Chloroacetamides Affect the Plasma Membrane

2002 ◽  
Vol 57 (9-10) ◽  
pp. 843-852 ◽  
Author(s):  
Bernd Matthes ◽  
Peter Böger
Keyword(s):  
Fatty Acids ◽  
Plasma Membrane ◽  
Fatty Acid ◽  
De Novo ◽  
Fatty Acid Content ◽  
Direct Consequence ◽  
Two Phase ◽  
Phase Partitioning ◽  
Microsomal Membranes ◽  
And Function

In the present study membrane fatty acids were analyzed to find a link between the biosynthesis inhibition of very-long-chain fatty acids and the phytotoxic effects of herbicidal chloroacetamides. Accordingly,we have isolated membranes of cucumber seedlings (Cucumis sativus) by two-phase partitioning and analyzed their fatty acid content. Saturated VLCFAs ranging from C20 to C26 were found in high amounts (22%) in the plasma membrane fraction. Nonmodified VLCFAs were predominantly present in phospholipids, while saturated 2-hydroxylated VLCFAs were identified in cerebrosides. Treatment of intact seedlings with chloroacetamides markedly reduced the VLCFA content in the plasma membrane. This result could be specified by fatty-acid labeling using [14C]malonate as a substrate for fatty acid elongation. De novo incorporation of VLCFAs into the plasma membrane and into microsomal membranes, respectively, was severely impaired by chloroacetamides with I50 values between 10 to 100 nm. These results confirm the previous finding that chloroacetamides inhibit VLCFA biosynthesis localized in the microsomes (Böger et al., Pest Manage. Sci. 56, 497D508, 2000). The direct consequence of this inhibition is a strong decrease of VLCFAs required as constituents of the plasma membrane and the substitution by shorter acyl chains. Apparently, physical properties and function of the plasma membrane are affected eventually leading to death of the plant.

EXTH-27. MOLECULAR CHARACTERIZATION AND PRECLINICAL DEVELOPMENT OF NOVEL SMALL MOLECULE INHIBITOR SPECIFIC FOR WILD-TYPE IDH1 FOR FERROPTOSIS INDUCTION IN GLIOBLASTOMA

2021 ◽  
Vol 23 (Supplement_6) ◽  
pp. vi169-vi169
Author(s):  
Kevin Murnan ◽  
Serena Tommasini-Ghelfi ◽  
Lisa Hurley ◽  
Corey Dussold ◽  
Daniel Wahl ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Cell Death ◽  
Plasma Membrane ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
De Novo ◽  
De Novo Lipogenesis ◽  
Therapeutic Modality ◽  
Wild Type ◽  
Genetic Ablation

Abstract Increased de novo synthesis, mobilization and uptake of fatty acids are required to provide sufficient lipids for membrane biogenesis in support of rapid tumor cell division and growth. In addition to their structural roles as components of the plasma membrane, fatty acid-derived lipids regulate ferroptotic cell death, a type of programmed cell death, when oxidized by iron-dependent lipoxygenase enzymes. De novo lipogenesis and the defense against oxidative lipid damage require large amounts of cytosolic NADPH. Our group has recently found that HGG up-regulate wild-type Isocitrate dehydrogenase 1 (referred to hereafter as ‘wt-IDH1high HGG’) to generate large quantities of cytosolic NADPH. RNAi-mediated knockdown of wt-IDH1, alone and in combination with radiation therapy (RT), slows the growth of patient-derived HGG xenografts, while overexpression of wt-IDH1 promotes intracranial HGG growth. Isotope tracer and liquid chromatography-based lipidomic studies indicated that wt-IDH1 supports the de novo biosynthesis of mono-unsaturated fatty acids (MUFAs) and promotes the incorporation of monounsaturated phospholipids into the plasma membrane, while displacing polyunsaturated fatty acid (PUFA) phospholipids. In addition, enhanced NADPH production in wt-IDH1high HGG increases glutathione (GSH) level, reduces reactive oxygen species (ROS), activates the phospholipid peroxidase glutathione peroxidase 4 (GPX4)-driven lipid repair pathway, and dampens the accumulation of PUFA-containing lipid peroxides, known executioners of ferroptosis. To pharmacologically target wt-IDH1,we have used and characterized wt-IDH1i-13, a first-in-class competitive α,β-unsaturated enone (AbbVie). wt-IDH1i-13 potently inhibits wt-IDH1 enzymatic activity, by covalently binding to the NADP+ binding pocket. Our data indicate that wt-IDH1i-13 promotes ferroptosis, which can be rescued by pre-treatment of cells with the peroxyl scavenger and ferroptosis inhibitor ferrostatin. wt-IDH1i-13 is brain-penetrant, and similar to genetic ablation, reduces progression and extends the survival of wt-IDH1high HGG bearing mice, alone and in combination with RT. These studies credential to wt-IDH1i-13 as a novel therapeutic modality for the treatment of wt-IDH1 gliomas.

