PA, 39.0% sn‐2 PA, and 60.4% %sn‐2 PA, respectively. The similarity of the product to HMF was assessed by the evaluation model, and the achievement of high scores indicated it has potential for use as Fat substitute in infant formulas. Practical applications: Basa catfish oil was found to contain around 30% total PA with more than 45% sn‐2 PA, which is a new alternative starting material suitable for HMFS production. Basa catfish is widely cultured in southern Vietnam in floating cages with annual production of 15 000 tonnes. Preparation of HMFSs from basa catfish oil is thus important for the development of HMFSs. This process reported preparation of HMFSs by combination of enzymatic acidolysis and modeled blending, with the attributes of lower cost and higher similarity, has great potential for industrial uses. Human Milk Fat substitutes (HMFSs) were prepared from basa catfish oil by combination of Lipozyme RM IM‐catalyzed acidolysis and physical blending. In the acidolysis step, free Fatty acids from sesame oil were used as acyl donors to replace palmitic acid (PA) at sn‐1, 3 positions of basa catfish oil. In the blending step, with the Fatty acid profiles of Human Milk Fat (HMF) as a preferable goal, selected oils were added to the enzymatic product and the desirable formula was predicted by the physical blending model which could guarantee the maximum addition. The final product had 21.5% of total PA, 39.0% of PA at sn‐2 position,and the relative content of PA at the sn‐2 position was 60.4%. High scores for the similarity of the product to HMF were obtained, which was evaluated by the established model, indicating the great potential of the product as a Fat substitute for infant formulas.
Casimir C. Akoh - One of the best experts on this subject based on the ideXlab platform.
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Production of Human Milk Fat analogue containing docosahexaenoic and arachidonic acids.
Journal of agricultural and food chemistry, 2012Co-Authors: Dilek Turan, Neşe Şahin Yeşilçubuk, Casimir C. AkohAbstract:Human Milk Fat (HMF) analogue containing docosahexaenoic acid (DHA) and arachidonic acid (ARA) at sn-1,3 positions and palmitic acid (PA) at sn-2 position was produced. Novozym 435 lipase was used to produce palmitic acid-enriched hazelnut oil (EHO). EHO was then used to produce the final structured lipid (SL) through interesterification reactions using Lipozyme RM IM. Reaction variables for 3 h reactions were temperature, substrate mole ratio, and ARASCO/DHASCO (A:D) ratio. After statistical analysis of DHA, ARA, total PA, and PA content at sn-2 position, a large-scale production was performed at 60 °C, 3:2 A:D ratio, and 1:0.1 substrate mole ratio. For the SL, those results were determined as 57.3 ± 0.4%, 2.7 ± 0.0%, 2.4 ± 0.1%, and 66.1 ± 2.2%, respectively. Tocopherol contents were 84, 19, 85, and 23 μg/g oil for α-, β-, γ-, and δ-tocopherol. Melting range of SL was narrower than that of EHO. Oxidative stability index (OSI) value of SL (0.80 h) was similar to that of EHO (0.88 h). This SL can be used ...
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candida rugosa lipase lip1 catalyzed transesterification to produce Human Milk Fat substitute
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Anita Srivastava, Casimir C. Akoh, Shuwei Chang, Guan Chiun Lee, Jeifu ShawAbstract:Structured lipids (SLs) containing palmitic and oleic acids were synthesized by transesterification of tripalmitin with either oleic acid or methyl oleate as acyl donor. This SL with palmitic acid at the sn-2 position and oleic acid at sn-1,3 positions is similar in structure to Human Milk Fat triacylglycerol. LIP1, an isoform of Candida rugosa lipase (CRL), was used as biocatalyst. The effects of reaction temperature, substrate molar ratio, and time on incorporation of oleic acid were investigated. Reaction time and temperature were set at 6, 12, and 24 h, and 35, 45, and 55 degrees C, respectively. Substrate molar ratio was varied from 1:1 to 1:4. The highest incorporation of oleic acid (37.7%) was at 45 degrees C with methyl oleate as acyl donor. Oleic acid resulted in slightly lesser (26.3%) incorporation. Generally, higher percentage incorporation of oleic acid was observed with methyl oleate (transesterification) than with oleic acid (acidolysis). In both cases percentage incorporation increased with reaction time. Incorporation decreased with increase in temperature above 45 degrees C. Initially, oleic acid incorporation increased with increase in substrate molar ratio up to 1:3. LIP1 was also compared with Lipozyme RM IM as biocatalysts. The tested reaction parameters were selected on the basis of maximum incorporation of C18:1 obtained during optimization of LIP1 reaction conditions. Reaction temperature was maintained at 45, 55, and 65 degrees C. Lipozyme RM IM gave highest oleic acid incorporation (49.4%) at 65 degrees C with methyl oleate as acyl donor. Statistically significant (P < 0.05) differences were observed for both enzymes. SL prepared using Lipozyme RM IM may be more suitable for possible use in Human Milk Fat substitutes.
