Lipase-catalyzed synthesis and characterization of flaxseed oil-based structured lipids

The biosynthesis of structured lipids (SLs) was carried out by the interesterification of flaxseed oil (FO) and tricaprylin (TC) in an organic solvent medium (OSM), using selected commercial lipases, including Amano DF, Novozym 435, Lipozyme TL-IM and Lipozyme RM-IM. The fatty acyl chains of the synthesized triacylglycerols (TAGs) were identified by atmospheric pressure chemical ionization/mass spectrometric (APCI/MS) analysis, while the fatty acid positional distribution of the MLM- and MML-SLs (M-medium and L-long chain fatty acids) was determined by silver-ion high-performance liquid chromatographic (Ag⁺/HPLC) analysis. The effects of reaction temperature (T_r, 30–50 °C), enzyme concentration (E_c, 0.5–4%, w/v), initial water activity (a_w, 0.05–0.43) and reaction time (R_t, 0–72 h) on the efficiency of the enzymes, were studied. The bioconversion yield (%) of the synthesized MLM- and MML-SLs was monitored under the established reaction parameters for each lipase. The maximum yield of MLM-SLs was obtained in the order, of Novozym 435 > Lipozyme TL-IM > Lipozyme RM-IM > Amano DF. Moreover, considering the ratio of the MLM- to MML-SLs produced by each enzyme, Novozym 435 and Lipozyme TL-IM were selected as the most effective enzymes for interesterification of FO and TC.     

Lipase-catalyzed synthesis of O-lauroyl l-serinamide and O-lauroyl l-threoninamide

O-Lauroyl l-serinamide and O-lauroyl l-threoninamide were synthesized with an immobilized lipase using lauric acid and l-serinamide or l-threoninamide in water-miscible organic solvents, of which 2-methyl-2-propanol gave the highest conversion of 93% for O-lauroyl l-serinamide at 50 mmol-l-serinamide/L and 100 mmol-lauric acid/L. The addition of 4 Å 1/16 molecular sieves at 50 mg/mL increased the conversion to 53% for O-lauroyl l-threoninamide at 50 mmol-l-threoninamide/L and 150 mmol-lauric acid/L in 2-methyl-2-butanol. The difference of conversion between the two products was exactly proportional to the difference of solubility of aminoacid amides.     

Methyl ketone production from copra oil by Penicillium roqueforti spores

Bioconversion of copra oil by two strains of Penicillium roqueforti spores was studied in the presence or absence of exogenous lipase. Without exogenous lipase action, methyl ketone productivities were weak: 33 ± 1.9 to 61 ± 2.4 μmol g⁻¹ of oil, respectively, for strains 1 and 2. This formation results from the bioconversion of free fatty acids present in copra oil and appears strain-dependent. The major ketone was 2-undecanone, reflecting the high concentration of dodecanoic acid in the substrate. After lipolysis of copra oil by a Candida cylindracea lipase, a large increase of methyl ketone productivities (912 ± 13 and 1935 ± 26 μmol g⁻¹ of oil, respectively) is noticed with 2-heptanone predominating. This observation could result from the selectivity of the lipase used in the bioconversion process, or from the preferential oxidation due to spore specificity. When the reaction time was increased, the amount of methyl ketones decreased and other volatile compounds were formed..     

