Milk yield and composition during abomasal infusion of conjugated linoleic acids in dairy cows

Conjugated linoleic acids refer to a mixture of positional and geometric isomers of linoleic acid with conjugated double bounds. Three supplements of conjugated linoleic acids which differed in isomer enrichment were infused into the abomasum of lactating dairy cows to determine postruminal effect on milk yield and composition. Four Holstein cows were used in a 4 x 4 Latin square design. Treatments were 3-d abomasal infusion of 1) control, 5 kg of skim milk (carrier for conjugated linoleic acid supplements), 2) conjugated linoleic acid supplement 1 (28.8 g/d; 6.9 g of cis/trans 9,11; 6.4 g of cis/trans 8,10), 3) conjugated linoleic acid supplement 2 (48.5 g/d; 7.1 g of cis/trans 9,11; 4.1 g of cis/trans 8,10; 8.3 g of cis/trans 10,12; 5.5 g of cis/trans 11,13), and 4) conjugated linoleic acid supplement 3 (16.3 g/d; 7.1 g of cis/trans 9,11; 7.2 g of cis/trans 10,12). Infusions increased the conjugated linoleic acids content of milk fat from 0.43 g/100 g of fat for the control treatment to 1.02, 1.52, and 0.95 g/100 g of fat for conjugated linoleic acid supplements 1, 2, and 3, respectively. Apparent efficiency of transfer in milk fat was 25.2, 33.5, 21.0, and 28.4% for cis/trans 8,10, cis/trans 9,11, cis/trans 10,12, and cis/trans 11,13, respectively. Infusion of conjugated linoleic acids had no effect on dry matter intake, milk yield, and milk protein content. However, conjugated linoleic acid supplements reduced the content and yield of milk fat by 28 and 25%, respectively. The similarity of response for the different conjugated linoleic acid supplements did not allow us to identify the specific role of different isomers, but the changes in milk fatty acid composition indicated that effects were primarily on de novo fatty acid synthesis and the desaturation process.     

Effects of conjugated linoleic acid isomers on lipid metabolism and gluconeogenesis in monolayer cultures of bovine hepatocytes

The objective was to determine the effects of linoleic acid and different isomers of conjugated linoleic acid (CLA) at different concentrations on hepatic lipid and glucose metabolism in the bovine. Monolayer cultures of hepatocytes obtained from 7- to 10-d-old Holstein bull calves were exposed to treatments from 16 to 64 h after plating. The treatments included 1.0 mM palmitic acid plus either 0.1 or 1.0 mM of cis-9, cis-12 linoleic acid, cis-9, trans-11 CLA, or trans-10, cis-12 CLA. Metabolism of palmitic acid to cellular triacylglycerol (TAG) was decreased when media contained cis-9, trans-11 compared with trans-10, cis-12 CLA. Total cellular TAG content was increased for the CLA isomers compared to cis-9, cis-12 linoleic acid. Both CLA isomers increased palmitic acid incorporation into phospholipids, cholesterol, and media triacylglycerol compared with cis-9, cis-12 linoleic acid at a concentration of 1.0 mM. Increasing the concentration of treatment fatty acids from 0.1 to 1.0 mM decreased oxidation of palmitic acid to acid-soluble products, but no effects of fatty acids were observed. There was no treatment effect on rates of gluconeogenesis from propionic acid. Overall, CLA isomers elicited changes in palmitic acid metabolism to cellular and media triacylglycerol, and cellular phospholipids and cholesterol, but had little or no effect on other measured pathways of lipid metabolism or gluconeogenesis in bovine hepatocytes.     

An improved gas chromatography-based approach for characterisation of fatty acids in fresh basil seed oil

An improved gas chromatography-based analytical method for the simultaneous separation of seventy-two fatty acids was developed. Twenty-six types of trans fatty acids and conjugated linoleic acids were separated and identified with this method, especially trans C18 isomers. This method was confirmed to be high throughput and have high sensitivity and a low detection limit. It was successfully applied to separate and identify fatty acids in fresh basil seed oil. The linolenic acid content (51.67 g/100 g) was highest in basil seed oil, followed by linoleic acid (20.16 g/100 g) and oleic acid (12.70 g/100 g). These unsaturated fatty acids in fresh basil seed oil were transformed into trans fatty acids, conjugated linoleic acids and saturated fatty acids after heating to a certain temperature for an adequate duration, and the formation mechanisms were characterised.     

