Medium- and Long-Chain Triacylglycerol: Preparation, Health Benefits, and Food Utilization.

Medium- and long-chain triacylglycerol (MLCT) is a structured lipid with both medium- and long-chain fatty acids in one triacylglycerol molecule. Compared with long-chain triacylglycerol (LCT), which is mainly present in common edible oils, and the physical blend of medium-chain triacylglycerol with LCT (MCT/LCT), MLCT has different physicochemical properties, metabolic characteristics, and nutritional values. In this article, the recent advances in the use of MLCT in food formulations are reviewed. The natural sources and preparation of MLCT are discussed. A comprehensive summary of MLCT digestion, absorption, transport, and oxidation is provided as well as its health benefits, including reducing the risk of overweight, hypolipidemic and hypoglycemic effects, etc. The potential MLCT uses in food formulations, such as infant formulas, healthy foods for weight loss, and sports foods, are summarized. Finally, the current safety assessment and regulatory status of MLCT in food formulations are reviewed. Expected final online publication date for the Annual Review of Food Science and Technology, Volume 15 is April 2024. Please see http://www.annualreviews.org/page/journal/pubdates for revised estimates.

Combining antioxidants and processing techniques to improve oxidative stability of a Schizochytrium algal oil ingredient with application in yogurt.

Oxidative instability limits incorporation of ω-3 fatty acids (FAs) into some products. This research combined processing techniques with antioxidant addition to overcome these barriers. Oleogels, microencapsulates, and microencapsulated gel ingredients were prepared using Schizochytrium spp. algal oil (AO) in combination with α, ß, γ, and δ tocopherols or 1-o-galloylglycerol (GG) as antioxidants. Ingredients were tested for physicochemical stability and optimal ingredients were selected to prepare yogurts as a model food with ideal matrix. Yogurts were analyzed for physicochemical properties. After 24-days storage at 4 °C, yogurt containing microencapsulated oleogel with GG as antioxidant exhibited average peroxide and p-Anisidine values of 7.17 mmol O2/kg of oil and 118.85 abs/g, respectively. These values were similar to store-bought yogurt using saturated fat source, with values of 6.83 mmol O2/kg of oil and 117.95 absorbance/g, respectively. These results could lead to incorporation of ω-3 FAs into foods, cosmetics, and pharmaceuticals in the future.

Lipase-catalyzed one-step regioselective synthesis of 1,2-dioctanoylgalloylglycerol in a solvent-free system: Optimization of reaction conditions and structural elucidation.

A multi-functional galloylated structured lipid, 1,2-dioctanoylgalloylglycerol (DOGG), was synthesized enzymatically via a regioselective transesterification of propyl gallate and trioctanoate using an immobilized food-grade Candida antarctica lipase B (Lipozyme® 435) as the biocatalyst under solvent-free condition. The variables that affect the reaction, including reaction temperature, substrate ratio, reaction time, and enzyme load, were evaluated and optimized using Taguchi method and response surface methodology. Both methods predicted the same optimal reaction condition, resulting in a 68.8 ± 1.3% DOGG yield with reaction selectivity of 82.9 ± 0.6% at 90 °C, 25/1 trioctanoate/PG (mol/mol), 72 h reaction, and 25% enzyme load relative to the total substrate weight. The structure of the reaction product was elucidated using NMR spectroscopy and ESI-HRMS, confirming the regioselectivity of the reaction. Enzyme retained 50% of its activity after 5 cycles of reuse. It is feasible to synthesize DOGG as a potential antioxidant and nutraceutical using Lipozyme® 435.

Comparison of antioxidant activities of selected phenolic compounds in O/W emulsions and bulk oil.

Antioxidant activities of 1-o-galloylglycerol (GG), propyl gallate, rosmarinic acid (RA), tocopherols (TOC), and 1:1 combinations of GG/RA and GG/TOC were evaluated using in vitro assays including 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+), and ferric reducing antioxidant power (FRAP). Soybean oil stripped of TOC was utilized as bulk oil and as the oil phase in O/W emulsions for accelerated oxidation test with the selected phenolic compounds. Efficacies of antioxidants were evaluated by monitoring total oxidation (TOTOX) values and fatty acid profiles of oil and O/W samples during the accelerated oxidation. In bulk oil, GG outperformed other singular antioxidants, preventing 39.04% of oxidation for ω-3 fatty acids with a TOTOX value of 166.68. In emulsions, TOC outperformed other singular antioxidants, preventing 38.04% of oxidation with a TOTOX value of 196.72. Considering the polarities of the antioxidants and our testing systems, these results provide supporting evidence for the polar paradox theory.

