C18 Unsaturated Fatty Acids Research Articles

Selenate and selenite affect ruminal metabolism of C18 unsaturated fatty acids and fatty acid composition of lamb tissues

The main aim of our study was to investigate the influence of selenite (SeIV) or selenate (SeVI) added to ovine ruminal fluid with cis9cis12cis15C18:3 (LNA) on contents of fatty acids (FA), especially products of microbial isomerisation of LNA and biohydrogenation (BH) of unsaturated FA in vitro incubated fluids. The second goal of our study was to investigate the effects of SeVI added to a diet containing linseed oil (LO, rich in LNA) on the accumulation of BH products in selected tissues of lambs. Ruminal fluids were incubated in vitro at 39°C under CO2 either alone (the control fluid; RF) or with LNA (1.67 mg/ml), a low (1.33 μg/ml), a high (3.33 μg/ml) dose of Se (as SeIV or SeVI), with a combination of LNA with either a low (1.33 μg/ml) or a high (3.33 μg/ml) dose of Se as SeIV or SeVI. The tubes with incubated fluids were removed after 0, 6, 12, 18 or 24 h of in vitro incubation and then analysed to determine contents of FA. Both the doses of SeIV or SeVI in fluids with LNA revealed no significant effect on the contents of products of LNA isomerisation compared to incubated fluids with LNA. The contents of isomerisation products of LNA in incubated fluids with LNA, irrespective of the presence of SeIV and SeVI, rapidly increased in the fluids incubated for 6 h, followed by a slower rate of disappearance until 24 h. Contents of trans11C18:1 and trans11cis15C18:2 in fluids with LNA, regardless of the presence of both the doses of SeIV or SeVI, increased throughout incubations. The lower dose of SeVI in fluids with LNA increased the capacity of BH to trans11C18:1 in incubated fluids. SeVI added to the lambs’ diet with LO decreased contents of saturated FA (like C18:0) in the liver and musculus longissimus dorsi. LO added to the diets with or without SeVI most effectively increased the level of polyunsaturated FA (PUFA) in the liver, while the higher content of monounsaturated FA was observed in musculus biceps fermoris (MBF) when compared to the control group. The diets with LO, irrespective of the presence of SeVI, reduced the capacity of linoleic acid elongation to cis11cis14C20:2 in the liver and MBF compared to the control lambs. Further studies are required to clarify the effects of SeVI and long-chain PUFA on contents of FA, especially conjugated PUFA, in the ruminal microbiota and tissues of lambs.

Ruminal parameters and fatty acid composition of omasal digesta and milk in cows fed sugarcane-based diets supplemented with sunflower oil

This study evaluates the intake and digestion of nutrients, parameters of rumen fermentation and degradation, omasal digesta and milk fatty acid composition, productive performance, and the concentration of serum metabolites in cows fed 600 g kg-1 sugarcane-based diets containing 0 (control), 15, 30, and 45 g kg-1 sunflower oil (SO) on a dry matter (DM) basis. Four rumen-cannulated Holstein x Gyr cows yielding 15±5 kg day-1 with 110±10 days in milk were allocated in a 4 x 4 Latin square design. Data were analyzed using mixed models, and significant differences were declared at P < 0.05. There was no effect of SO on the intake and apparent digestibility of DM, crude protein, neutral detergent fiber (NDF) and nonfibrous carbohydrates, but there was a linear increase in the intake and digestibility of ether extract. Dietary SO levels did not alter the ruminal degradability parameters for DM and NDF, rumen pH and contents of ammonia N, acetate, propionate and volatile fatty acids. Milk fat content and yield were linearly decreased, whereas a linear increase in milk protein content was observed in response to increasing levels of SO, but with no effect on milk yield. Linear reductions in palmitic and ?-linolenic acid contents, a linear increase in trans-10 C18:1 and elaidic acids, and a quadratic effect on vaccenic and rumenic acids were observed in omasal digesta of cows fed increasing levels of SO. Overall, up to 45 g kg-1 SO can be included on DM of chopped sugarcane-based diets without reducing consumption, apparent digestibility and rumen degradability of DM and fiber. Supplementing chopped sugarcane-based diets with 30 to 45 g kg-1 SO (DM basis) promotes milk fat depression due to the inhibition of mammary lipogenesis by specific rumen-derived fatty acid intermediates of the biohydrogenation of unsaturated C18 fatty acids. The inclusion of 15 to 45 g kg-1 SO in chopped sugarcane-based diets improves the nutritional quality of milk fat, with increases in the levels of oleic, vaccenic and rumenic acids, beneficial to human health, and a reduction in the levels of the hypercholesterolemic lauric, myristic and palmitic acids.

