Digestion of the 1-O-alkyl diacylglycerol ethers of atlantic dogfish liver oils by Atlantic salmon Salmo salar

Dogfish (Squalus acanthias) liver poses a waste disposal problem in Canada because it is not utilized for any commercial purpose. The liver of Atlantic dogfish, which is often up to 20% of the weight of the fish, contains 40–70% oil. The oil contains about 30–40% 1-O-alkyl diacylglycerol ethers (DAGE) which render it unacceptable for human use, and it has also not been considered satisfactory for animal feed use. Polyunsaturated fatty acids (20∶5n−3 and 22∶6n−3) are present in dogfish liver oils at levels comparable to those in herring oil. Dogfish liver oil could be a source of essential fatty acids for Atlantic salmon (Salmo salar), but their ability to hydrolyze DAGE from dogfish oil has not been examined. Experiments were designed to measure the digestibility of fatty acids of DAGE in salmon. The fatty acid moieties were liberated by the digestive enzymes of the fish and made readily available as a source of energy. The 1-O-alkylglycerol ether moiety was absorbed to a small extent but should not constitute a health problem in either the fish or the human fish consumer. The long-chain polyunsaturated fatty acids were particulary well absorbed, with an apparent digestibility in salmon of 87–95% when feeding on dogfish liver oil. The total fatty acids and other lipids were in fact both absorbed to the extent of approximately 85%. Presented in part at the Annual Meeting of the American Oil Chemists’ Society, Atlanta, Georgia, May 1994.     

Nutritional Value of Various Ray Fish Liver Oils to the Pacific White Shrimp <Emphasis Type="Italic">Litopenaeus vannamei</Emphasis>

A 32-day comparative feeding trial was performed to evaluate the nutritional value of four different ray fish liver oils to the Pacific white shrimp Litopenaeus vannamei. Four feeds were prepared with liver oil extracted from Dasyatis brevis, Rhinoptera steindachneri, Aetobatus narinari, and R. bonasus. A control feed was prepared with Menhaden fish oil. Ray fish liver oils were mainly composed of poly- and highly unsaturated fatty acids and contained levels of 20:5n-3 and 22:6n-3 comparable in magnitude to those of Menhaden fish oil, except for A. narinari liver oil, which had moderately low concentrations of 20:5n-3 and 22:6n-3 but showed a particularly high level of 20:4n-6, more than six times greater than that of Menhaden fish oil. Dietary fatty acids significantly influenced the fatty acid composition of shrimp muscle tissue, e.g., the diet with Menhaden fish oil elicited significantly higher shrimp muscle DHA level than diets with oil from D. brevis, and A. narinari, but not than diets with oil from R. steindachneri and R. bonasus. In spite of these differences, all four ray fish liver oils evaluated were as efficient in promoting growth and survival of L. vannamei as Menhaden fish oil, an ingredient known for its adequate nutritional quality to shrimp and fish. This study demonstrated one of the many possible applications of a locally-available resource that is currently being wasted.     

Studies of the fatty acid specificity of the lipase fromRhizomucor miehei toward 20:1n-9, 20:5n-3, 22:1n-9 and 22:6n-3

The fatty acid specificity of the lipase fromRhizomucor miehei toward 20:1n-9, 20:5n-3, 22:1n-9 and 22:6n-3 has been determined by comparing the alcoholysis (byn-propanol) of various mixtures of C₂₀ and C₂₂ fatty acids (FFA) or the corresponding ethyl esters (FAEE) inn-heptane. For all the fatty acids examined, the degree of conversion was much higher when using FFA rather than FAEE. When comparing the experiments with either single FAEE or FAEE mixtures, it was found for all four fatty acids that the degree of conversion depended on whether the FAEE was alone or together with other fatty acids in the reaction mixture. The lipase showed a strong specificity toward 20:1n-9, whereas the polyunsaturated fatty acids were much poorer substrates, especially 22:6n-3. The degrees of conversion for the two n-3 fatty acids show a clear preference for 20:5n-3 over 22:6n-3, not only when present alone but also in the different mixtures examined. The results obtained in the present experiments therefore suggest that when using the lipase fromR. miehei for enrichment of fish oils with n-3 fatty acids, it should not only be possible to diminish the content of 20:1 and 22:1 present in the outer positions in the triacylglycerols, but also to incorporate relatively more 20:5n-3 than 22:6n-3 into the triglycerides.     