癞葡萄籽油脂肪酸组成的GC/MS分析

采用2-氨基-2-甲基丙醇(AMP)衍生化,GC/MS法分析癞葡萄籽油的脂肪酸组成。测定结果为:软脂酸1.65%,硬脂酸31.78%,油酸5.52%,亚油酸3.86%,十八碳共轭三烯酸55.13%,未定出成分2.07%。癞葡萄籽油的主要成分为十八碳脂肪酸,其中十八碳不饱和脂肪酸占64.51%。AMP衍生化GC/MS法可对不饱和脂肪酸双键的位置准确定位,将癞葡萄籽油中的3种共轭三烯酸的顺反异构体分开。     

Effect of the feeding system on intramuscular fatty acids and conjugated linoleic acid isomers of beef cattle,with emphasis on their nutritional value and discriminatory ability

Thirty two Alentejano purebred bulls were used to investigate the effect of four feeding systems (pasture only, pasture feeding followed by 2 or 4 months of finishing on concentrate, and concentrate only) on meat fatty acid composition (GC-FID), including conjugated linoleic acid (CLA) isomeric distribution (Ag[+]–HPLC–DAD). In addition, meat fatty acids and CLA isomers were used to elucidate the impact of the different feeding regimens on the nutritional value of intramuscular fat and their usefulness as chemical discriminators of meat origin. The diet had a major impact on the fatty acid composition of beef (affected 27 of 36 fatty acids and 10 of 14 CLA isomers), which was independent of the fatty acid concentration. Beef fat from pasture-fed animals had a higher nutritional quality relative to that from concentrate-fed bulls. Finally, meat fatty acid composition was an effective parameter to discriminate between ruminant feeding systems, including different finishing periods on concentrate.     

Direct quantification of fatty acids in dairy powders with special emphasis on trans fatty acid content

In this study a validated procedure for accurate determination of fatty acids in dairy products, with special emphasis on total trans fatty acids (TFA) content is presented. Dairy fat naturally contains 4–6% of trans fatty acids, mainly trans-octadecenoic acids (i.e. vaccenic acid), and 0.3–1.5% of conjugated linoleic acids (CLA). The proposed procedure does not require lipid extraction, and transesterification of lipids could be carried out directly on dairy products. Optimal analytical conditions have been developed to allow accurate determination of TFA content without prior fractionation of cis/trans FAME isomers by thin-layer chromatography. The methodology requires the use of a highly polar open tubular capillary column having at least 100 m length. CLA and other fatty acids from C4:0 (butyric) acid to long-chain polyunsaturated fatty acids (LC-PUFAs) could also be analyzed. Therefore, the methodology presented is versatile and could be used for both targeted analysis (e.g. determination of TFA in dairy products) and determination of the broad fatty acid profile in dairy products.     

11种品牌玉米油脂肪酸及异构体的主成分分析

对市售的11种品牌玉米油开展了脂肪酸(包括脂肪酸及其异构体)组成与含量的调查研究。采用气相色谱技术,结合主成分分析法,分析了不同品牌玉米油中脂肪酸的差异性和相关性。结果表明,11种品牌玉米油中共鉴定出19种脂肪酸,包括7种饱和脂肪酸,5种不饱和脂肪酸,6种反式脂肪酸(TFAs)和1种共轭亚油酸(t,t-CLAs),平均含量分别为14.18×10~(-2) g/g,80.32×10~(-2) g/g,1.47×10~(-2) g/g和0.23×10~(-2) g/g;其中,亚油酸(C18:2-9c12c)、油酸(C18:1-9c)和棕榈酸(C16:0)依次是玉米油中含量最多的3种脂肪酸;不同品牌玉米油中脂肪酸含量存在显著性差异(p0.05)。主成分分析揭示了不同品牌玉米油在脂肪酸含量上的相似性、差异性及脂肪酸之间相关程度,TFAs和CLAs正相关程度高。本研究为评价市售玉米油脂肪酸品质特征提供了较为全面的数据支撑。     

Effect of dietary conjugated linoleic acid (CLA) supplementation on CLA isomers content and fatty acid composition of dry-cured Parma ham

