Decomposition of linoleic acid hydroperoxides by radicals

Summary Methyl 13-hydroperoxy-cis,trans-9,11-octa-decadienoate (LMPO) was incubated with di-t-butyl peroxyoxalate for 3 h at 38 °C. In the presence of oxygen LMPO decomposed to numerous products among which were methyl 13-oxo-trans,trans-9,11- and methyl 9-oxo-trans,trans-10,12-octadecadienoate, methyl 13-oxo-trans-9,10-epoxy-trans-11-and methyl 9-oxo-trans-12,13-epoxy-trans-10-octadecenoate, methyl 9-hydroxy-trans-12,13-epoxy-trans-10-and methyl 13-hydroxy-trans-9,10-epoxy-trans-11-octadecenoate. Flushing the reaction system with nitrogen reduced the breakdown of LMPO and altered the reaction route in such a manner that a dimethyloctadecadienoate peroxide appeared as the major product.

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Abbau von Linolsäurehydroperoxiden durch RadikaleI. Strukturen der Produkte aus dem 13-Hydroperoxy-cis,traus-9,11-octadecädiensäuremethylester

Zusammenfassung 13-Hydroperoxy-cis,trans-9,11-octadecadiensäuremethylester (LMPO) wurde mit ditert-Butylperoxyoxalat 3 Std bei 38 °C incubiert. In Gegenwart von Sauerstoff wurde das LMPO zu zahlreichen Produkten abgebaut unter denen sich befanden: Methyl-13-oxo-trans,trans-9,11- und Methyl-9-oxo-trans,trans-10,12-octadecadienoat, Methyl-13-oxo-trans-9,10-epoxy-trans-11-und Methyl-9-oxo-trans-12,13-epoxy-trans-10-octadecenoat, Methyl-9-hydroxy-trans-12,13-epoxy-trans-10-und Methyl-13-hydroxy-trans-9,10-epoxy-traps-11-octadecenoat. Begasung des Reaktionssystems mit Stickstoff minderte den LMPO-Abbau und veränderte den Reaktionsverlauf derart, daß ein Di-methyloctadecadienoat-peroxid als Hauptprodukt erschien.

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These results have been presented in part at the 14th ISF Congress in Brighton (September 17th–21st 1978)     

On lipoxygenase and enzymes which decompose linoleic acid hydroperoxides in rye (author's transl)]

An enzyme fraction from rye containing lipoxygenase activity was investigated. The molecular weight of lipoxygenase was found to be about 102000. Two bands groups with isoelectric points between 5.1-5.5 and 5.8-6.4 were obtained by isoelectric focusing. Three isoenzymes could be separated by ion exchange chromatography. Lipoxygenase has optimum activity at pH 7.3-7.5 and predominantly forms 13-hydroperoxy-9-cis, 11-trans-octadecadienoic acid (13-LHPO). In rye the 13-LHPO is converted to alpha-ketols by a high molecular protein fraction. This isomerase converts the LHPO formed by rye lipoxygenase predominantly to 12,13-ketohydroxy acids. The Michaelis Constant of isomerase is 3-5 X 10(-5), using LHPO as substrate. At low protein concentrations the reaction velocity of LHPO-conversion increases linearly with protein concentration.     

亚油酸的微胶囊化研究

研究了喷雾干燥法微胶囊化亚油酸的工艺。选用HI-CAP100为主要壁材,并以微胶囊化效率为响应值,用响应面分析法(RSA)对亚油酸微胶囊化工艺进行了优化,确定的最优工艺参数为:溶液固形物含量为40%,经一级均质(压力为26.5 MPa),在进风温度为190℃,出风温度为90℃的条件下进行喷雾干燥,产品中亚油酸的载量可达50%,微胶囊化效率为92.11%。     

植物乳杆菌转化合成共轭亚油酸的培养基条件优化

生物法转化合成共轭亚油酸,产物中异构体组成单一,具有很好的应用前景。通过一株植物乳杆菌(Lactobacillus plantarum)合成共轭亚油酸的培养基成分进行优化,确定最优的培养基组成:葡萄糖20g/L,酵母浸出物40g/L,硫酸镁0.5g/L,硫酸锰0.5g/L,乙酸钠2g/L,磷酸氢二钾1g/L。优化后,共轭亚油酸产量达到0.259g/L,相比优化前(0.0455g/L)有了较大的提升。      

共轭亚油酸转化菌株的筛选

针对性地从特定环境采集土样,筛选出了2株能够将亚油酸转化为共轭亚油酸的菌株,并对菌株的形态学、生长规律和转化条件进行了初步研究.这两株菌株形态差异较大.但是在MRS培养基中,转化亚油酸为共轭亚油酸的最佳条件类似:最适亚油酸的浓度是0.51%(v/v),最适培养时间是36～48h.     

