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1.
Tripalmitin-enriched triacylglycerols were concentrated from palm stearin by acetone fractionation and as the substrate reacted with a mixture of equimolar quantities of fatty acids (C8:0-C18:3). The incorporation degree and acyl migration level of the fatty acids and acylglycerols composition were investigated, providing helpful information for the production of human milk fat substitutes. Higher incorporation degrees of the fatty acids were obtained with lipase PS IM, Lipozyme TL IM, and Lipozyme RM IM followed by porcine pancreatic lipase and Novozym 435-catalyzed acidolysis. During reactions catalyzed by Lipozyme TL IM, Lipozyme RM IM, and lipase PS IM, incorporation degrees of C12:0, C14:0, C18:1, and C18:2 were higher than those of other fatty acids at operated variables (molar ratio, temperature, and time), and the triacylglycerols content reached the highest (82.09%) via Lipozyme RM IM-catalyzed acidolysis. On the basis of significantly different levels of acyl migration to the sn-2 position, lipases were in the order of lipase PS IM < Lipozyme TL IM < Lipozyme RM IM.  相似文献   

2.
Structured lipids (SLs) containing palmitic, oleic, stearic, and linoleic acids, resembling human milk fat (HMF), were synthesized by enzymatic acidolysis reactions between tripalmitin, hazelnut oil fatty acids, and stearic acid. Commercially immobilized sn-1,3-specific lipase, Lipozyme RM IM, obtained from Rhizomucor miehei was used as the biocatalyst for the enzymatic acidolysis reactions. The effects of substrate molar ratio, reaction temperature, and reaction time on the incorporation of stearic and oleic acids were investigated. The acidolysis reactions were performed by incubating 1:1.5:0.5, 1:3:0.75, 1:6:1, 1:9:1.25, and 1:12:1.5 substrate molar ratios of tripalmitin/hazelnut oil fatty acids/stearic acid in 3 mL of n-hexane at 55, 60, and 65 degrees C using 10% (total weight of substrates) of Lipozyme RM IM for 3, 6, 12, and 24 h. The fatty acid composition of reaction products was analyzed by gas-liquid chromatography (GLC). The fatty acids at the sn-2 position were identified after pancreatic lipase hydrolysis and GLC analysis. The results showed that the highest C18:1 incorporation (47.1%) and highest C18:1/C16:0 ratio were obtained at 65 degrees C and 24 h of incubation with the highest substrate molar ratio of 1:12:1.5. The highest incorporation of stearic acid was achieved at a 1:3:0.75 substrate molar ratio at 60 degrees C and 24 h. For both oleic and stearic acids, the incorporation level increased with reaction time. The SLs produced in this study have potential use in infant formulas.  相似文献   

3.
Sitostanol has been converted in high to near-quantitative extent to the corresponding long-chain acyl esters via esterification with oleic acid or transesterification with methyl oleate or trioleoylglycerol using immobilized lipases from Rhizomucor miehei (Lipozyme IM) and Candida antarctica (lipase B, Novozym 435) as biocatalysts in vacuo (20-40 mbar) at 80 degrees C, whereas the conversion was markedly lower at 60 and 40 degrees C. Corresponding conversions observed with papaya (Carica papaya) latex lipase were generally lower. High conversion rates observed in transesterification of sitostanol with methyl oleate at 80 degrees C using Lipozyme IM were retained even after 10 repeated uses of the biocatalyst. Saturated sterols such as sitostanol and 5alpha-cholestan-3beta-ol were the preferred substrates as compared to Delta(5)-unsaturated cholesterol in transesterification reactions with methyl oleate using Lipozyme IM. Transesterification of cholesterol with dimethyl 1,8-octanedioate using Lipozyme IM in vacuo yielded methylcholesteryl 1,8-octanedioate (75%) and dicholesteryl 1,8-octanedioate (5%). However, transesterification of cholesterol with diethyl carbonate and that of oleyl alcohol with ethylcholesteryl carbonate, both catalyzed by Lipozyme IM, gave ethylcholesteryl carbonate and oleylcholesteryl carbonate, respectively, in low yield (20%). Moreover, cholesterol was transesterified with ethyl dihydrocinnamate using Lipozyme IM to give cholesteryl dihydrocinnamate in moderate yield (56%), whereas the corresponding reaction of lanosterol gave lanosteryl oleate in low yield (14%).  相似文献   

