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Total fat and fatty acid levels of Ulva linza (Linnaeus 1753), Enteromorpha flexuosa (Agardh, 1883), and Taonia atomaria (Agardh, 1848) collected from Viransehir, Taskiran, and Karaduvar coasts were determined. The total oil level of the samples was found to be 1.31-1.91%, 1.23%, 7.78% for U. linza, E. flexuosa and T. atomaria, respectively. The dominant saturated fatty acids are palmitic acid and stearic acid. The highest level of palmitic acid (32.27%) was found in E. flexuosa in Viransehir beach. The highest level of stearic acid was found on the coast of Viransehir (7.20%), U. linza. The highest level of ΣSFA was found in the U. linza species on Taskiran coast (37.89%), and the lowest level was determined in the T. atomaria species on the Taskiran coast (18.13%). It is oleic acid that has a high level of monounsaturated fatty acids. The highest level of this fatty acid (10.35%) was found in E. flexuosa species in Viransehir beach. The highest level of ΣMUFA was found in the Viransehir coast (16.67%) and the lowest level (11.39%) in the U. linza on the Viransehir beach. The highest level of linolelaidic acid in polyunsaturated fatty acids was found in E. flexuosa in Viransehir beach (3.34%). The highest level of linoleic acid (4.85%) was found in U. linza on the coast of Viransehir. The highest level of ΣPUFA was found in T. atomaria on the Taskiran coast (16.56%), and the lowest level (7.03%) was found in U. linza.

Freshwater microalgae Chlorella sp. was isolated from the water body of Taman Gelora, Kuantan, Pahang. The isolated monoculture was cultured in different concentration of POME (10%, 20%, 30%, 40% and 50%, v/v) as substrate. The maximal growth and biomass productivity were found in 30% (v/v) of POME. The maximal dry biomass 1.56 g/L was obtained and extracted 39.1% lipid, approximating similar productivity as in conventional BG-11 medium 1.65 g/L of biomass and 41.5% lipid. Gas chromatography-mass spectrometry analysis shows the composition of fatty acids such as linolelaidic acid, oleic acid, palmitic acid, stearic acid, elaidic acid, and α-linoleic acid dominant. The highest fatty acid is linolelsidic acid (41.69%). POME has the potential to be used as a substrate for microalgae Chlorella sp. cultivation.

Background Previous studies on health effects of trans fatty acids (TFA) have focused mainly on cardiovascular health. Little is known about the association of TFA with brain or mental health. In this study, we examined the associations of objectively-measured plasma TFA concentrations with depression in a large population-based cross-sectional study among U.S. adults. Methods We included 2136 non-pregnant participants aged 20 years or older from the National Health and Nutrition Examination Survey 2009–2010. Four major TFAs, including palmitelaidic acid (C16:1n-7t), elaidic acid (C18:1n-9t), vaccenic acid (C18:1n-7t), and linoelaidic acid (C18:2n-6t, 9t), were measured in fasting plasma using gas chromatography/mass spectrometry. Depressive symptoms were assessed using the validated Patient Health Questionnaire-9. Results Participants with depressive symptoms had a higher plasma concentration of total TFA compared with those without depressive symptoms (6.6 vs 6.0 μmol/g lipids, P = 0.046). After adjustment for other major risk factors, the odds ratio (OR) of depressive symptoms comparing the highest with lowest tertile of TFAs was 1.44 (95% CI, 0.86–2.39) for total TFAs (P for trend 0.15). For each individual type of TFA, the corresponding OR was 1.78 (1.03–3.07) for elaidic acid (P for trend 0.049), 1.23 (0.76–2.00) for linoelaidic acid (P for trend 0.37), 1.19 (0.75–1.87) for palmitelaidic acid (P for trend 0.46), and 1.20 (0.75–1.94) for vaccenic acid (P for trend 0.43). Limitations The cross-sectional study design limited causal inferences of the findings. Conclusions In a nationally representative population, plasma elaidic acid, a major trans fatty acid, was positively associated with depressive symptoms in adults. A positive but non-significant association of depressive symptoms was observed for total TFAs, linolelaidic acid, palmitelaidic acid, and vaccenic acid.

Sperm cryopreservation represents a powerful tool for horse breeding. To improve the efficiency of artificial insemination in the horse using cryopreserved spermatozoa, an adequate understanding of the underlying biophysical properties that affect sperm cryosurvival needs to be reached yet. In this pilot study, we described isolation and analysis of the main fatty acids from sperms of stallions classified as good and poor freezers (7 GF and 5 PF, according to sperm motility and viability, before and after cryopreservation). Fatty acid profiles were only assessed in pre-thaw sperms. Eight main fatty acids were identified, using gas chromatography, and their contents were expressed as percentage of the total lipid content. We found that lauric, myristic and oleic acid (C12:0, C14:0 and C18:1n9c) turned out to be about 2-fold more abundant in the sperm cells of the GFs compared with PFs. Moreover, we described for the first time the presence of a very high amount of a trans geometrical isomer of linoleic acid, linolelaidic acid (C18:2n6t), in pre-thaw PF spermatozoa. Notably, we found in fresh sperms of PF stallions a ratio of unsaturated fatty acids to saturated fatty acids which was twice that of those of GF group, suggesting a positive effect of a high saturated-to-unsaturated fatty acid ratio for the “freezability” of equine spermatozoa. Finally, principal component analysis (PCA) confirmed the relationships between specific fatty acids and cryotolerance of equine spermatozoa, also providing a graphical classification and additional information about the dominant variables governing the classification process.

Background: Trans fatty acids are considered to impair health and some ω fatty acids are protective against atherosclerosis and diabetes mellitus. Trans fatty acids are said to be formed by the partial hydrogenation of vegetable oils. Some amounts are produced in digestive organs of ruminants and present in dairy products or meat. It is important how much these intaken fatty acids influence their plasma levels. Methods: Plasma levels of fatty acids including transforms of healthy old men are measured by gas chromatography and correlations between various foods intakes and plasma levels of trans fatty acids, and ω fatty acids are examined. Results: Intake of fish resulted in increase in plasma levels of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) but intake of meat such as beef, cow and chicken meat did not increase plasma levels of arachidonic acid (AA). Intakes of oils increased plasma levels of dihomo-g-linolenic acid significantly and AA to some extent. Conclusion: Plasma levels of EPA and DHA increased upon intakes of fish in Japanese old men. Oil intake but not meat intake increased DGLA significantly. These results may explain low incidence of cardiovascular diseases in Japanese people compared with American people whose plasma levels of DHA and EPA are lower.

Sterculia tragacantha Lindl. plants are endemic plants existing in Papua and have the potential of secondary metabolite compounds. This research aimed to determine the antioxidant activity and fatty acid composition of S. tragacantha Lindl. leaf extract. The extract was obtained by maceration using methanol and n-hexane solvents. The antioxidant activity testing was carried out using DPPH (1,1-diphenyl 2-picrylhydrazyl) free radicals while the identification of fatty acid compounds was done using Gas Chromatography-Mass Spectrometry (GCMS). The results showed that the methanol and n-hexane extracts of S. tragacantha Lindl. leaves had a strong antioxidant activity of 2.25 ±0,09 ppm and 27,24 ± 1,25 ppm respectively. Meanwhile, the fatty acid main contents of the methanol and n-hexane extracts of S. tragacantha Lindl. leaves were Methyl palmitate, Methyl linolenate, Linolelaidic acid methyl ester, trans-9-elaidic acid methyl ester, and Methyl palmitoleate. Keywords: Antioxidants, Fatty Acid, FTIR, Sterculia, GCMS

Background: The consumption of trans fatty acids (TFAs) is associated with an increased risk of cardiovascular disease, and reducing their consumption is a major public health objective. Food intake studies have provided estimates for TFA concentrations in the US population; however, there is a need for data on TFA blood concentrations in the population.Objective: The objective of this study was to determine plasma TFA concentrations in a nationally representative group of fasted adults in the US population in NHANES samples from 1999-2000 and 2009-2010.Design: Four major TFAs [palmitelaidic acid (C16:1n-7t), trans vaccenic acid (C18:1n-7t), elaidic acid (C18:1n-9t), and linoelaidic acid (C18:2n-6t,9t)] were measured in plasma in 1613 subjects from NHANES 1999-2000 and 2462 subjects from NHANES 2009-2010 by gas chromatography-mass spectrometry. Geometric means and distribution percentiles were calculated for each TFA and their sum by age, sex, and race/ethnicity (non-Hispanic white, non-Hispanic black, Mexican American), and covariate-adjusted geometric means were computed by using a model that included these demographic and other dietary factors, as well as survey year and any significant interaction terms.Results: These nationally representative data for the adult US population show that TFA concentrations were 54% lower in NHANES 2009-2010 than in NHANES 1999-2000. Covariate-adjusted geometric means for the sum of the 4 TFAs were 81.4 μmol/L (95% CI: 77.3, 85.6 μmol/L) and 37.8 μmol/L (95% CI: 36.4, 39.4 μmol/L) in NHANES 1999-2000 and 2009-2010, respectively. Even with the large decline in TFA concentrations, differences between demographic subgroups were comparable in the 2 surveys.Conclusion: The results indicate an overall reduction in TFA concentrations in the US population and provide a valuable baseline to evaluate the impact of the recent regulation categorizing TFAs as food additives.