Modification of palm-based oil blend via interesterification: Physicochemical properties, crystallization behaviors and oxidative stabilities.

Interesterification is widely employed as an effective technique to modify oils and fats. This study utilizes palm-based oil (palm olein: palm kernel oil: palm stearin, 5:3:2, w/w/w) as the raw material for the interesterification process performed in a pilot-scale packed bed reactor. Enzymatic interesterification (EIE) was catalyzed by Lipozyme TL IM (813.0 g) at 60℃ with reaction flow rate of 100 mL/min. Chemical interesterification (CIE) was catalyzed using sodium methoxide (0.3 wt%) as catalyst at 105 °C for 30 min. The results showed that the EIE fats had lower solid fat content tendency compared to that of CIE fats. The crystallization onset temperature was higher in EIE fats (23.09℃) compared to that of CIE (19.08℃). The results were consistent with the crystallization kinetics whereby the Avrami K constants of EIE fats were higher than that of CIE fats at various temperatures, indicating rapid crystallization and instant nucleation. Linear growth mechanism was dominant and the crystals formed were smaller in size as observed using polarized light microscope. The interesterified fats exhibited the presence of ß and ß'-crystals. While most of the tocopherol content was retained after EIE (386.18 ug/g), the molecular distillation process reduced the tocopherol concentration (110.01 ug/g) which consequently affected the oxidative stability. The findings in this work contribute to the fundamental understanding on the differences between CIE and EIE fats and provides data to support the preparation of modified fats via EIE that shows great potential as a controllable technique for industrialization.

Phenolic compounds as antioxidants to improve oxidative stability of menhaden oil-based structured lipid as butterfat analog.

Phenolic compounds, including propyl gallate, 1-o-galloylglycerol, ferulic, gallic, caffeic, rosmarinic, and carnosic acids, tocopherols, and butylated hydroxytoluene (BHT), were investigated as antioxidants to improve the oxidative stability of a structured lipid (SL) produced by the enzymatic acidolysis of menhaden oil with caprylic and stearic acids. SL had similar physical properties to butterfat but was more susceptible to oxidation. The above phenolic compounds were each added to SL as antioxidants. SL with 1-o-galloylglycerol, rosmarinic acid, or BHT showed the highest oxidative stability during an accelerated oxidation test with the total oxidation (TOTOX) value around 250 after 18 days. Oxidation induction time (OIT) using differential scanning calorimetry showed a good correlation with the accelerated oxidation test. A mixture of 1-o-galloylglycerol and tocopherols at 50:50 ppm had the strongest protective effect on SL (OIT = 115.1 min) compared to the other tested compounds or combinations at the same concentration (OIT < 100 min).

Solvent-free enzymatic synthesis of 1,2-dipalmitoylgalloylglycerol: Characterization and optimization of reaction condition.

A novel diacylglycerol-based galloyl structured lipid, 1,2-dipalmitoylgalloylglycerol (DPGG), was synthesized using the enzymatic transesterification of propyl gallate (PG) and tripalmitin under solvent-free condition. An immobilized and commercially available food-grade Candida antarctica lipase B, Lipozyme® 435, was used as the biocatalyst. The reaction variables that affect the yield of DPGG were optimized using a 33 full factorial design. At 70 °C, DPGG was obtained at a yield of 33.0 ± 2.0% with PG conversion at 44.8 ± 1.8% when the following condition was used: 25 substrate molar ratio of tripalmitin to PG, 120 h reaction time, and 25% enzyme load relative to the total substrate weight. The structure of reaction product was elucidated using Fourier-transform infrared spectroscopy (FT-IR), electrospray ionization high-resolution accurate-mass tandem mass spectrometry (ESI-HRAM-MS/MS), and 1D and 2D nuclear magnetic resonance spectroscopy (NMR). The effects of different lipases and galloyl donors/acceptors on the transesterification were also investigated.