Effects of exogenous C18 unsaturated fatty acids on milk lipid synthesis in bovine mammary epithelial cells.

We determined the effects of a combination of C18 unsaturated fatty acids (C18-UFAs) consisting of oleic, linoleic, and linolenic acids on milk lipogenesis in bovine mammary epithelial cells (BMECs). By orthogonal experiments to determine cellular triacylglycerol (TAG) accumulation, a combination of 200 μmol/l C18 : 1, 50 μmol/l C18 : 2, and 2 μmol/l C18 : 3 was selected as C18-UFAs combination treatment, and culture in medium containing fatty acid-free bovine serum albumin was used as the control. The expression of genes related to milk lipid synthesis and intracellular FA composition was measured. The results showed that cytosolic TAG formation was higher under C18-UFAs treatment than under control treatment. The mRNA expression of acetyl-CoA carboxylase-α (ACACA), fatty acid synthase (FASN), and peroxisome proliferator-activated receptor gamma (PPARG) did not differ between treatments. The abundance of stearoyl-CoA desaturase (SCD) and acyl-CoA synthetase long-chain family member 1 (ACSL1) was higher, whereas that of sterol regulatory element binding transcription factor 1 (SREBF-1) was lower after C18-UFAs treatment compared to control treatment. The C16 : 0 and SFA content was decreased following C18-UFAs treatment compared to control treatment, while the cis-9 C18 : 1 and UFA content was increased. In conclusion, C18-UFAs could stimulate triglyceride accumulation, increase the cellular UFA concentration, and regulate lipogenic genes in BMECs.

In vitro ruminal biohydrogenation of C18 fatty acids in mixtures of Indigofera zollingeriana and Brachiaria decumbens

This research was aimed at studying the in vitro ruminal biohydrogenation (BH) of C18 fatty acids (FA) in mixtures of Indigofera zollingeriana and Brachiaria decumbens. Four combinations of experimental rations of I. zollingeriana : B. decumbens were tested i.e., IZ 1 (45%:45%), IZ 2 (60%:30%), IZ 3 (75%:15%), and IZ 4 (90%:0%). The remaining 10% in in each ration was rice bran. The experimental design was based on a completely randomized design with five replicates. Results revealed that there was a statistically significant difference (P<0.01) in the composition of C18 unsaturated FA (UFA) and saturated FA (SFA) for each in vitro incubation period of 1, 2, 4, 8 and 24 h. The highest accumulation of C18 UFA at 24 h was observed in the incubation of IZ 4 (19.87%). The BH of C18:3, C18:2, and C18:1 showed no differences (P>0.05). Composition of C18:0 after incubation showed a significant difference (P<0.01) with the lowest composition was observed in IZ 2 (22%). In conclusion, combination of I. zollingeriana and B. decumbens at different ratio has minor inhibition effect on BH of C18 UFA.

Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity

Bioassay-guided separation of a methanol extract of Tricleocarpa jejuensis by monitoring algicidal activity against the red tide phytoplankton Chattonella antiqua led to the isolation of an active fraction consisting of a mixture of four isomeric compounds. The active compounds were identified as (E)-9-hydroxyoctadec-10-enoic acid (1), (E)-10-hydroxyoctadec-8-enoic acid (2), (E)-11-hydroxyoctadec-12-enoic acid (3) and (E)-12-hydroxyoctadec-10-enoic acid (4) by NMR, IR and mass spectral data. The structures were confirmed by comparison of the NMR and MS data with those of authentic samples of 1–4 obtained by unambiguous syntheses. Synthesized hydroxy acids 1–4 and related compounds were assessed for algicidal activity against C. antiqua and it was found that all of 1–4 had high activity (>80% mortality at 24 h) at a concentration of 20 μg/mL. A structure–activity relationship study using 11 related compounds revealed that the presence of the hydroxyl group is important for the activity and the double bond may be replaced with a triple bond.

