Dietary medium- and long-chain triacylglycerols accelerate diet-induced thermogenesis in humans

This study investigated the effects of a liquid meal containing medium- and long-chain triacylglycerols (MLCT) on diet-induced thermogenesis (DIT) and was conducted in double-blind cross-over manner. Twenty subjects participated in this examination. The subjects consumed the liquid meal, which was made with 14 g of canola oil (LCT, long-chain triacylglycerols) or MLCT containing about 12% medium-chain fatty acids (MCFA). Oxygen consumption and carbon dioxide production were measured by indirect calorimetry. Resting energy expenditure (REE) was determined based on there parameters, applying the equation of Weir. Increase in DIT after ingesting the liquid meal with MLCT during 6h was significantly greater than with LCT (P<0.05). The results suggest that the substitution of MLCT for cooking oil is useful to control body weigh and fat in subjects.     

Production of Structured Triacylglycerol via Enzymatic Interesterification of Medium-Chain Triacylglycerol and Soybean Oil Using a Pilot-Scale Solvent-Free Packed Bed Reactor

Oils rich in medium- and long-chain triacylglycerols (MLCT) serve as functional oils to help reduce body fat accumulation and weight gain. However, most of the MLCT-rich products on the market are physical blends of medium- and long-chain triacylglycerols (MCT and LCT, respectively) that are not structured triacylglycerols (TAG). In this study, an efficient pilot-scale packed bed reactor (PBR) of immobilized lipase from Thermomyces lanuginosus (Lipozyme® TL IM, Novozymes, Bagsvaerd, Denmark) was employed for producing structured MLCT via 1,3-specific interesterification of TAG enriched in caprylic and capric acyl groups and soybean oil (SBO). The PBR was operated under continuous recirculation mode in the absence of solvent. Optimal reaction conditions were determined to be: caprylic/capric TAG: SBO ratio (45:55 w/w), reaction temperature (75 °C) and residence time (16.0 min) on MLCT production were studied. When employing a pilot-scale PBR (100 kg day⁻¹) under optimal conditions, a product containing 76.61 wt% MLCT was produced. Lipozyme TL IM was reused for 25 successive batch reactions (125 kg substrates) with no significant reduction in catalytic efficiency. The light yellow MLCT-enriched product had a high level of saturated fatty acids (SFA, 82.74 wt%) in its sn-2 position as a result of the enzyme's 1,3-positional specificity. One-stage molecular distillation and methanol extraction were used to remove the free fatty acids, mono-, and diacylglycerols generated from hydrolysis. With distillation temperature of 150 °C and oil-to-methanol ratio of 1:3 v/v, MLCT content was further increased to 80.07 wt%. The enzymatic PBR was therefore effective in producing structured MLCT at a pilot-scale under solvent-free conditions.     

Lipase-Catalyzed Interesterification of Schizochytrium sp. Oil and Medium-Chain Triacylglycerols for Preparation of DHA-Rich Medium and Long-Chain Structured Lipids

DHA-rich medium and long-chain structured lipids (MLSL) were successfully synthesized by lipase-catalyzed interesterification of microbial oil from Schizochytrium sp. with medium-chain triacylglycerols (MCT) containing 99% of caprylic acid. Parameters that affected the reaction process were investigated and the conditions were selected as follows: lipase from Aspergillus oryzae, NS40086; reaction time, 8 hours; substrate molar ratio (MCT/microbial oil), 1:1; lipase load, 8 wt%; reaction temperature, 60 °C. Under these conditions, the proportions of MCT, MLSL, and long-chain triacylglycerols (TAG) in the final products were 12.5%, 62.8%, and 24.6%, respectively. The final product was then subjected to UPLC-MS/MS. Eighty-three types of TAG were identified, in which 54 types contained MCFA and MLSL species with relatively high contents were 22:6–8:0–8:0 (6.8%), 8:0–8:0–16:0 (7.5%), and 16:0–16:0–8:0 (7.5%). This product rich in MLSL with DHA and MCFA in the same TAG molecule is beneficial for fat digestion and absorption in infant and thus can increase the bioavailability of DHA at the molecular level.     

