Non-conjugated cis/trans 18:2 in Beef Fat are Mainly Δ-9 Desaturation Products of trans-18:1 Isomers

Human liver cells (HepG2) were cultured with individual trans (t) 18:1 including t6‐, t12‐, t13‐, t14‐, t15‐ and t16‐18:1, and retention times of their Δ‐9 desaturation products were determined using 100‐m biscyanopropyl‐polysiloxane and SLB‐IL111 columns. Corresponding peaks were found in beef adipose tissues known to have different delta‐9 desaturase activities. Further lines of evidence indicating the presence of Δ‐9 desaturation products of t‐18:1 isomers in beef fat were developed by analysis of fatty acid methyl esters (FAME) fractionated using Ag⁺‐TLC, and by GC/MS. Some of the Δ‐9 desaturation products of t‐18:1 have been previously identified in ruminant fat (c9, t12‐ and c9, t13‐18:2). Some of the Δ‐9 desaturation products of t‐18:1 (c9, t14‐ and c9, t15‐18:2) have been previously tentatively identified as different fatty acids, and for the first time we provide evidence of the presence of c9, t16‐18:2, and where t6, c9‐18:2 may elute during analysis of FAME from beef fat.     

气相色谱法测定食品油脂中的十八碳反式脂肪酸

反式脂肪酸是在油脂的加氢反应或高温精炼过程中伴随产生的一类不饱和脂肪酸,过多的食用这些成分可能会对人体健康产生危害。食品油脂中以十八碳反式脂肪酸最为常见。采用气相色谱法对食品中十八碳反式脂肪酸的检测进行了实验摸索,获得了一套准确度高、精确度好的方法,可应用于日常监督检测。     

Gene expression after dietary intervention with trans fatty acids (trans‐11/trans‐12 18:1) in humans

Gene‐by‐diet interactions play an important role in the prevention of several diseases. Conjugated linoleic acids (CLA) are ligands of gene regulators [e.g. peroxisome proliferator‐activated receptors (PPAR)] and have anti‐inflammatory properties. The aim of the study was to investigate the changes in gene expression in monocytes during the intervention with two trans fatty acids (trans‐11 18:1 and trans‐12 18:1) and endogenous CLA from trans‐11 18:1 as precursor in humans. Monocytes were isolated at baseline and after a 6‐week intervention period. The female and male test groups received Σ6.0 g trans‐11 and trans‐12 18:1/day (1 : 1). The control group received control oil. The expression of candidate genes was determined by quantitative RT‐PCR. Gender‐ and treatment‐related gene expression was found. Due to trans fatty acid intake in both gender subgroups, the relative PPARγ expression was up‐regulated. In the female test group, the expression of FAT, SCD, COX2 and BCL2 were induced, while in the male test group E‐FABP, CYP, GLUT4 and PBE were induced. In the male test group compared to controls, a clear increase in gene expression of PPARγ and GLUT4 was shown. The results reveal a gender‐ and treatment‐related gene expression. There is no clear indication as to what extent the supplemented trans fatty acids and the synthesized cis‐9,trans‐11 CLA were involved.     

Trans10,cis15 18:2 Isolated from Beef Fat Does Not Have the Same Anti-Adipogenic Properties as Trans10,cis12–18:2 in 3T3-L1 Adipocytes

During ruminal biohydrogenation of α‐linolenic acid, a non‐conjugated non‐methylene interrupted dienoic acid is formed containing a t10 double bond, namely t10,c15–18:2. The present study was designed to examine whether t10,c15–18:2 would exert similar anti‐adipogenic effects compared to t10,c12–18:2 in 3T3‐L1 adipocytes. Differentiated 3T3‐L1 adipocytes were treated with 35 or 70 µM of LNA, t10,c12–18:2, t10,c15–18:2, or bovine serum albumin (BSA) vehicle control for 120 h. Cellular triacylglycerol and protein were quantified using commercial colorimetric kits. Cells were analyzed for fatty acid composition and gene expression using gas chromatography and quantitative PCR, respectively. Trans10,cis12–18:2 decreased (P < 0.05) the adipocyte triacylglycerol (TAG) content, which was mainly related to a reduction in saturated fatty acids (SFA; e.g., 16:0 and 15:0) and cis monounsaturated fatty acids (c‐MUFA; e.g., c9–16:1 and c9–18:1). Trans10,cis12 also decreased (P < 0.05) the expression of genes related to fatty acid synthesis (ACACA, FASN), delta‐9 desaturation (SCD1), fatty acid elongation (ELOVL5), and fatty acid uptake (LPL) and upregulated (P < 0.05) the expression of the rate‐liming enzyme involved in fatty acid β‐oxidation (CPT1). In contrast, LNA and t10,c15–18:2 did not affect the gene expression and cellular content of the TAG, SFA, c‐MUFA, or SCD1 indices in adipocytes. Our findings suggest that t10,c15–18:2, despite having structural similarity to t10,c12–18:2 (presence of a trans‐10 double bond), does not exert anti‐adipogenic effects in 3T3‐L1 adipocytes.     