4.
Incorporation of stearic acid into canola oil to produce trans-free structured lipid (SL) as a healthy alternative to partially hydrogenated fats for margarine formulation was investigated. Response surface methodology was used to study the effects of lipozyme RM IM from Rhizomucor miehei and Candida rugosa lipase isoform 1 (LIP1) and two acyl donors, stearic acid and ethyl stearate, on the incorporation. Lipozyme RM IM and ethyl stearate gave the best result. Gram quantities of SLs were synthesized using lipozyme RM IM, and the products were compared to SL made by chemical catalysis and fat from commercial margarines. After short-path distillation, the products were characterized by GC and RPHPLC-MS to obtain fatty acid and triacylglycerol profiles, 13C NMR spectrometry for regiospecific analysis, X-ray diffraction for crystal forms, and DSC for melting profile. Stearic acid was incorporated into canola oil, mainly at the sn-1,3 positions, for the lipase reaction, and no new trans fatty acids formed. Most SL products did not have adequate solid fat content or beta' crystal forms for tub margarine, although these may be suitable for light margarine formulation.  相似文献   

5.
Lipase-catalyzed interesterification of butterfat blended with rapeseed oil (70/30, w/w) was investigated both in batch and in continuous reactions. Six commercially available immobilized lipases were screened in batch experiments, and the lipases, Lipozyme TL IM and Lipozyme RM IM, were chosen for further studies in a continuous packed bed reactor. TL IM gave a fast reaction and had almost reached equilibrium with a residence time of 30 min, whereas RM IM required 60 min. The effect of reaction temperature was more pronounced for RM IM. TL IM showed little effect on the interesterification degree when the temperature was raised from 60 degrees C to 90 degrees C, whereas RM IM had a positive effect when the temperature was increased from 40 degrees C to 80 degrees C. Even though TL IM is an sn-1,3 specific lipase, small changes in the sn-2 position of the triacylglycerol could be seen. The tendency was toward a reduction of the saturated fatty acid C14:0 and C16:0 and an increase of the long-chain saturated and unsaturated fatty acids (C18:0 and C18:1), especially at longer residence times (90 min). In prolonged continuous operation the activity of TL IM was high for the first 5 days, whereafter it dramatically decreased over the next 10 days to an activity level of 40%. In general, the study shows no significant difference for butterfat interesterification in terms of enzyme behavior from normal vegetable oils and fats even though it contains short-chain fatty acids and cholesterol. However, the release of short-chain fatty acids from enzymatic reactions makes the sensory quality unacceptable for direct edible applications.  相似文献   

6.
Structured triacylglycerols (ST) from canola oil were produced by enzymatic acidolysis in a packed bed bioreactor. A commercially immobilized 1,3-specific lipase, Lipozyme IM, from Rhizomucormiehei, was the biocatalyst and caprylic acid the acyl donor. Parameters such as substrate flow rate, substrate molar ratio, reaction temperature, and substrate water content were examined. High-performance liquid chromatography was used to monitor the reaction and product yields. The study showed that all of the parameters had effects on the yields of the expected di-incorporated (dicaprylic) ST products. Flow rates below 1 mL/min led to reaction equilibrium, and lower flow rates did not raise the incorporation of caprylic acid and the product yield. Incorporation of caprylic acid and the targeted di-incorporated ST was increased by approximately 20% with temperature increase from 40 to 70 degrees C. Increasing the substrate molar ratio from 1:1 to 7:1 increased the incorporation of caprylic acid and the product yield slightly. Water content in the substrate also had a mild influence on the reaction. Water content at 0.08% added to the substrate gave the lowest incorporation and product yield. The use of solvent in the medium was also studied, and results demonstrated that it did not increase the reaction rate at 55 degrees C when 33% hexane (v/v) was added. The main fatty acids at the sn-2 position of the ST were C(18:1), 54. 7 mol %; C(18:2), 30.7 mol %; and C(18:3), 11.0 mol %.  相似文献   