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candida rugosa lipase lip1 catalyzed transesterification to produce Human Milk Fat substitute
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Anita Srivastava, Casimir C. Akoh, Shuwei Chang, Guan Chiun Lee, Jeifu ShawAbstract:Structured lipids (SLs) containing palmitic and oleic acids were synthesized by transesterification of tripalmitin with either oleic acid or methyl oleate as acyl donor. This SL with palmitic acid at the sn-2 position and oleic acid at sn-1,3 positions is similar in structure to Human Milk Fat triacylglycerol. LIP1, an isoform of Candida rugosa lipase (CRL), was used as biocatalyst. The effects of reaction temperature, substrate molar ratio, and time on incorporation of oleic acid were investigated. Reaction time and temperature were set at 6, 12, and 24 h, and 35, 45, and 55 °C, respectively. Substrate molar ratio was varied from 1:1 to 1:4. The highest incorporation of oleic acid (37.7%) was at 45 °C with methyl oleate as acyl donor. Oleic acid resulted in slightly lesser (26.3%) incorporation. Generally, higher percentage incorporation of oleic acid was observed with methyl oleate (transesterification) than with oleic acid (acidolysis). In both cases percentage incorporation increased with reaction tim...
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Human Milk Fat substitutes containing omega 3 Fatty acids
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nese Sahin, Casimir C. Akoh, Artemis KaraaliAbstract:Structured lipids resembling Human Milk Fat (HMF) enriched with omega-3 Fatty acids were synthesized by enzymatic acidolysis reactions between tripalmitin, hazelnut oil Fatty acids (FA), and omega-3 FA concentrate. Response surface methodology was used to model and optimize the incorporation of omega-3 FA and oleic acid into tripalmitin, in hexane, using immobilized sn-1,3-specific lipase, Lipozyme RM IM. The three factors chosen were substrate molar ratio, reaction temperature, and reaction time. Good quadratic models were obtained for the incorporation of eicosapentaenoic acid (EPA) plus docosahexaenoic acid (DHA) (response 1) and oleic acid (response 2) by multiple regression and backward elimination. The determination coefficient (R2) value for the models was 0.95. The adjusted R2 values were 0.91 and 0.92 for responses 1 and 2, respectively. The optimal conditions generated from the models for the targeted total EPA and DHA (5%) and oleic acid (40%) incorporation were 12.4 mol/mol, 55 degrees C, and 24 h for substrate ratio, temperature, and time, respectively. The model was verified, which led to the production of a HMF ingredient with 76.6% palmitic acid at the sn-2 position.
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enzymatic production of Human Milk Fat substitutes containing γ linolenic acid optimization of reactions by response surface methodology
Journal of the American Oil Chemists' Society, 2005Co-Authors: Casimir C. Akoh, Nese Sahin, Artemis KaraaliAbstract:Structured lipids resembling Human Milk Fat and containing GLA were synthesized by an enzymatic interesterification between tripalmitin, hazelnut oil FA, and GLA in n-hexane. Commercially immobilized 1,3-specific lipases, lipozyme® RM IM and Lipozyme® TL IM, were used as the biocatalysts. The effect of these enzymes on the incorporation levels was investigated. A central composite design with five levels and three factors—substrate ratio, reaction temperature, and time—were used to model and optimize the reaction conditions via response surface methodology. Good quadratic models were obtained for the incorporation of GLA (response 1) and oleic acid (response 2) by multiple regression and backward elimination. The determination coefficient (R 2) values for the models were found to be 0.92 and 0.94 for the reactions catalyzed by Lipozyme RM IM, and 0.92 and 0.88 for the reactions catalyzed by Lipozyme TL IM, respecitively. The optimal conditions generated from the models for the targeted GLA (10%) and oleic acid (45%) incorporation were 14.8 mol/mol, 55°C, and 24 h; 14 mol/mol, 55°C, and 24 h for substrate ratio (moles total FA/mol tripalmitin), temperature and time for the reactions catalyzed by Lipozyme RM IM and Lipozyme TL IM, respectively. Human Milk Fat substitutes containing GLA that can be included in infant formulas were success-fully produced using both Lipozyme RM IM and Lipozyme TL IM enzymes. The effect of the two enzymes on the incorporation of GLA and oleic acid were found to be similar.
Xiaoqiang Zou - One of the best experts on this subject based on the ideXlab platform.