Plant Unsaturated Fatty Acids: Biosynthesis and Regulation.

In most plants, major unsaturated fatty acids (UFAs) are three C18 species, namely, oleic (18:1), linoleic (18:2), and α-linolenic (18:3) acids. These simple compounds play multiple crucial roles in planta and are also important economic traits of oil crops. The enzymatic steps of C18 UFA biosynthesis have been well established. However, the associated FA/lipid trafficking between the plastid and the endoplasmic reticulum remains largely unclear, as does the regulation of the expression and activities of the involved enzymes. In this review, we will revisit the biosynthesis of C18 UFAs with an emphasis on the trafficking, and present an overview of the key enzymes and their regulation. Of particular interest is the emerging regulatory network composed of transcriptional factors and upstream signaling pathways. The review thereby provides the promise of using physical, biochemical and/or genetic means to manipulate FA composition and increase oil yield in crop improvement.

Realization of breeding values for milk fatty acids in relation to seasonal variation in organic milk

Prediction of detailed milk fatty acid (FA) composition by mid-infrared spectroscopy (MIRS) offers possibilities for high-throughput indirect measurements of detailed milk compositional parameters through the milk testing system, which can be used to differentiate the FA profile by genetics or specific management or on dairies for milk quality evaluation. Since 2015, milk samples from all Danish dairy cows under milk testing have been recorded using MIRS. The MIRS software from the FOSS Application Note 64 was used to predict contents of 7 FA groups and 4 individual FA. Data generated from the application note have been used to estimate breeding values for sires for percentage of saturated fat (SFA%) in milk. To investigate whether extreme SFA% breeding values of sires were reflected in the detailed milk FA profile from their daughters, milk samples from 194 cows in 7 organic herds were collected and the detailed FA composition measured by gas chromatography. From each cow, milk samples were collected twice to explore specific seasonal effects of pasture-based diets in relation to sires' estimated breeding value (EBV) for MIRS-predicted SFA% (MIRS-SFA%). The results showed a significant difference in SFA% measured from GC (GC-SFA%) in milk from daughters of sires having high SFA% EBV compared with daughters of sires having low SFA% EBV. The EBV group (low or high) also significantly affected most FA except C13:0, C15:0, C17:0, and C18:1 trans-11. Contents of SFA with even chain-lengths were all higher in the high EBV group, whereas C14:1, C16:1, and the other unsaturated C18 FA had a higher content in the low EBV group. All FA were significantly affected by season. The SFA% decreased from indoor spring feeding to summer pasture, as did FA with chain length ≤16 carbons, whereas long-chain FA (>C17) all increased during summer pasture. The results show that use of MIRS-predicted EBV for SFA% will most likely display a correlated response on the detailed FA composition in milk. In the current study, the combined action of feeding and genetics resulted in a 10 percentage-point difference on average when comparing milk SFA% from daughters of high SFA% EBV sires during indoor spring feeding from one farm to milk SFA% from daughters of low SFA% EBV sires during summer from another farm.

Conformational changes in bovine α-lactalbumin and β-lactoglobulin evoked by interaction with C18 unsaturated fatty acids provide insights into increased allergic potential.