Polymorphisms in genes in the SREBP1 signalling pathway and SCD are associated with milk fatty acid composition in Holstein cattle

2011 ◽  
Vol 79 (1) ◽  
pp. 66-75 ◽  
Author(s):  
Gonzalo Rincon ◽  
Alma Islas-Trejo ◽  
Alejandro R Castillo ◽  
Dale E Bauman ◽  
Bruce J German ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Candidate Genes ◽  
Acid Content ◽  
Milk Fat ◽  
De Novo ◽  
Saturated Fatty Acids ◽  
Fatty Acid Content ◽  
Signalling Pathway ◽  
Phenotypic Variance

Genes in the sterol regulatory element-binding protein-1 (SREBP1) pathway play a central role in regulation of milk fat synthesis, especially the de-novo synthesis of saturated fatty acids. SCD, a SREBP-responsive gene, is the key enzyme in the synthesis of monounsaturated fatty acids in the mammary gland. In the present study, we discovered SNP in candidate genes associated with this signalling pathway and SCD to identify genetic markers that can be used for genetic and metabolically directed selection in cattle. We resequenced six candidate genes in the SREBP1 pathway (SREBP1, SCAP, INSIG1, INSIG2, MBTPS1, MBTPS2) and two genes for SCD (SCD1 and SCD5) and discovered 47 Tag SNP that were used in a marker-trait association study. Milk and blood samples were collected from Holstein cows in their 1st or 2nd parity at 100–150 days of lactation. Individual fatty acids from C4 to C20, saturated fatty acid (SFA) content, monounsaturated fatty acid content, polyunsaturated fatty acid content and desaturase indexes were measured and used to perform the asociation analysis. Polymorphisms in the SCD5 and INSIG2 genes were the most representative markers associated with SFA/unsaturated fatty acid (UFA) ratio in milk. The analysis of desaturation activity determined that markers in the SCD1 and SCD5 genes showed the most significant effects. DGAT1 K232A marker was included in the study to examine the effect of this marker on the variation of milk fatty acids in our Holstein population. The percentage of variance explained by DGAT1 in the analysis was only 6% of SFA/UFA ratio. Milk fat depression was observed in one of the dairy herds and in this particular dairy one SNP in the SREBP1 gene (rs41912290) accounted for 40% of the phenotypic variance. Our results provide detailed SNP information for key genes in the SREBP1 signalling pathway and SCD that can be used to change milk fat composition by marker-assisted breeding to meet consumer demands regarding human health, as well as furthering understanding of technological aspects of cows' milk.

In vivo study of the biosynthesis of long-chain fatty acids using deuterated water

1995 ◽  
Vol 269 (2) ◽  
pp. E247-E252 ◽  
Author(s):  
H. O. Ajie ◽  
M. J. Connor ◽  
W. N. Lee ◽  
S. Bassilian ◽  
E. A. Bergner ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
De Novo ◽  
Chain Elongation ◽  
Deuterated Water ◽  
De Novo Synthesis ◽  
Isotopomer Distribution ◽  
Long Chain ◽  
Mass Isotopomer