This study determined effects of milk production, milk components, or fatty acids (FA) profile on live weight of suckling lambs till their weaning. Live weight (LW, kg) of 42 purebred Wallachian lambs (from 33 ewes) was recorded during four control days with approximately 30-day intervals during rearing. At the same time, their mothers were examined for milk production (kg), milk fat (g), proteins (g), lactose (g), and fatty acids (%) contents. Results investigated using linear regression analysis showed 5.93 kg (p &lt, 0.05) increase of lambs LW corresponded with 1 kg of ewe&rsquo, s daily milk production increase during the observed period. Similarly, significant 0.13 kg or 0.11 kg increases of lambs live weight corresponded with 1 g increase of milk protein or milk lactose at this time. Milk with higher prevalence of trans-palmitoleic acid, trans-vaccenic acid, cis-vaccenic acid, linolelaidic acid, linoleic acid, or conjugated linolenic acid (CLA) significantly improved lambs LW. Moreover, significantly positive Pearson partial correlation between LW and trans-vaccenic acid (r = 0.305) or CLA (r = 0.347) indicated on genetic correlation between these traits. Therefore, milk (natural or artificially supplied) with higher distribution of these specified FAs could improve lambs&rsquo, LW.

The rheological characteristics of oils isolated from the seeds of Afzelia africana and Detarium microcarpum were studied and compared with rapeseed oil. The effects of shear rate and temperature on the flow characteristics were evaluated. The shear stress- shear rate rheological models: Herschel-Bulkley, Power law, Binghan, Newtonian and Casson were used to determine the flow characteristics. All the oils exhibited non-Newtonian behaviour at shear rates rapeseed oil > Detarium oil. The activation energy of viscous flow followed the same order as viscosity of the oils. The most abundant fatty acids in A. africana oil were cis-11-eicosenoic acid (39 .06%), linolelaidic acid (18.38%) and nervonic acid (10.20%) and in D. microcarpum oil cis-13,16-dicosadienoic acid (20.51%) and linoleic acid (20.37%) and undecanoic acid (14.24%). A. africana contained higher amount of unsaturated fatty acids (92.26%) and long chain fatty acids (C ≥15; 96.00%) than D. microcarpum (unsaturated fatty acids, 66.27%; C ≥ 15; 79.41%). A. africana oil with the greater amount of long chain fatty acids had higher viscosity and activation energy of viscous flow. Key words: Afzelia africana, oil, rheological properties, fatty acid composition, Detarium microcarpum

The effects of plant oils on health are being intensively studied. Many fatty acids have attracted significant scientific attention since the studies pointed them as potential nutrients. An attempt was made to analyze the variation in three major Indian Garcinia fruits for their oils, lipid sub-classes, fatty acids and total amino acids. Solvent extraction and chromatographic techniques were used for the isolation, purification, separation and detection of these compounds. Three major Garcinia fruits G. gummi-gutta, G. indica and G. xanthochymus varied in their chemical composition. Oil content was significantly higher (p

It remains unclear how trans fatty acid (TFA) at low-level intake affect lipid levels and the development of acute coronary syndrome (ACS). The study aimed to investigate how plasma TFA composition differs between male patients with ACS and healthy men.Plasma fatty acid (FA) composition (as determined by gas chromatography) was analyzed in ACS patients on hospital admission and compared to that of age-adjusted healthy men.Total FA and TFA levels were similar between ACS and control subjects. Palmitelaidic acid, ruminant-derived TFA (R-TFA), levels were lower in ACS patients (0.17 ± 0.06 vs. 0.20 ± 0.06 of total FA, in ACS and control, respectively, p0.01), and were significantly directly associated with HDL cholesterol (HDL-C) (rho = 0.269) and n-3 polyunsaturated FA (n-3 PUFA) (rho = 0.442). Linoleic trans isomers (total C18:2 TFA), primary industrially-produced TFA (IP-TFAs), were significantly higher in ACS patients (0.68 ± 0.17 vs. 0.60 ± 0.20 of total FA, in ACS and control, respectively). Total trans-C18:1 isomers were comparable between ACS and control. Differences between ACS and controls in C18:1 trans varied by specific C18:1 trans species. Absolute concentrations of trans-C18:2 isomers were significantly directly associated with LDL-C and non-HDL-C in ACS men. The ACS patients showed significantly lower levels of both n-6 and n-3 PUFA (i.e., eicosapentaenoic, docosahexaenoic and arachidonic acids).There were several case-control differences in specific TFA that could potential affect risk for ACS. Japanese ACS patients, especially middle-aged patients, may consume less R-TFA.

With increasing presence of silver nanoparticles (AgNPs) into the environment, the chronic and low-dose effects of AgNPs are of vital concern. This study evaluated chronic physiological effects of AgNPs on Daphnia similis, which were exposed to two ambient encountered concentrations (0.02 and 1 ppb) of AgNPs for 21 days. It was observed that the low-dose AgNPs stimulated a significant increase in average length/dry mass, but inhibited reproduction compared to control specimens. Non-targeted metabolomics based on liquid chromatography-quadrupole-time of flight-mass spectrometry (LC-QTOFMS-MS) and gas chromatograph-quadrupole time of flight mass spectrometry (GC-QTOF-MS) were utilized to elucidate the underlying molecular mechanisms of these responses. Forty one metabolites were identified, including 18 significantly-changed metabolites, suggesting up regulation in protein digestion and absorption (amino acids, such as isoleucine, tryptophan, lysine, leucine, valine, aspartic acid, threonine, tyrosine) and down regulation of lipid related metabolism (fatty acids, such as arachidonic acid, stearidonic acid, linoelaidic acid and eicosapentaenoic acid) were key events in these responses. The increase in these amino acid contents explains the accelerated growth of D. similis from the metabolic pathway of aminoacyl-tRNA biosynthesis. Down regulation of fatty acid contents corresponds to the observed drop in the reproduction rate considering the fatty acid biological enzymatic reaction pathways. Significant changes in metabolites provided a renewed mechanistic understanding of low concentration chronic toxicity of AgNP toxicity on D. similis.

The effect of different individual TFA isomers on cardiovascular disease (CVD) has been a limited study, especially for stroke. We aimed to investigate the relationships between four major plasma TFA isomer (elaidic, vaccenic, palmitelaidic and linolelaidic acid) concentrations and the risk of CVD, stroke and non-stroke CVD. A cross-sectional study was conducted, utilising a nationally representative sample of US adults in the National Health and Nutrition Examination Survey. Among the 3504 participants, 304 participants self-reported CVD history. The highest quintile of elaidic acid intake was associated with a 233% higher CVD risk (p = .010). Adjusted for age, gender and race, palmitelaidic acid was associated with a decreased CVD risk, but the effect size was diminished in a subsequent analysis model. For stroke risk, we failed to identify any associations. In addition to elaidic acid, the health effect of palmitelaidic acid should be paid more attention in the future studies.

The present study was aimed to study the effect of the bee pollen extract on the broiler Ross 308 breast and thigh meat fatty acids. The experiment enrolled 90 chicks in one day old, which were divided into 3 groups (control, E1 and E2). The broiler has been bred in a cage condition for 42 days. To the experimental groups were added bee pollen extract in the amount (400, 800 mg.kg-1). The chickens have been bred in a cage conditions, each cage was equipped with feed dispenser and water intake was ensured ad libitum through a self feed-pump. The temperature was controlled during the fattening period and it was 33 °C at the first day and every week was reduced about 2 °C the end temperature was 23 °C. At the end of the experiment the fatty acids have beenevaluatedby using Agilent 7890A Gas Chromatograph apparatus (USA). The findings have been shown that the myristoleic acid, linoleic acid, linoelaidic acid, arachidonic acid, and archaic acid were decreased after using the bee pollen into broiler feed mixture otherwise, the bee pollen has been increased the polemic acids and oleic acid and there were found no significant differences (P ≥0.05) among all the experimental groups.From the recent experiment, we conclude that bee pollen extract has decreasedthe fattyacids except palmitoleic acid acid and oleic acid, whichwere higher compared to control groupand there were no significant differences (P ≥0.05) between experimental groups.