Bovine α-lactalbumin (BLA) and β-lactoglobulin (BLG) are the most common and severe food allergens in milk and they can bind C18 unsaturated fatty acids (UFAs) and their bioactivities were changed. This study aims to determine the effects of C18 UFAs on the structures of BLA and BLG and their allergic properties, such as antigenicity and allergenicity. We reveal that C18 UFAs can efficiently promote the gradual unfolding of the structures of BLA and BLG and increase their hydrophobicity. Moreover, the IgG binding ability and the expression of IgG-dependent activation marker CD200R3 on basophils were remarkably promoted after C18 UFA treatment. Finally, we also observed that C18 UFAs can enhance the IgE binding ability and the degranulation capacity of human basophil KU812 cells (intracellular Ca2+, histamine, β-Hex, and IL-6). Collectively, these results suggested that C18 UFAs changed the structures of BLA and BLG, which contributed to their increased allergic potential.

Effects of supplemental plant oils on rumen bacterial community profile and digesta fatty acid composition in a continuous culture system (RUSITEC)

Lipid supplementation of ruminant diets may trigger changes in the ruminal microbiota and in anaerobic digestion. Changes in the bacterial community composition and in the fatty acid hydrogenation caused by the addition of different supplemental plant oils to a high concentrate diet were investigated in vitro using RUSITEC (rumen simulation technique) fermenters. The control (CTR) diet was a high-concentrate total mixed ration for dairy sheep, with no supplementary oil. The other experimental diets were supplemented with olive (OLV), sunflower (SFL) or linseed (LNS) oils at 6% (dry matter basis). Four RUSITEC fermenters were used for each experimental diet, all inoculated with rumen digesta of sheep. Extent of dry matter and fat degradation, composition of the bacterial community and long-chain fatty acids in digesta were determined. The addition of plant oils increased (P < 0.001) apparent degradation of fat in the fermenters, whereas fermentation kinetics (gas production and average fermentation rate) were lower (P < 0.05) with the LNS than with the CTR diet. Hydrogenation of C18 unsaturated fatty acids (P < 0.05), in particular that of oleic acid (P < 0.001), and stearic acid proportion (P < 0.001) were reduced, and oleic acid proportion was increased (P < 0.001) with all oil supplements. Addition of OLV decreased linoleic and LNS increased α-linolenic (P < 0.001), whereas conjugated linoleic was increased with SFL oil (P = 0.025) and vaccenic increased with both SFL and LNS oils (P = 0.008). Addition of 6% OLV and LNS reduced (P < 0.05) microbial community diversity and quantity of total bacteria relative to the control. Some specific microbial groups were affected (P < 0.001) by oil addition, with less relative abundance of Clostridiales and Actinobacteria and increased Bacteroidales, Aeromonadales and Lactobacillales species. In conclusion, the supplementation of high-concentrate ruminant diets with plant oils, in particular from sunflower or linseed, causes shifts in the rumen microbiota and fatty acid hydrogenation in the rumen increasing the formation of vaccenic and conjugated linoleic acids.

Coproduction of lipids and extracellular polysaccharides from the novel green alga Parachlorella sp. BX1.5 depending on cultivation conditions

A novel strain of microalga Parachlorella sp. BX1.5 was isolated and its unique properties of producing lipids and extracellular polysaccharides (EPS) characterized. The cells could extracellularly produce a large amount of acidic EPS, when cultured in nitrogen-deficient BG110 medium (BG11–N) with 2 % CO2-air supply. The main component of intracellularly accumulated lipids was triacylglycerol (TAG), depending on the different cultivation conditions of BG11, BG11–N, BG11–P (phosphate depleted), and BG11–N–P (nitrogen and phosphate depleted). Fatty-methyl-esters (FAMEs), methyl-esterification of total lipids, consisted of abundant saturated C16 and unsaturated C18 fatty acids under the culture conditions. Cell spot assays on BG11 plates revealed the resistance of cells to pH 2–11, high temperatures of 50–70 °C, ultraviolet irradiation, and drought, under different culture conditions, thereby suggesting the biological significance of lipid and EPS accumulation. The prospects of BX1.5 as a dual producer has also been discussed for biorefineries.

