Response surface modelling of the production of structured lipids from soybean oil using Rhizomucor miehei lipase

The production of structured lipids (SLs) by the acidolysis of soybean oil (SO) with a free fatty acid (FFA) mixture obtained from Brazilian sardine oil, catalysed by Rhizomucor miehei lipase (Lipozyme RM IM) in a solvent-free medium, was optimised by response surface methodology (RSM) using a three-factor central composite rotatable design. The best reaction conditions to achieve an adequate n-6/n-3 FA ratio were: sardine-FFA:SO mole ratio of 3:1, initial water content of the enzyme of 0.87% w/w, reaction time of 12 h, reaction temperature of 40 °C and 10% by weight of the enzyme (% w/w). Under these conditions, the incorporation of eicosapentaenoic acid (EPA) + docosahexaenoic acid (DHA) into the soybean oil reached 9.2% (% of the total FAs), leading to a significant reduction in the n-6/n-3 FA ratio from 11:1 to 3:1. Analysis of variance (ANOVA) showed that 95% (R² = 0.95) of the observed variation was explained by the model. Lack of fit analysis revealed a non-significant value for the model equation, indicating that the regression equation was adequate for predicting the degree of EPA + DHA incorporation under any combination of values of the variables. Easy ambient sonic-spray ionisation mass spectrometry (EASI-MS) was used for instantaneous characterisation of TAGs. After the enzymatic reaction, a great variety of new TAGs were formed containing EPA, DHA or both in the same molecule.     

结构脂质的研究进展

结构脂质(Structured lipids,SLs)以其众多特殊生理功能而成为国内外关注的热点,极具开发潜力.对结构脂质的定义、代谢特征、功能特性、生产方法及纯化技术进行了详细介绍与展望.     

Enzymatic synthesis of structured lipids from liquid and fully hydrogenated high oleic sunflower oil

Structured lipids (SL) were synthesized via enzymatic (EI) and chemical interesterification of high oleic sunflower oil (SO) and fully hydrogenated high oleic SO with Lipozyme TL IM (Thermomyces lanuginose) for 3 h at 70°C, 300 rpm. Reaction showed changes in the triacylglycerols (TAGs) composition, solid fat content (SFC), thermal behavior, regiospecific distribution, microstructure, and polymorphism. Results revealed that the EI caused considerable rearrangement of the TAG species with lower levels of tri-saturated and tri-unsaturated TAG and higher levels of monoun- and diunsaturated TAG. The interesterified blends showed reduced SFC between 20 and 35°C, lowering the melting point. After 3-h incubation, EI produced acyl migration to some extent. The SL showed the required characteristics for application as bakery fats and as additives for lipid crystallization in the food industry.     

Enzymatic synthesis of structured lipids using a novel cold-active lipase from Pichia lynferdii NRRL Y-7723

Structured lipids (SL) were synthesized by the acidolysis of borage oil with caprylic acid using lipases. Six commercial lipases from different sources and a novel lipase from Pichia lynferdii NRRL Y-7723 were screened for their acidolysis activities and Lipozyme RM IM and NRRL Y-7723 lipase were selected to synthesize symmetrical SL since recently NRRL Y-7723 lipase was identified as a novel cold-active lipase. Both lipases showed 1,3-regiospecifity toward the glycerol backbone of borage oil. The effects of enzyme loading and temperature on caprylic acid incorporation into the borage oil were investigated. For Lipozyme RM IM and NRRL Y-7723 lipase, the incorporation of caprylic acid increased as enzyme loading increased up to 4% of total weight of the substrate, but significant increases were not observed when enzyme loading was further increased. The activity of NRRL Y-7723 lipase was higher than that of Lipozyme RM IM in the temperature range between 10 and 20 °C.     

无溶剂体系中酶催化合成结构脂质条件初探

以菜籽油和辛酸为原料,在无溶剂体系中用脂肪酶催化酸解合成结构脂质。对6种不同来源的脂肪酶进行筛选,结果表明Lipozyme RMIM催化活性高、Sn-1,3位特异性强。以Lipozyme RMIM为催化用酶,考察了反应时间、反应温度、底物比(菜籽油与辛酸摩尔比)、加酶量、体系水分含量对酸解反应的影响。结果表明,在反应时间15 h,反应温度50℃,底物比1∶4,加酶量10%条件下,辛酸合成率达40%。     

脂肪酶催化稻米油酯交换制备低热量结构脂及其动力学研究

以三丁酸甘油酯和稻米油为原料采用固定化脂肪酶Lipozyme RM IM酯交换合成低热量结构脂,研究了底物质量比、酶添加量、反应温度、反应时间对结构脂转化率的影响,并以乒乓机制为动力学模型,建立脂肪酶催化制备结构脂的动力学方程。通过单因素试验确定最佳结构脂制备条件为底物质量比4∶1,酶添加量10%,反应温度50℃,反应时间24 h。三丁酸甘油酯与稻米油在无溶剂体系中的进行酯交换反应的初速度的动力学反应模型为V=5.413×10~(-3)C_AC_B/0.169 2C_B+0.148 6C_A+C_AC_B,经验证表明计算值与实验值较吻合,反应符合乒乓机制。     

