Lipase-catalyzed production of pinolenic acid concentrate from pine nut oil using a recirculating packed bed reactor

Pinolenic acid (PLA) concentrate in fatty acid ethyl ester (FAEE) was efficiently produced from pine nut oil via lipase-catalyzed ethanolysis using a recirculating packed bed reactor (RPBR). The effects of reaction temperature, molar ratio, and residence time on the concentration of PLA were explored. Novozym 435 lipase from Candida antarctica showed less selectivity toward PLA esterified at the sn-3 position when temperature was increased from 45 to 55 °C. For the trials of molar ratio between 1: 50 and 1: 100 (pine nut oil to ethanol), there were no significant differences in the yield of PLA. Residence time of substrate in a RPBR affected significantly the PLA content as well as the yield of PLA. Optimal temperature, molar ratio (pine nut oil to ethanol), and residence time for production of PLA concentrate via lipase-catalyzed ethanolysis in a RPBR were 45 °C, 1: 50, and 3 min, respectively. Under these conditions, the maximal PLA content (36.1 mol%) in the concentrate was obtained during the initial 10 min of reaction.     

尿素包合法富集压榨松籽油中皮诺敛酸工艺优化

以压榨松籽油为原料,研究乙醇浓度、脂肪酸与尿素比、脂肪酸与乙醇比、包合时间、包合温度及包合次数对松籽油中皮诺敛酸的影响。在单因素试验的基础上,以皮诺敛酸含量和损失率的综合分为响应值,根据Box-Behnken中心组合试验设计原理,进行优化试验设计,并建立皮诺敛酸的尿素包合回归模型。研究表明:脂肪酸:尿素=1:2. 88(g/g),脂肪酸:乙醇=1:7. 98 (g/mL),包合时间23. 44 h,包合温度4. 18℃,该条件下对皮诺敛酸进行二次包合,含量可由一次包合的39. 27%提高到53. 36%,皮诺敛酸损失率为17. 24%,综合分值为0. 954 3,综合评价指标最高。     

超临界CO2对整粒松仁萃取的研究

采用超临界CO2萃取技术,从整粒松仁中萃取部分松子油.研究了萃取压力、温度和时间对出油率和整仁的影响.获得最佳的工艺条件为:压力30 MPa,萃取时间3 h,萃取温度35℃.     

酶法合成sn-2位富含DHA的中长链结构脂北大核心CSCD

采用两步酶法制备sn-2位富含DHA的中长链结构脂。首先,利用固定化脂肪酶Lipozyme 435催化DHA藻油发生醇解反应,溶剂萃取以获得富含DHA的单甘酯,再利用脂肪酶催化单甘酯和癸酸的酯化反应合成sn-2位富含DHA的中长链结构脂,并对中长链结构脂的组成进行分析。结果表明,最优酶法酯化反应条件为真空度0.05 MPa,单甘酯与癸酸摩尔比1∶3,固定化脂肪酶Lipozyme TL IM添加量为底物质量的8%,反应温度25℃,反应时间9 h。在最优条件下,酯化产物中甘油三酯(TAG)含量为96.55%,TAG脂肪酸组成中,DHA占总脂肪酸的40.04%,占sn-2位脂肪酸的72.15%。纯化的产品TAG中中长链结构脂占99.14%,含DHA的中长链结构脂占67.69%。     

酶促酯化反应合成共轭亚油酸油脂的工艺优化研究

研究了无溶剂体系中脂肪酶催化共轭亚油酸(CLA)与甘油酯化反应制备共轭亚油酸油脂的影响因素。考察了酶量、体系水分、温度、时间等因素对酯化反应的影响。结果表明,适宜的工艺条件为:酶量1%、水分含量1%、温度60℃,在上述条件下反应24h,酯化率可达94.11%。通过筛筐旋转反应酶重复利用5次后酯化率仍达87.28%。研究了脂肪酶对共轭亚油酸异构体的底物选择性,结果表明,脂肪酶催化10,12-十八碳二烯酸酯化反应优于9,11-十八碳二烯酸。     

Positional analysis of egg triacylglycerols and phospholipids from hens fed diets enriched with refined seal blubber oil