Fatty acids and proximate composition of eight Thai edible terricolous insects

Fatty acid composition and proximate analysis of eight terricolous insects namely dung beetle (Copris nevinsoni Waterhouse), short tailed cricket (Brachytrupes portentosus Lichtenstein), june beetle (Holotrichia sp.), queen caste (Oecophylla smaragdina Fabricius), weaver ant (Oecophylla smaragdina Fabricius), termite (Termes sp.), longan stink bug (Tessaratoma papillosa), cicada (Meimuna opalifera Walker) were determined. Polyunsaturated fatty acid (PUFA) was the most predominant fatty acid found in all analyzed insects, followed by saturated fatty acid (SFA) and monounsaturated fatty acid (MUFA). The concentration of total PUFA ranged from 213 in cicada to 1514 mg/100 g in dung beetle. There were five PUFAs; 18:3n ? 3, 20:3n ? 6, 20:4n ? 6, 20:5n ? 3 and 22:6n ? 3 detected in the insect samples. Two fatty acids, 20:3n ? 6, and 20:4n ? 6 were found in all analyzed insects, while, 20:5n ? 3 was only detected in dung beetle which lives in herbivore faeces, at concentration of 300 mg/100 g accounted for 13% of total fatty acid. The SFA content in ranged from 234 in termite to 733 mg/100 g in dung beetle. Only one MUFA, 18:1 was detected in the all analyzed insects. The protein content of insects ranged from 37% in queen caste to 54% in dung beetle. The highest amount of carbohydrate (16%) was found in cicada. Lipid contents ranged from 5% in june beetle to 37% in queen caste, while ash contents of edible insects ranged from 2% in queen caste to 12% in june beetle. We suggest that the insect could be considered as a good nutritional food source especially for fat and protein.     

Effect of the addition of fatty acids on rice starch properties

The effect of the addition of the two fatty acids (stearic and linoleic acid) on starch pasting, thermal properties and the leaching of amylose during the gelatinization process are presented. The addition of stearic acid (C18:0) at 1.0% level (w/w, on the basis of starch) significantly changed starch pasting characteristics in peak viscosity (P < 0.05), breakdown (P < 0.001) and time to peak viscosity (P < 0.001) as measured by RVA. In contrast, the addition of linoleic acid (C18:2) showed less impact on the three RVA parameters. Thermal studies with DSC suggested that the addition of both fatty acids did not significantly influence the starch gelatinization behaviour as reflected in peak width and enthalpy but there was a decrease in peak temperature. However, the addition of the saturated fatty acid produced a significant decrease in the retrogradation endotherm (P < 0.01) compared to that of native starch. It is suggested that the saturated fatty acid complexes with amylose and is preferentially introduced into the starch granule. The double bond in the linoleic acid apparently hinders complexation. After complexation, hydrophobicity was further enhanced with the content of amylose in the hot-water soluble fraction being significantly reduced (P < 0.01) as determined by HPLC.     

Oil composition,mineral nutrient and fatty acid distribution in the lipid classes of underutilized oils of Trilepisium madagascariense and Antiaris africana from Nigeria

Trilepisium madagascariense (TM) and Antiaris africana (AA) are two underutilized plants from Nigeria. They have been subjected to standard analytical techniques in order to evaluate the proximate composition, physico-chemical properties, mineral nutrient, fatty acid composition and distribution in the lipid classes of the seeds and seed oils. The carbohydrate composition of these seeds are high; TM is 62.73 ± 0.30% and AA is 53.97 ± 0.50%. Iodine value of TM was found to be 46.10 ± 0.70 mg iodine/g while that of AA was 88.24 ± 0.50 mg iodine/g. The mineral composition of the seeds and the oils varied with K having the highest concentration in the seed and Na the highest concentration in the oils. Linoleic acid is the dominant fatty acid in the oil of AA with the highest composition in the neutral lipids while palmitic acid is the dominant fatty acid in oil of TM. Vitamin E, Gamma-Sitosterol, α and β-Amyrin, Lupeol, Stigmast-4-en-3-one, and hydrocarbons were isolated from these oils. The results of the proximate, mineral nutrient compositions, chemical characterization and fatty acid distribution of these seeds and seed oils shows their possibility as potential resources.     