Acyl-CoA:lysophosphatidylcholine acyltransferases (LPCATs) of Camelina sativa seeds: biochemical properties and function

Main conclusionThe transfer of polyunsaturated fatty acids from phosphatidylcholine to other lipids involves several enzymes. In Camelina sativa seeds, acyl-CoA:lysophosphatidylcholine acyltransferases could be one of the most important players in this process.The transfer of polyunsaturated fatty acids from the location of their synthesis (phosphatidylcholine) to other lipids, e.g., triacylglycerol, remains insufficiently understood. Several enzymes could be involved in this process. One of these enzymes is acyl-CoA:lysophosphatidylcholine acyltransferases (LPCATs). In Camelina sativa seeds, LPCATs could be one of the most important players in this process. Our data clearly indicate that the CsLPCATs present in developing seeds have the potential to transfer almost all polyunsaturated fatty acids synthesised on phosphatidylcholine to the acyl-CoA pool. CsLPCAT activity is the highest at 30 °C, and the enzymes operate well at a pH of 7.0–11.0, with the best activity at a pH of 9.0. The activity of CsLPCATs was inhibited by calcium and magnesium ions at a concentration of 0.05–2 mM. In the forward reaction, CsLPCATs preferentially utilise 18:2-CoA; however, other C18 unsaturated fatty acids are also well accepted. In the backward reactions, there is no clear discrimination between the C18 unsaturated fatty acids utilised by the enzymes for phosphatidylcholine remodelling. The activity of CsLPCATs does not differ much between the stages of seed development.

Preparation and Characterization of PEGylated C18 Fatty Acids/Anti-SNAP25 Antibody-Targeted Liposomes

Background:Unsaturated C18 fatty acids, such as oleic acid (L1), linoleic acid (L2), and linolenic acid (L3), are a good choice of lipids to prepare liposomes. They are inexpensive, biocompatible, nontoxic, and readily available compared with phospholipids. Moreover, cis-double bonds of unsaturated fatty acids prevent the packing of molecules which increases membrane fluidity in liposomes making them a good choice of starting materials to prepare liposomes.Objective:Unsaturated C18 fatty acid liposomes, as well as their PEGylated and non- PEGylated antibody-targeted liposomes, were prepared and characterized.Methods:The particle size and zeta potential of the prepared liposomes (1 mM, pH = 7.4) for 28 and 14 days, respectively, were monitored and characterized. Membrane-bound antibodies Anti-SNAP25 (AS25) and DOPE PEG2000 (DP) were conjugated to pure C18 fatty acid liposomes to achieve stable fatty acid formulations.Results:The mean particle sizes of pure L1, L2, and L3 liposome solutions were 125, 129, and 122 nm respectively, while their polydispersity index values were 0.28, 0.21, and 0.40 respectively. A large negative zeta potential value of 45 mV was observed due to anionic carboxylate head-group of pure liposomes. The incorporation of AS25 into L1/DP, L2/DP, and L3/DP liposome solutions stabilized their mean particle size and zeta potential measurements over 28 and 14 days, respectively.Conclusion:L1/DP/AS25 was found to be the most stable PEGylated antibody-targeted liposome system because its particle size remained between 90 and 125 nm in 28 days. Transmission electron microscopy observations also supported the incorporation of AS25 and DP on the membrane surface as predicted.

LC-MS/MS analysis of free fatty acid composition and other lipids in skins and seeds of Vitis vinifera grape cultivars.

Lipids are important constituents of plant and animal cells, being essential due to their biological functions. Despite the significant role of these compounds in grape berries, knowledge of grape lipid composition is still limited. This study addresses the free fatty acid composition and other lipids in skins and seeds of several Vitis vinifera grape cultivars using LC-MS/MS. A different profile of free fatty acids was determined in the grape tissues, showing a higher proportion of unsaturated fatty acids in seeds (ca. 60%). Lignoceric acid was one of the main free saturated fatty acids found in grape skins, together with palmitic and stearic acids. Berry skins showed similar ranges of C18-unsaturated fatty acids, whereas linoleic acid was predominant in the seed fatty acid composition. Higher content of glycerophospholipids was determined in grape seeds. Uvaol and oleanolic acid were only quantified in skins (1.5-3.9 and 38.6-57.6 mg/kg fresh weight, respectively). These preliminary results suggest a certain diversity in grape lipids according to their location in the berry tissues and cultivar, providing useful information for the fermentation process due to their role in wine sensory profile and yeast growth.