Interactions between medium-chain and long-chain triacylglycerols in lipid and energy metabolism in growing chicks

The combined effects of dietary medium-chain triacylglycerols (MCT) and long-chain triacylglycerols (LCT) on lipid and energy utilization in chicks were investigated. Corn oil was used as the LCT source, and trioctanoin (8∶0) was used as the MCT source. The efficiency of dietary energy utilization (such as metabolizable energy values and fat and energy retention) decreased linearly as the level of MCT increased, but the efficiency of dietary protein utilization (protein retained per protein consumed) was not affected in a consistent manner. Fecal saturated and monounsaturated fatty acid composition was dependent on the dietary fatty acid composition, whereas fecal linoleic acid content was not. It is concluded that dietary MCT and LCT influence each other to some degree, with respect to protein and lipid metabolism in chicks. Moreover, in most cases, the nutritional characteristics of each triacylglycerol, including food efficiency and fat and energy retention, are independent of each other in growing chicks.     

Medium‐chain fatty acids – Nutritional function and application to cooking oil

Medium‐chain fatty acids, which are saturated fatty acids composed of 8–10 carbons, have unique nutritional characteristics different from those of long‐chain fatty acids. Medium‐chain triacylglycerol (MCT) is more readily digested and absorbed than long‐chain triacylglycerol (LCT), and easily utilized as energy. The use of MCT as an edible oil is limited because it has a low smoking point and easily foams during deep‐frying like lauric acid does. Medium‐ and long‐chain triacylglycerol (MLCT) prepared by transesterification between MCT and LCT has a higher smoking point and reduced foaming property. MLCT oil has been shown to result in less body fat accumulation in animal and human studies. It has been approved as a food for specified health use (FOSHU) and widely sold in Japan as a cooking oil less likely to lead to body fat accumulation.     

Fat Utilization in Healthy Subjects Consuming Diacylglycerol Oil Diet: Dietary and Whole Body Fat Oxidation

Several studies in animals and humans have reported beneficial effects of diacylglycerol (DAG) on lipid and energy metabolism. We assessed the effect of DAG versus triacylglycerol (TAG) treatment on total energy expenditure (TEE), total fat oxidation (Fox) and respiratory quotient (RQ), and measured the oxidation rate of each oil using a respiratory chamber and the 13C-stable isotope. Eleven healthy subjects participated in a double-blind, randomized crossover study. Subjects consumed an energy maintenance diet consisting of 55% of total calories from carbohydrate, 15% from protein and 30% from fat during both the 3-day pre-chamber and 36-h chamber period. Fifty percent of the fat was test oil, containing either DAG oil or TAG oil. The oxidation rate of ingested test oils was determined by monitoring 13CO2 excretion in the breath from 13C-labeled diolein or 13C-labeled triolein. There were no significant differences in TEE, RQ and total Fox between the DAG and TAG treatment in the overall analysis. In the subgroup analysis, DAG treatment decreased RQ significantly in subjects with a high fat ratio (HFR) compared to TAG treatment. In addition, ingested diolein oxidation in DAG treatment was significantly faster than triolein oxidation in TAG treatment in the HFR group. Enhanced fat utilization with DAG treatment and rapid oxidation of ingested DAG may, at least in part, explain the greater loss of body weight and body fat related to DAG consumption found in the weight-loss studies.     

Determination and Structural Elucidation of Triacylglycerols in Krill Oil by Chromatographic Techniques

The content of triacylglycerols (TAG) in krill oil is generally omitted from the labels of commercial supplements and unacknowledged in studies aimed at proving its health benefits. The present study demonstrates that TAG compounds, in addition to phospholipids and lysophospholipids, are an important lipid class in pure krill oil. The fatty acid composition of TAG molecules from krill oil and their distribution on the backbone of TAG structures were determined by gas chromatography and liquid chromatography tandem mass spectrometric, respectively. The content of omega 3 polyunsaturated fatty acids (n-3 PUFA) was similar to those reported in the literature for fish oil. It was estimated that 21 % of n-3 PUFA were at the sn-2 position of TAG structures. To our knowledge, this is the first determination and structural characterization of TAG in pure krill oil supplements.     