7.
Stearidonic acid (SDA, C18:4n-3) enriched soybean oil may be added to the diet to increase intake of omega-3 fatty acids (FAs). Human milk fat has ≥60% of palmitic acid (PA), by weight, esterified at the sn-2 position to improve absorption of fat and calcium in infants. Enzymatic interesterification of SDA soybean oil and tripalmitin produced structured lipids (SLs) enriched with PA at the sn-2 position of the triacylglycerol. Reactions were catalyzed by Novozym 435 or Lipozyme TL IM under various conditions of time, temperature, and substrate mole ratio. Response surface methodology was used to design the experiments. Model optimization conditions were predicted to be 1:2 substrate mole ratio at 50 °C for 18 h with 10% (by weight) Lipozyme TL IM resulting in 6.82 ± 1.87% total SDA and 67.19 ± 9.59% PA at sn-2; 1:2 substrate mole ratio at 50 °C for 15.6 h resulting in 8.01 ± 2.41% total SDA and 64.43 ± 13.69% PA at sn-2 with 10% (by weight) Novozym 435 as the biocatalyst. The SLs may be useful as human milk fat analogues for infant formula formulation with health benefits of the omega-3 FAs.  相似文献   

8.
Human milk fat (HMF) analogue containing docosahexaenoic acid (DHA) and arachidonic acid (ARA) at sn-1,3 positions and palmitic acid (PA) at sn-2 position was produced. Novozym 435 lipase was used to produce palmitic acid-enriched hazelnut oil (EHO). EHO was then used to produce the final structured lipid (SL) through interesterification reactions using Lipozyme RM IM. Reaction variables for 3 h reactions were temperature, substrate mole ratio, and ARASCO/DHASCO (A:D) ratio. After statistical analysis of DHA, ARA, total PA, and PA content at sn-2 position, a large-scale production was performed at 60 °C, 3:2 A:D ratio, and 1:0.1 substrate mole ratio. For the SL, those results were determined as 57.3 ± 0.4%, 2.7 ± 0.0%, 2.4 ± 0.1%, and 66.1 ± 2.2%, respectively. Tocopherol contents were 84, 19, 85, and 23 μg/g oil for α-, β-, γ-, and δ-tocopherol. Melting range of SL was narrower than that of EHO. Oxidative stability index (OSI) value of SL (0.80 h) was similar to that of EHO (0.88 h). This SL can be used in infant formulas to provide the benefits of ARA and DHA.  相似文献   

9.
Diacylglycerol (DAG) and triacylglycerol (TAG) as responses on optimization of DAG production using a dual response approach of response surface methodology were investigated. This approach takes the molecular equilibrium of DAG into account and allows for the optimization of reaction conditions to achieve maximum DAG and minimum TAG yields. The esterification reaction was optimized with four factors using a central composite rotatable design. The following optimized conditions yielded 48 wt % DAG and 14 wt % TAG: reaction temperature of 66.29 degrees C, enzyme dosage of 4 wt %, fatty acid/glycerol molar ratio of 2.14, and reaction time of 4.14 h. Similar results were achieved when the process was scaled up to a 10 kg production in a pilot packed-bed enzyme reactor. Lipozyme RM IM did not show any significant activity losses or changes in fatty acid selectivity on DAG synthesis during the 10 pilot productions. However, lipozyme RM IM displayed higher selectivity toward the production of oleic acid-enriched DAG. The purity of DAG oil after purification was 92 wt %.  相似文献   

