Quantitative determination of triacylglycerol profile of structured lipid by capillary supercritical fluid chromatography and high-temperature gas chromatography

Two analytical methods have been developed for the qualitative and quantitative analyses of triacylglycerol profile of structured lipid (SL)-containing medium-chain and long-chain fatty acids. Supercritical fluid chromatography (SFC) was used in the first method. The SL was dissolved in chloroform/methanol, 95:5 (vol/vol), and analyzed directly using a super-critical fluid chromatograph equipped with temperature and density programming capabilities. No derivatization was required for sample preparation. An SB-methyl-100 capillary column (10 m, 100 μ i.d., 0.25 μ film thickness) was used for the separation of the triacylglycerol species and a flame-ionization detector (FID) was used for the detection. Supercritical fluid carbon dioxide was used as the mobile phase. In the second method, the SL was hydrogenated to complete saturation prior to analysis using gas chromatography at high temperatures of up to 375°C. A DB-5HT capillary column (30 m × 0.32 mm i.d., 0.1 μ film thickness) was used for the separation. FID was used for the detection and helium gas was used as mobile phase. The triacylglycerol species were separated and identified based on their equivalent carbon number (ECN), the total carbon number of the acyl side chains. A calibration curve was constructed using a triacylglycerol mixture containing known amounts of monoacyltriacylglycerol standard materials ranging from ECN 18 (trihexanoin) to ECN 66 (tridocosanoin). The novel triacylglycerol species, ECN 32–43, created by the interesterification of medium-chain triacylglycerol (MCT) and long-chain triacylglycerol (LCT) were separated and identified based on their retention times. These triacylglycerols, ECN 32–43, were absent in the physical mixture of MCT and LCT. The unique triacylglycerol specieis, ECN 32-43, were therefore selected as the fingerprinting region for the qualitative identification of the SL. Quantitation of the novel triacylglycerol species in the SL was achieved by using the integrated peak area of the new species. Both methods were employed successfully to distinguish the physical mixture from the corresponding interesterified SL. Results generated by the two methods were compared and found to be in good agreement.     

Effects of the degree of unsaturation of coexisting triacylglycerols on cholesterol oxidation

In order to evaluate the effects of the degree of unsaturation of triacylglycerols on cholesterol oxidation, mixtures of purified sardine oil triacylglycerols (iodine value, IV=182.6) and cholesterol; of partially hydrogenated sardine oil triacylglycerols (IV=174.5) and cholesterol; and of fully hydrogenated sardine oil triacylglycerols (IV=92.0) and cholesterol were incubated at 25°C in the dark. The oxidative stability of the samples decreased with increasing degree of unsaturation of the triacylglycerols in the sample mixtures; the induction period for peroxide values (PV) of the sardine oil triacylglycerols and cholesterol was shorter than that of the partially hydrogenated sardine oil triacylglycerols and cholesterol. Certain polyunsaturated fatty acids (PUFAs) in the constituent fatty acids of sardine oil triacylglycerols started to decrease after a shorter induction period compared with that of the partially hydrogenated triacylglycerols. The prominent cholesterol oxides accumulated in the samples were 7β-hydroxycholesterol, 7-ketocholesterol, β-epoxide and cholestane triol. The tendency for accumulation of cholesterol oxides in the time course coincided with the changes in PV as well as the decrease in PUFAs. Cholesterol was oxidized in conjunction with autoxidation of coexisting fish oil triacylglycerols. Although lowering the degree of unsaturation of fish oil triacylglycerols was effective in prolonging the induction period of cholesterol oxidation, the rate of cholesterol oxidation in the cholesterol oxides' formation phase after the induction period was not affected by the difference in the proportion of highly unsaturated fatty acids in the natural and partially hydrogenated triacylglycerols of fish oils.     

Continual conversion of free fatty acid in rice bran oil to triacylglycerol by immobilized lipase

Rice bran oil containing 30–50% free fatty acid was continually converted to an oil containing more than 75% of triacylglycerol (TG) by means of immobilized lipase. The reaction was carried out at 60°C for 24 h with dehydration and reactant mixing by dry nitrogen flow under a positive nitrogen atmosphere. Enzymatic TG synthesis with evaporation by heating was not suitable because of the increasing peroxide value of the oil. Part of this article was presented at the annual meeting of the Japan Oil Chemists' Society at Sendai, Japan, October, 16, 1990.     