Preparation of Omega-3 PUFA Concentrates from Fish Oils via Urea Complexation

The effect of weight ratio of urea to fatty acids and the urea-fatty acid adduct crystallization temperature on the enrichment of eicosapentaenoic acid from marine oil fatty acids was studied. The optimum ratio of urea to fatty acids was found to be 3 : 1 for laboratory scale preparations and the optimum temperature for the formation of urea-fatty acid adduct was 1°C. At very low temperatures (?12, ?18, ?35°C) the recovery efficiency for EPA was reduced. Using these optimum values, enrichment of EPA and other n-3 polyunsaturated fatty acids via urea complexation was carried out on a pilot plant scale in a variety of North Atlantic and North Pacific fist oils and a seal oil. Irrespective of hte type of starting oil, all the oils gave a concentrate with 69–85% total n-3 PUFA with an overall yield of 17–20%. Menhaden is clearly an ideal oil for preparation of EPA concentrate, as the starting oil usually has a higher proportion of EPA to DHA than most of the other commercial fish oils.     

Capillary supercritical fluid chromatographic analysis of shark liver oils

The liver oils of six different shark species have been analyzed by supercritical fluid chromatography (SFC). The liver oils were from the species Pseudotriakis microdon (False catshark), Centroscymnus coelepsis (Portuguese dogfish), Centrophorus squanosus (Leafscalp gulper shark), Deanea calceus (Birdbeak dogfish), Etmopterus princips (Greater lantern shark), and Centroscymnus crepidater (Longnose velvet dogfish). The method was capable of direct quantitation of squalene and cholesterol, while quantitation of triacylglycerols, cholesterol esters, and diacylglycerol ethers required thin-layer chromatographic fractionation prior to SFC analysis. The iodine values of the liver oil samples gave a linear correlation when plotted against the squalene content found by SFC. The variation of squalene content within one shark species is large, and there are large differences in squalene content from species to species. The squalene contents varied between 0.22 and 82.54 wt%. The identity of the glycerol ethers was investigated by SFC of the unsaponifiable matter. The major glycerol ethers contained chimyl, batyl, and selachyl alcohol.     

Conifer seeds: Oil content and fatty acid composition

The seed oils from twenty-five Conifer species (from four families—Pinaceae, Cupressaceae, Taxodiaceae, and Taxaceae) have been analyzed, and their fatty acid compositions were established by capillary gas-liquid chromatography on two columns with different polarities. The oil content of the seeds varied from less than 1% up to 50%. Conifer seed oils were characterized by the presence of several Δ5-unsaturated polymethylene-interrupted polyunsaturated fatty acids (Δ5-acids) with either 18 (cis-5,cis-9, 18∶2,cis-5,cis-9,cis-12 18∶3, andcis-5,cis-9,cis-12,cis-15 18∶4 acids) or 20 carbon atoms (cis-5,cis-11 20∶2,cis-5,cis-11,cis-14, 20∶3, andcis-5,cis-11,cis-14,cis-17 20∶4 acids). Pinaceae seed oils contained 17–31% of Δ5-acids, mainly with 18 carbon atoms. The 20-carbon acids present were structurally derived from 20∶1n-9 and 20∶2n-6 acids. Pinaceae seed oils were practically devoid of 18∶3n-3 acid and did not contain either Δ5-18∶4 or Δ5-20∶4 acids. Several Pinaceae seeds had a Δ5-acid content higher than 50 mg/g of seed. The only Taxaceae seed oil studied (Taxus baccata) had a fatty acid composition related to those of Pinaceae seed oils. Cupressaceae seed oils differed from Pinaceae seed oils by the absence of Δ5-acids with 18 carbon atoms and high concentrations in 18∶3n-3 acid and in Δ5-acids with 20 carbon atoms (Δ5-20∶3 and Δ5-20∶4 acids). Δ5-18∶4 Acid was present in minute amounts. The highest level of Δ5-20∶4 acid was found inJuniperus communis seed oil, but the best source of Δ5-acids among Cupressaceae wasThuja occidentalis. Taxodiaceae seed oils had more heterogeneous fatty acid compositions, but the distribution of Δ5-acids resembled that found in Cupressaceae seed oils. Except forSciadopytis verticillata, other Taxodiaceae species are not interesting sources of Δ5-acids. The distribution profile of Δ5-acids among different Conifer families appeared to be linked to the occurrence of 18∶3n-3 acid in the seed oils.     