Antioxidant property and characterization data of 1-o-galloylglycerol synthesized via enzymatic glycerolysis.

This article provides comprehensive experimental data characterizing antioxidant activity, as well as chemical and physical properties of 1-o-galloylglycerol (GG), synthesized by enzymatic glycerolysis of propyl gallate (PG) using a food-grade lipase (Lipozyme® 435) [1]. GG was characterized by Fourier-transform infrared spectroscopy (FT-IR), 1H, 13C, 1H-1H gradient correlation spectroscopy (gCOSY), 1H-13C gradient heteronuclear single quantum coherence (gHSQC), 1H-13C gradient heteronuclear multiple quantum coherence (gHMQC), and 1H-13C gradient heteronuclear multiple bond correlation (gHMBC) nuclear magnetic resonance spectroscopies (NMR), and ultraviolet-visible spectrophotometry (UV-Vis). The antioxidant property of GG, which was evaluated through 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2,2'-azinobis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+), ferric reducing antioxidant power (FRAP), and hydrogen peroxide (H2O2) scavenging assays, is also presented.

Enzymatic synthesis of 1-o-galloylglycerol: Characterization and determination of its antioxidant properties.

1-o-Galloylglycerol (GG) was synthesized by the enzymatic glycerolysis of propyl gallate (PG) using a food-grade lipase (Lipozyme® 435). The reaction conditions affecting the yield of GG were optimized and a yield of 76.9% ±â€¯1.2% was obtained. GG was characterized by various techniques after being separated from the reaction mixture using liquid-liquid extraction. The water solubility and hydrophilicity of GG were significantly higher than those of gallic acid (GA) and PG. The antioxidant properties, measured by the ferric reducing antioxidant power (FRAP) and hydrogen peroxide (H2O2) scavenging assays, showed that GG exhibited the highest scavenging capacity (GG > GA > PG). From the results of the 1,1-diphenyl-2-picrylhydrazyl (DPPH•) and 2,2'-azinobis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+) assays, GG and GA exhibited greater scavenging capacity than PG (GG = GA > PG). These results suggest that GG may be used as a water-soluble antioxidant alternative to GA for food and cosmetic applications.

Oxidative stability of cod liver oil in the presence of herring roe phospholipids.

The aim of this research was to investigate the effect of herring roe phospholipids (PLs) on the oxidative stability of cod liver oil during storage. The effect of PLs on the oxidative stability of cod liver oil was assessed in terms of peroxide value, free fatty acids, secondary oxidation products and pyrrolisation. The results show that the PV was lower in cod liver oil containing PLs (P < 0.05) than in the control without PLs. Benzaldehyde, 2,5-dimethylpyrazine, 2-methyl-2-pentenal, 1-penten-3-ol and 3-methylbutanal were the main volatiles. In addition, significant pyrrolisation was observed after 28 days when PLs were added to cod liver oil. The results suggested that cod liver oil with dispersed PLs was oxidized during storage followed by non-enzymatic browning reactions. The findings indicated that the ratio between pyrroles formed and α-tocopherol may influence the formation of new peroxides and secondary oxidation products.

Effect of Oil Type and Emulsifier on Oil Absorption of Steam-and-fried Instant Noodles.

The effects of four different frying oils and three emulsifiers on oil absorption by steam-and-fried instant noodles were evaluated. The blended oil (high oleic sunflower oil/soybean oil/palm oil = 24:25:1 (v/v/v)) containing approximately 50% oleic acid was chosen as the proper frying oil due to lower oil absorption by instant noodle compared to palm, soybean, and high oleic sunflower oils. Among the four oils, the interfacial tension between high oleic sunflower oil and instant noodle was the lowest (0.073 mN/m), resulting in the highest oil uptake (15.47%), while the lowest interfacial tension (0.30 mN/m) between blended oil and instant noodle resulted in the lowest oil uptake by the fried product (12.63%). Scanning electron microscopy (SEM) and confocal laser scanning microscopy (CLSM) were used to observe surface properties and oil distribution. The instant noodle fried in blended oil was found to have uniform oil distribution and smooth surface. After selecting the proper frying oil, three emulsifiers (soybean lecithin, Tween-80, Span-80, at 0.2% (v/v)) were added to the blended frying oil. Adding emulsifier into frying oil significantly decreased the interfacial tension between frying oil and instant noodle. Among the three emulsifiers, addition of soybean lecithin resulted in the lowest interfacial tension (0.010 mN/m) and the highest oil uptake (18.36%). Therefore, from this study, we do not recommend adding emulsifier into frying oil.