Self-assembled vesicles formed by C18 unsaturated fatty acids and sodium dodecyl sulfate as a drug delivery system

Fatty acids, as anionic surfactants, can form different self-assembled structures in alkaline solutions. It has been reported that unsaturated fatty acids (UFAs) are more likely to form vesicles in this condition. Generally, fatty acid vesicles are formed near their respective pKa (8–9), which is far from the neutral range to which the life system fits. Furthermore, vesicles formed by UFAs are extremely sensitive to pH, which limit their application. To solve this problem, we added sodium dodecyl sulfate (SDS), an anionic surfactant, to the vesicles formed by C18 UFAs to adjust the ionic effect in aqueous solution. Thereby, the formed pH windows of vesicles are migrated and expanded, which can be close to the pH range of physiological environment. Meanwhile, the vesicles formed by SDS-UFAs were determined by cryogenic transmission electron microscopy (cryo-TEM) and particle size analyzer to obtain nanocarriers with a particle size of 200–300 nm. Afterwards, the hemolysis, cytotoxicity, sustained release behavior and cellular uptake of drug-loaded nanocarriers were evaluated in vitro. This result can provide theoretical guidance for the application of drug-loaded vesicles in drug delivery system.

Effects of soybean oil supplement to diets of lactating dairy cows, on productive performance, and milk fat acids profile: a meta-analysis

The aim of this paper was to investigate the effects of soybean oil, an oilseed rich in the polyunsaturated fatty acid C18:2, on dry matter intake (DMI), milk yield (MY) and milk composition (including fatty acid profile) of dairy cows by using a meta-analysis approach. In the meta-analysis, effect size for all outcomes was reported as standardised means difference with 95% confidence intervals. Q test and I2 were calculated to detect the heterogeneity, with a meta-regression also used to investigate sources of heterogeneity. Results of the meta-analysis indicated that adding soybean oil to the diet of dairy cows decreased DMI, milk fat percentage (MFP), milk fat yield (MFY) and milk protein percentage (MPP), whilst significantly increasing MY. Unsaturated fatty acids C18:2, C18:1 trans-11 and C18:2 cis-9 trans-11 conjugated linoleic acid (CLA) all significantly increased with soybean oil inclusion in the diet, whereas C18:3 was numerically higher but not significantly different. Milk composition, including MFP, MFY, MPP, short-chain and medium-chain fatty acids (C4–C20) and unsaturated fatty acids showed a significant percentage of heterogeneity. Results of the meta-regression indicated that dose of soybean oil, total fatty acids in the diet, and the concentration of C18:2 between groups receiving soybean oil and control are the most important factors affecting this heterogeneity. By performing meta-analysis and meta-regression it can be concluded that dietary supplementation of soybean oil to lactating dairy cows decreased DMI, and increased MY and the amount of unsaturated fatty acids in milk.HighlightsSoybean oil dietary supplementation to dairy cows increased milk yield but reduced milk fat content.Milk fat in soybean oil dietary supplemented cows has a lower content of short-chain fatty acids, associated with de novo synthesis.Milk fat in soybean oil dietary supplemented cows has a higher content of C18:1 trans-11, C18:2 and CLA.

Draft Genome and Description of Eisenbergiella massiliensis Strain AT11T: A New Species Isolated from Human Feces After Bariatric Surgery.