Strongylocentrotus intermedius is an important commercial species of sea urchin distributed in the coastal waters of China. However, the metabolomic changes that accompany its gonadal growth and development stages remain unclear. In this study, we have histologically observed gonad growth stages, analyzed the fatty acid composition, and employed an untargeted metabolomic approach to investigate the metabolites associated with the gonadal growth and development of S. intermedius, as well as the biosynthesis and metabolism of polyunsaturated fatty acids (PUFAs) at different stages and in different sexes. The gonad mass of sea urchin increased from 0.70 ± 0.18 g in January (at the recovering stage) to 8.78 ± 2.89 g in July (the reproductive stage), with the GSI increasing from 4.02 ± 0.88% to 16.86 ± 2.79%. We have analyzed 34 types of fatty acids, such as arachidonic acid, eicosapentaenoic acid, etc., of which PUFAs were the dominant fatty acid class in this species, accounting for >48.55% of the total. In the metabolomic analysis, linolelaidic acid, sciadonic acid, cis-8,11,14,17-eicosatetraenoic acid, adrenic acid, docosapentaenoic acid, and tetracosapentaenoic acid were detected in the differentially expressed metabolites of the unsaturated fatty acids biosynthesis pathway. We found that the most significant functional pathways during gonadal growth and development were “arachidonic acid metabolism”, “alpha-linolenic acid metabolism” and “linoleic acid metabolism”, which are all related to fatty acid metabolism. These results will provide valuable information on the possible presence of both exogenous and endogenous fatty acids in sea urchin gonads and the metabolomic changes in S. intermedius during gonadal growth periods, and will further our understanding of the intermediary metabolism and the molecular bases of growth traits in this species.

The p resent study investigated the influence of seasonality (summer and winter) on the pro ximate co mposition and on the amount of polyunsaturated fatty acids in milk fat. The amounts of lipid and protein were greater in the winter. The quantity of conjugated linoleic acid (CLA, ru menic acid, 18:2c9t11) in type B pasteurized milk (10.38 ± 0.69 in summer and 7.44 ± 0.82 in winter) was higher than in type C milk (9.90 ± 0.64 in summer and 7.25 ± 0.85 in winter) in both seasons. The amount of trans linolelaidic acid (18:2n-6t), linoleic acid (18:2n-6) and linolen ic acid (18:3n-3) had no variation between seasons and types of milk. Furthermore, the n-6/n-3 ratio of the milks analy zed after pasteurization has reduced significantly fro m (p

Epidemiological data have shown an association of the intake of industrial produced trans fatty acids (TFA) and sudden cardiac death. The present study examines the impact of elaidic acid (t18:1n-9) and linoelaidic acid (t18:2n-6) on the human aortic endothelial cell functional response. Trans fatty acids predominately incorporated into the phospholipid component while only a minute fraction of the total fatty acids (FA) incorporated into triacylglycerol. Trans fatty acids incorporated into the plasma membranes at the expense of the saturated-FA, stearic, palmitic, and to a lesser extent, myristic acid. Both t18:1n-9 and t18:2n-6 induced a pro-inflammatory response by elevating surface expression of intercellular adhesion molecule-1 (ICAM-1). Neither oleic nor linoleic evoked a pro-inflammatory phenotype under the maximal 50 µM treatments. Both TFA and stearic acid increased phosphorylation of the ICAM-1 transcriptional regulator, nuclear factor-κβ (NF-κβ), while oleic and linoleic acids did not appear to alter the phosphorylation status. Elaidic acid minimally affected endothelial cell growth, whereas linoelaidic acid completely inhibited growth at 100 µM and imparted limited cytotoxicity up to 300 µM. Stearic acid induced cytotoxicity at concentrations above 75 µM, while oleic and linoleic acids evoked gradual dose-dependent growth inhibition with cytotoxicity occurring only at linoleic acid concentrations greater than 200 µM. In conclusion, t18:1n-9 and t18:2n-6 fatty acids effectively incorporated into the phospholipid component of endothelial cells and subsequently induce a pro-inflammatory phenotype.

In order to automatically identify fatty acids in plant seed oils, a method was developed to search all saturated fatty acid methyl esters in the sample, subsequently calculate the ECL value of each fatty acid, and finally identify the molecular structure for each component by comparing the ECL of the interest and that in the customised database. Our method was applied to analyse the fatty acid composition of Eucommia ulmoides seed oil. The results show that major polyunsaturated fatty acids are α-linolenic acid (56.5093% of total fatty acids, TFAs) and linolelaidic acid (12.6563% of TFAs). Meanwhile, the main monounsaturated fatty acid is oleic acid whose percentage in the TFAs is 15.8008. Palmitic acid and steartic acid are the dominant saturated fatty acids representing 9.8165% and 2.5942% of TFAs, respectively. The UFA/SFA ratio (6.57) is higher than the recommended value (3) by nutritionists.

Background Converging evidence suggests that people at ultra-high risk (UHR) for psychosis have depleted levels of several fatty acids (FAs), and that changes in omega-3 (n-3) FA levels may indicate a higher risk for transition to psychosis. However, limited information is available on how FA deficiencies relate to psychopathology in individuals with UHR phenotypes. Here, we report the relationship between membrane FA levels and symptom severity in a study of individuals at UHR for psychosis. Methods Data from 280 of 304 (92%) of participants of the NEURAPRO study, a multi-centre randomized-controlled trial of omega-3 fatty acids versus placebo, were used for the present analysis. All participants were aged between 13 and 40 years and met criteria for UHR for psychosis. Blood samples were collected at study baseline and month 6 (end-of-intervention). Membrane fatty acids were analysed using mass spectrometry as percentage of total fatty acids in erythrocytes. Pearson correlation coefficients were calculated between baseline erythrocyte fatty acid levels and scores on the Scale for the Assessment of Negative Symptoms (SANS) and Brief Psychiatric Rating Scale (BPRS). Results Negative symptoms were positively correlated with one saturated FA (Tetracosanoic acid [24:0], R=0.272, p

The objective of the study was to determine how the partial supplementation of Moringa oleifera whole seed meal (MOWSM) would affect layer performance, egg quality and egg fatty acid profile. One hundred and forty-four Hy-Line hens in early-lay (20-weeks-old), with an average body weight of 1.45 kg were randomly allocated to four dietary treatments which were formulated to meet or exceed the National Research Council standards for brown-egg laying hens. Dietary treatments consisted of 0 (control), 1, 3, and 5% MOWSM. Layer performance was monitored over a period of 8 weeks. The inclusion of MOWSM in layer diets reduced feed intake, bodyweight, the rate of lay, egg weight, and egg mass. Yolk colour was significantly improved by 1, 3 and 5% inclusion levels, while the albumen height decreased. The albumen weight, yolk weight, eggshell weight, eggshell thickness, and egg shape index showed no statistical differences across all treatment groups. Similarly, the saturated fatty acid profile was also not affected. Palmitoleic acid decreased with the increase in MOWSM inclusion, whilst linolelaidic acid increased. The atherogenicity index was not affected by MOWSM inclusion, while the thrombogenicity index increased when compared to the control diet. It was concluded that, although MOWSM inclusion improved yolk colour, maintained external egg quality, and improved the fatty acid profile, the deleterious effect that it had on layer performance indicated that it may not be fed to early-lay hens at these respective levels. Keywords: Alternative protein, egg production, laying hens, oil seeds

The products formed by thermally induced isomerization of trilinolein and trilinoelaidin at 250 degrees C were studied by infrared spectroscopy and gas chromatography. The triglycerides of the 9c12c and 9t12t fatty acids, linoleic and linoelaidic acid respectively, were subjected to thermal treatment under nitrogen in glass. The products were removed at regular intervals and analysed by infrared spectroscopy using a single reflectance attenuated total internal reflectance crystal accessory. Trans-esterification of the products provided the corresponding fatty acid methyl esters which were studied by gas chromatography. The results show that the samples undergo decomposition and isomerization. Thermally induced 9c12c fatty acid (linoleic acid) molecules in the trilinolein molecules isomerize into 9c12t, 9t12c and 9t12t isomers. Thermally induced 9t12t fatty acid (linoelaidic acid) molecules in the trilinoelaidin molecules isomerize into 9c12t, 9t12c and 9c12c isomers. However, the concentration profiles are different for these two triglyceride samples. The rates of formation of isomers from linoleic acid are higher than the rates of formation of isomers from linoelaidic acid. In addition, these two fatty acids also isomerize into conjugated linoleic acids (CLAs). The profiles of the CLAs are identical in both cases.

