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Medium‐chain fatty acids – Nutritional function and application to cooking oil
Abstract
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.
... Although C4 : 0 occurs at the relatively low content of 3-4% by weight of total milk fatty acids (MacGibbon and Taylor 2006), about onethird of all milk fat triacylglycerol molecules contains a C4 : 0 residue (Parodi 1970). Fatty acids of chain length C4 : 0 to C10 : 0 present within triacylglycerol are readily hydrolysed, absorbed directly in to the portal blood stream, and transported to the liver where they are rapidly metabolised in to energy (Takeuchi et al. 2008). Consequently, they are less likely to accumulate as body fat and contribute to obesity. ...
Effect of herd nutrition, time of year and season of calving on milk fat composition and physical properties were examined on irrigated commercial dairy farms in northern Victoria that made use of split-calving and a diverse range of feeding systems. Twenty-four farms were included in the study, and from each farm, morning and evening milk samples were collected from 16 cows that calved in autumn and 16 cows that calved in spring. There were no significant effects of season of calving on the concentration of fatty acids or phospholipids in milk fat, but there were interactions between season of calving and time of year (P<0.001). These differences could be attributed to changes in energy balance and body condition with stage of lactation. The phospholipids comprising mainly phosphotidylcholine (PC), phosphtidylethanolamine (PE) and sphingomyelin (SP) also varied, with PC and PE being highest in late lactation and SP lowest during peak and mid lactation for both calving groups. Milk fat colour and the concentrations of free fatty acids were more influenced by factors associated with time of year rather than stage of lactation. Milk fat colour in particular showed strong seasonal variation being distinctly lighter in summer-early autumn when compared with rest of the year. Increasing the amount of concentrates fed was associated with decreases in short-chain fatty acid concentration and increases in the solid fat content of milk fat. Variations in nutritional management practices had only small (non-significant) effects on fat composition.
... The long-term safety of medium-chain fatty acids in laboratory animals and humans was also confirmed in the period of 1950-60s, and its clinical application for mal-digestion/ mal-absorption syndrome was initiated. Currently, medium chain fatty acids (MCFA) containing TAG (MCT) is used as powdered oil, cooking oil, therapeutic diets, internal nutrients and transfusion solutions (Takeuchi et al. 2004). ...
Structured lipids were prepared from mustard oil by enzymatic acidolysis reaction with capric acid (C10) using lipase enzyme TLIM from Thermomyces lanuginosus as biocatalyst. Parameters such as substrate molar ratio, enzyme concentration, reaction temperature, stirring speed and time of maximum incorporation, were studied for the optimization of the reaction. The optimized set of process conditions was predicted by response surface methodology (RSM) and genetic algorithm (GA). The robustness of GA and RSM was evaluated using regression coefficient and p value. The R2 found out by GA was 0.996 while from RSM was 0.973. The results proved that GA models have better performance than RSM models. From the result, it could be concluded that optimal conditions for synthesis of capric acid rich mustard oil were: Temperature = 39.5 °C ; time = 21.1 hr; Substrate ratio = 3.5; Enzyme content = 8.8%; Speed = 570.8 rpm.
... Meanwhile, compared with the long-chain triacylglycerols, MCTs are digested more easily and absorbed more rapidly in the body (Papamandjaris et al., 1998;Tsuji et al., 2001;Han et al., 2003). It is reported that MCTs increase energy expenditure and lower body fat (Takeuchi et al., 2008). Therefore, many researchers focus on incorporation of MCT oil into new functional lipids (Adhikari et al., 2010a(Adhikari et al., , 2012Tang et al., 2012). ...