10.
Solvent-free lipase-catalyzed preparation of diacylglycerols   总被引：6，自引：0，他引：6  
Various methods have been applied for the enzymatic preparation of diacylglycerols that are used as dietary oils for weight reduction in obesity and related disorders. Interesterification of rapeseed oil triacylglycerols with commercial preparations of monoacylglycerols, such as Monomuls 90-O18, Mulgaprime 90, and Nutrisoft 55, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo at 60 degrees C led to extensive (from 60 to 75%) formation of diacylglycerols. Esterification of rapeseed oil fatty acids with Nutrisoft, catalyzed by Lipozyme RM in vacuo at 60 degrees C, also led to extensive (from 60 to 70%) formation of diacylglycerols. Esterification of rapeseed oil fatty acids with glycerol in vacuo at 60 degrees C, catalyzed by Lipozyme RM and lipases from Thermomyces lanuginosus (Lipozyme TL IM) and Candida antarctica (lipase B, Novozym 435), also provided diacylglycerols, however, to a lower extent (40-45%). Glycerolysis of rapeseed oil triacylglycerols with glycerol in vacuo at 60 degrees C, catalyzed by Lipozyme TL and Novozym 435, led to diacylglycerols to the extent of 相似文献   

11.
Stearidonic acid soybean oil (SDASO) is a plant source of n-3 polyunsaturated fatty acids (n-3 PUFAs). Solvent-free enzymatic interesterification was used to produce structured lipids (SLs) in a 1 L stir-batch reactor with a 1:2 substrate mole ratio of SDASO to tripalmitin, at 65 °C for 18 h. Two SLs were synthesized using immobilized lipases, Novozym 435 and Lipozyme TL IM. Free fatty acids (FFAs) were removed by short-path distillation. SLs were characterized by analyzing FFA and FA (total and positional) contents, iodine and saponification values, melting and crystallization profiles, tocopherols, and oxidative stability. The SLs contained 8.15 and 8.38% total stearidonic acid and 60.84 and 60.63% palmitic acid at the sn-2 position for Novozym 435 SL and Lipozyme TL IM SL, respectively. The SLs were less oxidatively stable than SDASO due to a decrease in tocopherol content after purification of the SLs. The saponification values of the SLs were slightly higher than that of the SDASO. The melting profiles of the SLs were similar, but crystallization profiles differed. The triacylglycerol (TAG) molecular species of the SLs were similar to each other, with tripalmitin being the major TAG. SDASO's major TAG species comprised stearidonic and oleic acids or stearidonic, α-linolenic, and γ-linolenic acids.  相似文献   

12.
A kind of low-calorie structured lipid (LCSL) was obtained by interesterification of tributyrin (TB) and methyl stearate (St-ME), catalyzed by a commercially immobilized 1,3-specific lipase, Lipozyme RM IM from Rhizomucor miehei . The condition optimization of the process was conducted by using response surface methodology (RSM). The optimal conditions for highest conversion of St-ME and lowest content LLL-TAG (SSS and SSP; S, stearic acid; P, palmitic acid) were determined to be a reaction time 6.52 h, a substrate molar ratio (St-ME:TB) of 1.77:1, and an enzyme amount of 10.34% at a reaction temperature of 65 °C; under these conditions, the actually measured conversion of St-ME and content of LLL-TAG were 78.47 and 4.89% respectively, in good agreement with predicted values. The target product under optimal conditions after short-range molecular distillation showed solid fat content (SFC) values similar to those of cocoa butter substitutes (CBS), cocoa butter equivalent (CBE), and cocoa butters (CB), indicating its application for inclusion with other fats as cocoa butter substitutes.  相似文献   

13.
Production in a batch reactor with a solvent-free system of structured triacylglycerols containing short-chain fatty acids by Lipozyme RM IM-catalyzed acidolysis between rapeseed oil and caproic acid was optimized using response surface methodology (RSM). Reaction time (t(r)), substrate ratio (S(r)), enzyme load (E(l), based on substrate), water content (W(c), based on enzyme), and reaction temperature (T(e)), the five most important parameters for the reaction, were chosen for the optimization. The range of each parameter was selected as follows: t(r) = 5-17 h; E(l) = 6-14 wt %; T(e) = 45-65 degrees C; S(r) = 2-6 mol/mol; and W(c) = 2-12 wt %. The biocatalyst was Lipozyme RM IM, in which Rhizomucor miehei lipase is immobilized on a resin. The incorporation of caproic acid into rapeseed oil was the main monitoring response. In addition, the contents of mono-incorporated structured triacylglycerols and di-incorporated structured triacylglycerols were also evaluated. The optimal reaction conditions for the incorporation of caproic acid and the content of di-incorporated structured triacylglycerols were as follows: t(r) = 17 h; S(r) = 5; E(l) = 14 wt %; W(c) = 10 wt %; T(e) = 65 degrees C. At these conditions, products with 55 mol % incorporation of caproic acid and 55 mol % di-incorporated structured triacylglycerols were obtained.  相似文献   