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preparation of Human Milk Fat substitutes from basa catfish oil combination of enzymatic acidolysis and modeled blending
European Journal of Lipid Science and Technology, 2016Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Zheng Guo, Xingguo WangAbstract:Human Milk Fat substitutes (HMFSs) were prepared from basa catfish oil by combination of Lipozyme RM IM‐catalyzed acidolysis and physical blending. In acidolysis step, sesame oil Fatty acids were used as acyl donors to replace palmitic acid (PA) at sn‐1, 3 positions of basa catfish oil, and the enzymatic product had 23.8% PA, 48.3% PA at sn‐2 position (sn‐2 PA), and 67.7% distribution probability of sn‐2 PA among total PA (%sn‐2 PA) under the selected conditions: Enzyme load, 8 wt%; temperature, 40°C; substrate molar ratio, 1:3; water content, 3.5 wt%; and reaction time, 2 h. In blending step, with Fatty acid profiles of Human Milk Fat (HMF) as a preferable goal, selected oils were added to the enzymatic product, and the desirable formula predicted by the blending model which guaranteed the maximum addition constituted enzymatic product/flaxseed oil/sunflower oil/palm kernel oil/palm stearin/algal oil/microbial oil at a mole ratio of 1: 0.1319: 0.0353: 0.1775: 0.0674: 0.0078: 0.0128. The blending product had 21.5% PA, 39.0% sn‐2 PA, and 60.4% %sn‐2 PA, respectively. The similarity of the product to HMF was assessed by the evaluation model, and the achievement of high scores indicated it has potential for use as Fat substitute in infant formulas. Practical applications: Basa catfish oil was found to contain around 30% total PA with more than 45% sn‐2 PA, which is a new alternative starting material suitable for HMFS production. Basa catfish is widely cultured in southern Vietnam in floating cages with annual production of 15 000 tonnes. Preparation of HMFSs from basa catfish oil is thus important for the development of HMFSs. This process reported preparation of HMFSs by combination of enzymatic acidolysis and modeled blending, with the attributes of lower cost and higher similarity, has great potential for industrial uses. Human Milk Fat substitutes (HMFSs) were prepared from basa catfish oil by combination of Lipozyme RM IM‐catalyzed acidolysis and physical blending. In the acidolysis step, free Fatty acids from sesame oil were used as acyl donors to replace palmitic acid (PA) at sn‐1, 3 positions of basa catfish oil. In the blending step, with the Fatty acid profiles of Human Milk Fat (HMF) as a preferable goal, selected oils were added to the enzymatic product and the desirable formula was predicted by the physical blending model which could guarantee the maximum addition. The final product had 21.5% of total PA, 39.0% of PA at sn‐2 position,and the relative content of PA at the sn‐2 position was 60.4%. High scores for the similarity of the product to HMF were obtained, which was evaluated by the established model, indicating the great potential of the product as a Fat substitute for infant formulas.
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preparation and characterization of Human Milk Fat substitutes based on triacylglycerol profiles
Journal of the American Oil Chemists' Society, 2016Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Zheng Guo, Xingguo WangAbstract:Human Milk Fat substitutes (HMFS) having similarity in (TAG) composition to Human Milk Fat (HMF) were prepared by Lipozyme RM IM-catalyzed interesterification of lard blending with selected oils in a packed bed reactor. Four oil blends with high similarity in Fatty acid profiles to HMF were first obtained based on the blending model and then the blending ratios were screened based on TAG composition similarity by enzymatic interesterification in a batch reactor. The optimal ratio was determined as lard:sunflower oil:canola oil:palm kernel oil:palm oil:algal oil:microbial oil = 1.00:0.10:0.50:0.13:0.12:0.02:0.02. This blending ratio was used for a packed bed reactor and the conditions were then optimized as residence time, 1.5 h; reaction temperature, 50 °C. Under these conditions, the obtained product showed high degrees of similarity in Fatty acid profile with 39.2 % palmitic acid at the sn-2 position, 0.5 % arachidonic acid (n-6) and 0.3 % docosahexaenoic acid (n-3) and the scores for the degree of similarity in TAG composition was increased from 58.4 (the oil blend) to 72.3 (the final product). The packed bed reactor could be operated for 7 days without significant decrease in activity. The final product presented similar melting and crystallization profiles to those of HMF. However, due to the loss of tocopherols during deacidification process, the oxidative stability was lower than that of the oil blend. This process for the preparation of HMFS from lard with high similarity in TAG composition by physical blending and enzymatic interesterification, as optimized by mathematical models in a packed bed reactor, has a great potential for industrialization.