Fatty acid composition of melon seed oil lipids and phospholipids

Fatty acid compositions of crude melon seed oil from two different sources were compared. Melon seeds fromCitrullus vulgaris (syn.C. lanatus) contained phosphatidylcholine (PC), lysophosphatidylcholine (LPC) and phosphatidylserine (PS), whereas melon seeds fromCitrullus colocynthis contained only PC and LPC, but not PS. Analysis of the total lipids revealed that the major fatty acid of the oils was 18:2n-6.Citrullus vulgaris seed oil contained 71.3% andC. colocynthis contained 63.4% of 18:2n-6. The predominant fatty acids in theC. vulgaris PC were 18:2n-6 (32.2%), 18:1n-9 (26.4%) and 16:0 (22.2%), whereas theC. colocynthis PC contained 44.6% of 18:1n-9 as the major fatty acid. The level of monoenes in theC. colocynthis variety (46.2%) was different from theC. vulgaris (27.3%). The major fatty acid in the LPC was 18:1n-9 for both varieties. Notably, theC. colocynthis variety did not contain any PS. The major fatty acids in theC. vulgaris PS were 18:1n-9 (37.9%) and 18:2n-6 (33.7%). Of all the phospholipids, LPC contained the greatest amount of monoenes, 48.6–52.4%.     

The ratio of n-6 to n-3 polyunsaturated fatty acids in the rat diet alters serum lipid levels and lymphocyte functions

Previous studies have reported that feeding rats diets rich in fish oils, which contain high proportions of the n-3 polyunsaturated fatty acids (PUFA) eicosapentaenoic and docosahexaenoic acids, results in lowering of blood lipid levels and suppression of lymphocyte functions testedex vivo andin vivo. The effects of other n-3 PUFA, such as α-linolenic acid, which is found in high proportions in linseed oil, are not as well documented. Therefore, in the present study, weanling male rats were fed for six weeks on one of five high-fat (20% by weight) diets made by mixing together sunflower and linseed oils; the resulting blends had n-6/n-3 PUFA ratios of 112.5:1 (pure sunflower oil), 14.8:1, 6.5:1, 0.8:1, and 0.33:1 (pure linseed oil); the levels of all other components in the diet were identical. The final body weight and total dissectable fat were lowest in rats fed the pure linseed oil diet. Serum cholesterol, triacylglycerol and nonesterified fatty acid concentrations decreased as the n-6/n-3 PUFA ratio of the diet decreased. The fatty acid composition of the serum and of spleen lymphocytes was influenced by the diet fed-there was a progressive decrease in the proportions of linoleic and arachidonic acids and a progressive increase in the proportion of α-linolenic acid as the n-6/n-3 PUFA ratio of the diet decreased. Eicosapentaenoic and docosahexaenoic acids were detected in the serum but not in spleen lymphocytes. Inclusion of α-linolenic acid in the diet resulted in significant suppression of spleen lymphocyte proliferation in response to the T-cell mitogen concanavalin A and in spleen lymphocyte natural killer cell activity, both measuredex vivo. The localized graft vs. host response, a measure of cellmediated immunityin vivo, progressively decreased as the n-6/n-3 PUFA ratio of the diet decreased. Thus, this study shows that dietary α-linolenic acid results in lowered blood lipid levels and suppressed lymphocyte functionsex vivo andin vivo. With respect to these effects, α-linolenic acid is as potent as dietary fish oil.     