Dietary fat in the prevention of cardiovascular disease — a review

In developed countries atherosclerotic cardiovascular disease is the reason for about 50% of all deaths. With growing prosperity coronary heart disease (CHD) is becoming the major cause of premature death. Most complications of atherosclerosis occur unexpectedly and more than 50% of the patients developing a myocardial infarction do not survive more than one year. Because of the severe morbidity and high mortality primary prevention is likely to be the only solution. Epidemiological studies show a strong, positive relationship between plasma cholesterol concentrations and the incidence of CHD. People who immigrate from low‐risk to high‐risk areas usually acquire similar plasma cholesterol levels as the native population and a similar CHD risk. This demonstrates that environmental rather than genetic factors lead to the differences in cardiovascular risk and supports the notion that nutrition and lifestyle play a major role. The association between dietary intake of fat and cholesterol and the extent of atherosclerosis and CHD has been recognized in previous studies. The amount of saturated fat in the diet correlates stronger with the incidence of CHD than with total fat intake. The consumption of unsaturated fatty acids, however, appears to be beneficial, since it is inversely correlated with the plasma cholesterol concentration and risk of myocardial infarction. Lately additional nutritional factors like trans fatty acids with a negative influence on risk as well as positive factors like linolenic acid have attracted much attention. In conclusion, as a challenge to public health, preventive medicine needs to focus on changes in dietary habits with priority, particularly fat modification. A nutrition low in total fat primarily avoiding saturated and trans fatty acids, but rich in fruit and vegetables should be recommended.     

Thermodynamic analysis of the kinetics reactions of the production of FAME and FAEE using Novozyme 435 as catalyst

Biodiesel is a biofuel expected to become a substitute for petroleum diesel. One of the most promising technologies for production of biodiesel is enzymatic catalysis. However, low catalytic performance of most of the enzymes employed makes such processes expensive and time-consuming. This work describes a kinetic study of the enzymatic production of biodiesel at different temperatures using either methanolysis or ethanolysis, using immobilized lipase from Candida antarctica (Novozym 435) as catalyst. Reactions kinetics were followed by GC, and data were used to perform thermodynamic analysis of the transition state using Arrhenius equation. We found that methanolysis is faster than ethanolysis at temperatures above 13 °C. Thermodynamic analysis of the kinetics of reactions showed that methanol is favored as acyl acceptor due to the positive activation entropy change of reaction. These data may be useful in the development of new enzymes and new processes for enzymatic production of biodiesel.     

Camelina oil and its unusual cholesterol content

The oil in Camelina sativa L. Crantz has a combined linolenic and linoleic acid content that is greater than 50% and a relatively low saturated FA content (∼10%). Although the FA composition has been reported, no information is available on the sterol composition of camelina oil. The derivatized plant sterols were separated and quantified with capillary GC and their identity confirmed with GC-MS. The refined camelina oil sample contained approximately 0.54 wt% unsaponifiables, and over 80% of the unsaponifiables were desmethylsterols. Perhaps the most unusual characteristic of camelina oil is its relatively high content of cholesterol, particularly for a vegetable oil, since it contains several times the cholesterol found in other “high-cholesterol” vegetable oils. Camelina oil also contains relatively large amounts of another unusual sterol, brassicasterol. The major sterols identified in the camelina oil included cholesterol (188 ppm), brassicasterol (133 ppm), campesterol (893 ppm), stigmasterol (103 ppm), sitosterol (1,884 ppm), and Δ⁵-avenasterol (393 ppm).     

Characterization of enzymatically synthesized structured lipids containing eicosapentaenoic, docosahexaenoic, and caprylic acids

Structured lipids (SL) containing n-3 polyunsaturated (eicosapentaenoic or docosahexaenoic) and mediumchain (caprylic) fatty acids were synthesized in gram quantities and characterized. Tricaprylin was mixed with n-3-rich polyunsaturated fatty acids in a 1:2 molar ratio and transesterified by incubating at 55°C in hexane with SP 435 lipase (10% by wt of total substrates) in a 125-mL Erlenmeyer flask as the bioreactor. After several batches of reaction, the products were pooled and hexane was evaporated. Short-path distillation was used for purification of synthesized SL. The distillation conditions were 1.1 Torr and 170°C at a feed flow rate of 3 mL/min. Up to 240 g of SL was isolated and deacidified by alkaline extraction or ethanol-water solvents. The fatty acid profile, free fatty acid value, saponification number, iodine value, peroxide value, thiobarbituric acid, and conjugated diene contents were determined. Oxidation stability, with α-tocopherol as antioxidant, and the oxidative stability index were also determined.     