酶促酸解合成结构脂反应中酰基迁移的研究进展

酶促酸解合成结构脂具有显著的优越性,其中酰基迁移副反应是结构脂合成中亟需研究和控制的关键。对酶催化酸解反应中酰基迁移的理论和实践研究进行综述,归纳总结温度、时间、酶、载体、水分活度、溶剂、底物比、甘油酯结构等因素对酰基迁移的影响。目前,对酰基迁移的研究主要在酶促反应水平上,机理尚不深入,且优化酶促酸解条件提高接入率、产率与减少酰基迁移是不可兼得的矛盾关系。今后需要进行酰基迁移在复杂体系下的影响机制和评测方法的深入研究,以期更高效地开发特殊用途的结构脂产品。     

大豆肽减肥降血脂作用的研究

采用大豆肽对Wistar大鼠进行实验,研究大豆肽的减肥降血脂作用。大豆肽减肥作用实验中,低剂量300 mg/kg.bw灌胃Wistar大鼠,其脂体比下降了34.85%。大豆肽降血脂作用实验中,低剂量300 mg/kg.bw灌胃Wistar大鼠,其血清总胆固醇下降了20.74%,同时其低密度脂蛋白下降了14.05%;中剂量600 mg/kg.bw灌胃Wistar大鼠,其高密度脂蛋白增加了9.03%,中剂量600 mg/kg.bw和高剂量1200 mg/kg.bw灌胃Wistar大鼠,其甘油三酯分别下降了45.10%和51.20%。研究结果表明大豆肽具有一定的减肥降血脂保健作用。     

Effects of pharmacological amounts of S‐allylcysteine on lipids in normal and isoproterenol‐induced myocardial infarction in rats

The present study evaluates the effect of S‐allylcysteine on marker enzymes, serum and myocardial lipids in normal and isoproterenol‐induced myocardial infarction in male Wistar rats. A significant increase in the activities of marker enzymes such as creatine kinase, lactate dehydrogenase, aspartate transaminase and alanine transaminase in serum of isoproterenol (150 mg kg^?1)‐treated rats was observed. The levels of serum lipids (cholesterol, triglycerides, free fatty acids and phospholipids) were significantly increased, while the levels of myocardial cholesterol, triglycerides and free fatty acids were significantly increased in isoproterenol‐administered rats. The concentration of myocardial phospholipids was significantly decreased in isoproterenol‐administered rats. Oral pretreatment with S‐allylcysteine at doses of 50, 100 and 150 mg kg^?1 using an intragastric tube daily for a period of 45 days positively modulated the biochemical alterations caused by isoproterenol. The effect of S‐allylcysteine at a dose of 150 mg kg^?1 showed a better cardioprotective effect than the other two doses (50 and 100 mg kg^?1). α‐Tocopherol (60 mg kg^?1) administration orally using an intragastric tube to rats daily for 45 days also exhibited a significant cardioprotective effect. The effect of S‐allylcysteine was compared with α‐tocopherol. Oral administration of S‐allylcysteine (50, 100 and 150 mg kg^?1) to normal rats did not show any significant change in this study. Thus, from the present study it can be concluded that a pharmacological dose of S‐allylcysteine exerts a protective effect against isoproterenol‐induced myocardial infarction in rats. Copyright © 2006 Society of Chemical Industry     

酶法合成1-油酸-2-棕榈酸-3-亚油酸甘油三酯结构脂的研究

在Lipozyme RM IM脂肪酶的催化作用下,将分提后的棕榈硬脂与油酸和亚油酸反应,通过酶法酸解合成富含1-油酸-2-棕榈酸-3-亚油酸甘油三酯(OPL)的结构脂,通过单因素实验对酶法合成反应条件进行了优化。结果表明,合成OPL结构脂的最优反应条件为:棕榈硬脂、油酸、亚油酸摩尔比1∶7∶7,酶添加量8%,反应温度60℃,反应时间6 h。在最优条件下,进行50倍放大实验,合成产物中OPL和sn-2位棕榈酸的含量分别为48.37%和84.70%。     