An approach based on an in silico analysis predicted that CYP77A4, a cytochrome P450 that so far has no identified function, might be a fatty acid-metabolizing enzyme. CYP77A4 was heterologously expressed in a Saccharomyces cerevisiae strain (WAT11) engineered for cytochrome P450 expression. Lauric acid (C12:0) was converted into a mixture of hydroxylauric acids when incubated with microsomes from yeast expressing CYP77A4. A variety of physiological C18 fatty acids were tested as potential substrates. Oleic acid (cis-Δ9C18:1) was converted into a mixture of ω-4- to ω-7-hydroxyoleic acids (75%) and 9,10-epoxystearic acid (25%). Linoleic acid (cis,cis-Δ9,Δ12C18:2) was exclusively converted into 12,13-epoxyoctadeca-9-enoic acid, which was then converted into diepoxide after epoxidation of the Δ9 unsaturation. Chiral analysis showed that 9,10-epoxystearic acid was a mixture of 9S/10R and 9R/10S in the ratio 33 : 77, whereas 12,13-epoxyoctadeca-9-enoic acid presented a strong enantiomeric excess in favor of 12S/13R, which represented 90% of the epoxide. Neither stearic acid (C18:0) nor linolelaidic acid (trans,trans-Δ9,Δ12C18:2) was metabolized, showing that CYP77A4 requires a double bond, in the cis configuration, to metabolize C18 fatty acids. CYP77A4 was also able to catalyze the in vitro formation of the three mono-epoxides of α-linolenic acid (cis,cis,cis-Δ9,Δ12,Δ15C18:3), previously described as antifungal compounds. Epoxides generated by CYP77A4 are further metabolized to the corresponding diols by epoxide hydrolases located in microsomal and cytosolic subcellular fractions from Arabidopsis thaliana. The concerted action of CYP77A4 with epoxide hydrolases and hydroxylases allows the production of compounds involved in plant–pathogen interactions, suggesting a possible role for CYP77A4 in plant defense.

We screened the inhibitor of mouse inosine 5′-monophosphate dehydrogenase (IMPDH) type II from natural compounds, and found that a fatty acid, linoleic acid (C18:2), inhibited IMPDH activity. In the C18:2 fatty acid derivatives, all trans -configuration (i.e., linoelaidic acid), ester form, alcohol form, and addition of the hydroxyl group of linoleic acid had no effect on inhibitory activity. Therefore, both parts of a carboxylic acid and an alkyl chain containing cis -type double bonds of fatty acid might be essential for inhibition. Among the various carbon atom lengths and double bonds of fatty acids examined, the strongest inhibitor was C20:2-fatty acid, eicosadienoic acid, and 50% inhibition was observed at a concentration of 16.1 μM. Eicosadienoic acid induced the inhibition of IMPDH activity and was competitive with respect to IMP ( K i = 3.1 μM). For inhibitory effect, the C20-fatty acids ranked as follows: C20:2 > C20:3 > C20:1 > > C20:4 > C20:5, and C20:0 showed no inhibition. The energy-minimized three-dimensional structures of linear-chain C20-fatty acids were calculated, and it was found that a length of 20.7–22.5 A and width of 4.7–7.2 A in the fatty acid molecular structure was suggested to be important for IMPDH inhibition. Docking simulation of C20-fatty acids and mouse IMPDH type II, which was homology modeled from human IMPDH type II (PDB code: 1NF7), was performed, and the fatty acid could bind to Cys331, which is a amino acid residue of the active site, competitively with IMP. Based on these results, the IMPDH-inhibitory mechanism of fatty acids is discussed.

Conjugated linoleic acid (CLA) and some trans fatty acids (FA) decrease tumor growth and alter tumor and host lipid uptake and storage. The goal of this study was to test the hypothesis that the acute inhibitory effects of CLA isomers and trans FAs on FA transport in tumors and white adipose tissue are mediated via an inhibitory G-protein coupled (GPC), FFA receptor (FFAR). Experiments were performed in hepatoma 7288CTC and inguinal fat pads in Buffalo rats during perfusion in situ. CLA isomers and trans FAs (0.03-0.4 mmol/L, in plasma) were added to the arterial blood, and FA uptake or release was measured by arterial minus venous difference. In hepatoma 7288CTC, the CLA isomers, t10,c12-CLA > (±)-9-HODE [13-(S)-hydroxyoctadecadienoic acid] > t9,t11-CLA, and the trans FAs, linolelaidic = vaccenic > elaidic, decreased cAMP content and inhibited FA uptake, 13(S)-HODE release, extracellular signal-regulated kinase p44/p42 phosphorylation, and [ 3 H]thymidine incorporation. Other CLA isomers, c9,t11-CLA, 13-(S)-HODE, c9,c11-CLA, and c11,t13-CLA, had no effect. In inguinal fat pads, FA transport was inhibited by t10,c12-CLA = linolelaidic acid > trans vaccenic acid, whereas c9,t11-CLA had no effect. In both hepatoma 7288CTC and inguinal fat pad, addition of either pertussis toxin or 8-Br-cAMP to the arterial blood reversed the inhibitions of FA transport. These results support the idea that an inhibitory GPC FFAR reduces cAMP and controls FA transport by CLA isomers and trans FAs. Ligand activity is conferred by the presence of a trans double bond proximal to the carboxyl group. J. Nutr. 134: 1989-1997, 2004.

Objective: Mulberry is a nontoxic commonly eaten plant, belongs to the Morus and used in folk medicine in the remedy of dysentery, antiphlogistic, diuretic, expectorant, and antidiabetic. The purpose of this study is to evaluate the antiproliferative and radical scavenging activity of the total alcoholic and successive fractions thereof of Morus alba and Morus rubra fruits. In addition, the chemical composition of the bioactive fractions of each species was investigated. Methods: The antiproliferative potential of 8 extracts on 4 human cancer cell lines, hepatocellular carcinoma (HepG2), Caucasian breast adenocarcinoma (MCF7), prostate (PC3), and colon carcinoma (HCT116) in addition to one normal cell line namely human normal immortalized skin fibroblast cells (BJ1) were carried out. Cell viability was determined using MTT assay. The potency was compared with the reference drug doxorubicin. These extracts were also assayed for 1,1-diphenyl-2-hydrazyl free radical scavenging activities. After saponification of the n-hexane fraction, unsaponifiable matter and fatty acid methyl esters were analyzed by gas liquid chromatography (GLC). The chemical composition of the bioactive fractions was investigated using gas chromatography/mass spectrometry (GC/MS) analysis. Results: All the extracts showed significant free radical scavenging activity dose-dependently. The n -hexane and dichloromethane (DCM) fractions of M. rubra exhibited potent cytotoxic activity on almost cancer cell lines. In the same pattern, ethyl acetate (EtOAc) of M. rubra has moderate cytotoxic activity against all cell lines except HepG2. DCM fraction of M. alba possessed both radical scavenging and high potential antiproliferated activities against HCT116 and MCF7 with inhibitory concentration of 43.9 and 32.3 μg/ml, respectively, while it showed no cytotoxic effect on BJ1. GLC analysis showed the major hydrocarbons in M. alba and M. rubra were heptacosane and docosane, respectively. Sterols were similar in both species but with different ratios and cholesterol was the major one. Palmitic and margaric were the major saturated fatty acid while arachidonic was the major unsaturated fatty acid in both species. GC/MS analysis showed the main compound in DCM fraction of each Morus species was palmitic acid. Furthermore, 1,11- bis -(methoxycarbonyl-ethenyl)-10,2-dihydroxy-cycloeicosane and linolelaidic acid, methyl ester were the main compounds in the EtOAc fraction of each Morus species. Whereas, the main compounds in alcoholic extract of M. alba and M. rubra were methyl-14-methyl-pentadecanoate and 1,2- O -isopropylyidene-4-nonene-1,2,3-triol, respectively. Conclusions: The results observed remarkable biological activity of the successive fractions of M. rubra more than those of M. alba and confirmed its importance as a natural bioactive source. Morus species are good candidates to be promising as possible sources for future antitumor and antioxidants in food and pharmaceutical formulations. The strong activity partly explains the potential effects of Morus species for the treatment of cancer and degenerative diseases caused by free radicals.