一株植物乳杆菌转化生成共轭亚油酸的特性研究

报道了一株植物乳杆菌(L.plantarumLT2-6)发酵转化亚油酸(LA)生成共轭亚油酸(CLA)的特性研究。微氧环境有利于CLA的生成;温度为37℃、初始pH为7.0、底物LA浓度为0.075%时,菌体生长及CLA生成量较高。时间曲线结果表明,接种后8h,CLA开始生成;发酵24h时,CLA生成量达到最高(0.29g/L),LA转化率为387%。生成的CLA产物主要为cis9,trans11/trans9,cis11-CLA。     

植物乳杆菌转化亚油酸为共轭亚油酸条件的研究

研究了植物乳杆菌AS1.555转化亚油酸为共轭亚油酸的条件。该菌株在MRS培养基中经0.1%(v/v)的亚油酸诱导培养后,所得的洗涤细胞具有很强的转化能力。通过单因素实验和正交实验得到植物乳杆菌转化亚油酸为共轭亚油酸的优化反应条件:反应温度30℃、反应时间48h、游离亚油酸浓度1.5%(v/v)、0.1mol/L磷酸缓冲液pH7.0。     

Conjugated linoleic acid concentration as affected by lactic cultures and added linoleic acid

Six lactic cultures: Lactobacillus acidophilus (CCRC14079), L. delbrueckii subsp. bulgaricus (CCRC14009), L. delbrueckii subsp. lactis (CCRC14078), Lactococcus lactis subsp. cremoris (CCRC12586), Lc. lactis subsp. lactis (CCRC10791), and Streptococcus salivarius subsp. thermophlius (CCRC12257) were tested for the effects of addition of 1000 and 5000 μg/ml linoleic acid, and incubation time from 0 to 48 h. The levels of conjugated linoleic acid (CLA) formation were determined by gas chromatography. A sharp increase in CLA level was observed in linoleic acid added cultures. Incubation of L. acidophilus in 1000 μg/ml linoleic acid added-skim milk medium for 24 h was most effective in promoting CLA formation. Increasing linoleic acid addition from 1000 to 5000 μg/ml and prolonging incubation from 24 to 48 h did not appear to enhance CLA formation.     

超临界CO2体系中固定化亚油酸异构酶催化合成共轭亚油酸

以固定化亚油酸异构酶和亚油酸(LA)为原料,在考察超临界CO2(SC-CO2)处理对酶稳定性影响的基础上,采用单因素试验和响应面法研究SC-CO2中LA质量浓度、反应温度、压力、反应时间对共轭亚油酸(CLA)合成的影响。结果表明:固定化亚油酸异构酶在SC-CO2压力小于30MPa,处理温度低于40℃,处理时间小于2 h时,相对酶活较高,具有较好的稳定性;响应面法优化CLA合成条件为LA质量浓度0.05 g/mL,反应温度36℃,压力30 MPa,反应时间1.5 h;在此条件下,CLA的含量为60.58 mg/g;固定化亚油酸异构酶重复使用3次,CLA保持较高的含量。     

共轭亚油酸的合成

共轭亚油酸(CLA)是亚油酸(LA)的同分异构体,是一种非常重要的功能性油脂,在医药保健、食品工业、饲料等方面的应用有着广阔的应用前景.从CLA的生产方法着手,重点描述了传统CLA的制备方法-化学异构化法、羟基脂肪酸脱水法,生物合成法和光异构化法.并对这些方法的研究手段、国内外研究水平、存在的问题、解决措施、优缺点和应用前景进行了介绍.尤其是生物合成法,由于其产物选择性高、异构体种类少、培养易于控制等,具有很好的商业应用前景.     

新型功能性油脂-共轭亚油酸

共轭亚油酸是天然存在于食品中的亚油酸异构体,具有抑制癌症和肿瘤的形成、减肥、抗动脉粥样硬化、改善免疫功能、降低胆固醇、促进生长等多种功能,是一种新型功能性油脂。本文综述了共轭亚油酸的生理功能、来源、合成及纯化方面的研究进展。     

共轭亚油酸的微乳及其性质研究

制备了共轭亚油酸/EL-35和EL-10/乙醇/水体系的O/W型微乳液.考察了温度、防腐剂和pH对微乳液区域的影响;动态光散射测定了微乳液的粒径;利用粘度计测定不同水含量的微乳液的粘度变化来观察微乳液流变性:对O/W、W/O、B.C.中的共轭亚油酸的微乳液和共轭亚油酸乙醇溶液进行了光稳定性研究,还分析了温度和pH对微乳液和乙醇溶液中共轭亚油酸稳定性的影响.结果表明,温度升高,防腐剂苯甲酸钠浓度变大和pH降低使微乳区稍有减小;微乳液粒径在制备三个月后仍保持在80～90nm之间;共轭亚油酸对光热和酸都比较敏感,但同环境条件下,O/W型微乳液中的共轭亚油酸比较稳定.     