13C nuclear magnetic resonance spectroscopic analysis of the triacylglycerol composition ofBiota orientalis and carrot seed oil

¹³C nuclear magnetic resonance (NMR) spectroscopic analysis of the whole oil (triacylglycerols) ofBiota orientalis seeds confirms the presence of oleate [18:1(9Z)], linoleate [18:2(9Z, 12Z)], linolenate [18:3((9Z, 12Z, 15Z)], 20:3 (5Z, 11Z, 14Z), 20:4(5Z, 11Z, 14Z, 17Z), and saturated fatty acids in the acyl groups by comparing the observed carbon shifts with previously established shift data for model triacylglycerols. This technique shows that the saturated, 20:3 and 20:4 fatty acids are distributed mainly in the α-acyl positions, whereas oleate, linoleate, and linolenate are randomly acylated to the α- and β-positions of the glycerol “backbone”. Stereospecific hydrolysis of theBiota oil with pancreatic lipase, followed by chromatographic analysis of fatty esters, reveals the presence of trace amounts of 16:0(0.7%), 18:0(0.5%), 20:3 (0.4%), and 20:4 (1.3%) in the β-position of the glycerol “backbone”, which are undetectable by¹³C NMR technique on the whole oil. Semiquantitative assessment of the¹³C NMR signal intensities gives the relative percentages of the fatty acid distribution as: saturated 16:0, 18:0 (12.0% α-acyl), oleate (7.7% α-acyl 8.7% β-acyl), total linoleate and linolenate (31.7% α-acyl; 24.2% βacyl), total 20:3 and 20:4 (15.7% α-acyl). The¹³C NMR spectroscopic analysis of carrot seed oil identifies the presence of saturated (18:0), 18:1(6Z), 18:1(9Z), and 18:2(9Z, 12Z). The saturated fatty acid is found in the α-acyl positions. Semi-quantitative assessment of the signal intensities gives the relative percentages of the fatty acids as: 18:0 (4.5% α-acyl), 18:1(6Z) (49.6% α-acyl; 19.7% β-acyl), oleate (6.5% α-acyl; 8.6% β-acyl) and linoleate (5.2% α-acyl; 6.9% β-acyl).     

Variations in the composition of acyl lipids and triacylglycerol molecular species of pumpkin seeds (Cucurbita spp.) following microwave treatment

Whole pumpkin seeds (Cucurbita spp.) of two cultivars were exposed to microwaves for 6, 12, 20 or 30 min at a frequency of 2450 MHz. The kernels were separated from the whole seeds, and were investigated not only for the different acyl lipids and their fatty acid compositions, but also for the molecular species of triacylglycerols (TAGs). A modified argentation TLC procedure, developed to optimize the separation of the complex mixture of total TAGs, provided 11 different groups of TAGs, based on both the degree of unsaturation and the chain‐length of fatty acid groups. With a few exceptions, dioleopalmitin (5.8–18.8 wt‐%), dipalmitolinolein (8.1–8.8 wt‐%), triolein (6.3–20.5 wt‐%), palmitoleolinolein (15.0–16.1 wt‐%), dioleolinolein (16.7–23.0 wt‐%), dilinoleopalmitin (4.6–15.4 wt‐%) and dilinoleolein (6.7–19.4 wt‐%) were the main TAG components. When pumpkin seeds were microwaved for 20 min or more, significant differences (p <0.05) occurred in the acyl lipids as well as their fatty acid distributions with a few exceptions. Therefore, microwave roasting caused a significant decrease (p <0.05), not only in TAGs molecular species containing more than 4 double bonds, but also in the amounts of diene species present in triacylglycerols. These results contribute to the study of the functional properties of pumpkin seed products.     

Activation of Free Fatty Acid Receptor 4 (FFA4) Ameliorates Ovalbumin-Induced Allergic Asthma by Suppressing Activation of Dendritic and Mast Cells in Mice