To evaluate the effects of dietary conjugated linoleic acid (CLA) supplementation on cis-9, trans-11 and trans-10, cis-12 isomer content and on the fatty acid composition of subcutaneous adipose tissue and intramuscular lipids of biceps femoris, the lipids of 24 dry cured Parma hams, obtained from Large White pigs fed isoenergetic diets supplemented with either 0 (CON) or 0.25% (T1) CLA from 97 to 172kg live weight, were analysed by Ag(+)-HPLC and capillary GLC. The dietary treatment had no influence on lipid content of BF and subcutaneous adipose tissue but increased (P<0.01) the content of both isomers, more markedly in the latter tissue. CLA supplementation increased (P<0.01) myristic, palmitic, palmitoleic and total saturated fatty acids, and decreased oleic and eicosenoic acids in both tissues. In adipose tissue, an increase (P<0.05) in stearic acid content was observed. Supplementing the finishing diet of heavy pigs with CLA has thus shown to be an effective tool for increasing the CLA content in cured ham and, also, the saturated:unsaturated ratio of the lipids, a positive effect from a technological point of view. From a human nutritional standpoint, the changes occurring in fatty acid composition negatively affect the atherogenic and thrombogenic indexes, but probably these changes are of no particular concern, as they would only partly offset the progressive increase in the degree of unsaturation of heavy pig lipids that has occurred in recent years, as a consequence of reduced adipose depots in carcasses.     

Technical note: Common analytical errors yielding inaccurate results during analysis of fatty acids in feed and digesta samples

The basic rules governing the proper fatty acid analysis of feed and digesta samples are sometimes overlooked, leading to potential errors in reporting the fatty acid content or composition of feed and digesta samples. The direct transesterification procedure of Sukhija and Palmquist (1988, J. Agric. Food Chem. 36:1202-1206) has become popular in analyzing fatty acids in feed and digesta samples obtained from animal feeding trials. One shortcoming of the Sukhija and Palmquist transesterification procedure is inaccurate analysis of fatty acids with conjugated double bonds. Digesta and milk samples from ruminant species typically contain a multitude of conjugated linoleic acid (CLA) isomers that easily undergo isomerization and epimerization following prolonged exposure to methanolic HCl. Modifications to the Sukhija and Palmquist procedure are given in this paper that allow successful determination of CLA isomers. Errors in fatty acid analysis also occur from misuse of internal standards; use of an internal standard is recommended in the Sukhija and Palmquist procedure as the preferred method to quantify total fatty acid content. The choice of internal standard may sometimes be important for obtaining accurate results. As an example, applying the direct transesterification procedure to a fat supplement high in saturated fatty acids yielded 613 mg/g of total fatty acids when C17 was used as the internal standard compared with 930 mg/g total fatty acids when C19 was used as the internal standard. Fatty acid content further increased to 952 mg/g when a unique unsaturated fatty acid (C13:1) was used as the internal standard.     

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.     

Conjugated fatty acids in food and their health benefits

Conjugated fatty acids (CFAs) are a mixture of positional and geometric isomers of polyunsaturated fatty acids with conjugated double bonds. Reports indicate that CFAs have potent beneficial effects, including antitumor, antiobese, antiatherogenic and antidiabetic activities. The molecules have also been shown to prevent the onset of hypertension. Recent reports suggest that each CFA isomer has different functions, for example the 10trans,12cis isomer of conjugated linoleic acid (CLA) has anticarcinogenic, antiobese and antidiabetic effects, whereas the 9cis,11trans-CLA isomer exerts an anticancer effect. Although it would be interesting to know the effects of CFAs on humans, there are only few reports concerning the anticancer and antiobese effects of CLA in humans. More detailed evaluations of the physiological bioactivities of CFA isomers on lifestyle-related diseases in humans and animals will be of great interest in future studies.     

Effect of cooking methods on fatty acids,conjugated isomers of linoleic acid and nutritional quality of beef intramuscular fat

The effect of boiling, microwaving and grilling on the composition and nutritional quality of beef intramuscular fat from cattle fed with two diets was investigated. Longissimus lumborum muscle from 15 Alentejano young bulls fed on concentrate or pasture was analyzed. Cooking losses and, consequently, total lipids, increased directly with the cooking time and internal temperature reached by meat (microwaving > boiling > grilling). The major changes in fatty acid composition, which implicated 16 out of 34 fatty acids, resulted in higher percentages in cooked beef of SFA and MUFA and lower proportions of PUFA, relative to raw meat, while conjugated linoleic acid (CLA) isomers revealed a great stability to thermal processes. Heating decreased the PUFA/SFA ratio of meat but did not change its n−6/n−3 index. Thermal procedures induced only slight oxidative changes in meat immediately after treatment but hardly affected the true retention values of its individual fatty acids (72–168%), including CLA isomers (81–128%).     

