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Background: Medium- and long-chain triacylglycerols (MLCTs) and sn-2 palmitate constitute approximately 70~80% of total breast milk fat. The structured lipid MLCTs and sn-2 palmitate, mimicking human milk, have demonstrated improvement in lipid absorption and energy metabolism in vitro and in animal experiments. However, clinical trials on infant formula supplied with MLCTs and sn-2 palmitate have yet to be conducted. Objectives: This study was designed to evaluate the effects on growth and lipid absorption of a novel formula with structured lipid MLCTs and sn-2 palmitate on healthy infants born at term. Methods: Infants were enrolled at 30 d postpartum and assigned to three groups based on their feeding conditions: (1) a novel formula with MLCTs and sn-2 palmitate (Novel-F group, n = 65); (2) a control formula with vegetable oils and no structured lipids (Contr-F group, n = 46); or (3) breastfeeding (BF group, n = 66). Growth measurements (including weight, length, and head circumference), stool characteristics, and fecal lipid composition (both soap and non-soap fatty acids) were analyzed at both baseline (30 d postpartum) and endline visits (90 d postpartum). Results: The Novel-F group had significantly higher weight gains (2195 ± 595 g) during the intervention compared to the Contr-F group (1897 ± 483 g) but similar weight gains to the BF group (2081 ± 614 g), with the changes in Zw/a following a similar pattern. Zl/a increased in the Novel-F group (0.04, (95% CI: −0.21 to 0.28)) and decreased in both the Contr-F (−0.23 (95% CI: −0.52 to 0.06)) and BF groups (−0.20 (95% CI: −0.44 to 0.05)). The stools of infants in the Novel-F group had similar undigested triacylglycerols and total fatty acids compared to breastfed infants but had significantly lower levels than infants fed with the control formula at both baseline and endline visits. Conclusions: The novel infant formula with MLCTs and sn-2 palmitate is safe and well tolerated, and supports adequate weight gain and improves lipid absorption.

A few studies suggested high stereo-specifically numbered (sn)-2 palmitate in a formula might favor the gut Bifidobacteria of infants. The initial colonization and subsequent development of gut microbiota in early life might be associated with development and later life functions of the central nervous system via the microbiota–gut–brain axis, such as children with autism. This study aims to assess the hypothesized effect of increasing the amount of palmitic acid esterified in the sn-2 position in infant formula on neurodevelopment in healthy full-term infants and to explore the association of this effect with the altered gut Bifidobacteria. One hundred and ninety-nine infants were enrolled in this cluster randomized clinical trial: 66 breast-fed (BF group) and 133 formula-fed infants who were clustered and randomly assigned to receive formula containing high sn-2 palmitate (sn-2 group, n = 66) or low sn-2 palmitate (control group, n = 67), where 46.3% and 10.3% of the palmitic acid (PA) was sn-2-palmitate, respectively. Infants’ neurodevelopmental outcomes were measured by the Ages and Stages Questionnaire, third edition (ASQ-3). Stool samples were collected for the analysis of Bifidobacteria (Trial registration number: ChiCTR1800014479). At week 16, the risk of scoring close to the threshold for fine motor skills (reference: scoring above the typical development threshold) was significantly lower in the sn-2 group than the control group after adjustment for the maternal education level (p = 0.036) but did not differ significantly versus the BF group (p = 0.513). At week 16 and week 24, the sn-2 group (week 16: 15.7% and week 24: 15.6%) had a significantly higher relative abundance of fecal Bifidobacteria than the control group (week 16: 6.6%, p = 0.001 and week 24:11.2%, p = 0.028) and did not differ from the BF group (week 16: 14.4%, p = 0.674 and week 24: 14.9%, p = 0.749). At week 16, a higher relative abundance of Bifidobacteria was associated with the decreased odds of only one domain scoring close to the threshold in the formula-fed infants group (odds ratio (OR), 95% confidence interval (CI): 0.947 (0.901–0.996)). Elevating the sn-2 palmitate level in the formula improved infants’ development of fine motor skills, and the beneficial effects of high sn-2 palmitate on infant neurodevelopment was associated with the increased gut Bifidobacteria level.