To determine the contributions of preexisting fatty acid, de novo synthesis, and chain elongation in long-chain fatty acid (LCFA) synthesis, the synthesis of LCFAs, palmitate (16:0), stearate (18:0), arachidate (20:0), behenate (22:0), and lignocerate (24:0), in the epidermis, liver, and spinal cord was determined using deuterated water and mass isotopomer distribution analysis in hairless mice and Sprague-Dawley rats. Animals were given 4% deuterated water for 5 days or 8 wk in their drinking water. Blood was withdrawn at the end of these times for the determination of deuterium enrichment, and the animals were killed to isolate the various tissues for lipid extraction for the determination of the mass isotopomer distributions. The mass isotopomer distributions in LCFA were incompatible with synthesis from a single pool of primer. The synthesis of palmitate, stearate, arachidate, behenate, and lignocerate followed the expected biochemical pathways for the synthesis of LCFAs. On average, three deuterium atoms were incorporated for every addition of an acetyl unit. The isotopomer distribution resulting from chain elongation and de novo synthesis can be described by the linear combination of two binomial distributions. The proportions of preexisting, chain elongation, and de novo-synthesized fatty acids as a percentage of the total fatty acids were determined using multiple linear regression analysis. Fractional synthesis was found to vary, depending on the tissue type and the fatty acid, from 47 to 87%. A substantial fraction (24-40%) of the newly synthesized molecules was derived from chain elongation of unlabeled (recycled) palmitate.

scholarly journals Effect of Nitrogen Fertilisation and Inoculation with Bradyrhizobium japonicum on the Fatty Acid Profile of Soybean (Glycine max (L.) Merrill) Seeds

Agronomy ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 941
Author(s):  
Ewa Szpunar-Krok ◽  
Anna Wondołowska-Grabowska ◽  
Dorota Bobrecka-Jamro ◽  
Marta Jańczak-Pieniążek ◽  
Andrzej Kotecki ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Acid Composition ◽  
Bradyrhizobium Japonicum ◽  
Field Experiments ◽  
Fatty Acid Content ◽  
Soybean Seeds ◽  
Oilseed Crop ◽  
Soybean Cultivars

Soybean is a valuable protein and oilseed crop ranked among the most significant of the major crops. Field experiments were carried out in 2016–2019 in South-East Poland. The influence of soybean cultivars (Aldana, Annushka), nitrogen fertilizer (0, 30, 60 kg∙ha−1 N) and inoculation with B. japonicum (control, HiStick® Soy, Nitragina) on the content of fatty acids (FA) in soybean seeds was investigated in a three-factorial experiment. This study confirms the genetic determinants of fatty acid composition in soybean seeds and their differential accumulation levels for C16:0, C16:1, C18:1n9, C18:2, C18:3, and C20:0 as well saturated (SFA), monounsaturated (MUFA), and polyunsaturated (PUFA) fatty acids. Increasing the rate from 30 to 60 kg ha−1 N did not produce the expected changes, suggesting the use of only a “starter” rate of 30 kg ha−1 N. Inoculation of soybean seeds with a strain of Bradyrhizobium japonicum (HiStick® Soy, BASF, Littlehampton, UK and Nitragina, Institute of Soil Science and Plant Cultivation–State Research Institute, Puławy, Poland) is recommended as it will cause a decrease in SFA and C16:0 acid levels. This is considered nutritionally beneficial as its contribution to total fatty acids determines the hypercholesterolemic index, and it is the third most accumulated fatty acid in soybean seeds. The interaction of cultivars and inoculation formulation on fatty acid content of soybean seeds was demonstrated. An increase in the value of C16:0 content resulted in a decrease in the accumulation of C18:1, C18:2, and C18:3 acids. The content of each decreased by almost one unit for every 1% increase in C16:0 content. The dominant effect of weather conditions on the FA profile and C18:2n6/C18:3n3 ratio was demonstrated. This suggests a need for further evaluation of the genetic progress of soybean cultivars with respect to fatty acid composition and content under varying habitat conditions.

scholarly journals Effect of Pork Meat Replacement by Fish Products on Fatty Acid Content, Physicochemical, and Sensory Properties of Pork Pâtés