酶法合成高含量共轭亚油酸甘油酯

选用AB-8大孔弱极性树脂对脂肪酶进行固定化,固定化脂肪酶的活力为210U／g。用此固定化酶催化共轭亚油酸乙酯和大豆油合成富含共轭亚油酸（CLA）的改性大豆油,最佳反应条件为：底物摩尔比（n（CLA乙酯）：n（大豆油））1：0．33,酶加量21U／g,反应温度60℃。放大反应体系,对反应产物中的CLA含量进行检测分析表明,其含量可达37％。     

瘤胃内共轭亚油酸(CLA)的形成

对瘤胃内共轭亚油酸（CLA）的形成机制、参与氢化的微生物及影响氢化的因素进行了综述，并对如何提高牛乳中CLA含量进行简要概述。     

共轭亚油酸在凝固型酸乳中的应用研究

在脱脂乳中分别添加了含量为0.05%、0.10%、0.20%、0.30%、0.40%、0.50%的共轭亚油酸(CLA),发酵凝固后,通过测定添加不同含量的CLA的酸奶的特征指标,如酸度、黏度、保水力、口感等的变化,从而确定酸奶中CLA的最适合添加量。结果表明,CLA添加量为0.2%时,酸奶的产黏性特性、产酸特性、保水性以及口感风味较好。     

植物乳杆菌ZS2058转化亚油酸为共轭亚油酸条件的初步研究

研究了植物乳杆菌ZS2058转化亚油酸为共轭亚油酸的条件,在培养基中添加10g/L吐温-80制成LA-吐温-80胶束溶液,可以提高CLA的转化率,最佳转化温度为35℃,添加1mg/mL的LA有较高的转化率和CLA产量。在MRS、SKM、KPB三种转化体系中SKM的转化率较高。在含LA的培养基中预培养12h,可以提高CLA的转化率。最佳转化接种量在1%～2%之间。      

Conjugated linoleic acid in ewe milk fat

Ewe milk fat from five different herds was studied to determine the content of conjugated linoleic acid (CLA) isomers. Research was carried out by combining gas chromatography-mass spectrometry (GC-MS) of fatty acid methyl esters (FAME) and 4,4-dimethyloxazolyne derivatives (DMOX) with silver ion-high performance liquid chromatography (Ag+-HPLC). Reconstructed mass spectral profiles of CLA characteristic ions from DMOX were used to identify positional isomers and Ag+-HPLC to quantify them. Total CLA content varied from 0.57 to 0.97 g/100 g of total fatty acids. FAME and DMOX were separated into a complex mixture of minor isomers and major rumenic acid (9-cis 11-trans C18:2) by GC-MS using a 100-m polar capillary column. Rumenic acid would represent more than 75% of total CLA. 11-trans 13-trans, 11-13 cis/trans plus trans/cis and 7-9 cis/trans plus trans/cis were the main CLA isomers after rumenic acid. Minor amounts of 8-10 and 10-12 C18:2 isomers were also found. Although most of the isomers were present in each herd's milk, differences in content were observed for some CLA species.     

Conjugated linoleic acid (CLA) content of milk from cows offered diets rich in linoleic and linolenic acid

Two experiments were conducted to determine the conjugated linoleic acid (CLA) content of milk from cows offered diets rich in linoleic and linolenic acid. In experiment 1, 36 cows were assigned to a control and five treatment groups. Cows in the control group received a diet containing 51% forage and 49% grain on a dry matter basis. In the treatment group, grain was partly replaced by either 18% raw cracked soybeans, 18% roasted cracked soybeans, 3.6% soybean oil, 2.2% linseed oil, or 4.4% linseed oil. Experimental diets were fed for 5 wk. Average CLA contents in milk fat from wk 2 through 5 were 0.39% in control and 0.37, 0.77, 2.10, 1.58, and 1.63% of total fatty acids in the raw soybean, roasted soybeans, soybean oil, 2.2% linseed oil, and 4.4% linseed oil treatments, respectively. In experiment 2, 36 cows were assigned to a control and 5 treatment groups. Cows in the control group received a diet containing 55% forage and 45% grain. In the treatment groups, grain was partly replaced by soybean oil at 0.5, 1.0, 2.0, 4.0, or by linseed oil at 1.0% of the dietary dry matter. Experimental diets were fed for 5 wk. Average CLA contents in milk fat from wk 2 through 5 were 0.50% in control and 0.75, 0.76, 1.45, 2.08, and 0.73% of total fatty acids in 0.5, 1.0, 2.0, 4.0 soybean oil and 1.0% linseed oil treatments, respectively. Diets rich in linoleic or linolenic acid can increase CLA content of milk when dietary oil is accessible to the rumen microorganisms.