A novel strain of a Gram-stain negative, non-motile, non-spore forming rod-shaped, obligate anaerobic bacterium, designated AT11T, was isolated from a stool sample of a morbidly obese woman living in Marseille, France. This bacterium was characterized using biochemical, chemotaxonomic, and phylogenetic methods. The 16S rRNA gene sequence analysis showed that strain AT11T had a 97.8% nucleotide sequence similarity with Eisenbergiella tayi strain B086562T, the closest species with standing in nomenclature. The major cellular fatty acids of the novel isolate were C16:0 followed by saturated or unsaturated C18 fatty acids (C18:1n9, C18:1n5 and C18:0). The draft genome of strain AT11T is 7,114,554bp long with 48% G+C content. 6176 genes were predicted, including 6114 protein-coding genes and 62 were RNAs (with 2 5S rRNA genes, two 16S rRNA genes, two 23S rRNA genes, and 56 tRNA genes). The digital DNA-DNA hybridization (dDDH) relatedness between the new isolate and E. tayi strain B086562T was 23.1% ± 2.2. Based on the phenotypic, chemotaxonomic, genomic, and phylogenetic characteristics, Eisenbergiella massiliensis sp. nov., is proposed. The type strain is AT11T (= DSM 100838T = CSUR P2478T).

Biosynthesis of Oxylipins by Rhizoctonia solani with Allene Oxide and Oleate 8S,9S-Diol Synthase Activities.

Oxylipin biosynthesis by fungi is catalyzed by both the lipoxygenase (LOX) family and the linoleate diol synthase (LDS) family of the peroxidase-cyclooxygenase superfamily. Rhizoctonia solani, a pathogenic fungus, infects staple crops such as potato and rice. The genome predicts three genes with 9-13 introns, which code for tentative dioxygenase (DOX)-cytochrome P450 fusion enzymes of the LDS family, and one gene, which might code for a 13-LOX. The objective was to determine whether mycelia or nitrogen powder of mycelia oxidized unsaturated C18 fatty acids to LDS- or LOX-related metabolites. Mycelia converted 18:2n-6 to 8R-hydroxy-9Z,12Z-octadecadienoic acid and to an α-ketol, 9S-hydroxy-10-oxo-12Z-octadecenoic acid. In addition to these metabolites, nitrogen powder of mycelia oxidized 18:2n-6 to 9S-hydroperoxy-10E, 12Z-octadecadienoic, and 13S-hydroperoxy-9Z,11E-octadecadienoic acids; the latter was likely formed by the predicted 13-LOX. 18:1n-9 was transformed into 8S-hydroperoxy-9Z-octadecenoic and into 8S,9S-dihydroxy-10E-octadecenoic acids, indicating the expression of 8,9-diol synthase. The allene oxide, 9S(10)epoxy-10,12Z-octadecadienoic acid, is unstable and decomposes rapidly to the α-ketol above, indicating biosynthesis by 9S-DOX-allene oxide synthase. This allene oxide and α-ketol are also formed by potato stolons, which illustrates catalytic similarities between the plant host and fungal pathogen.

Mutagenesis of the FAE1 genes significantly changes fatty acid composition in seeds of Camelina sativa

Camelina sativa is a re-emerging low-input oilseed crop that has great potentials. It is necessary to ameliorate camelina oils for optimized fatty acid composition that can meet different application requirements. Camelina seed contains significant amounts of C20-C24 very long-chain fatty acids (VLCFAs) that may not be desirable. We demonstrated that these VLCFAs can be effectively reduced by deactivating the Fatty Acid Elongase1 (FAE1) in camelina. The allohexaploid camelina contains three alleles of FAE1 genes. Ethyl methanesulfonate (EMS) induced mutation at the FAE1-B gene caused over 60% reduction of VLCFAs in seed. Homozygous knockout mutants were successfully created in a single generation by simultaneously targeting three FAE1 alleles using the CRISPR technology with an egg cell-specific Cas9 expression. VLCFAs were reduced to less than 2% of total fatty acids compared to over 22% in the wild type, and the C18 unsaturated fatty acids were concomitantly increased. The fae1 mutants were indistinguishable from wild type in seed physiology and plant growth. This study demonstrated that the CRISPR/Cas9 technology can be effectively applied to the polyploid crop camelina to rapidly obtain desired traits such as optimal fatty acid composition in its seed oil. Knocking out FAE1 also provides a means to increase the levels of oleic acid or α-linolenic acid in camelina oils that are desirable for industrial or food/feed uses.