Physicochemical Characterization of Yellow Cake Prepared with Structured Lipid Oleogels.

Oleogels were produced using a phytosterol blend of ß-sitosterol/γ-oryzanol or a blend of sucrose stearate/ascorbyl palmitate (SSAP) as oleogelators. Four lipid phases were compared in oleogel formation for each oleogelator blend: menhaden oil, structured lipid (SL) of menhaden oil and 30 mol% caprylic acid (SL-C), SL of menhaden oil and 20 mol% stearic acid (SL-S), and SL of menhaden oil and 14 mol% each of caprylic and stearic acid (SL-CS). All SLs were produced enzymatically using a recombinant lipase from Candida antarctica as the biocatalyst. Menhaden oil, SL, phytosterol, or SSAP oleogels were evaluated as alternatives to shortening in the preparation of yellow cake in terms of batter and cake physicochemical properties. The shortening, phytosterol, and SSAP oleogel batters exhibited statistically similar specific gravities (0.85). The shortening, and menhaden oil phytosterol and SSAP oleogel batters, exhibited similar Power-Law values (n: 0.78, k: 31 Pa sn ), while all SL (and respective oleogels) batters typically had lower flow index values (n: 0.68 to 0.72), and higher consistency index values (k: 45 to 79 Pa sn ). All SL (and respective oleogels) cakes exhibited lower hardness (5 to 8 N) and chewiness (4 to 6 N) than the shortening cake (12 N, 9 N). Menhaden oil and SL-S phytosterol oleogel cakes, and SL-CS SSAP oleogel cake, showed similar textural properties to the shortening cake. Both phytosterol and SSAP oleogels were acceptable as zero trans-fat substitutes for shortening in yellow cake. PRACTICAL APPLICATION: The oleogels in this study may be a suitable replacement for shortening in yellow cake. These oleogels, which contain health beneficial omega-3 fatty acids, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), have the potential to lower consumer consumption of total saturated fat when used in foods.

Source, Extraction, Characterization, and Applications of Novel Antioxidants from Seaweed.

Driven by a general demand for clean labels on food and cosmetic products, these industries are currently searching for efficient natural antioxidants to replace synthetic antioxidants. Seaweed contains several compounds with antioxidative properties (phlorotannins, pigments, tocopherols, and polysaccharides). It is possible to extract these compounds via different extraction techniques, which are discussed in this review. Among the abovementioned compounds, phlorotannins are probably the most important in terms of the antioxidative potential of seaweed extracts. We review how the different antioxidative compounds can be characterized. We discuss the current knowledge of the relationship between phlorotannin's structure and antioxidant properties in in vitro studies as well as in food systems. Concerning food systems, most studies on the antioxidative effect of seaweed extracts have been performed with extracts prepared from Fucus vesiculosus, despite the fact that this species is less available than other species, such as Ascophyllum nodosum, which also has high phlorotannin content.

Mango kernel fat fractions as potential healthy food ingredients: A review.

Mango kernel fat (MKF) has been reported to have high functional and nutritional potential. However, its application in food industry has not been fully explored or developed. In this review, the chemical compositions, physical properties and potential health benefits of MKF are described. MKF is a unique fat consisting of 28.9-65.0% of 1,3-distearoyl-2-oleoyl-glycerol with excellent oxidative stability index (58.8-85.2 h at 110 °C), making the fat and its fractions suitable for use as high-value added food ingredients such as cocoa butter alternatives, trans-free shortenings, and a source of natural antioxidants (e.g., sterol, tocopherol and squalene). Unfortunately, the long period of dehydration of mango kernels at hot temperature results in the hydrolysis of triacylglycerols. The high levels of hydrolysates (mainly free fatty acids and diacylglycerols) limit the application of MKF in manufacturing these food ingredients. It is suggested that the physico-chemical and functional properties of MKF could be further improved through moderated refining (e.g., degumming and physical deacidification), fractionation, and interesterification.