Zero-trans interesterified fats were produced from camellia seed oil (CSO), palm stearin (PS) and coconut oil (CO) with three weight ratios (CSO/PS/CO, 50:50:10, 40:60:10 and 30:70:10) using Lipozyme TL IM. Results showed that the interesterified products contained palmitic acid (34.28–42.96%), stearic acid (3.96–4.72%), oleic acid (38.73–47.95%), linoleic acid (5.92–6.36%) and total medium-chain fatty acids (MCFA)s (∑MCFAs, 5.03–5.50%). Compared with physical blends, triacylglycerols of OOO and PPP were decreased and formed new peaks of equivalent carbon number (ECN) 44 in the interesterified products. The product CPC3′ showed a slip melting point of 36.8 °C and a wide plastic range of solid fat content (SFC) (45.8–0.4%) at 20–40 °C. Also, the major β′ form was determined. These data indicated that the zero-trans interesterified fats would have a potential functionality for margarine fats. Subsequently, the antioxidative stabilities of interesterified products with the addition of α-tocopherol (α-TOH) and ascorbyl palmitate (AP) were investigated. The results indicated that AP had a dose-dependent effect at concentrations of 100, 200 and 400 ppm.
Lipid concomitants are the main trace substances that determine the oxidative stability of oils. Over 90% of oils are composed of triglycerides, which affect oxidative stability. Oils typically enter living organism as emulsions. This study investigated the physical properties and cellular antioxidant activity (CAA) of emulsions in two model oils, namely, rice bran oil (RBO) with long-chain unsaturated triglycerides and coconut oil (CNO) with medium-chain saturated triglycerides. The results were as follows: the mean particle sizes were all approximately 250 nm; the polydispersity index (PDI) values were below 0.2; and the zeta potential values were more negative than −30 mV. The droplet size distribution of CNO emulsions was more concentrated than that of RBO emulsions. Rice bran oil-S (RBO-S) emulsions exhibited the highest CAA value, but the CAA value of coconut oil-C (CNO–C) emulsions was higher than that of rice bran oil-D (RBO-D) emulsions, indicating that CAA was influenced by the combined effect of triglycerides and minor constituents. Moreover, the medium-chain saturated triglycerides in vegetable oil emulsions resulted in a stronger CAA than that of long-chain saturated triglycerides.
Obesity is related to an increasing risk of chronic diseases. Medium- and long-chain triacylglycerols (MLCT) have been recognized as a promising choice to reduce body weight. In this study, three MLCT with different contents of medium-chain fatty acids (MCFA) (10%-30%, w/w) were prepared, and their effects on lipid metabolism and fecal gut microbiota composition of C57BL/6J mice were systematically investigated. MLCT with 30% (w/w) MCFA showed the best performance in decreasing body weight gain as well as optimizing serum lipid parameters and liver triacylglycerol content. The expression levels of genes encoding enzymes for fatty acid degradation increased markedly and expression levels of genes encoding enzymes for de novo fatty acid biosynthesis decreased significantly in the liver of mice treated with MLCT containing 30% (w/w) MCFA. Interestingly, the dietary intake of a high fat diet containing MLCT did significantly decrease the ratio of Firmicutes to Bacteroidetes and down-regulate the relative abundance of Proteobacteria that may attribute to the weight loss. Furthermore, we found a notable increase in the total short-chain fatty acid (SCFA) content in feces of mice on a MLCT containing diet. All these results may be synergistically responsible for the anti-obesity effect of MLCT with relatively high contents of MCFA.
Lauric fat blends could be prepared from formulation of different melting triacylglycerol (TAG) group to obtain various desired SFC profiles as required by different fat rich products such as margarine and shortening. At the interval temperature from 0 to 20 °C, an increase ratio of body and heated (BH) melting TAG group in the fat blends imposed higher SFC values with steeper SFC slopes. Meanwhile, at the interval temperature from 20 to 40 °C, an increase ratio of heated (H) melting TAG group resulted higher SFC values with comparable SFC slopes. The use of Palm Stearin (PS) or Fully Hydrogenated Rapeseed Oil (FHRO) as the hard fat gave comparable SFC profiles but the fat blends with FHRO melted completely (SFC 0 %) at higher temperature (60 °C) while those of PS did not. In addition, the crystallization and melting behaviors of lauric fat blends as measured by DSC were influenced by different ratio of TAG distribution formulated at H15 (varied BH) and BH50 (varied H). Fat blends with PS also showed different crystal morphology compared to those with FHRO as measured by PLM.