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preparation of Human Milk Fat substitutes from lard by lipase catalyzed interesterification based on triacylglycerol profiles
Journal of the American Oil Chemists' Society, 2014Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Jianhua Huang, Zheng Guo, Lingzhi Cheong, Xingguo WangAbstract:Human Milk Fat substitutes (HMFSs) with triacylglycerol profiles highly similar to those of Human Milk Fat (HMF) were prepared from lard by physical blending followed by enzymatic interesterification. Based on the Fatty acid profiles of HMF, different vegetable and single-cell oils were selected and added to the lard. Blend ratios were calculated based on established physical blending models. The blended oils were then enzymatically interesterified using a 1,3-regiospecific lipase, Lipozyme RM IM (RML from Rhizomucor miehei immobilized on Duolite ES562; Novozymes A/S, Bagsvaerd, Denmark), to approximate HMF triacylglycerol (TAG) profiles, particularly with respect to the distribution of palmitic acid in the sn−2 position. The optimized blending ratios were determined to be: lard:sunflower oil:canola oil:palm kernel oil:palm oil:algal oil:microbial oil = 1.00:0.10:0.50:0.13:0.12:0.02:0.02. The optimized reaction conditions were determined to be: enzyme load of 11 wt%, temperature of 60 °C, water content of 3.5 wt%, and reaction time of 3 hours. The resulting product was evaluated for total and sn−2 Fatty acids, polyunsaturated Fatty acids, and TAG composition. A high degree of similarity was obtained, indicating the great potential of the product as a Fat alternative for use in infant formulas.
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characterization and oxidative stability of Human Milk Fat substitutes enzymatically produced from palm stearin
Journal of the American Oil Chemists' Society, 2014Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Jianhua Huang, Zheng Guo, Yuanfa Liu, Lingzhi Cheong, Xingguo WangAbstract:Production of Human Milk Fat substitutes (HMFSs) from three types of palm stearin with palmitic acid (PA) of 91.3, 70.3 and 62.6 %, respectively, was scaled up to a kilogram scale. The physiochemical properties of these products including Fatty acid profiles, triacylglycerol compositions, tocopherol contents, oxidative stability and melting and crystallization profiles were compared with those of HMFSs from lard, butterFat and tripalmitin and Fats from infant formulas. Based on their chemical compositions, HMFSs from palm stearin with PA contents of 70.3 and 62.6 % produced by enzymatic acidolysis were found to have the highest degree of similarity to Human Milk Fat, which indicated that these HMFSs were the most suitable for use in infant formulas. However, HMFSs from palm stearin with PA content of 91.3 % had the highest tocopherol contents. By investigation of the primary and secondary oxidation products during accelerated oxidation, the oxidative stability of HMFSs was found to be positively correlated to the contents of tocopherols, and the volatile oxidation compounds with the highest relative contents in HMFSs were aldehydes analyzed by solid-phase microextraction-GC–MS. All HMFSs had final melting points lower than body temperature.
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lipid composition analysis of Milk Fats from different mammalian species potential for use as Human Milk Fat substitutes
Journal of Agricultural and Food Chemistry, 2013Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Jianhua Huang, Zheng Guo, Yuanfa Liu, Lingzhi Cheong, Xingguo WangAbstract:The lipid compositions of commercial Milks from cow, buffalo, donkey, sheep, and camel were compared with that of Human Milk Fat (HMF) based on total and sn-2 Fatty acid, triacylglycerol (TAG), phospholipid, and phospholipid Fatty acid compositions and melting and crystallization profiles, and their degrees of similarity were digitized and differentiated by an evaluation model. The results showed that these Milk Fats had high degrees of similarity to HMF in total Fatty acid composition. However, the degrees of similarity in other chemical aspects were low, indicating that these Milk Fats did not meet the requirements of Human Milk Fat substitutes (HMFSs). However, an economically feasible solution to make these Milks useful as raw materials for infant formula production could be to modify these Fats, and a possible method is blending of polyunsaturated Fatty acids (PUFA) and 1,3-dioleoyl-2-palmitoylglycerol (OPO) enriched Fats and minor lipids based on the corresponding chemical compositions of HMF.
Qingzhe Jin - One of the best experts on this subject based on the ideXlab platform.
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biosynthesis of structured lipids enriched with medium and long chain triacylglycerols for Human Milk Fat substitute
Lwt - Food Science and Technology, 2020Co-Authors: Tinglan Yuan, Wei Wei, Xingguo Wang, Qingzhe JinAbstract:Abstract Human Milk Fat is rich in medium and long-chain triacylglycerol (MLCT), especially the triacylglycerol with one medium-chain Fatty acid and two long-chain Fatty acids (MLL type). To obtain Human Milk Fat substitutes having similarity in medium and long-chain triacylglycerol (MLCT) composition to Human Milk, structured lipids (SLs) enriched with medium-chain Fatty acid and high content of 16:0 at sn-2 position of glycerol backbone were synthesized from catfish oil and coconut oil through enzymatic interesterification. The different immobilized lipases and the reaction conditions (substrate ratio, temperature, enzyme load and reaction time) were investigated. Under the optimal conditions, the content of MLCT and MLL reached 62.14% and 39.85%, respectively. Moreover, the relative content of 16:0 at the sn-2 position was 46.14%, and the most abundant TAGs in the final SL were 12:0/16:0/18:1, 12:0/18:1/18:1, 12:0/14:0/18:1, 12:0/12:0/18:1. The novel SLs as Human Milk Fat substitutes enriched with MLCTs was produced and have potential application in infant formulas.