Human milk fat substitute (HMFS) is a structured lipid designed to resemble human milk fat. It contains 60–70 % palmitic acid at the sn-2 position and unsaturated fatty acids at the sn-1,3 positions in triacylglycerol structures. HMFS is synthesized by the enzymatic interesterification of vegetable oils, animal fats or a blend of oils. The efficiency of HMFS synthesis can be enhanced through the selection of appropriate substrates, enzymes and reaction methods. This review focuses on the synthesis of HMFS by lipase-catalyzed interesterification and provides a detailed overview of biocatalysts, substrates, synthesis methods, factors influencing the synthesis and purification process for HMFS production. Major challenges and future research in the synthesis of HMFS are also discussed. This review can be used as an information for developing future strategies in producing HMFS.

Background Human milk palmitic acid (PA) is mainly esterified at the sn-2 position of triacylglycerols, while infant formula contains palmitate predominantly in the sn-1/3 positions. Current evidence on long-term health effects of increasing sn-2 palmitate in formula remains insufficient. This study investigated the effects of high sn-2 PA formula (> 40%) on fecal saponified fatty acid, calcium, magnesium and stool characteristics in healthy full-term infants. Methods In this cluster-randomized controlled trial, healthy infants < 14 d were assigned to breastfeeding (BF group, n  = 66), high sn-2 palmitate formula (sn-2 group, n  = 66, 46.3% sn-2 PA) or low sn-2 palmitate formula (control group, n  = 67, 10.3% sn-2 PA). Infant demographics, feeding status, stool characteristics, physical exams, and stool samples were collected at 6, 16, and 24 weeks. Per-protocol analysis was used. Results The sn-2 group exhibited a significant time-dependent decline in fecal saponified PA and calcium over time ( P h for Trend < 0.001). The BF group declined faster than the sn-2 group ( P adjusted for Group*Time < 0.001). Fecal saponified PA proportion in sn-2 group was significantly lower than controls at all timepoints. At week 24, fecal calcium was lower in the sn-2 group vs. control (0.9 vs. 1.3 mg/g, P  = 0.010). No significant difference was found in stool frequency, consistency or size between sn-2 and control groups at any point. Conclusion Infant formula enriched with > 40% sn-2 palmitate reduces fecal fatty acid and calcium excretion, supports efficient lipid and calcium absorption, shows a fecal magnesium pattern similar to breastfed infants, but does not alter stool characteristics relative to the control formula. Trial registration The trial is registered at Chinese Clinical Trial Registry: ChiCTR1800014479; 30/Jan./2018.

The binding ratio of palmitic acid (PA) at the sn-2 position of triacylglycerols in infant formulas is lower than that in breast milk, resulting in higher levels of fecal PA. Even if the ratio is increased to 40–50%, fecal PA levels in formula-fed infants remain higher than those in breast–fed infants. In Japan, infant formulas with 50% or more of PA bound to sn-2 (high sn-2 PA milk) are commercially available; however, their effects on PA excretion have not been investigated. Therefore, this observational study aimed to preliminarily evaluate whether the feeding volume of high sn-2 PA milk is significantly associated with fecal total/soaped PA levels in newborns. Infant formulas were classified as high (≥50% of PA bound to sn-2) or low sn-2 (<50%) PA milk. Associations between feeding volume of high or low sn-2 PA milk and fecal PA levels were evaluated using multiple regression analysis models. The results showed that the feeding volume of low sn-2 PA milk was positively associated with fecal total/soaped PA levels, while there was no significant association between those of high sn-2 PA milk and fecal total/soaped PA levels. Our preliminary study suggests that high sn-2 PA milk may reduce increased fecal PA levels in formula-fed newborns.