Medium-chain triglycerides (MCTs), sunflower seed oil, soybean oil, rapeseed oil and n-hexane were used as co-solvents to promote supercritical carbon dioxide (SC-CO2) extraction of lutein esters from marigold (Tagetes erecta L.). The steepest ascent method was used to determine the most effective co-solvent in improving the extraction yield, followed by an application of response surface methodology (RSM) to optimize SC-CO2 extraction conditions with the best co-solvent—MCT. The results showed that the second-order polynomial model could well describe and predict the responses of lutein ester yield. The independent variable of pressure, the quadratics of temperature, pressure and concentration of MCT, and the interaction between pressure and concentration of MCT were most influential on the yield of lutein esters. The optimum extraction conditions within the experimental range were predicted to be: extraction pressure of 46.8MPa, temperature of 65.9°C and MCT concentration of 1.5% (w/w of CO2), with a CO2 flow rate of 10kg/h and extraction time of 3h. The maximum yield of lutein esters under these conditions was predicted to be 1263.62mg/100g marigold.
It is known that Cinnamomum camphora seed oil (CCSO) is rich in medium-chain fatty acids (MCFAs) or medium-chain triacylglycerols (MCTs). The purpose of the present study was to produce zero-trans MCTs-enriched plastic fat from a lipid mixture (500 g) of palm stearin (PS) and CCSO at 3 weight ratios (PS:CCSO 60:40, 70:30, 80:20, wt/wt) by using lipase (Lipozyme TL IM, 10% of total substrate) as a catalyst at 65 °C for 8 h. The major fatty acids of the products were palmitic acid (C16:0, 42.68% to 53.42%), oleic acid (C18:1, 22.41% to 23.46%), and MCFAs (8.67% to 18.73%). Alpha-tocopherol (0.48 to 2.51 mg/100 g), γ-tocopherol (1.70 to 3.88 mg/100 g), and δ-tocopherol (2.08 to 3.95 mg/100 g) were detected in the interesterified products. The physical properties including solid fat content (SFC), slip melting point (SMP), and crystal polymorphism of the products were evaluated for possible application in shortening or margarine. Results showed that the SFCs of interesterified products at 25 °C were 9% (60:40, PS:CCSO), 18.50% (70:30, PS:CCSO), and 29.2% (80:20, PS:CCSO), respectively. The β' crystal form was found in most of the interesterified products. Furthermore, no trans fatty acids were detected in the products. Such zero-trans MCT-enriched fats may have a potential functionality for shortenings and margarines which may become a new type of nutritional plastic fat for daily diet.
To develop an easy-energy-supply agent, medium-chain fatty acids (MCFAs) liposomes were prepared by thin-layer dispersion, freeze-thawing and dynamic high pressure microfluidization (DHPM)-freeze-thawing methods. Results showed that MCFAs nanoliposomes obtained by the novel method (DHPM-freeze-thawing) exhibited a smaller size (72.6 ± 4.9 nm), narrower size distribution (PDI = 0.175 ± 0.005), higher zeta potential (-41.27 ± 1.16 mV) and entrapment efficiency (45.9 ± 6.0%) compared to the other two methods. In the weight-loaded swimming test of the mice, the high-dose group of MCFAs nanoliposomes indicated a significantly longer swimming time (105 ± 31 min, p < 0.05), a lower serum urea nitrogen (839.5 ± 111.9 mg/L, p < 0.05) and blood lactic acid (5.7 ± 1.0 mmol/L, p ≤ 0.001), and a higher hepatic glycogen (15.0 ± 3.6 mg/g, p ≤ 0.001) than those of the control group (53 ± 13 min, 1153.6 ± 102.5 mg/L, 12.5 ± 1.9 mmol/L and 8.8 ± 3.3 mg/g, respectively). However, no significant difference was found between the high-dose group and MCFAs group. The results suggested that MCFAs nanoliposomes could be used as a potential easy-energy-supply agent.