Stereospecific analysis of fish oil triacyl-sn-glycerols

Stereospecific analysis of fish oil triacyl-sn-glycerols was carried out by novel high-performance liquid chromatography on a chiral stationary phase. The positional distributions of fatty acids were determined without accumulation of errors in a particular position and preferential hydrolysis for a particular fatty acid. High-resolution gas-liquid chromatography on an open tubular column detailed the distribution of unsaturated fatty acid isomers having olefinic bonds in different positions. The distribution of fatty acids was not independent of other fatty acids. The distribution of long-chain highly unsaturated fatty acids 22:6(n-3), 22:5(n-3) and 20:5(n-3) was governed by total amounts of 20:1 and 22:1 in triacyl-sn-glycerols. Long-chain monounsaturated acids 20:1 and 22:1 were influenced by the position of the olefinic bond in 20:1 occurring in triacyl-sn-glycerols. Shorter-chain C14-C18 fatty acids seemed to be influenced by total fatty acid composition. These results introduce a concept of mutual interaction between fatty acids to the investigation of positional distribution of fatty acids.     

Effects of Rice Bran Oil Enriched with n-3 PUFA on Liver and Serum Lipids in Rats

Lipase-catalyzed interesterification was used to prepare different structured lipids (SL) from rice bran oil (RBO) by replacing some of the fatty acids with α-linolenic acid (ALA) from linseed oil (LSO) and n-3 long chain polyunsaturated fatty acids (PUFA) from cod liver oil (CLO). In one SL, the ALA content was 20% whereas in another the long chain n-3 PUFA content was 10%. Most of the n-3 PUFA were incorporated into the sn-1 and sn-3 positions of triacylglycerol. The influence of SL with RBO rich in ALA and EPA + DHA was studied on various lipid parameters in experimental animals. Rats fed RBO showed a decrease in total serum cholesterol by 10% when compared to groundnut oil (GNO). Similarly structured lipids with CLO and LSO significantly decreased total serum cholesterol by 19 and 22% respectively compared to rice bran oil. The serum TAGs level of rats fed SLs and blended oils were also significantly decreased by 14 and 17% respectively compared to RBO. Feeding of an n-3 PUFA rich diet resulted in the accumulation of long chain n-3 PUFA in various tissues and a reduction in the long chain n-6 PUFA. These studies indicate that the incorporation of ALA and EPA + DHA into RBO can offer health benefits.     

Cessation of polyunsaturated fatty acid formation in four selected filamentous fungi when grown on plant oils

Four fungi,Conidiobolus nanodes, Entomophthora exitalis, Mortierella isabellina, andMucor circinelloides, were grown on various oils (triolein, sesame, safflower, linseed, and oil fromM. isabellina) and produced lipids in which the fatty acids were predominantly the same as those of the original staring substrate. Only in the first two cases was there evidence of a small amount of chain elongation and of fatty acid desaturation taking place. The extent of this was only about 10% of that seen in glucose-grown cells. The apparent repression of the fatty acid desaturases and elongases was not reversed by growing cells on glucose and oils as mixed substrates—the fatty acid profiles were the same as when the fungi had grown in oils alone. Neither was the cessation of polyunsaturated fatty acid synthesis due to the presence of nonoil components (NOC) in the oil. Only the NOC from sesame oil affected one single conversion, that of 20∶3n-3 to 20∶4n–6. We conclude that fatty acid desaturase and elongase systems are repressed either partially or completely in a filamentous fungi grown on triacylglycerol oils.     

Influence of lipase-catalyzed interesterification on the oxidative stability of melon seed oil triacylglycerols

Melon seeds are rich in oil. However, the stability of melon seed oil (MSO) is low because of its high content of the essential fatty acid, linoleic acid (18:2n-6). MSO was physically blended or enzymatically interesterified with higholeic sunflower oil (HOSO). The fatty acid composition of MSO was remarkably changed after interesterification. Palmitic (16:0), stearic (18:0), and oleic (18:1n-9) acid contents increased at the sn-2 position of triacylglycerols, whereas 18:2n-6 decreased due to interesterification. The oxidative stability of the physical and Pseudomonas sp. (PS30) lipase-interesterified blends was assessed with the Oxidative Stability Instrument, peroxide value, and conjugated diene methods. The stability of MSO increased with increased proportions of HOSO, which was the source of 18:1n-9 in the blends. The ratio of 18:1n-9/18:2n-6 improved from 0.18 in MSO to 1.47 in the enzymatically interesterified blend. Calculated oxidizability and the results of oxidation tests of the blends confirmed the improvement in MSO stability by both physical blending and enzymatic interesterification.     