Triacylglycerols and Polar Lipids in Cow and Goat Milk are Differentially Affected by Various Lipid Supplemented Diets

This study characterizes milk triacylglycerol (TAG) and polar lipid (PL) fractions from cows and goats fed various lipid supplements modulating milk fat content. Twelve Holstein cows and 12 Alpine goats, at 86 ± 24.9 and 61 ± 1.8 days in milk, respectively, are allocated to one of 4 groups to receive diets supplemented with either corn oil [5% dry matter intake (DMI)] plus wheat starch (COS), marine algae powder (MAP; 1.5% DMI) or hydrogenated palm oil (HPO; 3% DMI), or a no-added-lipid control diet (CTL), according to a 4 × 4 Latin square design with 28 d experimental periods. Milk TAG and PL contents are determined by liquid chromatography-mass spectrometry (LC-MS). Multivariate analysis and ANOVA demonstrate major between-species differences in diet effects. In cows, COS specifically increases TAG 54:3 and 54:4 associated with milk fat depression (MFD), and increases the sum of phosphatidylcholines (PC) and phosphatidylinositols (PI). In addition to causing a MFD, MAP diet increases long-chain polyunsaturated TAG in both species, with higher magnitude in cows than in goats, and decreases the sum of PI in goats. HPO increases TAG 52:1 and the sum of PI in cows, but not in goats. Practical applications: Feed strategies can quickly and efficiently modulate the ruminant milk fat production and composition to improve nutritional quality for consumers. Certain starch-rich diets supplemented with polyunsaturated fatty acids (PUFA)-rich vegetable oils and diets supplemented with marine products (long-chain PUFA) reduce milk fat secretion and modify the milk fatty acid (FA) profile in cows, but not—or less so—in goats. Advanced analysis of both the TAG and PL fractions of milk fat is required to unravel these differences in lipid metabolism between cows and goats fed various lipid-supplemented diets. This study brings new insight on using nutritional strategies to control milk lipid composition according to ruminant species.     

Triacylglycerols Oxidation in Oils and Fats Monitored by Easy Ambient Sonic-Spray Ionization Mass Spectrometry

Oxidation is the major cause of fat and oil deterioration which produces rancid and unpleasant flavors that drastically reduces their quality and nutritional value. The primary oxidation products are triacylglycerols (TAG) containing unsaturated fatty acyl hydroperoxides formed by a chain process occurring through free radical intermediates. The Rancimat method is currently the gold standard for measuring the oxidative stability of oils and fats. In this report, easy ambient sonic-spray ionization mass spectrometry (EASI-MS) is demonstrated to function as a direct (no pre-separation or sample preparation steps), fast and accurate method to monitor oils and fats oxidation, providing detailed overviews of the most immediate TAG hydroperoxide products. The EASI-MS results were compared to those obtained via the classical Rancimat test.     

Lipidemic effects of an interesterified mixture of butter, medium-chain triacylglycerol and safflower oils

The objective of this study was to determine if the positional structure of dietary triacylglycerol affected lipidemic responses. Thirty healthy adults (16 men and 14 postmenopausal women) with low-density lipoprotein cholesterol (LDL-C) concentrations >3.37 mM (130 mg/dl) enrolled in a prospective, single-blind, cross-over outpatient clinical trial that consisted of two 5-wk dietary phases. After baseline screening, subjects were instructed to follow individualized meal plans (weight maintenance diets with 36% of total energy from fat, half of which was from a test oil) and randomized to receive either butter (B) or an interesterified mixture (IM) of butter, medium-chain triacylglycerol (MCI), and safflower oils. Blood drawn during weeks 5 and 10 of feeding was analyzed for total cholesterol (TC), high density lipoprotein cholesterol (HDL-C), LDL-C, and triacylglycerols (TAG). Mean plasma levels of TC (B, 6.98±1.06 mM; IM, 7.09±1.20 mM), HDL-C (B,1.30±0.35 mM; IM, 1.29±0.34 mM), and LDL-C (B, 4.91±0.95 mM; IM, 492±1.10 mM) were not significantly different between the two dietary treatments. Mean TAG levels were higher for the interesterified B-MCT mixture (B, 1.75±0.72 mM; IM, 1.96±0.86 mM, P<0.05). We conclude that an IM of B, MCT and safflower oils as compared to native B has no appreciable effect on plasma cholesterol concentrations but is associated with a modest rise in plasma TAG.     