Physical and oxidative stability of high fat fish oil-in-water emulsions stabilized with sodium caseinate and phosphatidylcholine as emulsifiers.

The physical and oxidative stability of high-fat omega-3 delivery systems such as fish oil-in-water emulsions stabilized with combinations of sodium caseinate (CAS) and phosphatidylcholine (PC) was optimized. The influence of fish oil content (50, 60 and 70%, w/w), amount of total emulsifier CAS + PC (1.4, 2.1 and 2.8%, w/w) and ratio between CAS and PC (0.4, 1.2 and 2) on physical and oxidative parameters was investigated. Creaming and droplet size significantly decreased when the amount of fish oil, total emulsifier and ratio of CAS to PC were increased. Viscosity decreased significantly with decreasing fish oil content, whereas the ratio of CAS to PC did not have a significant influence. Decreasing the ratio of CAS to PC led to emulsions with a significantly lower concentration of 1-penten-3-ol, while no significant effect was found for other volatiles such as (E)-2-pentenal, (E)-2-hexenal and (E,E)-2,4-heptadienal.

Physicochemical characterization of organogels prepared from menhaden oil or structured lipid with phytosterol blend or sucrose stearate/ascorbyl palmitate blend.

The purpose of this research was to produce organogels using two different organogelator blends and two different oil substrates and compare their physicochemical properties. A medium-long-medium (MLM)-type structured lipid (SL) containing 37.44 mol% MLM-type triacylglycerols (TAG) was produced by enzymatic modification of menhaden oil with ethyl caprate. Menhaden oil and SL were used as oil substrates to form organogels. One organogel was formed using a phytosterol blend of ß-sitosterol and γ-oryzanol (molar ratios of 2 : 1, 1 : 1, and 1 : 2 at 4, 6, and 8% (w/w) in oil), and another was formed with a blend of sucrose stearate (HLB value: 2) and ascorbyl palmitate (SSAP) (molar ratios of 3 : 1, 1 : 1, and 1 : 3 at 8, 10, and 12% (w/w) in oil). Organogels were formed for all ratios except 2 : 1 and 3 : 1 for the phytosterol and SSAP blend, respectively. For both organogels, the 1 : 1 molar ratio was optimal. This ratio produced organogels with higher melting completion temperatures than menhaden oil and SL (13.6 and 14.3 °C). The SSAP blend had higher melting completion temperatures (72.3 and 72.4 °C) than the phytosterol blend (69.2 and 68.4 °C) for organogels formed using menhaden oil and SL, respectively. All 1 : 1 molar ratio blends exhibited ß' polymorphic form with short spacing peaks at 4.20, 3.97, and 3.71 Å. All organogels improved the oxidative stability of the menhaden oil and SL. These organogels have the potential for use as nutraceuticals or health beneficial low saturated fat alternatives to saturated and/or trans-fats.

Lipase - catalyzed Modification of Rice Bran Oil Solid Fat Fraction.