Effects of endogenous flour lipids on the quality of short‐dough biscuits

Fractionation and reconstitution techniques were used to study the contribution of endogenous flour lipids to the quality of short‐dough (shortcake type) biscuits. Biscuit flour was defatted with chloroform and baked with bakery fat, but without endogenous lipid. Short‐dough biscuits baked from defatted flour had smaller diameters, and were flatter, denser and harder than control biscuits. Defatted flour shortcake doughs exhibited different rheological behaviour from the control samples, showing higher storage and loss moduli (G′ and G″ values), ie higher viscoelasticity. Functionality was restored when total non‐starch flour lipids were added back to defatted flour. The polar lipid fraction had a positive effect in restoring flour quality whereas the non‐polar lipid fraction had no effect. Both fractions were needed for complete restoration of both biscuit quality and dough rheological characteristics. A study of the microstructure of defatted biscuits revealed that their gluten protein was more hydrated and developed than the gluten of the control biscuits. This conclusion was supported by the higher water absorption of the defatted gluten. Copyright © 2004 Society of Chemical Industry     

Effect of hesperidin and naringin on the plasma lipid profile and plasma antioxidant activity in rats fed a cholesterol‐containing diet

The objective of this study was to compare the influence of hesperidin and naringin, the main flavonones of orange and grapefruit, on plasma lipid profile and antioxidant activity in rats fed a cholesterol‐containing diet. Sixty male Wistar rats were randomly divided into six groups of 10, named Control, Hesperidin, Naringin, Chol, Chol/Hesperidin and Chol/Naringin. The Control group was fed a basal diet (BD) and 1–2 mL of distilled water. To the BD of the other five groups were added 0.1–0.2 mg of hesperidin dissolved in 1–2 mL of distilled water (Hesperidin group), 0.46–0.92 mg of naringin in 1–2 mL of water (Naringin group), 1% of non‐oxidised cholesterol (NOC) and 1–2 mL of water (Chol), 1% of NOC and 0.1–0.2 mg of hesperidin in 1–2 mL of water (Chol/Hesperidin), 1% of NOC and 0.46–0.92 mg of naringin in 1–2 mL of water (Chol/Naringin). After 30 days of the experiment it was found that the diets supplemented with hesperidin and naringin increased the plasma antioxidant activity. In conclusion, diets supplemented with hesperidin and naringin significantly hindered the increase in plasma lipid levels caused by cholesterol feeding. Hesperidin and naringin, bioactive compounds of citrus fruits, are powerful plasma lipid lowering and plasma antioxidant activity increasing flavonones. Copyright © 2007 Society of Chemical Industry     

Influence of sn‐1,3‐lipase‐catalysed interesterification on the oxidative stability of soybean oil‐based structured lipids

The oxidative stability of structured lipids (SLs) synthesised by specific sn‐1,3‐lipase catalysed interesterification of soybean oil (SBO) with caprylic acid (CA) in a stirred batch reactor was studied. SLs contained considerable amounts of tocopherol (TOH) isomers, although they lost almost 25% of endogenous TOHs during production. The effects of the addition of different TOH homologues (α, β, γ, δ), ascorbyl palmitate (AP, 200 ppm), lecithin (Le, 1000 ppm), butylated hydroxytoluene (BHT, 100 ppm) and butylated hydroxyanisole (BHA, 100 ppm) on the oxidative stability of SLs were investigated. Induction time (IT) of SBO, determined by the Rancimat method, decreased from 8.4 to 5.8 h at 110 °C after the modification. On the other hand, purified SLs and purified SBO had the same IT due to the tocopherol reduction during silica purification. No significant difference was observed between IT of SLs and SLs plus different α‐tocopherol concentrations (50, 100, 150, 200, 300, 500 and 1000 ppm) (P > 0.05). However, the addition of Le and/or AP significantly improved oxidative stability of purified SLs and SBO. The ternary blend containing δ‐TOH, AP and Le had higher IT than ternary blends of α‐TOH, β‐TOH or γ‐TOH. Furthermore, ternary blend containing BHA, AP and Le had higher IT than ternary blends of BHT, AP and Le. In addition, there was an increase in peroxide value (PV), conjugated diene (CD) content and p‐anisidine value (AV) during oxidation of oils at 60 °C. Antioxidant mixtures of α‐TOH (50 ppm) and δ‐TOH (500 ppm) with AP and Le decreased PV, CD and AV effectively. Copyright © 2006 Society of Chemical Industry     

Effects of yoghurt butter oils on rat plasma lipids,haematology and liver histology parameters in a 150‐day study

Although yoghurt butter oil as a fermented dairy product is widely consumed in several countries, its metabolic effects have not been fully elucidated. In this study, male Wistar rats were treated with standard diet, standard diet enriched with 10% or 20% (W/W) of either cow yoghurt butter oil (CYBO), sheep yoghurt butter oil (SYBO) or cottonseed oil (COT) for 20 weeks. Treatment of rats with CYBO or SYBO (at both concentrations) did not significantly influence haematological parameters, plasma lipids and liver histological structure. However, in contrast to popular belief, COT treatment at the higher dose induced leukocytosis, dyslipidaemia and liver steatosis.