Medium-chain fatty acids (MCFA) are widely used in diets for patients with obesity. To develop a delivery system for suppressing dietary fat accumulation into adipose tissue, MCFA were encapsulated in nanoliposomes (NL), which can overcome the drawbacks of MCFA and keep their properties unchanged. In the present study, crude liposomes were first produced by the thin-layer dispersion method, and then dynamic high-pressure microfluidisation (DHPM) and DHPM combined with freeze-thawing methods were used to prepare MCFA NL (NL-1 and NL-2, respectively). NL-1 exhibited smaller average size (77.6 (SD 4.3) nm), higher zeta potential (- 40.8 (SD 1.7) mV) and entrapment efficiency (73.3 (SD 16.1) %) and better stability, while NL-2 showed narrower distribution (polydispersion index 0.193 (SD 0.016)). The body fat reduction property of NL-1 and NL-2 were evaluated by short-term (2 weeks) and long-term (6 weeks) experiments of mice. In contrast to the MCFA group, the NL groups had overcome the poor palatability of MCFA because the normal diet of mice was maintained. The body fat and total cholesterol (TCH) of NL-1 (1.54 (SD 0.30) g, P = 0.039 and 2.33 (SD 0.44) mmol/l, P = 0.021, respectively) and NL-2 (1.58 (SD 0.69) g, P = 0.041 and 2.29 (SD 0.38) mmol/l, P = 0.015, respectively) significantly decreased when compared with the control group (2.11 (SD 0.82) g and 2.99 (SD 0.48) mmol/l, respectively). The TAG concentration of the NL-1 group (0.55 (SD 0.14) mmol/l) was remarkably lower (P = 0.045) than the control group (0.94 (SD 0.37) mmol/l). No significant difference in weight and fat gain, TCH and TAG was detected between the MCFA NL and MCFA groups. Therefore, MCFA NL could be potential nutritional candidates for obesity to suppress body fat accumulation.
As a fat source in our diet, medium-chain triglycerides (MCTs) result in lower fat deposition when compared by 2 methods to long-chain triglycerides. Using data from 10 animal studies, the calculated energy loss during utilization of MCTs was 16%, resulting in a net energy value (NEV) of 6.97 kcal/g. The NEV calculated from the molecular composition of 9 MCTs with widely varying caprylic:capric fatty acid ratios was 6.72 ± 0.16 kcal/g. For 5 MCTs with completely defined fatty acid compositions, the NEV was 6.80 ± 0.15 kcal/g. Establishing the NEV for dietary MCTs at 6.8 kcal/g is proposed.
The effects of a liquid-formula diet supplement containing structured medium- and long-chain triacylglycerols (SMLCT) composed of medium- (10%) and long-chain (90%) fatty acids were compared with those of long-chain triacylglycerols (LCT) on bodyfat accumulation in 13 healthy male volunteers aged 18–20 years. The subjects were randomly assigned the SMLCT or LCT group. The subjects in each group received a liquid-formula diet supplement of the SMLCT or LCT, which provided 1040 kJ plus daily energy intake for 12 weeks. Mean energy intake containing liquid diet throughout the 12-week period did not differ between the SMLCT and LCT groups. Bodyweight of subjects in both groups increased slightly from the baseline throughout the 12-week period, but the differences were not significant. Rates of variation of bodyfat percentage were significantly lower in the SMLCT group than in the LCT group throughout the 12-week period. Comparisons between the SMLCT and LCT groups at baseline and 12 weeks showed no significant differences in any of the biochemical blood parameters. These results suggest that replacing LCT with SMLCT over long periods of time could produce bodyfat loss in the absence of reduced energy intake.
The purpose of this study was to investigate the hypothesis that a single dose of structured medium- and long-chain triacylglycerols (SMLCTs) composed of medium-chain (20%) and long-chain (80%) fatty acids would increase the metabolic rate more than a dose of long-chain triacylglycerols (LCTs) in 15 healthy young women aged 18 to 28 years. The effects on postingestive energy expenditure were compared for SMLCTs versus LCTs. On the experimental days, the subjects fasted overnight and then ingested 1,680 kJ SMLCTs or LCTs each day. Energy expenditure and the respiratory quotient (RQ) were measured before and after SMLCT and LCT ingestion by indirect calorimetry. Blood samples were collected before and after ingestion to obtain plasma and serum. Postingestive total energy expenditure (PTEE) was significantly higher after SMLCT ingestion versus LCT ingestion (26.9 +/- 1.0 v 25.5 +/- 1.1 kJ/kg/6 h, P < .05). The thermic effects of the test oil were also significantly greater after SMLCT ingestion compared with LCT ingestion (3.02 +/- 0.49 v 1.47 +/- 0.82 kJ/kg/6 h, P < .01). Plasma glucose and serum triacylglycerol concentrations were not significantly different. Serum free fatty acid and 3-hydroxybutyric acid concentrations were higher after SMLCT ingestion versus LCT ingestion. These results suggest that long-term substitution of SMLCTs for LCTs will produce body fat loss if energy intake remains constant.