Plant Stanol Supplementation Decreases Serum Triacylglycerols in Subjects with Overt Hypertriglyceridemia

Evidence is accumulating that high serum concentrations of triacylglycerols (TAG) are, like LDL cholesterol, causally related to cardiovascular disease. A recent meta-analysis has indicated that plant stanol ester (PSE) intake not only lowered LDL cholesterol, but also serum TAG concentrations, especially in subjects with high baseline TAG concentrations. We therefore evaluated the effects of PSE supplementation on lipid metabolism in a population with elevated fasting TAG concentrations. In a randomized, placebo-controlled, parallel study, 28 subjects with elevated TAG concentrations (>1.7 mmol/L) were studied. After a 1-week run-in period during which a control margarine was used, subjects consumed for 3 weeks either control or PSE-enriched margarine (2.5 g/day of plant stanols). Serum plant stanol concentrations increased in all subjects receiving the PSE-enriched margarines, demonstrating good compliance. PSE supplementation significantly decreased serum total (6.7%, P = 0.015) and LDL cholesterol (9.5%, P = 0.041). A significant interaction between baseline TAG concentrations and PSE intake was found; PSE intake lowered TAG concentrations, particularly in subjects with high baseline TAG concentrations (>2.3 mmol/L; P = 0.009). Additionally, a significant interaction between baseline total number of LDL particles (LDL-P) and PSE intake was found (P = 0.020). PSE consumption lowered LDL-P, primarily in subjects with elevated baseline values; this was mainly due to a non-significant decrease in the number of atherogenic small LDL-P. Circulating levels of hs-CRP, glucose, and insulin were not changed after PSE intake. Taken together, PSE supplementation not only lowered LDL cholesterol, but also serum TAG concentrations, especially in subjects with overt hypertriglyceridemia.     

Lymphatic transport of a physical mixture of medium-and long-chain TAG in rats

Lymphatic transport of a mixture of medium-chain TAG (MCT) and long-chain TAG (LCT) was studied in lymph-cannulated rats. Animals were administered a test emulsion containing either triolein, tricaprylin, or a 1∶1 mixture of triolein and tricaprylin, and the lymph was collected for 24 h. The lymphatic recovery rate of medium-chain FA (MCFA) was significantly higher in rats given the TAG mixture than in those given MCT alone. The lymphatic recovery rate of long-chain FA (LCFA) also was significantly higher in rats given the TAG mixture than in those given LCT alone. No TAG containing three MCFA (i.e., MCT) was detected, and 37.7% of TAG containing one or two MCFA was detected in the lymph TAG when rats were given the TAG mixture. These results indicate that lymphatic transport of MCFA and LCFA can be modified by the combination of MCT and LCT.     

Relationships between Very Low-Density Lipoproteins–Ceramides, −Diacylglycerols,and –Triacylglycerols in Insulin-Resistant Men

This short report describes the relationships between concentrations of ceramides (CER), diacylglycerols (DAG), triacylglycerols (TAG) in very low-density lipoproteins (VLDL) particles, and hepatic lipid accumulation. VLDL particles were isolated from male subjects (n = 12, mean ± SD, age 42.1 ± 5.4 years, BMI 37.4 ± 4.1 kg/m², ALT 45 ± 21 U/L) and apolipoprotein B100 (apoB100), VLDL-TAG, -CER, and -DAG quantified. The contents of all three lipids were highly correlated with VLDL particle number (r ≥ 0.768, p ≤ 0.003). The molar quantity of VLDL-TAG was 3× that of DAG and 137× that of CER (14,053 ± 5714, 5004 ± 2714, and 105 ± 49 mol/mol apoB100, respectively). Reduced VLDL-CER concentrations were associated with both higher insulin levels (r = −0.645, p = 0.024) and intrahepatic-TAG (r = −0.670, p = 0.017). In fatty liver, the secretion of hepatic TAG, CER, and DAG may be suppressed and contribute to intrahepatic lipotoxicity. The mechanisms by which hepatic-CER and -DAG synthesis and assembly into VLDL is coordinately controlled with TAG will be important in understanding the emerging role of elevated CER contributing to cardiometabolic disease.     