Enrichment of the conjugated linoleic acid content of bovine milk fat by dry fractionation

This study investigated the effect of fat fractionation on the conjugated linoleic acid (cis-9, trans-11-C_18 : 2) content of bovine milk fat. Anhydrous milk fat was fractionated into hard and soft fractions using controlled cooling and agitation. Fractionation of milk fat pre-melted at 60°C using a temperature programme of 33–10°C and a cooling rate of 0.58°C h⁻¹ yielded a soft fraction containing 63.2% more conjugated linoleic acid (2.22 g 100 g⁻¹ FAME), which was also enriched in polyunsaturated fatty acids and vaccenic acid (trans-11-C_18 : 1) compared with the parent fat. Agitation following fractionation was found to have a negative effect on the conjugated linoleic acid content of the soft fraction. Refractionation of the soft fraction did not increase the yield of conjugated linoleic acid. The conjugated linoleic acid and trans fatty acid content of 26 selected food products ranging in milk fat content from 0 to 100% is reported. Conjugated linoleic acid concentrations ranged from 0 to 16.2 mg g⁻¹ fat and were generally lower than the trans fatty acid content which ranged from 0 to 155.7 mg g⁻¹ fat. Spreads containing vegetable oils contained higher trans fatty acid and lower conjugated linoleic acid contents than milk fat-containing products. This study highlights that a milk fat fraction enriched in conjugated linoleic acid may be achieved by dry fractionation.     

Microbiological and chemical changes during the manufacture of Kefir made from cows’ milk,using a commercial starter culture

The counts of total aerobic mesophilic bacteria, lactic acid bacteria (in three different culture media, M17 agar, MSE agar, and Rogosa agar) and yeasts, and some biochemical parameters (levels of lactose, glucose, galactose, L(+)- and D(−)-lactic acids, ethanol, titratable acidity and pH) were determined during 196 h of fermentation in five batches of Kefir made from cows’ milk using a commercial starter culture. Lactococcus spp. predominated during the first 48 h of fermentation (∼8 log₁₀ cfu g⁻¹); Lactobacillus spp. became the predominant species after 48 h (∼8.5 log₁₀ cfu g⁻¹). During the first 24 h of fermentation, the lactose content decreased from a mean value of 4.92% (w/w) to 4.02% (w/w); the concentration of L(+)-lactic acid increased from 0.01% to 0.76% (w/w) and the pH decreased to 4.24 over the same period. After 24 h of fermentation, the changes in the levels of lactose and L(+)-lactic acid, and in pH, occurred more slowly. Neither glucose nor galactose were detected during fermentation. The production of ethanol was limited, reaching a mean final value of 0.018% (w/w).     

Prediction of fatty acid composition using a NIRS fibre optics probe at two different locations of ham subcutaneous fat

NIR technology was used to analyze the fatty acid composition of fat tissue from conjugated linoleic acid fed pigs by direct application of a fibre optics probe on two different locations of subcutaneous fat. One hundred and fifty-three pigs were fed three different diets and the fatty acid profile of subcutaneous fat from Gluteus medius was analyzed using gas chromatography and FT-NIR in a longitudinal and transversal cut. Spectra were acquired using a Bruker Optics Matrix-F duplex spectrometer equipped with a fibre optics probe (IN-268-2). Total saturated, monounsaturated and polyunsaturated together as well as oleic and stearic fatty acids were predicted accurately (R² > 0.70), myristic, and linoleic fatty acids were predicted with lower accuracy (0.60 < R² < 0.70), while palmitic, asclepic and α-linolenic fatty acids were poorly predicted (R² < 0.60). Results indicated that NIR technology has potential as a rapid tool to discriminate carcasses from animals fed diets with different fatty acid composition by a direct measurement on the fat from the ham.     

Synthesis and Characterization of 2-monoacylglycerols from Canarium Oil (Canarium Indicum)

This paper studies synthesis and characterization of 2-monoacylglycerols (2-MAGs), generally used for structured lipid production. Synthesis used canarium oil by enzymatic reaction using immobilized lipase from Mucor miehei that has a specific activity on the sn-1 and 3 of the triacylglycerol structure. Characterization of 2-MAGs by thin layer chromatography using a standard of 2-oleoylglycerol followed by isolation and purification to determine the fatty acids composition.The highest composition of fatty acids on 2-MAGs were unsaturated fatty acids, namely oleic acid (939.8 ppm) and linoleic acid (445.5 ppm), therefore it could be used for the synthesis of structured lipid.     