Effect of triacylglycerols containing medium- and long-chain fatty acids (TML) on body fat accumulation was studied in rats. Male Wistar rats were fed an experimental diet containing 25% soybean oil or TML for 6 weeks. The food intake for 6 weeks did not significantly differ between the two diet groups. However, the perirenal and mesenteric adipose tissue weight and carcass fat content were significantly lower in the TML diet group than in the soybean oil diet group. The epididymal adipose tissue weight and liver triacylglycerol content did not significantly differ between the two diet groups. The digestibility of dietary fat did not significantly differ between the two diet groups. These results suggest that an intake of TML decreases body fat accumulation compared to an intake of soybean oil in rats.
We investigated the effect of long-term ingestion of dietary medium-chain triacylglycerols (MCT) on body weight and fat in humans. Using a double-blind, controlled protocol, we assessed the potential health benefits of MCT compared with long-chain triacylglycerols (LCT) in 78 healthy men and women [body mass index (BMI) > or = 23 kg/m(2): n = 26 (MCT), n = 30 (LCT); BMI < 23 kg/m(2): n = 15 (MCT), n = 7 (LCT)]. Changes in anthropometric variables, body weight and body fat during the 12-wk MCT treatment period were compared with those in subjects consuming the LCT diet. The subjects were asked to consume 9218 kJ/d and 60 g/d of total fat. The energy, fat, protein and carbohydrate intakes did not differ significantly between the groups. Body weight and body fat in both groups had decreased by wk 4, 8 and 12 of the study. However, in the subjects with BMI > or = 23 kg/m(2), the extent of the decrease in body weight was significantly greater in the MCT group than in the LCT group. In subjects with BMI > or = 23 kg/m(2), the loss of body fat in the MCT group (-3.86 +/- 0.3 kg) was significantly greater than that in the LCT group (-2.75 +/- 0.2 kg) at 8 wk. In addition, in subjects with BMI > or = 23 kg/m(2), the decrease in the area of subcutaneous fat in the MCT group was significantly greater than that in the LCT group at wk 4, 8 and 12. These results suggest that the MCT diet may reduce body weight and fat in individuals (BMI > or = 23 kg/m(2)) more than the LCT diet.
We investigated whether a structured medium- and long-chain triacylglycerols (MLCT) diet could decrease accumulation of body fat in healthy humans. The study was conducted under a double-blind randomized design. Ninety-three subjects participated in this study. However, 10 subjects could not consume the specified meal, and one subject wished to opt out. Consequently, the study included 82 subjects. The experimental subjects consumed the test bread, which was made with 14 g of MLCT containing 1.7 g MCFA, daily at breakfast during the study period of 12 weeks, and the control subjects consumed bread made with long-chain triacylglycerols (LCT). All subjects consumed the same standard packaged meals. Body composition parameters were body weight, total body fat and abdominal fat, and blood analyses included serum cholesterol, triacylglycerols and phospholipids. Significant decreases of body weight, the amount of body fat, subcutaneous and visceral fat were noted in the MLCT group as compared with those of the LCT group for 12 weeks (P<0.05). Furthermore, a significant decrease in serum total cholesterol was noted in the MLCT group as compared with that of the LCT group at 8 weeks (P<0.05). However, other serum parameters were not different between the MLCT and LCT groups. The results suggest that the daily intake of MLCT diet could result in a reduction in body weight and in accumulation of body fat, and, moreover, it could reduce serum total cholesterol.