Corn steep liquor (CSL) is a liquid byproduct generated by the corn wet-milling industry. This agroindustrial residue is obtained when corn is digested with warm water and SO2 in the presence of different spontaneously growing microorganisms. The microbial population of CSL includes lactic acid bacteria, which are widely known to produce biosurfactants. However, there is no information available about the possible existence of surface-active compounds in CSL. In this work the surface tension activity of CSL was evaluated and the biosurfactant contained in this residue was extracted with different organic solvents and characterized. The biosurfactant obtained from CSL was analyzed by Fourier transform infrared spectroscopy, and the composition in fatty acid was analyzed by gas chromatography–mass spectrometry. The hydrophobic chain of the biosurfactant contained in CSL comprised 50–55.2% linolelaidic acid, 15.7–22.2% oleic and/or elaidic acid, 5.9–14.6% stearic acid, and 14.9–19.6% palmitic acid.

To estimate the relative significance of exogenous and endogenous fatty acid substrates in decreasing hepatic triacylglycerol secretion after sesamin feeding, livers from rats fed diets supplemented with and without sesamin (sesamin : episesamin, 1:1, w/w) were perfused in the presence and absence of an exogenous di-trans isomer of linoleic acid (linolelaidic acid, trans,trans-9,12-octadecadienoic acid). Both exogenous trans fatty acid and dietary sesamin, as compared with respective controls, resulted in a marked increase in hepatic ketogenesis; however, the beta-hydroxybutyrate to acetoacetate ratio was elevated by exogenous fatty acid and decreased by dietary sesamin. On the other hand, hepatic secretions of triacylglycerol, phospholipid and cholesterol were markedly lowered in rats fed sesamin, especially when exogenous fatty acid substrate was provided. The relative significance of the exogenous fatty acid was observed in the dietary sesamin-induced decrease in hepatic secretion of triacylglycerol. These results suggest that increased fatty acid oxidation by dietary sesamin, as reflected by enhanced ketone body production, leads to decreased partition of fatty acid substrates to the esterification pathways, and this in turn reduces the synthesis and secretion of triacylglycerol. The altered metabolism of exogenous fatty acids in the liver was therefore a major determinant for the synthesis and secretion of triacylglycerol.

A series of fatty acid N-acyloxymethyl derivatives of theophylline was prepared to determine the effects of varying the nature of the fatty acid on their in vitro rates of hydrolysis using porcine liver esterase and human plasma. The carboxylic acids examined include acetic (Ac), valeric (VA), nonanoic (NA), stearic (SA), oleic (OA), linoleic (LA), γ-linolenic (GLA), α-linolenic (ALA), eicosapentaenoic (EPA), elaidic (EA) and linoelaidic acid (LEA). When exposed to porcine liver esterase the NA acid derivative was hydrolyzed about 80 times faster than the triple bond GLA and ALA derivatives, which were hydrolyzed about four times as fast as the double bond LA derivative, which was hydrolyzed three times as fast as the single bond OA derivative. In human plasma the VA acid derivative was hydrolyzed over 100 times faster than the GLA derivative. Both the trans fatty acid EA and LEA derivatives were hydrolyzed slower than their cis counterparts. In both porcine esterase and human plasma, the derivatives displayed the classical parabolic relationship when the logarithm of the rate constant, k, was plotted versus the lipophilicity index, log K. Although the unsaturated fatty acid derivatives with three or more double bonds are not hydrolyzed at the maximum rate, they are hydrolyzed at markedly faster rates than the corresponding saturated or mono-unsaturated derivatives and as such still may serve as a delivery vehicle for other drugs.

To estimate the relative significance of exogenous vs. endogenous fatty acids in increasing hepatic triacylglycerol secretion following an inhibition of fatty acid oxidation by emeriamine, livers from 2-d-fasting rats were perfused with or without an inhibitor in the presence of a geometrical isomer of linoleate (linolelaidic acid, trans, trans-9, 12octadecadienoic acid). Emeriamine added to the perfusion medium at 2 h of the recirculating perfusion period caused immediate and complete cessation of ketone body production while it increased triacylglycerol and cholesterol secretion by the liver without affecting uptake of exogenous linolelaidic acid. The increase in the triacylglycerol secretion by emeriamine was accompanied by a marked increase in the proportion of linolelaidic acid in this lipid molecule in the perfusate and in the liver. The calculated amounts of exogenous linolelaidate, compared with those of endogenous fatty acids in the secretory triacylglycerol, suggested that the former compared with the latter contributes more to the drug-mediated increase in triacylglycerol secretion. This drug caused a marked reduction of mitochondrial carnitine palmitoyltransferase activity in perfused liver. These results suggest that a blockade of fatty acid oxidation by emeriamine, through an inhibition of carnitine palmitoyltransferase, diverts predominantly the exogenous free fatty acids from oxidation to the esterification pathway and subsequently stimulates the synthesis and secretion of triacylglycerol-rich lipoproteins.

Various fatty acids were fed to the yeast Dipodascopsis uninucleata UOFS Y 128, and the extracted samples were analyzed for the accumulation of 3-hydroxy metabolites with the help of electron impact gas chromatography-mass spectrometry. Fatty acids containing of 5Z,8Z-diene system (5Z,8Z,11Z-eicosatrienoic, 5Z,8Z,11Z,14Z-eicosatetraenoic, and 5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acids) yielded the corresponding 3-hydroxy-all-Z-eicosapolyenoic acids. Moreover, linoleic acid (9Z,12Z-octadecadienoic acid) and 11Z,14Z,17Z-eicosatrienoic acid were converted to the 3-hydorxylated metabolites of shorter chain length, e,g., 3-hydroxy-5Z,8Z-tetradecadienoic acid and 3-hydroxy-5Z,8Z,11Z-tetradecatrienoic acid, respectively. In contrast, no accumulation of a 3-hydroxy metabolite was observed with oleic acid (9Z-octadecenoic acid), linolelaidic acid (9E,12E-octadecadienoic acid), gamma-linolenic acid (6Z,9Z,12Z-octadecatrienoic acid), and eicosanoic acid as substrate. These findings pinpoint that the 3-hydroxylation of a fatty acid in Dipodascopsis uninucleata requires a 5Z,8Z-diene system either directly or following initial incomplete beta-oxidation. Following analysis of the enantiomer composition, the arachidonic acid metabolite was identified as 3R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, which rules out a normal beta-oxidation as biosynthetic route to this new class of oxylipins.

Reversed-phase high-performance liquid chromatography (HPLC) methods were developed for the separation of molecular species of 45 synthetic triacylglycerols and diacylglycerols. These methods used linear gradients of methanol-isopropanol and UV detection at 205 nm as well as radioactive flow detection, which we add for metabolic studies. The elution orders of triacylglycerols and diacylglycerols depend on the polarity of their fatty acid constituents with elution time increasing as polarity decreases. The elution orders of triacylglycerols depending on their fatty acid constituents were as follows: ricinoliec acid

Context: Sacha inchi (Plukenetia volubilis L.) is a potential oilseed crop because it is rich in α-linolenic acid (ALA) (omega-3 fatty acid). Objective: To evaluate the exposure of fatty acids after a single oral administration of sacha inchi or sunflower oil in healthy volunteers. Material and methods: Plasma fatty acids concentrations were assayed by Gas Chromatography with Flame Ionization Detector in 18 adult subjects. After fasting, blood samples were obtained at 0, 0.5, 1, 2, 4, 8 and 24 h after ingestion of 10 or 15 ml of sacha inchi oil or sunflower oil. Results: The proportion ALA/linoleic acid was 1.37 in sacha inchi oil and 0.01 in sunflower oil. ALA, lauric acid, palmitic acid, linolelaidic acid, cis-8,11,14-eicosatrienoic acid, cis-13,16-docosadienoic acid and cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) levels changed over time after sacha inchi oil ingestion but not with sunflower oil. The time at maximal concentration (tmax) for ALA was 2 h after sacha inchi oil ingestion. No ALA in plasma was observed after sunflower oil consumption. The maximal concentration of ALA was 2.84 ± 0.36 mg/ml in women and 0.94 ± 0.57 mg/ml in men, p 0.05). There is a trend for higher plasma ALA levels with 15 ml sacha inchi oil. After 2 h of consumption, plasma delta triacylglycerol were reduced with sunflower oil but slightly increased with sacha inchi oil. A reduction in plasma delta triacylglycerol-rich lipoprotein cholesterol was observed with both oils. Conclusion: Consumption of sacha inchi oil increased ALA and DHA in plasma.