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Human Milk Fat substitutes past achievements and current trends
Progress in Lipid Research, 2019Co-Authors: Wei Wei, Qingzhe Jin, Xingguo WangAbstract:The first commercial infant formula, invented in 1867, contained lipids mainly from cow's Milk. We now know that Human Milk Fat differs from the Milk Fat of other mammals and even more from vegetable oils. Human Milk Fat is one of the most complex natural lipid mixtures with a unique Fatty acid composition, distribution, and numerous complex lipids. Therefore, to mimic Human Milk Fat, Human Milk Fat substitutes (HMFSs) have been produced through the enzymatic/chemical modification of natural lipids. Researchers have become increasingly interested in use of HMFSs as functional lipids due to their nutritional effects on the growth and development of formula-fed infants. This paper discusses the history and recent advances in HMFSs. A comprehensive summary of the composition of Human Milk Fat (Fatty acids, sn-2 Fatty acids, triacylglycerols, and complex lipids) and its structure (Human Milk Fat globules), as well as the changes during the lactation period. Nutritional bases, preparation methods, and applications of HMFSs (long-chain polyunsaturated Fatty acids, sn-2 palmitate, medium-chain triacylglycerols, and Milk Fat globule membrane supplements) have been reviewed. Legislation relating to the Fat fraction of infant formulae are also presented in this paper.
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preparation of Human Milk Fat substitutes from basa catfish oil combination of enzymatic acidolysis and modeled blending
European Journal of Lipid Science and Technology, 2016Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Zheng Guo, Xingguo WangAbstract:Human Milk Fat substitutes (HMFSs) were prepared from basa catfish oil by combination of Lipozyme RM IM‐catalyzed acidolysis and physical blending. In acidolysis step, sesame oil Fatty acids were used as acyl donors to replace palmitic acid (PA) at sn‐1, 3 positions of basa catfish oil, and the enzymatic product had 23.8% PA, 48.3% PA at sn‐2 position (sn‐2 PA), and 67.7% distribution probability of sn‐2 PA among total PA (%sn‐2 PA) under the selected conditions: Enzyme load, 8 wt%; temperature, 40°C; substrate molar ratio, 1:3; water content, 3.5 wt%; and reaction time, 2 h. In blending step, with Fatty acid profiles of Human Milk Fat (HMF) as a preferable goal, selected oils were added to the enzymatic product, and the desirable formula predicted by the blending model which guaranteed the maximum addition constituted enzymatic product/flaxseed oil/sunflower oil/palm kernel oil/palm stearin/algal oil/microbial oil at a mole ratio of 1: 0.1319: 0.0353: 0.1775: 0.0674: 0.0078: 0.0128. The blending product had 21.5% PA, 39.0% sn‐2 PA, and 60.4% %sn‐2 PA, respectively. The similarity of the product to HMF was assessed by the evaluation model, and the achievement of high scores indicated it has potential for use as Fat substitute in infant formulas. Practical applications: Basa catfish oil was found to contain around 30% total PA with more than 45% sn‐2 PA, which is a new alternative starting material suitable for HMFS production. Basa catfish is widely cultured in southern Vietnam in floating cages with annual production of 15 000 tonnes. Preparation of HMFSs from basa catfish oil is thus important for the development of HMFSs. This process reported preparation of HMFSs by combination of enzymatic acidolysis and modeled blending, with the attributes of lower cost and higher similarity, has great potential for industrial uses. Human Milk Fat substitutes (HMFSs) were prepared from basa catfish oil by combination of Lipozyme RM IM‐catalyzed acidolysis and physical blending. In the acidolysis step, free Fatty acids from sesame oil were used as acyl donors to replace palmitic acid (PA) at sn‐1, 3 positions of basa catfish oil. In the blending step, with the Fatty acid profiles of Human Milk Fat (HMF) as a preferable goal, selected oils were added to the enzymatic product and the desirable formula was predicted by the physical blending model which could guarantee the maximum addition. The final product had 21.5% of total PA, 39.0% of PA at sn‐2 position,and the relative content of PA at the sn‐2 position was 60.4%. High scores for the similarity of the product to HMF were obtained, which was evaluated by the established model, indicating the great potential of the product as a Fat substitute for infant formulas.