Diversity of compounds in femoral secretions of Galápagos iguanas (genera: Amblyrhynchus and Conolophus), and their potential role in sexual communication in lek-mating marine iguanas (Amblyrhynchus cristatus).

BackgroundChemical signals are widely used in the animal kingdom, enabling communication in various social contexts, including mate selection and the establishment of dominance. Femoral glands, which produce and release waxy secretions into the environment, are organs of central importance in lizard chemical communication. The Galápagos marine iguana (Amblyrhynchus cristatus) is a squamate reptile with a lek-mating system. Although the lekking behaviour of marine iguanas has been well-studied, their potential for sexual communication via chemical cues has not yet been investigated. Here we describe the diversity of the lipophilic fraction of males’ femoral gland secretions among 11 island populations of marine iguanas, and compare it with the composition of its sister species, the Galápagos land iguana (Conolophus subcristatus). We also conducted behavioural observations in marine iguana territorial males in order to explore the possible function of these substances in the context of male dominance in leks.MethodsFemoral secretions were analysed by gas chromatography coupled to mass spectrometry (GC–MS), and chromatography with a flame ionisation detector (GC-FID) in order to characterise the lipophilic composition. To understand the potential role of femoral secretions in marine iguana intraspecific communication, territorial males were sampled for their femoral glands and monitored to record their head bob rate—a territorial display behaviour in males—as well as the number of females present in their leks.ResultsWe found that the gland secretions were composed of ten saturated and unsaturated carboxylic acids ranging in chain length between C16 and C24, as well as three sterols. Cholesterol was the main compound found. Intriguingly, land iguanas have a higher diversity of lipophilic compounds, with structural group of lipids (i.e. aldehydes) entirely absent in marine iguanas; overall the chemical signals of both species were strongly differentiated. Lipid profiles also differed among populations of marine iguanas from different islands, with some islands demonstrating a high diversity of lipophilic compounds (i.e. full spectra of compounds), and others lacking one or more compounds. Among the compounds most frequently found missing were 11- and 13-eicosenoic acids. Gland secretions of males with a better body condition and with a higher dominance status (i.e. those accompanied by females and with higher head bob display) were proportionately richer in C20-unsaturated fatty acids (11-eicosenoic acid).DiscussionLand and marine iguanas strongly diverged in their chemical composition of the femoral glands likely due to ecological differences between both species. Despite that marine iguana populations varied in their femoral gland composition that was not related to their genetic structure. Our results indicated that 11-eicosenoic acid may play an important role in intraspecific chemical communication in marine iguanas.

Interaction between C18 fatty acids and DOPE PEG2000 in Langmuir monolayers: effect of degree of unsaturation.

In this study, we address the effect of the cis-double bond in 1,2-dioleoyl-sn-glycero-3-phosphoethanolamide-N-[methoxy(polyethylene glycol)-2000, DOPE PEG2000 (DP), on the Langmuir monolayer of C18 fatty acids-namely, stearic acid (SA), oleic acid (L1), linoleic acid (L2), and linolenic acid (L3)-with the same head group but different degrees of saturation on their hydrocarbon chains. Negative values of Gibbs free energy of mixing (ΔG mix) were obtained throughout the investigated ranges of the unsaturated C18 fatty-acid (L1, L2 and L3) mixed systems, indicating that very strong attractions occurred between molecules in the monolayers. The bend and kink effects from the cis-double bond(s) in the hydrocarbon chain affected the membrane fluidity and molecular packing in the monolayers, which resulted in a greater interaction between unsaturated C18 fatty acids and DP. The most thermodynamically stable mole composition of unsaturated C18 fatty acids to DP was observed at 50:1; this ratio is suggested to be the best mole ratio and will be subsequently used to prepare DP-C18 fatty-acid nanoliposomes. The presence of cis-double bonds in both hydrocarbon chains of DOPE in DP also created an imperfection in the membrane structure of lipid-drug delivery systems, which is expected to enhance lipid-based systems for antibody conjugation and drug encapsulation.