Role of the conjugated linoleic acid in the prevention of cancer

There are multiple lines of evidence that a variety of natural fatty acids are effective in health promotion. Among these fatty acids, conjugated linoleic acid (CLA)--a collective term referring to a mixture of positional and geometric isomers of linoleic acid (LA, cis-9, cis-12-octadecadienoic acid)--is currently under intensive investigation due to its health-promotion potential. The antitumor activity of CLA is of special interest, since it shows inhibitory effects against multistage carcinogenesis at relatively low dietary levels. Many studies using in vivo and in vitro models have shown that CLA suppresses the development of multistage carcinogenesis at different sites. The research to date on CLA has provided a vast amount of information about the mechanism on how CLA functions in the prevention of cancer. This article discusses characteristics of CLA in the prevention of cancer in both in vivo and in vitro studies and the possible underlying chemoprevention mechanisms.     

C18 : 1, C18 : 2 and C18 : 3 trans and cis fatty acid isomers including conjugated cis δ9,trans δ11 linoleic acid (CLA) as well as total fat composition of German human milk lipids

In particular with respect to infant nutrition knowledge of the current contents of trans fatty acids (TFA) and of conjugated linoleic acid (CLA) in human milk lipids is of interest. After pre-separation by Ag-TLC 11 trans-C18 : 1 isomers could be quantified by GC with a mean total content of 2.40 ± 0.60 wt% in samples from 40 German women. For the positional isomers t4, t5, t6–8, t9, t10, t11, t12, t13, t14, t15 and t16 contents of 0.02, 0.02, 0.21, 0.37, 0.32, 0.68, 0.23, 0.15, 0.18, 0.09 and 0.14 wt% were established, with vaccenic acid being the predominant isomer. Further, small trans-C14 : 1 and trans-C16 : 1 contents of 0.08% and 0.15% on average were found. As the trans-C18 : 1 isomers also the trans-C16 : 1 isomers of human milk lipids could for the first time be baseline-resolved by GC to a great extent. Moreover, besides a mean CLA (c9,t11) content of 0.40 ± 0.09% further 6 cis/trans isomers of linoleic acid with a total content of 1.07 ± 0.56% on average (w/o CLA) were determined. Further, 4 trans isomers of α-linolenic acid could be baseline-resolved exhibiting a total content of 0.11%. Altogether German human milk lipids on average were found to contain 3.81 ± 0.97% TFA with a range of 2.38–6.03%. Direct connections between the dietary intake of trans-C18 : 1 isomers and the composition of human milk lipids could be established. The major fatty acids exhibited the following contents (wt%): C4: 0.16, C6: 0.18, C8: 0.06, C10: 0.58, C12: 3.12, C14: 6.43, C16: 25.28, C18: 7.41, C18 : 1 (total): 33.67, C18 : 2 (total): 10.63 and α-C18 : 3: 0.87.     

Production of conjugated fatty acids by lactic acid bacteria

Conjugated fatty acids have attracted much attention as a novel type of biologically beneficial functional lipid. Some isomers of conjugated linoleic acid (CLA) reduce carcinogenesis, atherosclerosis, and body fat. Considering the use of CLA for medicinal and nutraceutical purposes, a safe isomer-selective process is required. The introduction of biological reactions for CLA production could be an answer. We screened microbial reactions useful for CLA production, and found several unique reactions in lactic acid bacteria. Lactic acid bacteria produced CLA from linoleic acid. The produced CLA comprised a mixture of cis-9,trans-11-octadecadienoic acid (18:2) and trans-9,trans-11-18:2. Lactobacillus plantarum AKU 1009a was selected as a potential CLA producer. Using washed cells of L. plantarum AKU 1009a as a catalyst, CLA production from linoleic acid reached 40 mg/ml under the optimized conditions. The CLA-producing reaction was found to consist of two successive reactions, i.e., hydration of linoleic acid to 10-hydroxy-12-octadecenoic acid and dehydrating isomerization of the hydroxy fatty acid to CLA. On the basis of these results, the transformation of hydroxy fatty acids by lactic acid bacteria was investigated. Lactic acid bacteria transformed ricinoleic acid (12-hydroxy-cis-9-octadecenoic acid) to CLA (a mixture of cis-9,trans-11-18:2 and trans-9,trans-11-18:2). Castor oil, which is rich in the triacylglycerol form of ricinoleic acid, was also found to act as a substrate for CLA production by lactic acid bacteria with the aid of lipase-catalyzed triacylglycerol hydrolysis. L. plantarum AKU 1009a produced conjugated trienoic fatty acids from alpha- and gamma-linolenic acid. The trienoic fatty acids produced from alpha-linolenic acid were identified as cis-9,trans-11,cis-15-octadecatrienoic acid (18:3) and trans-9,trans-11,cis-15-18:3. Those produced from gamma-linolenic were cis-6,cis-9,trans-11-18:3 and cis-6,trans-9,trans-11-18:3. The conjugated trienoic fatty acids produced from alpha- and gamma-linolenic acid were further saturated by L. plantarum AKU 1009a to trans-10,cis-15-18:2 and cis-6,trans-10-18:2, respectively.     