The fatty acid composition of the membrane of the conditional auxotroph fabB2 can be altered by allowing the cells to grow at non-permissive temperature (37°C) in the presence of a cis-unsaturated fatty acid. The phage 9NA, a virulent phage of Salmonella typhimurium, can not multiply in fabB2. Synthesis and maturation of the phage DNA are differentially affected by variation in the fatty acid composition of the cell membrane. The replicating DNA associates with the membrane complex, the site of DNA synthesis. The association is comparatively weak in oleic, claidic, palmitoleic, palmitelaidic and linolelaidic acid enriched cells. When the cells are grown in the presence of palmitoleic acid, a large pool of concatemeric phage DNA accumulates in the cytoplasm within 10 min of infection. The conversion of concatemeric DNA to monomeric one i.e., mature phage length DNA, is inhibited in such cells. The presence of concatemeric DNA can be visualized by electron microscope. Such a situation is not observed when the cells are grown in media supplemented with other types of unsaturated fatty acids. The mechanism by which the host cell membrane lipid controls phage development is yet to be worked out.

Arabidopsis thaliana (L.) Heynh. expressing the Crepis palaestina (L.) linoleic acid delta12-epoxygenase in its developing seeds typically accumulates low levels of vernolic acid (12,13-epoxy-octadec-cis-9-enoic acid) in comparison to levels found in seeds of the native C. palaestina. In order to determine some of the factors limiting the accumulation of this unusual fatty acid, we have examined the effects of increasing the availability of linoleic acid (9cis, 12cis-octadecadienoic acid), the substrate of the delta12-epoxygenase, on the quantity of epoxy fatty acids accumulating in transgenic A. thaliana. The addition of linoleic acid to liquid cultures of transgenic plants expressing the delta12-epoxygenase under the control of the cauliflower mosaic virus 35S promoter increased the amount of vernolic acid in vegetative tissues by 2.8-fold. In contrast, the addition to these cultures of linoelaidic acid (9trans, 12trans-octadecadienoic acid), which is not a substrate of the delta12-epoxygenase, resulted in a slight decrease in vernolic acid accumulation. Expression of the delta12-epoxygenase under the control of the napin promoter in the A. thaliana triple mutant fad3/fad7-1/fad9, which is deficient in the synthesis of tri-unsaturated fatty acids and has a 60% higher level of linoleic acid than the wild type, was found to increase the average vernolic acid content of the seeds by 55% compared to the expression of the delta12-epoxygenase in a wild-type background. Together, these results reveal that the availability of linoleic acid is an important factor affecting the synthesis of epoxy fatty acid in transgenic plants.

Objectives Trans isomers of fatty acids (TFA) have been implicated in the initiation and progression of atherosclerosis. Previous studies have shown that trans-unsaturated fatty acids like their cis-unsaturated counterparts exert a modifying effect on platelet aggregation. The aim of this work was to determine the influence of TFA on the aforementioned enzymes: lipoxygenase and cycloxygenase/thromboxane synthase. Methods Two C18 cis–trans fatty acid pairs: oleic/elaidic and linoleic/linolelaidic were chosen. Fasting blood was sampled from 30 healthy volunteers without any lipid abnormalities and not on medication for at least 7 days prior to sampling. Platelet-rich plasma (PRP) was prepared and the platelet count was adjusted to 310 8 cellsml −1 . Fatty acids in hexane were added to a final concentration of 7 μM and evaporated to dryness under nitrogen, 500 μl of PRP was pipetted into each tube, thoroughly mixed and incubated at 37°C for 60 min. 12-P LOX activity was measured with a spectrophotometric method and expressed per mg protein. Cycloxygenase/thromboxane synthase activity was determined by TXB 2 production with an ELISA-based assay. Statistics were done with the Kruskal-Wallis test and Statistica software package. Results We have found that the activity of 12-P LOX was suppressed by all cis–trans fatty acids used by us. Cycloxygenase/thromboxane synthase activity was significantly inhibited by polyunsaturated fatty acids only. Linolelaidic acid was more potent in comparison to its monounsaturated (elaidic acid) counterpart. Conclusions We believe that the effects of fatty acids are demonstrated at the membrane level where fatty acids may produce a perturbation in specific lipid domains. TFA are able to interact with the platelet membrane and transmembrane proteins just as the cis isomers. By interacting with proteins exposed on the cytoplasmic membrane, TFA may modify the activity of receptors and other membrane proteins. In this way, changes on the membrane surface are propagated into the cell affecting the activity of cytoplasmic enzymes like 12-P LOX and cycloxygenase/thromboxane synthase.

The modulation of TREK-1 leak and Kv1.4 voltage-gated K+ channels by fatty acids and lysophospholipids was studied in bovine adrenal zona fasciculata (AZF) cells. In whole-cell patch-clamp recordings, arachidonic acid (AA) (1-20 microM) dramatically and reversibly increased the activity of bTREK-1, while inhibiting bKv1.4 current by mechanisms that occurred with distinctly different kinetics. bTREK-1 was also activated by the polyunsaturated cis fatty acid linoleic acid but not by the trans polyunsaturated fatty acid linolelaidic acid or saturated fatty acids. Eicosatetraynoic acid (ETYA), which blocks formation of active AA metabolites, failed to inhibit AA activation of bTREK-1, indicating that AA acts directly. Compared to activation of bTREK-1, inhibition of bKv1.4 by AA was rapid and accompanied by a pronounced acceleration of inactivation kinetics. Cis polyunsaturated fatty acids were much more effective than trans or saturated fatty acids at inhibiting bKv1.4. ETYA also effectively inhibited bKv1.4, but less potently than AA. bTREK-1 current was markedly increased by lysophospholipids including lysophosphatidyl choline (LPC) and lysophosphatidyl inositol (LPI). At concentrations from 1-5 microM, LPC produced a rapid, transient increase in bTREK-1 that peaked within one minute and then rapidly desensitized. The transient lysophospholipid-induced increases in bTREK-1 did not require the presence of ATP or GTP in the pipette solution. These results indicate that the activity of native leak and voltage-gated K+ channels are directly modulated in reciprocal fashion by AA and other cis unsaturated fatty acids. They also show that lysophospholipids enhance bTREK-1, but with a strikingly different temporal pattern. The modulation of native K+ channels by these agents differs from their effects on the same channels expressed in heterologous cells, highlighting the critical importance of auxiliary subunits and signaling. Finally, these results reveal that AZF cells express thousands of bTREK-1 K+ channels that lie dormant until activated by metabolites including phospholipase A2 (PLA2)-generated fatty acids and lysophospholipids. These metabolites may alter the electrical and secretory properties of AZF cells by modulating bTREK-1 and bKv1.4 K+ channels.

The objective of this study was to assess the relative long-term effects of linoleic (cis, cis 18:2), linolelaidic (trans, trans 18:2), and palmitic (16:0) acids on hepatic lipoprotein production in HepG2 cells. All fatty acids increased the mass of triglycerides (TG) in the medium and the incorporation of [(3)H]-glycerol into secreted TG; the increase was more pronounced with linoleic acid than with linolelaidic and palmitic acids. The net accumulation in the medium of apolipoprotein (apo) A-I was not affected by the fatty acids tested and moderate changes in that of apoB resulted in apoB/apoA-I mass ratios of 1.05, 1.27 and 0.86 with linoleic, linolelaidic and palmitic acids, respectively. The incorporation of [(14)C]-acetate into cellular plus secreted total sterols was 9.1%, 33.6% and 17.4% of total [(14)C]-labeled lipids with linoleic, linolelaidic and palmitic acids, respectively. Relative to linoleic acid, palmitic acid, and to a greater extent (P0.05) linolelaidic acid, increased the secretion and cellular accumulation of [(14)C]-labeled free cholesterol (FC) and cholesteryl esters and decreased those of TG and phospholipids (PL). Compared with linoleic acid, linolelaidic acid increased LDL-cholesterol (C) and HDL-C by 154% (P0.001) and 50% (P = 0.016), respectively, whereas palmitic acid increased LDL-C by 17% (P0.1) and did not affect HDL-C. The LDL-C to HDL-C ratios were 0.70, 1.18 and 0.96 with linoleic, linolelaidic and palmitic acids, respectively. These differences were not due to altered LDL receptor activity. The PL to C ratios of HDL particles were 1.61, 0.40 and 0.77 with linoleic acid, linolelaidic acid and palmitic acid, respectively. These results suggest that relative to cis polyunsaturated and saturated fatty acids, trans PUFA more adversely affect the concentration and composition of apoA-I- and apoB-containing lipoproteins secreted by HepG2 cells.