Production of medium chain saturated fatty acids with enhanced antimicrobial activity from crude coconut fat by solid state cultivation of Yarrowia lipolytica

Fatty acids profiles and antimicrobial activity of crude coconut fat hydrolysates obtained in solid-state cultivation system with a selected yeast strain Yarrowia lipolytica RO13 were performed. A preliminary step regarding extracellular lipase production and solid state enzymatic hydrolysis of crude fat at different water activity and time intervals up to 7 days was also applied. Gas chromatography–mass spectrometry analysis was used for quantification of medium chain saturated fatty acids (MCSFAs) and the results revealed a higher concentration of about 70% lauric acid from total fatty acids. Further, antimicrobial activity of fatty acids against some food-borne pathogens (Salmonella enteritidis, Escherichia coli, Listeria monocytogenes and Bacillus cereus) was evaluated. The minimum inhibitory concentration of the obtained hydrolysates varied from 12.5 to 1.56 ppm, significantly lower than values reported in literature. The results provide substantial evidence for obtaining biopreservative effects by coconut fat enzymatic hydrolysis.     

A one-pot ultrasound-assisted water extraction/cyclodextrin encapsulation of resveratrol from Polygonum cuspidatum

The ultrasound-assisted extraction (UAE) of resveratrol and other polyphenols from Polygonum cuspidatum has been carried out with the aim of developing an efficient and eco-friendly extraction process. The finely milled roots were sonicated (titanium horn, 19.5 kHz) in methanol, in different cyclodextrin water solutions [β-cyclodextrin (β-CD) or hydroxypropyl β-CD (HPβ-CD)] and also in pure water. UAE dramatically increased the yields and cut down extraction times compared to conventional extraction under stirring. Outstanding results have been achieved with the β-CD solution (1.5% w/w); in fact HPLC analysis showed that the selective inclusion properties of CDs toward phenolic stilbenes gave a much cleaner analytical extract profile. This green method gave 7.51 mg of total resveratrol (free + cleaved polydatin glucoside) per gram of dry plant. Thanks to polyphenol encapsulation within CDs, this extract showed excellent water dispersibility, higher stability and an antioxidant power which is comparable to that of the MeOH extract (DPPH, ORAC_FL). These important features should pave the road for its application in food supplements or phytochemical preparations.     

Seed oils of ten traditional Portuguese grape varieties with interesting chemical and antioxidant properties

To increase the potential and better exploring of grape seeds that are an important wine-industrial waste, oils of ten traditional Portuguese grape varieties were evaluated in relation to their vitamin E content (tocopherols and tocotrienols), fatty acid profile, as well as, antioxidant properties. Our results showed that the grape-seed oils were a good source of γ-tocotrienol (499–1575 mg/kg), α-tocopherol (85.5–244 mg/kg) and α-tocotrienol (69–319 mg/kg). Concerning fatty acid profile, linoleic (C18:2cc), oleic (C18:1), palmitic (C16:0) and stearic (C18:0) acids were the predominant. Grape-seed oils demonstrated to be a good source of polyunsaturated fatty acids (PUFAs) (63.64–73.53%), whereas monounsaturated fatty acid (MUFA) and saturated fatty acid (SFA) ranged between 14.19–21.29% and 11.64–14.94%, respectively. Interesting values of DPPH and ABTS radical scavenging activities were also obtained. This study demonstrated that these seeds may be reused and their oils incorporated in other food products, taking into account the compounds with positive effects on human health that are present in their composition.     