trans-Polyunsaturated fatty acids in French edible rapeseed and soybean oils

The fatty acid compositions of rapeseed and soybean oils marketed in France have been determined by gas liquid chromatography on a fused-silica capillary column coated with a 100% cyanopropyl polysiloxane stationary phase. Under the operating conditions employed, methyl esters of linolenic acid geometrical isomers could be separated and quantitated easily without any other complementary technique. With only one exception, all samples under study (eight salad oils and five food samples) contain geometrical isomers of linolenic acid in measurable, although variable, amounts. Totaltrans-18:3 acids may account for up to 3% of total fatty acids. This value corresponds to a degree of isomerization (percentage oftrans isomers relative to total octadecatrienoic acids) of 30%. Examination of our data indicates that the distribution pattern of linolenic acid geometrical isomers does not depend on the degree of isomerization. The two main isomers always have thec,c,t and thet,c,c configurations. These isomers occur in the almost invariable relative proportions of 47.8±1.7% and 41.1±1.0%, respectively. The third mono-trans isomer is present in lower amounts−6.5±0.7%. The only di-trans isomer that can be quantitated with sufficient accuracy is thet,c,t isomer (4.9±1.5%). Mono-trans isomers of linoleic acid are also present in these oils. However, their maximum percentages are lower than those determined for linolenic acid geometrical isomers. In the oils showing the highest degrees of isomerization,trans isomers of linoleic acid account for 0.5% (rapeseed oils) and 1% (soybean oils) of total fatty acids. Taking into account all data, it would appear that the probability of isomerization of linolenic acid is about 13–14 times that of linoleic acid.     

Influence of lipase-catalyzed interesterification on the oxidative stability of melon seed oil triacylglycerols

Melon seeds are rich in oil. However, the stability of melon seed oil (MSO) is low because of its high content of the essential fatty acid, linoleic acid (18:2n-6). MSO was physically blended or enzymatically interesterified with higholeic sunflower oil (HOSO). The fatty acid composition of MSO was remarkably changed after interesterification. Palmitic (16:0), stearic (18:0), and oleic (18:1n-9) acid contents increased at the sn-2 position of triacylglycerols, whereas 18:2n-6 decreased due to interesterification. The oxidative stability of the physical and Pseudomonas sp. (PS30) lipase-interesterified blends was assessed with the Oxidative Stability Instrument, peroxide value, and conjugated diene methods. The stability of MSO increased with increased proportions of HOSO, which was the source of 18:1n-9 in the blends. The ratio of 18:1n-9/18:2n-6 improved from 0.18 in MSO to 1.47 in the enzymatically interesterified blend. Calculated oxidizability and the results of oxidation tests of the blends confirmed the improvement in MSO stability by both physical blending and enzymatic interesterification.     

Fatty acids of canola Brassica campestris var candle seed and oils at various stages of refining

Fatty acids of oil of a current variety of canolaBrassica campestris var Candle, at 3 stages of commercial production and refining, were compared with authentic seed oils, and with the oil ofB. napus var Tower. The proportion ofcis- 9, cis- 12, trans- 15 andtrans- 9, cis-12, cis-lS-octadecatrienoates relative to the all-cis isomer was lower than that previously observed in processed oils. The minor C₁₄, C₁₅, C₁₇ fatty acids previously documented for Tower were also found in the same proportions in the Candle oil. The proportion of 22:1ω7 isomer (1.1% of a total 1.2% 22:1) was intermediate to that of a high erucic variety (0.9% out of 23% 22:1) and the very low 22:1 Tower (2.3% out of 0.1% 22:1). Thus the proportion of ω7 isomers is governed by total 22:1 present.     