Degradation of trans-unsaturated fatty acids was studied in the yeast Saccharomyces cerevisiae. Propagation of yeast cells on trans-9 elaidic acid medium resulted in transcriptional up-regulation of the SPS19 gene, whose promoter contains an oleate response element. This up-regulation depended on the Pip2p-Oaf1p transcription factor and was accompanied by induction of import-competent peroxisomes. Utilization of trans fatty acids as a single carbon and energy source was evaluated by monitoring the formation of clear zones around cell growth on turbid media containing fatty acids dispersed with Tween 80. For metabolizing odd-numbered trans double bonds, cells required the beta-oxidation auxiliary enzyme Delta(3)-Delta(2)-enoyl-CoA isomerase Eci1p. Metabolism of the corresponding even-numbered double bonds proceeded in the absence of Sps19p (2,4-dienoyl-CoA reductase) and Dci1p (Delta(3,5)-Delta(2,4)-dienoyl-CoA isomerase). trans-2,trans-4-Dienoyl-CoAs could enter beta-oxidation directly via Fox2p (2-enoyl-CoA hydratase 2 and d-specific 3-hydroxyacyl-CoA dehydrogenase) without the involvement of Sps19p, whereas trans-2,cis-4-dienoyl-CoAs could not. This reductase-independent metabolism of trans-2,trans-4-dienoyl-CoAs resembled the situation postulated for mammalian mitochondria in which oleic acid is degraded through a di-isomerase-dependent pathway. In this hypothetical process, trans-2,trans-4-dienoyl-CoA metabolites are generated by Delta(3)-Delta(2)-enoyl-CoA isomerase and Delta(3,5)-Delta(2,4)-dienoyl-CoA isomerase and are degraded by 2-enoyl-CoA hydratase 1 in the absence of 2,4-dienoyl-CoA reductase. Growth of a yeast fox2sps19Delta mutant in which Fox2p was exchanged with rat peroxisomal multifunctional enzyme type 1 on trans-9,trans-12 linolelaidic acid medium gave credence to this theory. We propose an amendment to the current scheme of the carbon flux through beta-oxidation taking into account the dispensability of beta-oxidation auxiliary enzymes for metabolizing trans double bonds at even-numbered positions.

Hibiscus (H.) sabdariffa (commonly known as “Karkadeh” in Arabic) is widely used in various pharmacological applications in Sudan. The present study was carried out to investigate the anti-inflammatory and analgesic activities of H. sabdariffa seed extracts using rat models. In acute anti-inflammatory models, oral administration of petroleum ether extract of H. sabdariffa seeds inhibited the hind paw edema (p

To understand how dietary fatty acids differentially modulate mouse skin tumorigenesis, the ability of specific fatty acids and their derivatives to activate murine epidermal protein kinase C (PKC) in vitro was investigated. Total PKC from untreated female SSIN mouse skin was partially purified and incubated with specific fatty acids at concentrations up to 300 microM in the presence of Ca2+ and phosphatidylserine. The cis-unsaturated fatty acids tested, ranging from 16:1 to 22:6, stimulated PKC activity in a similar dose-dependent manner with an approximate threefold maximum increase over control. Neither the number of cis-double bonds nor the chainlength of these fatty acids affected their relative ability to activate PKC. trans-Fatty acids, with the exception of linoelaidic acid (t,t-18:2n-6), exhibited about half of the potency of their corresponding cis-isomers in stimulating PKC at the plateau concentration (200 microM) or lower. Substitutions close to the double bond on cis-fatty acids abolished their ability to activate PKC. The hydroxylated metabolites of arachidonic acid (20:4n-6) and linoleic acid (c,c-18:2n-6), i.e., the hydroxyeicosatetraenoic acids (HETE) and hydroxyoctadecadienoic acids (HODE), also activated mouse skin PKC in vitro, but only about half as effectively as did the respective parent fatty acids. The results suggest that both hydroxyl substitution and trans-configuration of HETE and HODE are responsible for their reduced ability to activate PKC. Overall the data suggests that the reduced skin tumor yield observed in mice fed diets high in c,c-18:2n-6 is not likely to be due to differences in the ability of c,c-18:2n-6 or 20:4n-6, or their metabolites, to activate PKC.

Human or rat microsomal 5 alpha-reductase activity, as measured by enzymic conversion of testosterone into 5 alpha-dihydrotestosterone or by binding of a competitive inhibitor, [3H]17 beta-NN-diethulcarbamoyl-4-methyl-4-aza-5 alpha-androstan-3-one ([3H]4-MA) to the reductase, is inhibited by low concentrations (less than 10 microM) of certain polyunsaturated fatty acids. The relative inhibitory potencies of unsaturated fatty acids are, in decreasing order: gamma-linolenic acid greater than cis-4,7,10,13,16,19-docosahexaenoic acid = cis-6,9,12,15-octatetraenoic acid = arachidonic acid = alpha-linolenic acid greater than linoleic acid greater than palmitoleic acid greater than oleic acid greater than myristoleic acid. Other unsaturated fatty acids such as undecylenic acid, erucic acid and nervonic acid, are inactive. The methyl esters and alcohol analogues of these compounds, glycerols, phospholipids, saturated fatty acids, retinoids and carotenes were inactive even at 0.2 mM. The results of the binding assay and the enzymic assay correlated well except for elaidic acid and linolelaidic acid, the trans isomers of oleic acid and linoleic acid respectively, which were much less active than their cis isomers in the binding assay but were as potent in the enzymic assay. gamma-Linolenic acid had no effect on the activities of two other rat liver microsomal enzymes: NADH:menadione reductase and glucuronosyl transferase. gamma-Linolenic acid, the most potent inhibitor tested, decreased the Vmax. and increased Km values of substrates, NADPH and testosterone, and promoted dissociation of [3H]4-MA from the microsomal reductase. gamma-Linolenic acid, but not the corresponding saturated fatty acid (stearic acid), inhibited the 5 alpha-reductase activity, but not the 17 beta-dehydrogenase activity, of human prostate cancer cells in culture. These results suggest that unsaturated fatty acids may play an important role in regulating androgen action in target cells.

The effects of arachidonic acid (AA) and other long-chain fatty acids on voltage-dependent Ca channel current (ICa) were investigated, with the whole cell patch clamp method, in longitudinal smooth muscle cells of rabbit ileum. 10-30 microM AA caused a gradual depression of ICa. The inhibitory effect of AA was not prevented by indomethacin (10 microM) (an inhibitor of cyclooxygenase) or nordihydroguaiaretic acid (10 microM) (an inhibitor of lipoxygenase). 1-(5-Isoquinolinesulfonyl)-2-methylpiperazine (H7; 25-50 microM) or staurosporine (2 microM) (inhibitors of protein kinase C) did not block the AA-induced inhibition of ICa, and application of phorbol ester (a protein kinase C activator) (phorbol-12,13-dibutyrate, 0.2 microM) did not mimic the AA action. Some other cis-unsaturated fatty acids (palmitoleic, linoleic, and oleic acids) were also found to depress ICa, while a trans-unsaturated fatty acid (linolelaidic acid) and saturated fatty acids (capric, lauric, myristic, and palmitic acids) had no inhibitory effects on ICa. Myristic acid consistently increased the amplitude of ICa at negative membrane potentials. The present results suggest the possible role of AA, and perhaps other fatty acids, in the physiological and/or pathological modulation of ICa in smooth muscle.

Apart from the generation of potent inflammatory mediators, the effects of fatty acid oxygenase activation, per se, on the host cell have not been well-delineated. Fatty acid oxygenases were activated in rat basophilic leukemia cells (RBL-1) by incubating them for 2-4 hr with 33-300 microM of arachidonic acid (AA) or linoleic acid (LA). As a control, the cells were incubated with one of two analogs of these fatty acids which are not oxygenase substrates: eicosatetraynoic acid or linoelaidic acid. Effects of oxygenase activation on cell viability were monitored by an assay for mitochondrial function. Cytotoxicity occurred in incubations with exogenous AA or LA in direct proportion to the substrate concentration but was not found in the control incubations or in incubations with the principal monohydroxylated AA products, 5-, 15-, and 12-HETE. Nordihydroguaiaretic acid (80 microM) and alpha-tocopherol (100 microM) significantly decreased the cell death observed during incubations with AA or LA. It is concluded that extensive oxygenase activation can result in cell death from intermediates produced proximal to the stable monohydroxylated derivatives.