14.
Medium- and long-chain dialkyl 3,3'-thiodipropionate antioxidants such as dioctyl 3,3'-thiodipropionate, didodecyl 3,3'-thiodipropionate, dihexadecyl 3,3'-thiodipropionate, and di-(cis-9-octadecenyl) 3,3'-thiodipropionate were prepared in high yield by lipase-catalyzed esterification and transesterification of 3,3'-thiodipropionic acid and its dimethyl ester, respectively, with the corresponding medium- or long-chain 1-alkanols, i.e., 1-octanol, 1-dodecanol, 1-hexadecanol, and cis-9-octadecen-1-ol, in vacuo (80 kPa) at moderate temperatures (60-80 degrees C) without solvents. Immobilized lipase B from Candida antarctica (Novozym 435) was the most active biocatalyst for the preparation of medium- and long-chain dialkyl 3,3'-thiodipropionates showing enzyme activities up to 1489 units/g, whereas the immobilized lipases from Rhizomucor miehei (Lipozyme RM IM) and Thermomyces lanuginosus (Lipozyme TL IM) were by far less active ( approximately 10 enzyme units/g). Maximum conversions to dialkyl 3,3'-thiodipropionates were as high as 92-98% after 4 h of reaction time. Similarly, dihexadecyl 2,2'-thiodiacetate was prepared in high yield using 2,2'-thiodiacetic acid or diethyl 2,2'-thiodiacetate and 1-hexadecanol as the starting materials and Novozym 435 as the biocatalyst.  相似文献   

15.
Structured lipids (SLs) from stearidonic acid (SDA) soybean oil pre-enriched with palmitic acid (PA) at the sn-2 position with Novozym 435 (NSL) or Lipozyme TL IM (LSL) from previous research were further enriched with γ-linolenic acid (GLA) or docosahexaenoic acid (DHA). Small-scale acidolysis reactions with Lipozyme TL IM were performed to determine the optimal reaction conditions as 1:1 substrate mole ratio of NSL or LSL to free DHA at 65 °C for 24 h and a 1:0.5 substrate mole ratio of NSL or LSL to free GLA at 65 °C for 12 h. Optimized SL products were scaled up in a 1 L stir-batch reactor, and the resulting SLs of NSL:DHA (NDHA), LSL:DHA (LDHA), NSL:GLA (NGLA), and LSL:GLA (LGLA) were chemically and physically characterized. The SLs contained >54% PA at the sn-2 position with GLA >8% for the GLA SLs and DHA >10% for the DHA SLs. The oxidative stabilities of the SLs were increased by the addition of 200 ppm TBHQ, with NGLA being more stable due to higher tocopherol content than the other SLs. The melting and crystallization profiles did not differ between the DHA SLs or the GLA SLs. The triacylglycerol (TAG) species were similar for the GLA SLs but differed between the DHA SLs, with tripalmitin being the major TAG species in all SLs.  相似文献   

16.
Sterols (sitosterol, cholesterol, stigmasterol, ergosterol, and 7-dehydrocholesterol) and sitostanol have been converted in high to near-quantitative yields to the corresponding long-chain acyl esters via esterification with fatty acids or transesterification with methyl esters of fatty acids or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20-40 mbar) at 40 degrees C. Neither organic solvent nor water is added in these reactions. Under similar conditions, cholesterol has been converted to cholesteryl butyrate and steroids (5alpha-pregnan-3beta-ol-20-one or 5-pregnen-3beta-ol-20-one) have been converted to their propionic acid esters, both in moderate to high yields, via transesterification with tributyrin and tripropionin, respectively. Reaction parameters studied in esterification include the temperature and the molar ratio of the substrates as well as the amount and reuse properties of the C. rugosa lipase. Lipases from porcine pancreas, Rhizopus arrhizus, and Chromobacterium viscosum are quite ineffective as biocatalysts for the esterification of cholesterol with oleic acid under the above conditions.  相似文献   