This study used a rice bran oil solid fat fraction (RBOSF) to produce cocoa butter alternatives via interesterification reaction catalyzed by immobilized lipase (Lipozyme® RM IM) in hexane. Effects of reaction time (6, 12, and 18 h), temperature (55, 60, and 65°C), mole ratios of 3 substrates [RBOSF:palm olein:C18:0 donors (1:1:2, 1:2:3, and 1:2:6)] were determined. The substrate system was dissolved in 3 mL of hexane and 10% of lipase was added. Two sources of C18:0 donors, stearic acid (SAd) and ethyl stearate (ESd) were used. Pancreatic lipase - catalyzed sn-2 positional analysis was also performed on both substrates and structured lipids (interesterification products). Structured lipids (SL) were analyzed by gas - liquid chromatography (G40.35LC) for fatty acid composition. Major fatty acids of RBOSF were C18:1, oleic acid (OA, 41.15±0.01%), C18:2, linoleic acid (LA, 30.05±0.01%) and C16:0, palmitic acid (PA, 22.64±0.01%), respectively. A commercial raw cocoa butter (CB) contained C18:0, stearic acid (SA, 33.13±0.04%), OA (32.52±0.03%), and PA (28.90±0.01%), respectively. Fatty acids at sn-2 position of RBOSF were OA (46.52±0.63%) and LA (42.98±1.1%), while major fatty acid at sn-2 position of CB was OA (85.24±1.22%). The RBOSF had low SA (2.40±0.01%) compared to CB (33.13±0.04%). The content of OA (46.52±0.63%) at sn-2 position in RBOSF was half of that found in CB (85.24±1.22%). Optimal reaction was 1:2:6 mole ratio of the substrate (RBOSF:PO:SAd), at 65°C for 12 h. Fatty acid compositions of the SL were 31.72±0.99% SA, 30.91±0.53% LA, 23.18±0.32% OA, and 13.26±0.34% PA, respectively. Fatty acids at sn-2 position of the SL were 53.72±4.21% OA, 25.11±3.69% LA, 14.18±1.58% PA, and 6.99±0.02% SA, respectively. DSC curves showed the melting point of CB at 20.94°C, while those of the SL were 14.15 and 40.35°C, respectively. The melting completion temperature (Tmc) of CB was 25.5°C while that of SL was 43.9°C, respectively.

The impact of lactation and gestational age on the composition of branched-chain fatty acids in human breast milk.

Breast milk consumption reduces the incidence of necrotizing enterocolitis (NEC) in preterm infants compared to formula. Branched-chain fatty acids (BCFAs) are present in breast milk but not in most formulas intended for preterm infants. We aimed to determine the composition of BCFAs in the breast milk of mothers with preterm infants, and to understand the impact of gestational age at birth and stage of lactation on BCFA content. The main BCFAs in preterm breast milk were iso-14:0, iso-15:0, anteiso-15:0, iso-16:0, iso-17:0, and anteiso-17:0. Breast milk BCFAs as a percent of total fatty acids (g per 100 g, %) were significantly different across lactation stages, with the highest concentration in colostrum, followed by transitional and mature breast milk (median: 0.41, 0.31, and 0.28%, respectively, p < 0.05). Lower BCFAs in preterm breast milk compared to term breast milk may have been related to maternal intake, or the ability of the mammary gland to extract BCFA from plasma, or differences in mammary gland BCFA synthesis. BCFAs were mainly in the sn-2 position (52-65%), similar to palmitic acid. Overall, preterm and term breast milk BCFAs were similar and showed specific concentration patterns, resembling 16:0 with respect to sn-2 positional distribution. BCFAs were reduced with lactation stage, similar to highly unsaturated fatty acids.

Phospholipids composition and molecular species of large yellow croaker (Pseudosciaena crocea) roe.

The research aims to study phospholipids (PL) classes and molecular species of large yellow croaker (Pseudosciaena crocea) roe. Both gas chromatographymass spectroscopy (GC-MS) and high-performance liquid chromatography with evaporative light-scattering detection (HPLC-ELSD) were utilized to analyze and identify the PLs fatty acids compositions and classes in the P. crocea roe, respectively. Docosahexaenoic acid (DHA, C22:6) and eicosapentaenoic acid (EPA, C20:5) account for 35.0% and 6.9% of the PLs. Phosphatidylcholines (PC), lysophosphatidylcholines (LPC), phosphatidylethanolamines (PE) and phosphatidylinositols (PI) account for 76.36 ±â€¯0.62%, 12.30 ±â€¯0.55%, 9.12 ±â€¯0.02% and 1.09 ±â€¯0.01% of the total PLs, respectively. In addition, the PLs molecular species were characterized by ultra-high performance liquid chromatography-electrospray ionization-quadruple-time of flight-mass spectrometry (UPLC-Q-TOF-MS). A total of 92 PLs molecular species was identified, including 49 PCs, 13 PEs, 10 phosphatidic acids (PAs), 13 phosphatidylserines (PSs), 3 phosphatidylglycerols (PGs), 2 sphingomyelins (SMs), and 2 PIs of the P. crocea roe.