2020 ◽  
Vol 11 (1) ◽  
pp. 188
Author(s):  
Piotr Skałecki ◽  
Agnieszka Kaliniak-Dziura ◽  
Piotr Domaradzki ◽  
Mariusz Florek ◽  
Ewa Poleszak ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Acid Content ◽  
Raw Materials ◽  
Fatty Acid Content ◽  
Calorific Value ◽  
Thiobarbituric Acid ◽  
Acid Value ◽  
Sensory Properties ◽  
Control Group

The aim of the study was to assess the influence of the addition of fish raw materials (roe or fish meat) on the quality and nutritional value of pork pâtés. The control group (n = 4) consisted of pork pâtés, I experimental group (n = 6) of pâtés with 20% addition of roe (perch and pike), and II group of pâtés with 20% addition of fish (perch and pike meat) (n = 6). The pâtés’ pH, color, and profiled texture analysis were instrumentally measured and water, protein, fat, ash, and fatty acid content were determined by reference methods. To assess the oxidative stability of lipids the measurement of peroxide number, thiobarbituric acid reactive substances and content of conjugated dienes and trienes was used. The degree of fat hydrolysis was determined on the basis of acid value. Sensory analysis was carried out using the scaling method, taking into account 12 unit quality characteristics. Products with roe and meat contained less fat (accordingly 15.9% and 14.1%) and showed lower calorific value (accordingly 225.6 and 208.6 kcal/100 g) compared to pork pâtés (20.2% of lipids, 267 kcal/100 g). Moreover, the addition of fish raw materials improved the index of nutritional quality for protein (from 3.2 to 3.9) and beneficially reduced the nutritional index for fat (from 2.2 to 1.9). Fish constituents modified, to a certain extent, the color, texture, and sensory properties of pâtés, while maintaining full acceptability in consumer assessment. The addition of fish roe significantly increased the healthful quality by improving the fatty acid profile of pâtés, in which the significantly highest content of n-3 fatty acids, including eicosapentaenoic and docosahexaenoic acids (accordingly 252.21, 43.17, and 107.94 mg/100 g product), as well the highest concentration of saturated branched chain fatty acids were determined (18.75 mg/100 g product).

scholarly journals Meat Quality, Fatty Acid Content and NMR Metabolic Profile of Dorper Sheep Supplemented with Bypass Fats

Foods ◽  
2021 ◽  
Vol 10 (5) ◽  
pp. 1133
Author(s):  
Atique Ahmed Behan ◽  
Muhammad Tayyab Akhtar ◽  
Teck Chwen Loh ◽  
Sharida Fakurazi ◽  
Ubedullah Kaka ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Meat Quality ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Fatty Acid Content ◽  
Basal Diet ◽  
Negative Influence ◽  
Significant Difference ◽  
Dorper Sheep

The supplementation of rumen bypass fat (RBF) has remained one of the preferred approaches used to decrease undesirable saturated fatty acids (FA) and increase beneficial unsaturated FA in the meat. This study was planned to evaluate the influences of rumen bypass fats on meat quality, fatty acid and metabolic profiles in male Dorper sheep (n = 36) with 24.66 ± 0.76 kg (mean ± standard error) initial body weight. Treatment comprised a basal diet (30:70 rice straw to concentrate) with no added RBF as a control (CON), basal diet with prilled fat (PF), basal diet with prilled fat plus lecithin (PFL) and basal diet with calcium soap of palm fatty acids (CaS). The findings revealed that cooking loss, drip loss and shear force in longissimus dorsi (LD) muscle were not affected by RBF supplementation, while meat pH was significantly higher in the CaS on aging day 1. However, the diet supplemented with prilled fat and lecithin modified the meat’s fatty acid profile significantly by increasing unsaturated fatty acids and decreasing saturated fats. The relative quantification of the major differentiating metabolites found in LD muscle of sheep showed that total cholesterol, esterified cholesterol, choline, glycerophosphocholine and glycerophospholipids were significantly lower in CaS and PFL diets, while glycerol and sphingomyelin were significantly higher in CaS and PFL diets. Most of the metabolites in the liver did not show any significant difference. Based on our results, the supplementation of protected fats did not have a negative influence on meat quality and the meat from Dorper sheep fed prilled fat with lecithin contained more healthy fatty acids compared to other diets.