Synthesis of Chlorinated and Non-chlorinated Polyols from Model Cross-Metathesis Modified Triacylglycerols

Three pure triacylglycerols (TAG) containing decenoic acid (D), and stearic acid (S), were hydroxylated into chlorinated and non-chlorinated polyols and studied in detail. D is a fatty moiety that can result from the cross metathesis of small olefins with common vegetable oils such as soybean oil. A fundamental understanding relating chemical composition and derived structure, particularly the number and position of the hydroxyl groups, to physical properties was established allowing us to add some perspective to the growing body of knowledge on industrially relevant polyol and polyurethane systems produced with metathesis-modified TAG (MTAG). The hydroxyl value, crystallization and melting behaviors, thermal degradation behavior of the polyols were directly related to their peculiar shortened and primary functionality inherited from the parent MTAG. The effect of regiochemistry on the physical properties of the polyols was investigated with the chromatography fractions of the trichlorinated polyol of propane-1,2,3-triyl tris(dec-9-enoate), giving an unhindered insight into the role of short and terminal functionality of MTAG polyols that will help select the optimal isomer composition for designer polyurethane materials.     

Formation of Acrolein in the Autoxidation of Triacylglycerols with Different Fatty Acid Compositions

Fish, echium, linseed, and soybean oil triacyglycerols (TAGs) were oxidized at 50 or 60 °C to determine the effect of the polyunsaturated fatty acid composition on the volatile product formation. The analysis of the oxygen consumption and total volatile formation demonstrated that the soybean oil TAG had the highest oxidative stability followed by linseed, echium, and fish oil TAGs. Our results were in agreement with the expected average number of bis‐allylic positions of each TAG. Higher quantities of acrolein (2‐propenal) and propanal were detected using the static headspace gas chromatography method at the early stages of oxidation of echium and fish oil TAGs; however, a considerable amount of propanal and only a small amount of acrolein were found in the oxidized linseed oil TAG. The peak area ratios of acrolein to propanal were 0.115, 0.569, and 2.554 after the 8‐h oxidation of linseed, echium, and fish oil TAG, respectively, suggesting the preferential formation of acrolein, especially during the fish oil TAG oxidation. The acrolein quickly increased during the first stage of oxidation, but thereafter it either did not change or slightly decreased during the fish oil oxidation. Because fish oil induces flavor deterioration from the very early stage of the oxidation, the acrolein formation observed in the present study may be important for fish oil deterioration.     

Chemical and thermal characteristics of milk-fat fractions isolated by a melt crystallization

Anhydrous milk fat (AMF) was fractionated by a two-stage dry fractionation process to produce three fractions: high melting (HMF), middle melting (MMF), and low melting (LMF). The HMF (m.p. 42°C) exhibited a broad melting range similar to a plastic fat. The MMF (m.p. 33°C) resembled the original AMF (m.p. 31°C), but with slightly higher solid fat content. The LMF (m.p. 16°C) was liquid at ambient temperature. Differences in the thermal properties of these fractions were attributed to the triacylglycerols (TAG) and their fatty acid composition. Saturated TAG with carbon numbers of 36–54 were concentrated in the HMF; whereas unsaturated TAG of carbon number 36–54 predominated in the LMF. Likewise, the long-chain saturated fatty acids were significantly higher and the long-chain unsaturated fatty acids were significantly lower in the HMF fraction. Binary blends of milk-fat fractions with a range of melting profiles were produced by mixing HMF with AMF, MMF, or LMF. Laboratory-prepared fractions were similar to commercially available fractions.     