Sorghum distillers dried grain lipid extract increases cholesterol excretion and decreases plasma and liver cholesterol concentration in hamsters

Grain sorghum is a rich source of phytochemicals. In this study, male hamsters were fed AIN-93M diets supplemented with a hexane-extractable lipid fraction from sorghum distillers dried grains with solubles (DDGS). Diets contained 0.0%, 0.5%, 1.0%, and 5.0% (w/w) DDGS lipid extract. After 4 wk, the 5.0% DDGS lipids group had significantly lower plasma non-HDL cholesterol and liver esterified cholesterol concentration. Faecal neutral sterol (i.e., cholesterol) excretion was significantly higher in the 5.0% DDGS lipids group compared to the other treatments (66% higher compared to controls). Bile acid excretion was not affected by DDGS lipid intake. Faecal cholesterol excretion was negatively correlated with liver cholesterol concentration (r = ?0.97, P = 0.026), and liver cholesterol concentration was directly correlated with plasma total cholesterol concentration (r = 0.96, P = 0.041). Thus, lipid extract of sorghum DDGS exhibited cholesterol-lowering properties due, at least in part, to increased cholesterol excretion from the body and could provide health benefits when incorporated into human diets.     

A comparison of the proximate compositions and fatty acid profiles of zander (Sander lucioperca) from two different regions and climatic conditions

The proximate compositions and fatty acid profiles of the flesh of the fresh water fish zander (Sander lucioperca) obtained from Eğirdir Lake and from Seyhan Dam Lake were compared. The crude protein (18.8–18.1%), ash (1.37–0.75), and dry matter (20.67–20.09) contents of fish in Seyhan Dam Lake were observed to be higher than those in the other lake. Zander in Seyhan Dam Lake had a significantly (p < 0.05) higher lipid content than its Eğirdir counterpart. Differences were also observed in the fatty acid profiles. The percentages of total saturated fatty acids (SFA) and total monounsaturated fatty acids (MUFA) were higher in the zander in Seyhan Dam Lake than in Eğirdir Lake, whereas the corresponding total polyunsaturated fatty acids (PUFA) content was lower. Moreover, the fatty acid composition of these fish showed a relatively high ratio of PUFA/SFA (1.00). Both zanders showed palmitic acid, C16:0, to be predominant, (19.6–20.8%), followed by oleic acid, C 18:1 n − 9, (19.2–13.4%).The data obtained indicate that the % composition of n − 3 PUFAs is greater in the flesh of zander in Eğirdir Lake. This finding is in compliance with the fact that n − 3 fatty acids in fish living in cold climatic conditions have a higher % composition. It was concluded that the consumption of zander, widely found in Eğirdir Lake and having higher % composition of n − 3 PUFAs than those caught from Seyhan Dam Lake, is more beneficial for human health.     

Food matrices affect the bioavailability of (n − 3) polyunsaturated fatty acids in a single meal study in humans

The aim of this study was to investigate the role of the food matrix on bioavailability of (n − 3) PUFA and oxidative stress in plasma. The study was a randomized, cross-over study and included 12 healthy male participants. The participants ingested a test meal, which consisted of a fitness bar, a yoghurt drink, eight oil capsules, bread and butter; 4 g of fish oil was incorporated into one of the matrices. Blood samples were collected and fatty acid composition of chylomicrons was determined together with plasma levels of conjugated dienes and α-tocopherol. Fish oil incorporated into food products were absorbed differently from those simply administered as supplements alongside of food products, and yoghurt was the best matrix for providing fast absorption of lipids in general, including (n − 3) fatty acids. No significant difference was observed in the level of plasma α-tocopherol after ingestion of test meals.     

Effect of milk fat concentration and gel firmness on syneresis during curd stirring in cheese-making

An experiment was undertaken to investigate the effect of milk fat level (0%, 2.5% and 5.0% w/w) and gel firmness level at cutting (5, 35 and 65 Pa) on indices of syneresis, while curd was undergoing stirring. The curd moisture content, yield of whey, fat in whey and casein fines in whey were measured at fixed intervals between 5 and 75 min after cutting the gel. The casein level in milk and clotting conditions was kept constant in all trials. The trials were carried out using recombined whole milk in an 11 L cheese vat. The fat level in milk had a large negative effect on the yield of whey. A clear effect of gel firmness on casein fines was observed. The best overall prediction, in terms of coefficient of determination, was for curd moisture content using milk fat concentration, time after gel cutting and set-to-cut time (R² = 0.95).     