Background Formula-fed (FF) infants often have harder stools and higher stool concentrations of fatty acid soaps compared to breastfed infants. Feeding high sn -2 palmitate or the prebiotic oligofructose (OF) may soften stools, reduce stool soaps, and decrease fecal calcium loss. Methods We investigated the effect of high sn -2 palmitate alone and in combination with OF on stool palmitate soap, total soap and calcium concentrations, stool consistency, gastrointestinal (GI) tolerance, anthropometrics, and hydration in FF infants. This double-blind trial randomized 165 healthy term infants 25–45 days old to receive Control formula (n = 54), formula containing high sn -2 palmitate ( sn -2; n = 56), or formula containing high sn -2 palmitate plus 3 g/L OF ( sn -2+OF; n = 55). A non-randomized human milk (HM)-fed group was also included (n = 55). The primary endpoint, stool composition, was determined after 28 days of feeding, and was assessed using ANOVA accompanied by pairwise comparisons. Stool consistency, GI tolerance and hydration were assessed at baseline, day 14 (GI tolerance only) and day 28. Results Infants fed sn -2 had lower stool palmitate soaps compared to Control ( P =0.0028); while those fed sn -2+OF had reduced stool palmitate soaps compared to both Control and sn -2 (both P <0.0001). Stool total soaps and calcium were lower in the sn -2+OF group than either Control ( P <0.0001) or sn -2 ( P <0.0001). The HM-fed group had lower stool palmitate soaps, total soaps and calcium ( P <0.0001 for each comparison) than all FF groups. The stool consistency score of the sn -2+OF group was lower than Control and sn -2 ( P <0.0001), but higher than the HM-fed group ( P <0.0001). GI tolerance was similar and anthropometric z-scores were <0.2 SD from the WHO growth standards in all groups, while urinary hydration markers were within normal range for all FF infants. Conclusions Increasing sn -2 palmitate in infant formula reduces stool palmitate soaps. A combination of high sn -2 palmitate and OF reduces stool palmitate soaps, total soaps and calcium, while promoting softer stools. Trial registration This study was registered on http://www.clinicaltrials.gov: number NCT02031003 .

Sn-2 palmitate is widely used in infant formula. However, little is known about its effects on metabolism and body composition in middle-aged and elderly adults. In a double-blinded, randomized controlled trial, we enrolled Chinese adults aged 45–75 years with self-reported constipation. Individuals were randomly assigned in a 1:1 ratio to a 1,3-dioleoyl-2-palmitoyl-glycerol (OPO)-enriched oil (66% palmitic acid in the sn-2 position) or a control vegetable oil (24% palmitic acid in the sn-2 position) daily for 24 weeks. Skim milk powder was used as the carrier for both fats. Interviews and body composition were performed at baseline, week 4, week 12 and week 24. A fasting blood draw was taken except at week 4. This study was a secondary analysis and considered exploratory. A total of 111 adults (83 women and 28 men, mean age 64.2 ± 7.0 years) were enrolled, of whom 53 were assigned to the OPO group and 57 to the control group. During the intervention, blood glucose, triglyceride, the triglyceride-glucose index, total cholesterol, low-density lipoprotein cholesterol and remnant cholesterol remained stable, while high-density lipoprotein cholesterol decreased in both groups (p = 0.003). No differences in change were observed between the groups (all p > 0.05). From baseline to week 24, the level of visceral fat increased slightly (p = 0.017), while body weight, total body water, protein, soft lean mass, fat-free mass, skeletal muscle and skeletal muscle mass index (SMI) decreased in two groups (p < 0.01). At weeks 4, 12 and 24, the SMI decreased less in the OPO group than in the control group, with a trend towards significance (p = 0.090). A 24-week daily intake of sn-2-palmitate-enriched oil had no adverse impact on fasting blood glucose, lipids and body composition compared with the control vegetable oil in Chinese adults (funded by Chinese Nutrition Society National Nutrition Science Research Grant, National Key Research and Development Program of China and Wilmar (Shanghai) Biotechnology Research & Development Center Co., Ltd.; ChiCTR1900026480).