17.
The incorporations of oleate (endogenous) and ricinoleate (nonendogenous) into phosphatidylcholine (PC) and acylglycerol (AG) in immature soybean microsomes were compared. [(14)C]Oleate and [(14)C]ricinoleate were incubated individually with soybean microsomal preparations for up to 4 h, and molecular species of PC and AG incorporated were identified and quantified by HPLC. The activities of acyl CoA:lysoPC acyltransferase and phospholipase A(2) are in general not affected by the fatty acid (FA) chain at the sn-1 position. However, comparison between oleate and ricinoleate revealed that different FA incorporated at sn-2 of PC showed some different selection of the molecular species of lysoPC. The incorporation of [(14)C]ricinoleate into triacylglycerols (TAG) was slightly better than that of [(14)C]oleate and indicated that soybean was capable of incorporating ricinoleate into TAG when ricinoleate can be produced endogenously in a transgenic soybean. The incorporation of FA into TAG in soybean microsomes was much slower than that in castor microsomes.  相似文献   

18.
Structured lipids (SL) containing caprylic, stearic, and linoleic acids were synthesized by enzymatic transesterification using Lipozyme IM60. Pure trilinolein and free fatty acids were used as substrates. Incorporation of stearic acid was higher than that of caprylic acid in all parameters. Highest incorporations of both acids were achieved at 32 h, mole ratio of 1:4:4 (trilinolein/caprylic/stearic acids), water content of 1% (wt %), temperature of 55 degrees C, and 10% (wt %) enzyme load. The maximal incorporations of caprylic and stearic acids were 23.73 and 62.46 mol %, respectively. Reaction time, water content, and enzyme load had major influences on the reaction, whereas substrate mole ratio and temperature showed less influence. Lipozyme showed good stability over six reuses. Differential scanning calorimetric analysis of SL gave a melting profile with a very low melting peak of 0-3.3 degrees C and a solid fat content of 25.21% at 0 degrees C. The melting profile and solid fat content of SL were compared with those of fats extracted from commercially available solid and liquid margarine products. The data suggest that enzymatically produced SL could be used in liquid margarine products.  相似文献   

19.
The esterification and hydrolytic activities of free and immobilized Candida rugosa lipase isoform 1 (LIP1) were investigated. Esterification activity was determined by reacting caprylic acid with glycerol in the presence of molecular sieves (30%, w/w), and the volume of 1.0 M NaOH consumed by the reaction products upon titration was used to calculate esterification activity. Caprylic acid was also reacted with cottonseed oil, and the amount of caprylic acid incorporated after 12 h of reaction was determined. Results indicated that LIP1 had little esterification activity, which was not significantly improved upon immobilization. Hydrolytic activity was determined by incubating tricaprylin emulsion (15%, w/w) with the respective lipases for 60 min, and the reaction products were titrated against 0.5 M NaOH. LIP1 showed hydrolytic activity comparable to Lipozyme RM IM. The hydrolytic activity improved significantly upon immobilization. Immobilization on Celite 545 produced the highest increase in hydrolytic activity.  相似文献   

20.
Human milk fat substitutes (HMFSs) were synthesized by lipozyme RM IM-catalyzed acidolysis of chemically interesterified palm stearin (mp = 58 °C) with mixed FAs from rapeseed oil, sunflower oil, palm kernel oil, stearic acid, and myristic acid in a solvent-free system. Response surface methodology (RSM) was used to model and optimize the reactions, and the factors chosen were reaction time, temperature, substrate molar ratio, and enzyme load. The optimal conditions generated from the models were as follows: reaction time, 3.4 h; temperature, 57 °C; substrate molar ratio, 14.6 mol/mol; and enzyme load, 10.7 wt % (by the weight of total substrates). Under these conditions, the contents of palmitic acid (PA) and PA at sn-2 position (sn-2 PA) were 29.7 and 62.8%, respectively, and other observed FAs were all within the range of FAs of HMF. The product was evaluated by the cited model, and a high score (85.8) was obtained, which indicated a high degree of similarity of the product to HMF.  相似文献   

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