Compositional and thermal characteristics of palm olein-based diacylglycerol in blends with palm super olein

Palm olein-based diacylglycerol (POL-DAG) was blended with palm super olein (POoo) in various concentrations (10–90%), with increments of 10% (wt/wt) POL-DAG. The physical and chemical characteristics, i.e., iodine value, acylglycerol content, fatty acid composition, melting and crystallization profiles and solid fat content, for POL-DAG, POoo and their binary blends were evaluated. The mid-infrared FTIR was used to determine the absorption bands of the different concentrations of the oil blends. Only slight differences of FAC and IV were observed. POL-DAG:POoo blends showed significant changes (p < 0.05) in DAG content and decreases in TAG content with increasing POL-DAG content. The DSC thermograms showed that the addition of different concentrations of POL-DAG changed the melting and crystallization behavior of the oil blends (POL-DAG:POoo). The crystallization onset point increased (p < 0.05) with an increasing POL-DAG concentration (10–90%). POL-DAG has the same absorption bands as POoo, with the exception of several minor peaks that appeared at (I) 2954 cm^− 1, (II) 1267 cm^− 1, (III) 1199 cm^− 1, (IV) 1222 cm^− 1 and (V) 966 cm^− 1. This study will provide essential information for the palm oil industry to identify the most suitable POL-DAG blends with desirable physicochemical properties for food application purposes.     

Effects of a liquid egg product containing fish oil on selected cardiovascular disease risk factors: A randomized crossover trial

The objective of the present human study was to evaluate the potential for a liquid egg product containing fish oil (providing eicosapentaenoic acid (EPA) plus docosahexaenoic acid (DHA)) as a functional food to favourably modify circulating triglyceride levels and other risk factors for cardiovascular disease (CVD). A two-period randomized, controlled, crossover trial was conducted in 16 healthy males with moderately elevated triglyceride levels. The participants were randomly assigned to consume either a breakfast containing the liquid egg product providing 1.3 g/day of EPA/DHA combined or a control breakfast, each for 21 days.The breakfast containing the liquid egg product significantly decreased the plasma triglyceride levels by 32% (P < 0.05), the triglyceride:HDL-cholesterol ratio by 37% (P < 0.05), and moderately reduced blood pressures whereas no such effects were observed with the control breakfast. No effects on total cholesterol and LDL-cholesterol were observed. The fatty acid composition of serum phospholipid showed an increase of 210% (P < 0.001) in EPA and 96% (P < 0.001) in DHA and shifting to a lower risk status for the EPA/DHA sum. Use of this liquid egg product as a functional food could serve as a dietary intervention for supporting CVD risk management.     

Effects on growth performance,carcass characteristics,and the fat and meat fatty acid profile of rabbits fed diets with chia (Salvia hispanica L.) seed supplements

The effects of three levels (0%, 10%, or 15%) of chia (Salvia hispanica L.) seed (SHS) included in the diet on the growth performance, some carcass characteristics and fatty acid profile of rabbit meat and perirenal fat was studied. At the end of the experiment, there were no significant differences among the groups in live weight, live weight gain, feed consumption, feed efficiency, carcass yield or the percentages of edible organs. The percentage values of hind legs, fore legs, loin and abdominal wall, breast and ribs, skin and limbs, and head were not affected by the inclusion level of SHS. The polyunsaturated fatty acid (PUFA) concentration in the longissimus dorsi muscle and perirenal fat was significantly increased with increasing SHS inclusion, while the saturated fatty acid (SFA) decreased. The n − 6/n − 3 PUFA ratio of the rabbit meat decreased from 4.55 in the control group, to 1.03 in the 15% SHS group.