Background Beta-palmitate (sn-2 palmitate) mimics human milk fat, enabling easier digestion. Therefore, we hypothesized that infants consuming high beta-palmitate formula would have more frequent, softer stools and reduced crying compared to infants consuming low beta-palmitate formula. Methods Formula-fed infants were randomly assigned to receive either (1) formula with high beta-palmitate (HBP, n = 21) or (2) regular formula with a standard vegetable oil mix (LBP, n = 21). A matched group of breastfed infants served as a reference (BF, n = 21). Crying and stool characteristics data were recorded by the parents for 3 days before the 6- and 12-week visits. Results We found no significant differences in the stool frequency or consistency between the two formula groups. The percentage of crying infants in the LBP group was significantly higher than that in the HBP and BF groups during the evening at 6 weeks (88.2% vs. 56.3% and 55.6%, p < 0.05) and during the afternoon at 12 weeks (91.7% vs. 50.0% and 40%, p < 0.05). The infants fed HBP had significantly shorter crying durations when compared with infants fed LBP formula (14.90 ± 3.85 vs.63.96 ± 21.76 min/day, respectively; p = 0.047). Conclusions Our study indicates that consumption of a high beta-palmitate formula affects infant crying patterns during the first weeks of life. Comparable to breastfeeding, it reduced crying duration and frequency, primarily during the afternoon and evening hours, thereby improving the well-being of formula-fed infants and their parents. Trial registration NCT00874068 . Registration date March 31, 2009

Nadomjestak masti iz majčina mlijeka je strukturirani lipid koji nalikuje masti iz majčina mlijeka. Sadržava 60-70 % palmitinske kiseline na poziciji sn-2 i nezasićene masne kiseline vezane na pozicijama sn-1,3 u strukturi triacilglicerola. Nadomjestak mliječne masti se sintetizira enzimskom interesterifikacijom biljnih ulja, životinjske masti ili njihovom mješavinom. Učinkovitost sinteze nadomjeska masti iz majčina mlijeka može se povećati odabirom odgovarajućih supstrata, enzima i postupaka sinteze. U fokusu ovog revijalnog prikaza je sinteza nadomjeska mliječne masti postupkom interesterifikacije pomoću lipaze. Dan je detaljan pregled biokatalizatora, supstrata, postupaka sinteze i čimbenika koji utječu na sintezu i pročišćavanje dobivenih nadomjestaka. Također se raspravlja o glavnim izazovima u proizvodnji i budućnosti sinteze ovih proizvoda. Ovaj rad se može upotrijebiti kao izvor informacija za razvoj budućih strategija proizvodnje nadomjeska masti iz majčina mlijeka.

To study feeding tolerance in infants fed formula with increased sn-2 palmitate and oligofructose (sn-2+OF) in a real-world setting, healthy Chinese infants were enrolled in this 48-day observational study on their current feeding regimens: exclusively breastfed (BF; n = 147), exclusively sn-2+OF formula-fed (FF; n = 150), or mixed-fed with breast milk and sn-2+OF formula (MF; n = 163). Throughout the study, incidence (90% confidence interval) of hard stools was ≤2.1% (0.0-5.3) in FF and 0.8% (0.0-3.5) in MF, with no hard stools in BF. Incidence of watery stools was ≤5.0% (1.0-9.2) in FF and ≥5.1% (2.4-9.3) in MF and BF. Gastrointestinal tolerance scores, although low in all groups (lower scores indicating better tolerance), were slightly higher (P ≥ .03) in FF (17.5 ± 4.8) and MF (18.2 ± 5.0) versus BF (16.3 ± 3.2) at mid-study; this difference disappeared at study end. Overall, low incidences of hard and watery stools and good feeding tolerance were observed in infants fed sn-2+OF formula.