Influence of moderate amounts of trans fatty acids on the formation of polyunsaturated fatty acids

The effect of trans fatty acids from partially hydrogenated soybean oil and butterfat on the formation of polyunsaturated fatty acids was investigated. Five groups of rats were fed diets that contained 20 wt% fat. The content of linoleic acid was adjusted to 10 wt% of the dietary fats in all diets, whereas the amount of trans fatty acids from partially hydrogenated soybean oil (PHSBO) was varied from 4.5 to 15 wt% in three of the five diets. The fourth group received trans fatty acids from butterfat (BF), while the control group was fed palm oil without trans fatty acids. Trans fatty acids in the diet were portionally reflected in rat liver and heart phosphatidylethanolamine (PE), phosphatidylcholine (PC), phosphatidylinositol, and phosphatidylserine. Incorporation in the sn-1 position was compensated by a decrease in saturated fatty acids. Trans fatty acids were not detected in diphosphatidylglycerol. Compared to the presence in the dietary fats, 8t- and 10t-18:1 were discriminated against in the incorporation in PE and PC from liver and heart, whereas 9t- and 12t-18:1 were preferred. The formation of 20:4n-6 was not influenced by 4.5 wt% trans fatty acids (from PHSBO) but apparently was by 10 wt% in liver. In contrast, even a content of 2.5 wt% trans fatty acids from BF reduced the formation of 20:4n-6. The inhibitory effect of trans isomers on linoleic acid conversion was reflected less in heart than in liver and less for PE than for PC. Groups with trans fatty acids showed increased 22:6n-3 and 22:5n-3 deposition in liver and heart PE and PC.     

Some minor fatty acids of rapeseed oils

A number of minor unsaturated fatty acids of rapeseed oil (fromBrassica napus orcampestris) have been isolated by combinations of distillation preparatve gas liquid chromatography and silver nitrate thin layer chromatography, and were further identified by oxidative fission in BF₃-MeOH. Among the shorter chain, all-cis polyunsaturated fatty acids described are 16:3ω3, 16:2ω6 and 14:2ω6. A ubiquitous minor component inunproceessed oils was found to becis-9, cis-12, trans-15-octadecatrienoic acid, with lesser proportions of thetrans-9, cis-12, cis-15 isomer. Among others identified werecis-14:1ω9 and 15:1ω10, the latter accompanied by half as muchtrans-15:1ω10. Particular attention was paid to the proportions of the minor monoethylenic fatty acids of the ω7 series relative to the longer chain major ω9 monoethylenic fatty acids which have been reduced by plant breeding.     

Stereospecific analysis of triacyl-sn-glycerols in Docosahexaenoic acid-rich fish oils

This paper presents the positional distribution of fatty acids in docosahexaenoic acid (22∶6n-3)-rich fish oil triacyl-sn-glycerols (TG). Stereospecific analysis of TG was carried out by a nonenzymatic method. The TG of bonito head oil, obtained after a winterization process, contained 22∶6n-3 at concentrations of 28,7, and 49 mole % in thesn-1,sn-2, andsn-3 positions, respectively. In the TG of oil before the winterization process, 22∶6n-3 was concentrated in thesn-3 position, followed evenly by thesn-1 andsn-2 positions. Tuna orbital oil, obtained after winterization, showed the preferential association of 22∶6n-3 to thesn-3 position, followed by thesn-1 position. This distribution pattern was similar to that observed for seal oil TG rather than sardine oil TG. The bonito head and tuna orbital oils are useful as fish oils with characteristics different from those of common fish oils, such as menhaden, sardine, and herring oils.     

Differentiation of Fish Oils According to Species by <Superscript>13</Superscript>C-NMR Regiospecific Analyses of Triacyglycerols

The aim of this study was to use ¹³C-nuclear magnetic resonance (NMR) regiospecific analyses of triacylglycerols to distinguish fish oils from different fish species for authentication purposes. ¹³C-NMR data of muscle lipids from Atlantic salmon (Salmo salar L.), mackerel (Scomber scombrus) and herring (Clupea harengus) were obtained, and the distribution of omega-3 polyunsaturated fatty acids between the sn-1,3 and sn-2 glycerol chains calculated from the carbonyl region. The results show that there were significant differences in the sn-2 position specificity of the fatty acids 22:6n-3, 20:5n-3 and 18:4n-3 among the species investigated. The most pronounced difference was that herring had a higher proportion of its 22:6n-3 in the sn-2 position compared to the two other species. Principal component analysis of data points in the carbonyl-region showed that there were also differences in the level and regiospecific distribution of monounsaturated/saturated fatty acids, which made it possible to distinguish oils of these three species solely from the carbonyl region of ¹³C-NMR spectra.     

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.