The effect of feeding laying hens with refined seal blubber oil (SBO, containing 22.2% ω3 polyunsaturated fatty acids) on the fatty acids composition and regiospecific distribution of fatty acids in triacylglycerols (TAG) and phospholipids (PL) of egg produced was investigated. The hens were fed four diets containing 0 (control), 1.25, 2.5 or 5% SBO for 5 and 9 weeks. Comparison of the total fatty acids composition indicated that a 5 week feeding period was sufficient to obtain the highest amount of total polyunsaturated fatty acids in the eggs. The fatty acids composition of the egg lipids reflected the fatty acids composition of the diet. The substantial reduction in the ω6/ω3 ratio (ie 8.5 to 2.6) is of interest, and is in line with the recommendations of health authorities in several countries, where it has been suggested that the human diet should contain a ω6/ω3 ratio of 3–4. The greatest reduction of the ω6/ω3 ratio occurred for diet A (control) and diet B (1.25% SBO). Principal component analysis analysis of the fatty acids composition of egg lipid showed four clusters representing: (i) the control diet; (ii) the diet containing 1.25% SBO as well as samples obtained from feeding 2.5% SBO for 9 weeks; (iii) the diet with 5% SBO; and (iv) samples obtained from hens fed 2.5% SBO for 5 weeks. More ω‐3 polyunsaturated fatty acids (ω3 PUFA) were incorporated in phosphatidylethanolamine and phosphatidylcholine than in TAG. Although ω3 were predominantly linked in the position Sn‐1,3 of TAG in SBO, they were esterified in the Sn‐2 position of the TAG and PL of eggs obtained after feeding laying hens with enriched diets. Copyright © 2005 Society of Chemical Industry     

沙棘油脂肪酸、sn-2位脂肪酸及甘三酯的测定与分析

采用超临界CO_2萃取得到沙棘籽油和沙棘全果油,并采用气相色谱和超高效液相色谱-飞行时间质谱对其脂肪酸、sn-2位脂肪酸及甘三酯组成进行测定与分析。结果表明:沙棘籽油中亚油酸、亚麻酸和油酸的含量较多,分别为38.71%、25.66%和20.68%,这3种脂肪酸也是其主要的sn-2位脂肪酸,含量分别为46.46%、25.49%和23.02%;LOL(13.65%)、OLO(12.06%)和LLn O(11.23%)是沙棘籽油的主要甘三酯类型;沙棘全果油中棕榈油酸(36.86%)、棕榈酸(27.27%)和油酸(18.00%)的含量较高,主要的sn-2位脂肪酸为棕榈油酸(45.57%)和油酸(32.06%);沙棘全果油的主要甘三酯为POPo(14.38%)、PoOPo(13.77%)和OPO(12.06%)。     

超临界CO2状态下酶法合成富含中链脂肪酸的玉米油

研究了在超临界CO2状态下,采用脂肪酶催化辛酸与玉米油反应制备富含辛酸甘油酯玉米油的工艺,分别考察了酶用量、反应压力、温度和时间对辛酸酯化率的影响。最佳的工艺条件为:酶用量5%,反应温度60℃,反应时间24h,反应压力11MPa,在此条件下辛酸的酯化率可达到90.73%。反应产物的脂肪酸组成中,具有生理活性的中链脂肪酸含量高达32.00%。     

高油酸花生油酶促酯交换合成类可可脂工艺优化

为促进高油酸花生油的高值化利用,在无溶剂体系中以高油酸花生油为原料,棕榈酸乙酯、硬脂酸乙酯为酰基供体,酶促酯交换合成类可可脂。以目标甘三酯1,3-二棕榈酸-2-油酸(POP)、1-棕榈酸-2-油酸-3-硬脂酸(POS)、1,3-二硬脂酸-2-油酸(SOS)含量,硬脂酸指数和酰基位移率为评价指标,在单因素实验的基础上采用响应面法对酶促酯交换合成类可可脂的工艺条件进行优化。结果表明：酶促酯交换合成类可可脂的最佳工艺条件为硬脂酸乙酯与棕榈酸乙酯物质的量比1.3∶1、酰基供体与高油酸花生油物质的量比12∶1、加酶量2.7%(以底物质量计)、反应温度60℃、反应时间7 h,在该条件下产物甘三酯中POP、POS、SOS的含量分别为14.55%、48.87%、25.17%,硬脂酸指数为0.56,酰基位移率为7.35%。产物的目标甘三酯组成和脂肪酸组成与可可脂相近,可作为可可脂替代品应用。     

超临界CO2从松子仁中萃取亚麻酸油的工艺研究

探讨超临界CO_2从松子仁中萃取亚麻酸油的萃取压力和温度、精馏柱温度以及萃取时间对亚麻酸油产率的影响,通过正交实验方案摸索出超临界CO_2从松子仁中萃取亚麻酸油的最佳条件。并与精榨方法提取的亚麻酸油比较,表明超临界流体萃取的亚麻酸油收率高,活性成分保存好。     

Biodiesel fuel production from plant oil catalyzed by Rhizopus oryzae lipase in a water-containing system without an organic solvent