Influence of low linoleic and linolenic acids in milk replacer on calf performance and lipids in blood plasma, heart, and liver

In a 6-wk study with 3-d-old calves (n = 32), we compared effects of low or adequate essential fatty acids in milk replacers on calf performance, feed utilization, and fatty acids in blood plasma, heart, and liver lipids. Four dietary treatments were hydrogenated coconut oil, as low-essential fatty acid basal; basal plus linoleic acid; basal plus linoleic plus linolenic acids; tallow control. None of the calves fed low essential fatty acid diet developed any external deficiency signs seen in monogastric animals. Supplementation of basal diet with essential fatty acids had no influence on weight gains, feed efficiency, or digestibility of lipids, nitrogen, and dry matter. Effects of low essential fatty acid intake were decreased resistance of erythrocytes to lysis, and in tissue lipids, marked reduction of linoleic acid and elevation of trienoic acid, palmitoleic acid, and ratio of trienoic acid to arachidonic acid, all indicative of low essential fatty acid status. Essential fatty acid intake in milk replacer may be more important than indicated here for longer term vealer calves, and where stresses, such as infectious diseases and high environmental temperature, are present.     

新型食品营养强化剂-共轭亚油酸

共轭亚油酸 (Conjgatedlinoleicacid ,CLA)是一类含有共轭双键的亚油酸的异构体 ,由于具有特殊的脂肪链结构使得其具有多种生理功能。c9t11和t10cl2异构体是共轭亚油酸的主要活性异构体。本文对共轭亚油酸的生理功能、代谢、安全性等进行综述。     

Conjugated linoleic acid and C18:1 isomers content in milk fat of sheep and their transfer to Pecorino Toscano cheese

The aim of the study was to evaluate the transfer of conjugated linoleic acid (CLA) and of C18:1 isomers from sheep milk to Pecorino Toscano protected denomination of origin cheese and to monitor the stability of these fatty acids during ripening. The total content of C18:1 fatty acids was not affected by milk treatment but there were changes in the isomers profile. In particular, the milk trans11 C18:1 decreased with pasteurization and after starter culture addition. In contrast, trans10 C18:1 and cis9, trans11 C18:2 were enhanced by the thermal treatment of milk. The fatty acid profile of cheese reflected that of milk used for cheese making with the exception of the C18:1 and CLA isomer profile. The cheese ripening affected the percentage of cis9, trans11 C18:2, which increased more than 10% on total content of CLA.     

CHEMICAL CHARACTERIZATION AND STEREOSPECIFIC ANALYSIS OF LIPIDS SYNTHESIZED BY CERTAIN YEAST STRAINS

Fatty acid analysis of lipids from yeast strains, Apiotrichum curvatum ATCC 10567, Cryptococcus albidus ATCC 56297, Lipomyces starkeyi ATCC 12659, and Rhodosporidium toruloides ATCC 10788, grown on whey permeate revealed palmitic, stearic, oleic and linoleic acids as the predominant fatty acids in the triacylglycerol fractions. The phospholipid fractions were dominated by oleic and linoleic acids. The stereospecific distribution of fatty acids in the triacylglycerol fractions of lipids from two yeast strains, Apiotrichum curvatum ATCC 10567 and Lipomyces starkeyi ATCC 12659, was determined and revealed the presence of almost entirely unsaturated fatty acids at the sn-2 position (91.9% and 82.8%, respectively). The dominance of unsaturated fatty acids (in the range of 61.5 to 72.3%) at the sn-1 position was also observed. Oleic acid was the predominant fatty acid at positions sn-1 and sn-2 for both yeast strains. Position sn-3 had the greatest concentrations of saturated fatty acids, with palmitic acid as the predominant fatty acid.