Epidemiological and clinical studies have suggested that intake of n-3 polyunsaturated fatty acids (PUFA) reduces the incidence of allergic airway diseases and improves pulmonary function in patients with allergic asthma. However, the pharmacological targets of PUFA have not been elucidated upon. We investigated whether free fatty acid receptor 4 (FFA4, also known as GPR120) is a molecular target for beneficial PUFA in asthma therapy. In an ovalbumin (OVA)-induced allergic asthma model, compound A (a selective agonist of FFA4) was administrated before OVA sensitization or OVA challenge in FFA4 wild-type (WT) and knock-out (KO) mice. Compound A treatment of RBL-2H3 cells suppressed mast cell degranulation in vitro in a concentration-dependent manner. Administration of compound A suppressed in vivo allergic characteristics in bronchoalveolar lavage fluid (BALF) and lungs, such as inflammatory cytokine levels and eosinophil accumulation in BALF, inflammation and mucin secretion in the lungs. Compound A-induced suppression was not only observed in mice treated with compound A before OVA challenge, but in mice treated before OVA sensitization as well, implying that compound A acts on mast cells as well as dendritic cells. Furthermore, this suppression by compound A was only observed in FFA4-WT mice and was absent in FFA4-KO mice, implying that compound A action is mediated through FFA4. Activation of FFA4 may be a therapeutic target of PUFA in allergic asthma by suppressing the activation of dendritic cells and mast cells, suggesting that highly potent specific agonists of FFA4 could be a novel therapy for allergic asthma.     

Fatty acid and triacylglycerol compositions of seed oils of five Amaranthus accessions and their comparison to other oils

This paper reports the fatty acid and triacylglycerol (TAG) compositions of five Amaranthus accessions (RRC1011, R149, A.K343, A.K432, and A. K433) representing two species and a cross between one of these and a third species. Seed oils of these were analyzed by gas chromatography and reversed-phase high-performance liquid chromatography, and their compositional properties compared with buck-wheat (Fagopyrum esculentum), corn (Zea mays), rice bran (Oryza sativa), soybean (Glycine max L. Merr.), sesame (Sesamum indicum), quinoa (Chenopodium quinoa), and cottonseed (Gossypium hirsutum) oils. All Amaranthus accessions were relatively high in palmitic (21.4–23.8%) and low in oleic (22.8–31.5%) and linolenic (0.65–0.93%) acids when compared to most of the grain and seed oils. The fatty acid composition of Amaranthus accessions K343, K433, and K432 (group I) were different from R149 and RRC1011 (group II) in mono and polyunsaturated fatty acids, but the saturate/unsaturate (S/U) ratios were very similar. All Amaranthus accessions were similar in TAG type, but showed slight differences in percentage. High similarities in UUU, UUS, and USS composition were observed among Amaranthus K343, K433 and K432, and between R149 and RRC1011. The fatty acid compositions of Amaranthus oil (group I) and cottonseed oil were similar, but their TAG compositions were different. The grain and oilseed oils were different from each other and from the Amaranthus accessions oils in terms of fatty acid composition, S/U, and TAG ratios. The UUU, UUS, and USS percentages were very diverse in grain and seed oils. The percentages of squalene in the TAG sample from the Amaranthus accessions were 8.05% in K343, 11.10% in K433, 11.19% in K432, 9.96% in R149, and 9.16% in RRC1011. Squalene was also tentatively identified in quinoa and ricebran oils at levels of 3.39 and 3.10%, respectively.     

Aerobic Liquor Washing Improves the Quality of Crude Palm Oil by Reducing Free Fatty Acids and Chloride Contents

The presence of free fatty acids (FFA) and chloride contents in crude palm oil is not desirable because they have an impact on oil quality and food safety. This work presents a method to reduce these compounds by washing the crude palm oil (CPO) with treated aerobic liquor (AL). The effects of process parameters on the reduction of FFA and chloride in CPO and the resultant 3-monochloropropane-1,2 diol ester (3-MCPDE) formed after refining are investigated. The results show that the AL dosage, initial FFA content, mixing speed, and duration have significant influence on the reduction of FFA in the CPO. Meanwhile, the chloride content is reduced by approximately 50% regardless of the AL dosage used. Consequently, the 3-MCPDE content in the oil after refining is up to 53% lower than that of the refined oil produced from the untreated CPO. Furthermore, an oil recovery above 97% can be achieved after the AL-washing step. The implementation strategy of this method in the palm oil mills has also been proposed. In conclusion, an effective and sustainable method for in situ improvements of the quality and food safety of palm oil has been developed without the need for additional water or chemical. Practical Applications: Treated aerobic liquor can be used to wash the CPO in palm oil mill for in situ reductions of FFA and chloride contents in CPO to improve the oxidative stability of CPO. The lower content of chlorides in CPO could mitigate the formation of 3-MCPDE during refining, thus improving the food safety of palm oil. This method can readily be implemented by the industry and it is sustainable because it does not require the use of additional process water or chemical.     