Modifying egg fatty acid content by supplementation of laying hen diets with palm olein oil (POO)

2009 ◽  
Vol 2009 ◽  
pp. 212-212
Author(s):  
S J Hosseini Vashan ◽  
N Afzali ◽  
A Golian ◽  
M Malekaneh ◽  
A Allahressani
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Acid Content ◽  
Palm Olein ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Fatty Acid Content ◽  
Processing Plant ◽  
Optimum Level ◽  
Olein Oil

Palm oil is the most abundant of all oils produced globally. It is very high in saturated fatty acids specifically palmitic acid, but other fatty acids (monounsaturated (MUFA) and polyunsaturated) are presented at low concentrations. In the processing plant some high amount of oleic acid with some other unsaturated fatty acids are extracted and marketed as Palm olein oil, and used to reduce blood or egg cholesterol (Rievelles et al., 1994). The objective of this study was to determine the optimum level of dietary palm olein oil required to enrich the mono-unsaturated fatty acid content of yolk, egg cholesterol and antibody titre.

Prediction of Fatty Acid Content in Beef Neck Lean by near Infrared Reflectance Analysis

1998 ◽  
Vol 6 (1) ◽  
pp. 229-234 ◽  
Author(s):  
William R. Windham ◽  
W.H. Morrison
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Near Infrared ◽  
Fatty Acid Content ◽  
Reference Method ◽  
Nir Spectroscopy ◽  
Coefficient Of Determination ◽  
Longissimus Dorsi ◽  
Near Infrared Reflectance ◽  
Total Fatty Acids

Near infrared (NIR) spectroscopy in the prediction of individual and total fatty acids of bovine M. Longissimus dorsi neck muscles has been studied. Beef neck lean was collected from meat processing establishments using advanced meat recovery systems and hand-deboning. Samples ( n = 302) were analysed to determine fatty acid (FA) composition and scanned from 400 to 2498 nm. Total saturated and unsaturated FA values ranged from 43.2 to 62.0% and 38.3 to 56.2%, respectively. Results of partial least squares (PLS) modeling shown reasonably accurate models were attained for total saturate content [standard error of performance ( SEP = 1.10%); coefficient of determination on the validation set ( r2 = 0.77)], palmitic ( SEP = 0.94%; r2 = 0.69), unsaturate ( SEP = 1.13%; r2 = 0.77), and oleic ( SEP = 0.97; r2 = 0.78). Prediction of other individual saturated and unsaturated FAs was less accurate with an r2 range of 0.10 to 0.53. However, the sum of individual predicted saturated and unsaturated FA was acceptable compared with the reference method ( SEP = 1.10 and 1.12%, respectively). This study shows that NIR can be used to predict accurately total fatty acids in M. Longissimus dorsi muscle.

The composition and metabolism of fatty acids in Ips paraconfusus Lanier (Coleoptera: Scolytidae)

1972 ◽  
Vol 50 (10) ◽  
pp. 1263-1267 ◽  
Author(s):  
K. R. Penner ◽  
J. S. Barlow
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Sexual Dimorphism ◽  
Acid Composition ◽  
De Novo ◽  
Monounsaturated Fatty Acids ◽  
Ips Paraconfusus ◽  
Chain Elongation ◽  
De Novo Synthesis

The fatty acid composition of newly emerged Ips paraconfusus Lanier shows no sexual dimorphism and is approximately as follows: C14:0, 0.5%; C16:0, 23.0%; C16:1, 6%; C18:0, 3%; C18:1, 55%; C18:2, 9%; C18:3, 2%. Both sexes, but particularly the female, use up fatty acids, particularly the monounsaturated acids, during reproduction. Isotope from 1-14C-acetate injected into newly emerged females appeared in all saturated and monounsaturated fatty acids within 30 min. There was evidence of de novo synthesis of C14:0 and C16:0, chain elongation of C16:0 to C18:0, and desaturation of C16:0 and C18:0 to yield C16:1 and C18:1 respectively.

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