Recent investigations have identified a class of outwardly rectifying potassium channels activated directly by arachidonic acid (AA) and select other fatty acids (FA) that inhibit smooth muscle contractions. We hypothesized that lymphatic smooth muscle contains similar fatty acid activated channels. Fresh porcine tracheobronchial lymphatic vessel rings were mounted in organ baths and connected to force-velocity transducers. Contractile responses were measured following exposure to histamine alone, with AA, and following AA washout, demonstrating a 40-55% inhibition of histamine-induced contractility by AA. Despite addition of indomethacin and nordihydroguaiaretic acid to inhibit formation of active AA metabolites, AA still attenuated contractility by 24-31%. Myristic acid and linoelaidic acid, FA's that are not substrates for cyclooxygenase or 5-lipoxygenase, inhibited histamine-induced contractility by 19 and 15%, respectively. The effects of AA and the other FA's were eliminated by exposure to a high potassium solution. The data support the existence of AA-activated hyperpolarizing potassium channels in lymphatic smooth muscle. Arachidonic acid, in addition to its metabolites, may play a direct role in regulating lymphatic smooth muscle tone.

The transport of α-methyl-D-glucoside and two aminoacids, L-phenylalanine and L-leucine by a temperature sensitive fatty acid requiring mutant ofSalmonella typhimurium was studied under conditions of supplementation withcis or trans-unsaturated fatty acids. The results of such experiments definitely establish a relationship between the fatty acids composition of the membrane and the transport property of the cells. Cells grown in the presence of trans-unsaturated fatty acids cannot transport so efficiently as compared to the cis-unsaturated fatty acid-grown cells except linolelaidic acid, atrans-trans-unsaturated fatty acid. Protein: phospholipid ratio of the membrane also varies significantly under such conditions. The affinity of L-phenylalanine transport carrier for the substrate changes remarkably in cells grown in the presence of differentcis or trans-unsaturated fatty acids and indicate the possible role of membrane lipids in membrane assembly as well as regulation of the activity of L-phenylalanine transport system.

Unsaturated fatty acid monolayers on silica gel have been autoxidized, and the rate of fatty acid disappearance and products obtained from those membrane-like assemblies have been studied. Fatty acid monolayers consisting of pure linoleic acid, linolelaidic acid, and oleic acid were autoxidized at 60 C. The rates of autoxidation of linoleic acid and linolelaidic acid monolayers followed by the disappearance of substrates are considerably faster than that in bulk phase, and the rates conform to apparent first order kinetics. Autoxidation of linoleic and linolelaidic acid monolayers, unlike bulk phase, produced only a small amount of diene conjugation, and the major products formed were identified as 9,10-epoxy and 12,13-epoxyoctadecenoic acid in roughly equal quantities. The epoxidation is stereospecific, with cis and trans olefins giving cis and trans epoxides, respectively. Oleic acid was autoxidized to only a small extent during 27 hr and produced no detectable amount of epoxide.

Dietary fatty acids affect the synthesis and thus ultimate availability of prostaglandin precursors. During processing of edible fats a significant portion of the naturally occurring cis fatty acids is changed to the respective trans isomers. Trans fatty acids could have a wide variety of effects including their effect on prostaglandin synthesis. A comparative study on the effect of cis (oleic and linoleic) fatty acids and their corresponding trans isomers (elaidic and linoelaidic acids) on the in vitro prostaglandin biosynthesis in human blood platelets was made. Linoleic acid (0.5, 1.0 mM) showed the same effect on the various arachidonic acid (AA) metabolites as reported earlier by us, that is, increased generation of prostaglandins and thromboxanes and reduced amounts of HHT and HETE (26). Linoelaidic acid at these two concentrations had the same effect but to a lesser extent. Both linoleic and linoelaidic acids at 0.25 mM concentration reduced TxB2 formation. Oleic and elaidic acids (0.5, 1.0 mM) decreased the formation of TxB2 though not significantly. With oleic acid, the results in respect of other AA metabolites were similar to those reported by us earlier (26). MDA was reduced significantly in the presence of linoleic, linoelaidic and oleic acids; cis isomers being more effective. In the presence of linoleic and linoelaidic acids, prostaglandin endoperoxides were reduced significantly; there was no change in the presence of oleic and elaidic acids. Thus fatty acids seem to affect the platelet cyclo-oxygenase activity; this being more pronounced in the case of cis fatty acids compared to their trans isomers. Reduction in cyclo-oxygenase activity also depends upon the number of double bonds in the acids.

1. The behaviour of fatty acids in dilute bile salt solution and in dispersions of triglyceride in bile salt solution was examined. The properties of fatty acids in bile salt solution were defined in terms of their saturation ratio, and of the critical micellar concentration of bile salt for each fatty acid as solute. The partition of fatty acids between the oil phase and the micellar phase of the dispersions was defined as the distribution coefficientK M/O.The phases were separated by ultracentrifugation.2. Of the fatty acids examined, palmitic and stearic acids behaved in bile salt solution as typical non-polar solutes. Lauric, oleic and linoleic acids had properties similar to typical amphiphiles. The effectiveness of these and other amphiphiles was expressed in terms of an amphiphilic index.3. Thetrans-fatty acids, vaccenic acid and linolelaidic acid possessed solubility properties similar to theircis-isomers. The properties of elaidic acid were intermediate between those of the non-polar and the amphiphilic solutes.4. The distribution coefficients of fatty acids differed less significantly than their solubilities in bile salt solution, but were influenced to some extent by the composition of the oil phase.5. The effect of pH on the partition of fatty acids was similar for all fatty acids examined. There was a marked increase in the partition of fatty acids in the micellar phase as pH increased above 6.2.6. In the presence of Ca2+ions above a threshold concentration of I m-equiv./l. and at a pH higher than 6.4, the partition of stearic acid in the micellar phase of the bi-phasic system was restricted. No interaction of Ca2+ion and pH was observed with oleic acid.7. The effect of some amphiphiles on the distribution coefficient of stearic acid was examined. The capacity of lysolecithin to solubilize stearic acid in the micellar phase of dispersions was about twice that of I-mono-olein. The significance of the results in relation to fat absorption in the pig and the sheep is discussed.

Male weanling rats of the Sprague-Dawley strain were made essential fatty acid (EFA)-deficient by feeding them a fat-free diet for five months. The animals were then fed a supple-ment of methyltrans-9,trans-12-octadecadienoate (methyl linoelaidate), as 5% of the dietary calo-ries (approximately 400 mg/animal/day) for 19 days, and killed by exsanguination. The com-position of the liver, kidney, epididymal and plasma lipids was determined and compared with that obtained from EPA-deficient rats given oral supplements of methylcis-9,cis-12-octadeca-dienoate (linoleate) and methylcis-9,trans-12- octadecadienoate. Linoelaidic acid was depos-ited in the phospholipids, sterol esters and tri-glycerides in all of the tissues examined. Iso-lation analysis of the fatty acids showed no evidence that linoelaidic acid was converted to higher polyunsaturated fatty acids in the EFA-deficient rat.

Differences in the positional incorporation of 9-trans[1-(14)C] octadecenoic (elaidic) and 9-trans,12-trans[1-(14)C] octadecadienoic (linoelaidic) acids in fetal lecithin of rats were demonstrated. On the 20th day of gestation, a 14C-labeled albumin complex of elaidic or linoelaidic acid was injected into the jugular vein of pregnant rats. For comparative purposes, 9-cis[1-(14)C] octadecenoic (oleic) or 9-cis,12-cis[1-(14)C] octadecadienoic (linoleic acid) was injected into the maternal circulation of rats. Animals were killed 6 hr later. Distribution of label in total lipids and phospholipids (PL) of fetal issue was measured by TLC. Irrespective of the label, the highest percentage of total radioactivity was associated with PL-59 to 67%. Within PL, the major portion of radioactivity was found in choline phosphoglycerides (CPG)-53 to 67%, and in ethanolamine phosphoglycerides (EPG)-18 to 33%. While linoelaidic acid was predominantly esterified in the 2-position of CPG, elaidic acid was nearly equally distributed between positions 1 and 2 of lecithin. Distribution of radioactivity within fatty acid methyl esters (FAME) of CPG measured by radio-GLC suggested that oleic and possibly linoleic acids may be converted to nervonic and arachidonic acid, respectively, in the rat by the 20th day of gestation. Following injection of elaidate, radioacivity of FAME was distributed between palmitate and elaidic acid indicating that rat fetal tissue may metabolize elaidic acid via beta-oxidation. In contrast, following injection of linoelaidate, radioactivity of FAME was primarily associated with tt-18:2, suggesting little biotransformation to other fatty acids by fetal tissues.