Effect of feeding muscovy ducklings different protein sources: Performance, θ-3 fatty acid contents, and acceptability of their tissues

One hundred Muscovy ducklings, 5-wk-old, from each gender were assigned to five dietary treatments. Each treatment of each sex contained two replicates of 10 ducklings each. Ducks were fed, from 4–9 wk of age, five isonitrogenous diets that differed in protein source, i.e., commercial protein concentrate (CPC), soybean meal, meat meal (MM), herring fish meal (HFM), and mixed herring fish and meat meals (HFM + MM). At the end of the experiment, four ducks per treatment were slaughtered for carcass evaluation and the fatty acid profiles of their meat, adipose tissue, and plasma. Final body weight of both sexes showed no difference among protein sources, although males fed CPC or MM diets had the largest weight gain. No differences in feed consumption and conversion between sexes were shown, although differences in θ-3 fatty acid consumption due to protein source were significant. Feeding fish meal reduced the sensory acceptance of meat, whereas the plant protein diet improved it. Total lipid and cholesterol contents of the meat of males showed no differences between protein sources. Correlation between θ-3 fatty acid consumption and plasma cholesterol was negative (r=0.91; P=0.03). Moreover, correlation between plasma cholesterol and plasma lipid was positive (r=0.97; P=0.01). Feeding fish meal enriched total unsaturated fatty acid of adipose tissues, θ-3 fatty acid of adipose and meat tissues, and total unsaturated fatty acid of thigh meat. Total unsaturated fatty acid and θ-3 fatty acid of blood plasma from females were also enriched by feeding fish meal-containing diets. This work was presented at the 21st World Congress and Exhibition of the International Society for Fat Research (ISF) October 1–6, 1995, The Netherlands Congress Center, The Hague.     

Dietary trans α‐linolenic acid does not inhibit Δ5‐ and Δ6‐desaturation of linoleic acid in man

Dietary trans monoenes have been associated with an increased risk of heart disease in some studies and this has caused much concern. Trans polyenes are also present in the diet, for example, trans α‐linolenic acid is formed during the deodorisation of α‐linolenic acid‐rich oils such as rapeseed oil. One would expect the intake of trans α‐linolenic acid to be on the increase since the consumption of rapeseed oil in the western diet is increasing. There are no data on trans α‐linolenic acid consumption and its effects. We therefore carried out a comprehensive study to examine whether trans isomers of this polyunsaturated fatty acid increased the risk of coronary heart disease. Since inhibition of Δ6‐desaturase had also been linked to heart disease, the effect of trans α‐linolenic acid on the conversion of [U‐¹³C]‐labelled linoleic acid to dihomo‐γ‐linolenic and arachidonic acid was studied in 7 healthy men recruited from the staff and students of the University of Edinburgh. Thirty percent of the habitual fat was replaced using a trans ‘free’‐ or ‘high’ trans α‐linolenic acid fat. After at least 6 weeks on the experimental diets, the men received 3‐oleyl, 1,2‐[U‐¹³C]‐linoleyl glycerol (15 mg twice daily for ten days). The fatty acid composition of plasma phospholipids and the incorporation of ¹³C‐label into n‐6 fatty acids were determined at day 8, 9 and 10 and after a 6‐week washout period by gas chromatography‐combustion‐isotope ratio mass spectrometry. Trans α‐linolenic acid of plasma phospholipids increased from 0.04 ? 0.01 to 0.17 ? 0.02 and cis ? ‐linolenic acid decreased from 0.42 ? 0.07 to 0.29 ? 0.08 g/100 g of fatty acids on the high trans diet. The composition of the other plasma phospholipid fatty acids did not change. The enrichment of phosphatidyl ¹³C‐linoleic acid reached a plateau at day 10 and the average of the last 3 days did not differ between the low and high trans period. Both dihomo‐γ‐linolenic and arachidonic acid in phospholipids were enriched in ¹³C, both in absolute and relative terms (with respect to ¹³C‐linoleic acid). The enrichment was slightly and significantly higher during the high trans period (P<0.05). Our data suggest that a diet rich in trans α‐linolenic acid (0.6% of energy) does not inhibit the conversion of linoleic acid to dihomo‐γ‐linolenic and arachidonic acid in healthy middle‐aged men consuming a diet rich in linoleic acid.     

Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids

There are indications in the recent literature that the location of polyunsaturated fatty acids, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), in triacylglycerols (TAG) may influence their oxidative stability. To address that question, two types of structured lipids were designed and synthesized: firstly, a TAG molecule possessing pure EPA or DHA at the mid-position with stearic acid at the outer positions; and secondly, a TAG molecule possessing pure EPA or DHA located at one of the outer positions with stearic acid at the mid-position and the remaining end position. The former adduct was synthesized in two steps by a chemoenzymatic approach. In the first step 1,3-distearolyglycerol was afforded in good yield (74%) by esterifying glycerol with two equivalents of stearic acid in ether in the presence of silica gel using Lipozyme^TM as a biocatalyst. This was followed by a subsequent chemical esterification with pure EPA or DHA using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide as a coupling agent in the presence of 4-dimethylaminopyridine in dichloromethane in excellent yields (94 and 91, respectively). The latter adduct was synthesized in two enzymatic steps. In the first step tristearoylglycerol was prepared in very high yield (88%) by esterifying glycerol with a stoichiometric amount of stearic acid under vacuum at 70–75°C using an immobilized Candida antarctica lipase without a solvent. That adduct was subsequently treated in an acidolysis reaction with two equivalents of EPA or DHA without solvent at 70–75°C or in toluene at 40°C in the presence of Lipozyme to afford the desired product in moderate yields (44 and 29%, respectively). This work was presented at the Biocatalysis Symposium in April 2000, held at the 91st Annual Meeting and Expo of the American Oil Chemists’ Society, San Diego, CA.     

Lower Plasmatic Levels of Saturated Fatty Acids and a Characteristic Fatty Acid Composition in the Ovary Could Contribute to the High-Fertility Phenotype in Dummerstorf Superfertile Mice

In recent decades, fertility traits in humans as well as in farm animals have decreased worldwide. As such, it is imperative to know more about the genetics and physiology of increased or high fertility. However, most of the current animal models with reproductive phenotypes describe lower fertility or even infertility (around 99%). The “Dummerstorf high-fertility lines” (FL1 and FL2) are two unique mouse lines selected for higher reproductive performances, more specifically for higher number of pups per litter. We recently described how those superfertile mice managed to increase their reproductive phenotype by doubling the ovulation rate and consequently the litter size compared to the unselected mice of the same founder population. FLs show an unusual estrous cycle length and atypical levels of hormones that link reproduction and metabolism, such as insulin in FL1 and leptin in FL2. Moreover, we described that their higher ovulation rate is mostly due to a higher quality of their oocytes rather than their sheer quantity, as they are characterized by a higher quantity of high-quality oocytes in antral follicles, but the quantity of follicles per ovary is not dissimilar compared to the control. In the present study, we aimed to analyze the lipid composition of the fertility lines from plasma to the gonads, as they can connect the higher reproductive performances with their metabolic atypicalities. As such, we analyzed the fat content of FLs and fatty acid composition in plasma, liver, fat, oocytes of different quality, and granulosa cells. We demonstrated that those mice show higher body weight and increased body fat content, but at the same time, they manage to decrease the lipid content in the ovarian fat compared to the abdominal fat, which could contribute to explaining their ovarian quality. In addition, we illustrate the differences in fatty acid composition in those tissues, especially a lower level of saturated fatty acids in plasma and a different lipid microenvironment of the ovary. Our ongoing and future research may be informative for farm animal biology as well as human reproductive medicine, mostly with cases that present characteristics of lower fertility that could be reversed following the way-of-managing of Dummerstorf high-fertility lines.     

Lipase-catalyzed modification of borage oil: Incorporation of capric and eicosapentaenoic acids to form structured lipids

Two immobilized lipases, nonspecific SP435 from Candida antarctica and sn-1,3 specific IM60 from Rhizomucor miehei, were used as biocatalysts for the restructuring of borage oil (Borago officinalis L.) to incorporate capric acid (10:0, medium-chain fatty acid) and eicosapentaenoic acid (20:5n-3) with the free fatty acids as acyl donors. Transesterification (acidolysis) reactions were carried out in hexane, and the products were analyzed by gas-liquid chromatography. The fatty acid profiles of the modified borage oil were different from that of unmodified borage oil. Higher incorporation of 20:5n-3 (10.2%) and 10:0 (26.3%) was obtained with IM60 lipase, compared to 8.8 and 15.5%, respectively, with SP435 lipase. However, SP435 lipase was able to incorporate both 10:0 and 20:5n-3 fatty acids at the sn-2 position, but the IM60 lipase did not. Solvents with log P values between 3.5 and 4.5 supported the acidolysis reaction better than those with log P values between −0.33 and 3.0.