Distribution of Triacylglycerols and Fatty Acids in Soybean Oil with Thermal Oxidation and Methylene Blue Photosensitization

Profiles of triacylglycerols (TAG) and fatty acids were compared in soybean oil thermally oxidized at 180 °C for 60 min or methylene blue photosensitized for 10 h. Headspace oxygen in thermally oxidized and photosensitized soybean oil decreased significantly (p < 0.05) as oxidation time increased. Relative contents of linoleic and linolenic acids decreased and those of oleic acid increased during oxidation. In both thermal and photosensitized oxidation, TAG with lower than 44 equivalent carbon number including dilinoleoyllinolenoylglycerol (LLLn, 40), trilinolein (LLL, 42), oleoyllinoleoyllinolenoylglycerol (OLLn, 42), dilinoleoyloleoylglycerol (LLO, 44), and dilinoleoylpalmitoylglycerol (PLL, 44) significantly decreased, while those with dioleoyllinoleoylglycerol (OOL, 46) increased significantly in relative peak areas (p < 0.05). Photosensitized oxidation decreased TAG containing linoleic and linolenic acids significantly faster than thermal oxidation in soybean oil (p < 0.05), which may be due to the singlet oxygen reaction. Photosensitized soybean oils can be differentiated from thermally oxidized samples using the distributions of TAG by principal component analysis.     

Absorption difference between diacylglycerol oil and butter blend containing diacylglycerol oil

This study aims at investigating whether the intake of butter blends containing diacylglycerol (DAG) oil may result in reduced fat accumulation, in similarity to DAG oil, and the potential metabolic differences between butter blends and DAG oil. Four experimental diets containing either 10 wt% DAG butter blend (BDAG), triacylglycerol (TAG) butter blend (BTAG), DAG oil (ODAG) or TAG oil (OTAG) were prepared, and each was fed to a group of 8 male Wistar rats. The design of the experiment was a combined balance and feeding experiment. The rats fed the BTAG and ODAG‐diets had a significantly higher protein content than rats fed the BDAG and OTAG‐diets, and the fat content was significantly lower in rats fed the ODAG‐diet as compared to rats fed the OTAG and BDAG‐diets. A significantly higher content of ash was observed in rats fed the two TAG diets. The ratio of abdominal fat weight/body weight was significantly higher for rats fed the BDAG‐diet than for rats fed the BTAG and ODAG‐diets. To conclude, the beneficial effects of DAG oil in reducing body fat accumulation cannot be observed in DAG oil containing butter blends, and the effect of DAG on bone health requires further investigation.     

Lipidomic Profiling of Chylomicron Triacylglycerols in Response to High Fat Meals

Using lipidomic methodologies the impact that meal lipid composition and metabolic syndrome (MetS) exerts on the postprandial chylomicron triacylglycerol (TAG) response was examined. Males (9 control; 11 MetS) participated in a randomised crossover trial ingesting two high fat breakfast meals composed of either dairy-based foods or vegetable oil-based foods. The postprandial lipidomic molecular composition of the TAG in the chylomicron-rich (CM) fraction was analysed with tandem mass spectrometry coupled with liquid chromatography to profile CM TAG species and targeted TAG regioisomers. Postprandial CM TAG concentrations were significantly lower after the dairy-based foods compared with the vegetable oil-based foods for both control and MetS subjects. The CM TAG response to the ingested meals involved both significant and differential depletion of TAG species containing shorter- and medium-chain fatty acids (FA) and enrichment of TAG molecular species containing C16 and C18 saturated, monounsaturated and diunsaturated FA. Furthermore, there were significant changes in the TAG species between the food TAG and CM TAG and between the 3- and 5-h postprandial samples for the CM TAG regioisomers. Unexpectedly, the postprandial CM TAG concentration and CM TAG lipidomic responses did not differ between the control and MetS subjects. Lipidomic analysing of CM TAG molecular species revealed dynamic changes in the molecular species of CM TAG during the postprandial phase suggesting either preferential CM TAG species formation and/or clearance.