A new enzymatic method of synthesizing methyl esters from plant oil and methanol in a solvent-free reaction system was developed. It is anticipated that such plant oil methyl esters can be used as a biodiesel fuel in the future. Lipase from Rhizopus oryzae efficiently catalyzed the methanolysis of soybean oil in the presence of 4–30 wt% water in the starting materials; however the lipase was nearly inactive in the absence of water. The methyl ester (ME) content in the reaction mixture reached 80–90 wt% by stepwise additions of methanol to the reaction mixture. The kinetics of the reaction appears to be in accordance with the successive reaction mechanism. That is, the oil is first hydrolyzed to free fatty acids and partial glycerides, and the fatty acids produced are then esterified with methanol. Although R. oryzae lipase is considered to exhibit 1(3)-regiospecificity, a certain amount of 1,3-diglyceride was obtained during the methanolysis and hydrolysis of soybean oil by R. oryzae lipase solution. Therefore, the high ME content in the reaction mixture is probably attributable to the acyl migration from the sn-2 position to the sn-1 or sn-3 position in partial glycerides.     

α-亚麻酸单甘酯的合成工艺研究

在溶剂体系中,以亚麻籽油和甘油为反应底物,Lipozyme435为催化剂,制备富含α-亚麻酸的单甘酯,采用单因素实验与响应面分析法考察了制备过程中底物摩尔比、反应时间、油醇比、加酶量和反应温度对单甘酯得率的影响。结果表明,反应的最佳条件为底物摩尔比（亚麻籽油：甘油）=1：3,油醇比为39.66%,加酶量6.01wt%,反应温度为56.11℃,反应时间为10.48 h。在此反应条件下反应所得产物中单甘酯含量约达71.1%,经检验单甘酯中α-亚麻酸的含量达51.36%。     

Sn-2位富含棕榈酸甘油三酯的酶法制备研究

以棕榈硬脂为原料,以非专一性脂肪酶Novozym 435作催化剂,将棕榈酸作为酰基供体与棕榈硬脂进行酸解反应,制备Sn-2位富含棕榈酸的甘油三酯,为下一步制备母乳脂肪替代油脂提供原料。首先,通过单因素实验确定了各因素的范围,再应用Box-Behnken中心组合实验设计建立二次多项数学模型,进行响应面分析。结果表明,当棕榈酸与棕榈硬脂质量比1.09∶1,反应时间9.9h,反应温度54.7℃,加酶量21.9%时,反应所得甘油三酯中Sn-2位棕榈酸可达到60.59%,可满足下一步制备母乳脂肪替代油脂的要求。      

Efficient production of fatty acid methyl ester from waste activated bleaching earth using diesel oil as organic solvent

Fatty acid methyl ester (FAME) production from waste activated bleaching earth (ABE) discarded by the crude oil refining industry was investigated using fossil fuel as a solvent in the esterification of triglycerides. Lipase from Candida cylindracea showed the highest stability in diesel oil. Using diesel oil as a solvent, 3 h was sufficient to obtain a yield of approximately 100% of FAME in the presence of 10% lipase from waste ABE. Kerosene was also a good solvent in the esterification of triglycerides embedded in the waste ABE. Fuel analysis showed that the FAME produced using diesel oil as a solvent complied with the Japanese diesel standard and the 10% residual carbon amount was lower than that of FAME produced using other solvents. Use of diesel oil as solvent in the FAME production from the waste ABE simplified the process, because there was no need to separate the organic solvent from the FAME-solvent mixture. These results demonstrate a promising reutilization method for the production of FAME, for use as a biodiesel, from industrial waste resources containing waste vegetable oils.     

Positional distribution of fatty acids in triacylglycerols from subcutaneous adipose tissue of pigs fed diets enriched with conjugated linoleic acid, corn oil, or beef tallow

This study was conducted to determine the effects of dietary beef tallow, corn oil, and conjugated linoleic acid (CLA) on the distribution of fatty acids among positions within triacylglycerols. Crossbred barrows (n=6 per treatment group) received diets containing 1.5% beef tallow, 1.5% corn oil, or 1.5% CLA for 5 weeks. Subcutaneous adipose tissue samples were obtained immediately postmortem. The fatty acid composition was determined for the sn-2 positions of the triacylglycerols by digestion with Rhizopus arrhizus lipase. Fatty acids in the sn-1/3 position were calculated from these data. Feeding CLA increased (P<0.05) the concentration of total saturated fatty acids (SFA, especially 16:0) and isomers of CLA in adipose tissue lipids, but reduced (P<0.05) the concentration of total monounsaturated fatty acids (MUFA, especially 18:1n−9). Dietary CLA caused an accumulation of total SFA in the sn-1/3 position, with a proportional decrease in total MUFA and 18:2n−6 in the outer positions. Correspondingly, lipids extracted from CLA-fed pigs had slip points that were 10 °C higher (P<0.05) than those from corn oil- or tallow-fed pigs. These data suggest that dietary CLA increases the melting point of lipids in porcine adipose tissue by increasing the proportion of SFA at the sn-1/3 position of lipids.     