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preparation and characterization of Human Milk Fat substitutes based on triacylglycerol profiles
Journal of the American Oil Chemists' Society, 2016Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Zheng Guo, Xingguo WangAbstract:Human Milk Fat substitutes (HMFS) having similarity in (TAG) composition to Human Milk Fat (HMF) were prepared by Lipozyme RM IM-catalyzed interesterification of lard blending with selected oils in a packed bed reactor. Four oil blends with high similarity in Fatty acid profiles to HMF were first obtained based on the blending model and then the blending ratios were screened based on TAG composition similarity by enzymatic interesterification in a batch reactor. The optimal ratio was determined as lard:sunflower oil:canola oil:palm kernel oil:palm oil:algal oil:microbial oil = 1.00:0.10:0.50:0.13:0.12:0.02:0.02. This blending ratio was used for a packed bed reactor and the conditions were then optimized as residence time, 1.5 h; reaction temperature, 50 °C. Under these conditions, the obtained product showed high degrees of similarity in Fatty acid profile with 39.2 % palmitic acid at the sn-2 position, 0.5 % arachidonic acid (n-6) and 0.3 % docosahexaenoic acid (n-3) and the scores for the degree of similarity in TAG composition was increased from 58.4 (the oil blend) to 72.3 (the final product). The packed bed reactor could be operated for 7 days without significant decrease in activity. The final product presented similar melting and crystallization profiles to those of HMF. However, due to the loss of tocopherols during deacidification process, the oxidative stability was lower than that of the oil blend. This process for the preparation of HMFS from lard with high similarity in TAG composition by physical blending and enzymatic interesterification, as optimized by mathematical models in a packed bed reactor, has a great potential for industrialization.
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preparation of Human Milk Fat substitutes from lard by lipase catalyzed interesterification based on triacylglycerol profiles
Journal of the American Oil Chemists' Society, 2014Co-Authors: Xiaoqiang Zou, Qingzhe Jin, Jianhua Huang, Zheng Guo, Lingzhi Cheong, Xingguo WangAbstract:Human Milk Fat substitutes (HMFSs) with triacylglycerol profiles highly similar to those of Human Milk Fat (HMF) were prepared from lard by physical blending followed by enzymatic interesterification. Based on the Fatty acid profiles of HMF, different vegetable and single-cell oils were selected and added to the lard. Blend ratios were calculated based on established physical blending models. The blended oils were then enzymatically interesterified using a 1,3-regiospecific lipase, Lipozyme RM IM (RML from Rhizomucor miehei immobilized on Duolite ES562; Novozymes A/S, Bagsvaerd, Denmark), to approximate HMF triacylglycerol (TAG) profiles, particularly with respect to the distribution of palmitic acid in the sn−2 position. The optimized blending ratios were determined to be: lard:sunflower oil:canola oil:palm kernel oil:palm oil:algal oil:microbial oil = 1.00:0.10:0.50:0.13:0.12:0.02:0.02. The optimized reaction conditions were determined to be: enzyme load of 11 wt%, temperature of 60 °C, water content of 3.5 wt%, and reaction time of 3 hours. The resulting product was evaluated for total and sn−2 Fatty acids, polyunsaturated Fatty acids, and TAG composition. A high degree of similarity was obtained, indicating the great potential of the product as a Fat alternative for use in infant formulas.
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Lipase-catalyzed production of Human Milk Fat Substitutes (HMFS) containing gamma-linolenic acid
İTÜDERGİSİ d, 2011Co-Authors: Neşe Şahin Yeşilçubuk, Artemis KaraaliAbstract:Anne sütü yağına benzer yapılandırılmış yağların (YY) bitkisel kaynaklı yağlardan spesifik lipaz enzimlerinin katalizlediği interesterifikasyon (asidoliz) tepkimeleri ile üretilmeleri mümkün olmaktadır. Bu çalışmada gamma-linolenik asit (GLA) ile zenginleştirilmiş anne sütü yağına benzer YY’ların tripalmitin, fındık yağı serbest yağ asitleri (SYA) ve hodan (boraj) yağından elde edilen GLA konsantresi arasında gerçekleştirilen enzimatik asidoliz tepkimeleri ile üretilmesi ve tepki-yüzey yöntemi (TYY) ile reaksiyon koşullarının optimizasyonu amaçlanmıştır. Enzimatik asidoliz tepkimelerinde Rhizomucor miehei’den elde edilen ve bir sn-1,3 spesifik lipaz enzimi olan Lipozyme® RM IM kullanılmıştır. Tepki-yüzey yönteminde seçilmiş farklı faktörlerin etkilerinin incelenmesi ve optimum koşulların belirlenmesi amacıyla, 5 seviyeli Merkezil Bileşik Deney Tasarımı (CCD) kullanılmış ve "substrat mol oranı (Toplam yağ asitleri/Triaçilgliserol, Sr)", "reaksiyon sıcaklığı (T, ºC)" ve "reaksiyon süresi (t, saat)" değişken faktörler olarak seçilmiştir. Reaksiyonlar sonucunda seçilen tepkiler [oleik asit miktarı (%) ve GLA miktarı (%)] için, “çoklu regresyon” ve “geriye dönük eleme” yöntemleri uygulanarak başarılı kuadratik modeller elde edilmiştir. Hedeflenen özellikte ürün (%10 oranında GLA, %45 oranında oleik asit içeren) elde etmek için gerekli optimum koşullar [Sr: 14.8 mol/mol, T: 55ºC ve t: 24 saat] olarak bulunmuştur. Bu koşullarda modelin doğruluğu deneysel olarak da kontrol edilmiş ve çalışma sonucunda bebek beslenmesi ve sağlığı açısından önemli etkileri olan GLA ile zenginleştirilmiş ve anne sütü yağı ile benzer absorpsiyon özelliklerine ve yağ asidi kompozisyonuna sahip bir YY’ın üretimi mümkün olmuştur. Anahtar Kelimeler: Yapılandırılmış yağ, anne sütü yağı, gamma-linolenik asit, enzimatik asidoliz, tepki yüzey yöntemi.Breast Milk is the main and most preferred source of nutrients for infants and Human Milk Fat (HMF) is its component which supplies the highest fraction of the infant's required dietary energy. Human Milks are characterized by the dominance of triacylglycerols (TAG) (more than 98% of HMF) where the saturated 16-carbon palmitic acid (C16:0) (20-30%) is in the sn-2 position (60-70%) of the glycerol backbone, the sn-1 and sn-3 positions are being taken by unsaturated Fatty acids (FA). This unique structure is different from most vegetable oils and animal Fats. Previous reports provided convincing information that the higher Fatty acid (FA) and calcium absorption and efficient use of dietary energy was the result of this specific position of these Fatty acids in triacylglycerol (TAG) moiety. Structured lipids (SL) resembling TAGs of Human Milk Fat can be produced by interesterification from vegetable oils, using sn-1,3 specific lipases as biocatalyst and such TAG can be used in infant food formulations. There has also been a great interest for the supplementation of infant formulas with FA such as gamma-linolenic acid (GLA). In infant formulae, GLA-containing oil, especially borage oil is used for its health benefits and for its antagonist action on arachidonic acid (AA) metabolism. Since GLA is rapidly elongated to di-homo gamma-linolenic acid (DGLA) and subsequently ?5-desaturated to AA and is also cheaper and easier to produce than AA, an alternative way for supplementation of infant formulas with AA is to use GLA instead of highly active AA. Human Milk Fat substitutes (HMFS) containing GLA can be produced by enzymatic interesterification reactions. These formulae are also helpful where ?6-desaturase enzyme is insufficient. The purpose of the present work was to synthesize SLs resembling HMF enriched with GLA by enzymatic acidolysis reactions between tripalmitin, hazelnut oil FA and GLA in n-hexane. Commercially immobilized 1,3 specific lipase, Lipozyme® RM IM, obtained from Rhizomucor miehei, was used as the biocatalyst for the acidolysis reactions. Moreover it was aimed to model and optimize the reaction conditions via response surface methodology (RSM). For this purpose central composite design (CCD) with five levels and three factors; substrate molar ratio (Total FA/TAG, Sr)", "reaction temperature (T, ºC)" and "reaction time (t, hour)" were used. The reactions were optimized considering target GLA and oleic acid incorporation. Good quadratic models were obtained for the incorporation of GLA (response 1) and oleic acid (response 2) by "multiple regression" and "backward elimination". The determination coefficient (R2) values for the models were found to be 0.92 and 0.94. Based on the experimental results, the regression coefficients and significance (P) values were calculated. Among first order parameters substrate molar ratio had negative effect on the oleic acid incorporation. Time was the most significant first order parameter followed by temperature and substrate molar ratio for GLA incorporation. For both responses, second order parameters, temperature*temperature and time*time had negative effects and were found to be significant. The predicted values obtained from the models had a linear relationship with the observed values which indicates that the generated models adequately represent the relationship between the response and reaction parameters. The optimal conditions generated from the models for the targeted GLA (10%) and oleic acid (45%) incorporation were: 14.8 mol/mol, 55°C and 24 h for substrate molar ratio, reaction temperature and reaction time, respectively. Models were verified using the optimal conditions obtained with RSM. The SL resembling HMFS contained palmitic acid at 73.9 %, which is also close to that of HMF. In this study, a HMFS product containing GLA was successfully produced having both the associated health benefits of GLA and similar Fatty acid composition as well as similar absorption characteristics with Human Milk Fat. This SL may be an important ingredient for commercial use in infant formula and contribute to the infant's nutrition and development. Keywords: Structured lipids, Human Milk Fat, gamma-linolenic acid, enzymatic acidolyis, response surface methodology