Sequential Feeding of Lipid Supplement Enriches Beef Adipose Tissues with 18:3n-3 Biohydrogenation Intermediates

The present study was designed to determine if feeding steers extruded flaxseed and hay (25 and 75%; DM basis) together as a total mixed ration (TMR), or sequentially (non-TMR) would result in different enrichments of polyunsaturated fatty acids (PUFA) and their biohydrogenation intermediates (BHI) in beef adipose tissues [subcutaneous (SC) vs perirenal (PR) fat]. Forty-eight Angus cross steers (325 ± 16 kg) were stratified by weight to six pens, and pens were randomized to either TMR or non-TMR and fed ad libitum for an average of 242 days. The concentrations of α-linolenic acid increased by 18 mol% in both SC and PR in non-TMR steers compared to TMR steers (P < 0.01). trans 18:1 isomers were more concentrated in PR than SC (14.4 vs 9.5 mol%; P < 0.01) and increased by 10 mol% in both fat depots for non-TMR (P < 0.01). Other BHI including non-methylene-interrupted 18:2 (atypical dienes), conjugated linoleic acids and conjugated linolenic acids (CLnA) were affected by diet × tissue interactions (P < 0.01). The CLnA and CLA contents were higher in both fat depots when feeding the non-TMR, but the effect of diet was more pronounced in PR than in SC (P < 0.01). Atypical dienes were highest in PR from non-TMR and lowest in TMR fed steers (4.3 and 3.6 mol%) with SC contents being intermediate. The sequential feeding of lipid supplement can thus profoundly affect the enrichment of PUFA and their BHI in beef fat and their differentially enrichment is also fat depot dependant.     

Comparison of Soybean and Cottonseed Oils upon Hydrogenation with Nickel,Palladium and Platinum Catalysts

There is current interest in reducing the trans fatty acids (TFA) in hydrogenated vegetable oils because consumption of foods high in TFA has been linked to increased serum cholesterol content. In the interest of understanding the TFA levels, hydrogenation was carried out in this work on soybean oil and cottonseed oil at two pressures (2 and 5 bar) and 100 °C using commercially available Ni, Pd, and Pt catalysts. The TFA levels and the fatty acid profiles were analyzed by gas chromatography. The iodine value of interest is ~70 for all-purpose shortening and 95–110 for pourable oil applications. In all cases, higher hydrogen pressures produced lower levels of TFA. In the range of 70–95 iodine values for the hydrogenated products, the Pt catalyst gave the least TFA, followed closely by Ni, and then Pd, for both oils. For all three catalysts at 2- and 5-bar pressures and 70–95 iodine values, cottonseed oil contained noticeably less TFA than soybean oil; this is probably because cottonseed oil contains a lower total amount of olefin-containing fatty acids relative to soybean oil. Approximate kinetic modeling was also done on the hydrogenation data that provided additional confirmation of data consistency.     

Selective Enrichment of Conjugated Linoleic Acid Isomers in Their Mixtures Using Combined Chemical and Enzymatic Methods

The aim of this study was to selectively enrich t10,c12-conjugated linoleic acid (t10,c12-CLA) and c9,t11-CLA in commercial CLA mixtures using a combination of urea crystallization and lipase-catalyzed esterification. The objective of the urea fractionation is to remove saturated and monounsaturated fatty acids (FA) from the CLA mixtures. CLA-enriched free FA (FFA) mixtures containing 53.8 wt% t10,c12-CLA and 39.1 wt% c9,t11-CLA were produced from the CLA mixtures containing ~34 wt% each of the two CLA isomers by a urea crystallization using methanol and the urea-to-FA weight ratio of 2.5:1. The CLA-enriched FFA mixtures were partially esterified with dodecan-1-ol in a recirculating packed-bed reactor using an immobilized lipase from Candida rugosa to further enrich the t10,c12-CLA and c9,t11-CLA in an FFA fraction and an FA dodecyl ester fraction, respectively, under the optimal conditions, i.e., temperature, 20 °C; FA-to-dodecan-1-ol molar ratio, 1:1; water content, 2 wt% of total substrates; residence time, 5 min; and reaction time, 24 h (for t10,c12-CLA enrichment) and 12 h (for c9,t11-CLA enrichment). After the reaction, an FFA fraction with 72.6 wt% t10,c12-CLA was obtained. Another FFA fraction with 62.0 wt% c9,t11-CLA was recovered after the saponification of the FA dodecyl ester fraction. The yields of t10,c12-CLA and c9,t11-CLA in the FFA fractions were 43.6 and 21.5 wt%, respectively, based on their initial weights in the CLA mixtures.     

High trans,trans Conjugated Linoleic Acid-Rich Triacylglyceride Production by Photo-Irradiation

Recent studies have shown that a 20 % trans,trans conjugated linoleic acid (CLA)‐rich soy oil significantly reduces heart disease and diabetes risk factors in obese rats. Furthermore, trans,trans‐CLA has been reported to have superior anti‐carcinogenic activity than other CLA isomers. Therefore, a more concentrated source of trans,trans‐CLA oil would be highly desirable. The objectives of this study were to (1) determine the yield of trans,trans‐CLA isomers resulting from photo‐irradiation of Tonalin^® (BASF Global, Florham Park, NJ, USA) and identify trans,trans‐CLA positional isomers; and (2) derive a mathematical model of kinetics of trans,trans‐CLA TAG formation from Tonalin^®. Fifty‐five percent trans,trans‐CLA rich oil was obtained in about 140 min when Tonalin^® was photo‐isomerized with 0.35 % iodine, which is almost three times more than is possible with photo‐isomerized soy oil. Photo‐isomerization of Tonalin^® requires about 2 h, compared to 12 h for photo‐isomerization of soy oil. This reaction is a first‐order reversible reaction with the forward rate constant (k_f) = 13.17 × 10^?3min^?1 and backward rate constant (k_b) = 5.334 × 10^?3min^?1. The major isomers identified were trans‐9,trans‐11‐ and trans‐10,trans‐12‐CLA.