Generation of glycerophospholipid molecular species in the yeast Saccharomyces cerevisiae. Fatty acid pattern of phospholipid classes and selective acyl turnover at sn-1 and sn-2 positions

Acyl chains linked to phospholipids of the yeast, Saccharomyces cerevisiae, are mainly C16:1 and C18:1 accompanied by minor amounts of C14:0, C16:0 and C18:0. In view of this rather simple fatty acid composition, the question arose whether in yeast, as in higher eukaryotes, fatty acyl groups were characteristically distributed among the sn-1 and sn-2 positions of distinct phospholipid classes. Analysis of fatty acids linked to the sn-1 and sn-2 positions of the major phospholipids showed that indeed saturated fatty acyl groups predominated in the sn-1 positions. While the percentage of saturated fatty acids was low (10%) in phosphatidylcholine (PtdCho) and phosphatidylethanolamine (PtdEtn) from cells grown on rich medium, it was higher in phosphatidylserine (PtdSer) (25%) and highest in phosphatidylinositol (PtdIns) (41%). Oleate was mainly linked to position sn-2, while palmitoleate predominated in position sn-1. Striking differences in the fatty acid distribution of phospholipids that are metabolically closely related (e.g. PtdSer and PtdEtn, PtdEtn and PtdCho, and PtdIns and PtdSer) suggest that pathways must exist for the generation of distinct phospholipid molecular species within the different phospholipid classes. The highly selective incorporation of exogenous [¹⁴C]palmitic acid (90%) and [³H]oleic acid (99%) into the sn-2 position of PtdCho, and the preferential incorporation of these fatty acids into the sn-2 position of PtdEtn (70 and 90%, respectively, for palmitic and oleic acid) are compatible with the postulate that phospholipase A₂-mediated deacylation followed by reacylation of the lysophospholipids is involved in the generation of phospholipid species in yeast.     

红松仁蛋白氨基酸组成分析及营养评价

以红松仁为原料,利用氨基酸自动分析仪检测红松仁可溶性蛋白中的氨基酸组成,以氨基酸比值系数分和WHO/FAO氨基酸评分为评价标准,对红松仁蛋白质营养价值进行全面的评价。结果表明:红松仁蛋白中氨基酸种类齐全,谷氨酸含量最高,必需氨基酸的含量占氨基酸的总量为25%,属于优质植物蛋白。红松仁中水溶和盐溶蛋白占红松仁蛋白的67.7019%,水溶蛋白和醇溶蛋白的氨基酸组成及评分最为合理,是红松仁组成蛋白中较优的蛋白组分;按照氨基酸比值系数,红松仁组成蛋白中,水溶蛋白(82.9256)>碱溶蛋白(81.453)>醇溶蛋白(79.0838)>总蛋白(77.1625)>盐溶蛋白(46.3652)。总蛋白、水溶蛋白、盐溶蛋白的第一限制氨基酸为缬氨酸,碱溶蛋白和醇溶蛋白的第一限制性氨基酸为蛋氨酸和胱氨酸。     

Variation in oil content and fatty acid composition of the seed oil of Acacia species collected from the northwest zone of India

BACKGROUND: The oil content and fatty acid composition of the mature seeds of Acacia species collected from natural habitat of the northwest zone of the Indian subcontinent (Rajasthan) were analyzed in order to determine their potential for human or animal consumption. RESULTS: Oil content varied between 40 and 102 g kg^?1. The highest oil content was obtained in Acacia bivenosa DC. (102 g kg^?1) among the nine Acacia species. The fatty acid composition showed higher levels of unsaturated fatty acids, especially linoleic acid (～757.7 g kg^?1 in A. bivenosa), oleic acid (～525.0 g kg^?1 in A. nubica) and dominant saturated fatty acids were found to be 192.5 g kg^?1 palmitic acid and 275.6 g kg^?1 stearic acid in A. leucophloea and A. nubica respectively. Seed oils of Acacia species can thus be classified in the linoleic–oleic acid group. Significant variations were observed in oil content and fatty acid composition of Acacia species. CONCLUSION: The present study revealed that the seed oil of Acacia species could be a new source of high linoleic–oleic acid‐rich edible oil and its full potential should be exploited. The use of oil from Acacia seed is of potential economic benefit to the poor native population of the areas where it is cultivated. The fatty acid composition of Acacia seed oils is very similar to that reported for commercially available edible vegetable oils like soybean, mustard, sunflower, groundnut and olive. Hence the seed oil of Acacia species could be a new source of edible vegetable oil after toxicological studies. Copyright © 2012 Society of Chemical Industry