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Human Milk Fat substitutes containing omega 3 Fatty acids
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nese Sahin, Casimir C. Akoh, Artemis KaraaliAbstract:Structured lipids resembling Human Milk Fat (HMF) enriched with omega-3 Fatty acids were synthesized by enzymatic acidolysis reactions between tripalmitin, hazelnut oil Fatty acids (FA), and omega-3 FA concentrate. Response surface methodology was used to model and optimize the incorporation of omega-3 FA and oleic acid into tripalmitin, in hexane, using immobilized sn-1,3-specific lipase, Lipozyme RM IM. The three factors chosen were substrate molar ratio, reaction temperature, and reaction time. Good quadratic models were obtained for the incorporation of eicosapentaenoic acid (EPA) plus docosahexaenoic acid (DHA) (response 1) and oleic acid (response 2) by multiple regression and backward elimination. The determination coefficient (R2) value for the models was 0.95. The adjusted R2 values were 0.91 and 0.92 for responses 1 and 2, respectively. The optimal conditions generated from the models for the targeted total EPA and DHA (5%) and oleic acid (40%) incorporation were 12.4 mol/mol, 55 degrees C, and 24 h for substrate ratio, temperature, and time, respectively. The model was verified, which led to the production of a HMF ingredient with 76.6% palmitic acid at the sn-2 position.
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enzymatic production of Human Milk Fat substitutes containing γ linolenic acid optimization of reactions by response surface methodology
Journal of the American Oil Chemists' Society, 2005Co-Authors: Casimir C. Akoh, Nese Sahin, Artemis KaraaliAbstract:Structured lipids resembling Human Milk Fat and containing GLA were synthesized by an enzymatic interesterification between tripalmitin, hazelnut oil FA, and GLA in n-hexane. Commercially immobilized 1,3-specific lipases, lipozyme® RM IM and Lipozyme® TL IM, were used as the biocatalysts. The effect of these enzymes on the incorporation levels was investigated. A central composite design with five levels and three factors—substrate ratio, reaction temperature, and time—were used to model and optimize the reaction conditions via response surface methodology. Good quadratic models were obtained for the incorporation of GLA (response 1) and oleic acid (response 2) by multiple regression and backward elimination. The determination coefficient (R 2) values for the models were found to be 0.92 and 0.94 for the reactions catalyzed by Lipozyme RM IM, and 0.92 and 0.88 for the reactions catalyzed by Lipozyme TL IM, respecitively. The optimal conditions generated from the models for the targeted GLA (10%) and oleic acid (45%) incorporation were 14.8 mol/mol, 55°C, and 24 h; 14 mol/mol, 55°C, and 24 h for substrate ratio (moles total FA/mol tripalmitin), temperature and time for the reactions catalyzed by Lipozyme RM IM and Lipozyme TL IM, respectively. Human Milk Fat substitutes containing GLA that can be included in infant formulas were success-fully produced using both Lipozyme RM IM and Lipozyme TL IM enzymes. The effect of the two enzymes on the incorporation of GLA and oleic acid were found to be similar.
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lipase catalyzed acidolysis of tripalmitin with hazelnut oil Fatty acids and stearic acid to produce Human Milk Fat substitutes
Journal of Agricultural and Food Chemistry, 2005Co-Authors: Nese Sahin, Casimir C. Akoh, Artemis KaraaliAbstract:Structured lipids (SLs) containing palmitic, oleic, stearic, and linoleic acids, resembling Human Milk Fat (HMF), were synthesized by enzymatic acidolysis reactions between tripalmitin, hazelnut oil Fatty acids, and stearic acid. Commercially immobilized sn-1,3-specific lipase, Lipozyme RM IM, obtained from Rhizomucor miehei was used as the biocatalyst for the enzymatic acidolysis reactions. The effects of substrate molar ratio, reaction temperature, and reaction time on the incorporation of stearic and oleic acids were investigated. The acidolysis reactions were performed by incubating 1:1.5:0.5, 1:3:0.75, 1:6:1, 1:9:1.25, and 1:12:1.5 substrate molar ratios of tripalmitin/hazelnut oil Fatty acids/stearic acid in 3 mL of n-hexane at 55, 60, and 65 °C using 10% (total weight of substrates) of Lipozyme RM IM for 3, 6, 12, and 24 h. The Fatty acid composition of reaction products was analyzed by gas−liquid chromatography (GLC). The Fatty acids at the sn-2 position were identified after pancreatic lipase hyd...