Chain Unsaturated Fatty Acids Research Articles

Fatty Acid Profiles of Livers from Two Marine Fishes Inhabiting Sudanese Red Sea Coast

Fish livers a good source of long-chain polyunsaturated fatty acids and omega 3, are usually discarded as a waste when fish are processed for human consumption in Sudan. Highly fresh Triaenodon obesus and Hipposcarus harid fish were purchased from Port Sudan fish central market during December 2014. The fatty acid profiles of the livers of these commercially important fish were determined. The polyunsaturated and saturated fatty acids ratio in the livers oil of T. obesus and H. harid was 1:2.2 and 1:1.38, respectively. The Palmatic (16:0), Pentadecenoic (12:0) and Arachidic acids were the highest in both species. The poly chain unsaturated fatty acids Linolenic (18:3n - 3), Eicosapentaenoic (20:5n - 3) and Docosahexaenoic (22:6n - 3) were detected in the liver of both species. The highest values of above poly chain unsaturated fatty acids were detected in T. obesus.

Extracellular antibacterial substances in Anabaena fertilissima CCC597 kill bacteria by triggering oxidative radicals and destroying membrane integrity

An axenic culture of a cyanobacterium in the spent medium produced hexane-extracta- ble compound(s) that antagonized growth of several Gram+ve and –ve bacteria, including a few potential pathogens. Phylogenetic investigations classified the strain to be Anabaena fertilissima strain CCC597. Using Escherichia coli MTCC443 as a test organism, we have shown that ROS (O 2; H 2O 2) production and outer and inner membrane (OM: IM) permeabilization were induced upon such treatments. Consequently, leakage of proteins and cytosolic acidification processes were initi- ated. Suppression of cytoplasmic membrane-bound respiratory O 2consumption was most likely the physiological aberration that killed the bacteria. Several antioxidant enzymes viz. superoxide dis- mutase, catalase, and peroxidases showed concomitant increase in the enzymatic activities and band intensities in the corresponding substrate gels. Notwithstanding, the counteraction mechanism(s) was not preventive, and sufficient oxidative radicals still generated to manifest lipid peroxidation. Chemical analysis of the hexane-extract of A. fertilissima culture filtrates revealed presence of a number of long chain unsaturated fatty acids, including cis-13,16-docosadienoic acid, with proven antibacterial properties.

The unprecedented membrane deformation of the human nuclear envelope, in a magnetic field, indicates formation of nuclear membrane invaginations

Human nuclear membrane (hNM) invaginations are thought to be crucial in fusion, fission and remodeling of cells and present in many human diseases. There is however little knowledge, if any, about their lipid composition and dynamics. We therefore isolated nuclear envelope lipids from human kidney cells, analyzed their composition and determined the membrane dynamics after resuspension in buffer. The hNM lipid extract was composed of a complex mixture of phospholipids, with high amounts of phosphatidylcholines, phosphatidylinositols (PI) and cholesterol. hNM dynamics was determined by solid-state NMR and revealed that the lamellar gel-to-fluid phase transition occurs below 0 °C, reflecting the presence of elevated amounts of unsaturated fatty acid chains. Fluidity was higher than the plasma membrane, illustrating the dual action of Cholesterol (ordering) and PI lipids (disordering). The most striking result was the large magnetic field-induced membrane deformation allowing to determine the membrane bending elasticity, a property related to hydrodynamics of cells and organelles. Human Nuclear Lipid Membranes were at least two orders of magnitude more elastic than the classical plasma membrane suggesting a physical explanation for the formation of nuclear membrane invaginations.

Micellar Fd3m cubosomes from monoolein – long chain unsaturated fatty acid mixtures: Stability on temperature and pH response

HypothesisControl of the nanostructure of self-assembled systems may be achieved through manipulation of surfactant molecular packing and interfacial curvature. In order to phase engineer the inverse micellar cubosomes in some monoolein-fatty acid systems, lipids with wedge shaped molecular geometry were incorporated to promote the formation of this phase, that is of interest as potential sustained released nanocarriers. ExperimentsLiquid crystalline nanoparticle dispersions of monoolein with some cis unsaturated fatty acids were prepared and their partial temperature-composition phase diagrams and structure were established using high throughput Small Angle X-ray Scattering (SAXS) and cryogenic transmission electron microscopy (cryo-TEM). The pH responsiveness of these systems was evaluated in the presence of phosphate buffered saline (PBS). FindingsThe partial temperature-composition phase diagrams of five nanoparticle formulations containing monoolein and unsaturated fatty acids were established and identified the presence of micellar cubosomes in each of these systems. The results indicate that temperature, fatty acid concentration and structure, as well as pH all directly impact the formation and stability of this phase. Low energy inverse micellar cubic to emulsion phase transformations were identified in the monoolein with oleic acid and vaccenic acid systems at physiological temperatures that may be advantageous for staged therapeutic release strategies in nanomedicine.

Improving the Functional Properties of Buffalo Butter Oil Fractions Obtained by Multi-Step Dry Fractionation

Buffalo Milk fat has excellent properties; its variable physicochemical properties and its lack of functionality restrict its uses in food industry. The Multi-step dry fractionation was applied on buffalo butter oil (BO) for enhancement of the nutritional value and functionality at three different temperatures i.e. 35, 25 and 15 °C, three solids (S35, S25 and S15) and three liquid (L35, L25and L15) fractions was gained. LMF (L15and S15) was significantly higher not only in short chain fatty acids (SCFA) but also in long chain unsaturated fatty acids (LCUSFA), whereas, lower in medium saturated chain fatty acids (MCSFA) than those of BO, HMF(S35) and MMF (L25, S25 and L35) were detected. LMF had positive healthy effect of lower oxidative stability index (OSI) and of the highest nutritional (by ω6: ω3 3PUFA) than other fractions. differential scanning calorimeter (DSC) values for both solid and liquid fractions are significantly (P˂0.05) decreased with decreasing fractionation temperature even in melting or crystallization behaviors. Solid fat content (SFC) was significantly the lowest in LMF at 25OC. The liquid fractions had larger crystals size than those solid fractions and BO. Strong negative correlation between SFC at 20OC and (USFA, SCFA and IV) and strong positive correlation between SFC and (SFA, MCSFA, LCSFA and DSC) were observed. Results will increase the knowledge to improve the processing condition to produce buffalo butter oil fractions with increased functionality and more varieties for more dairy fat products. The chosen dry fractionation temperature resulted in an increase of the functional and nutritional properties of obtained buffalo butter oil fractions.

Total Synthesis of the Endocannabinoid Uptake Inhibitor Guineensine and SAR Studies.

Guineensine ((2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide) is a plant-derived natural product that inhibits reuptake of the endocannabinoid anandamide with sub-micromolar potency. We have established a highly efficient total synthesis of guineensine, which provided the natural product in only five steps from commercially available 3-nonyn-1-ol in 17 % overall yield, relying on the attachment of the benzodioxolyl moiety to the unsaturated fatty acid chain by means of a Suzuki coupling as the key step. Subsequent SAR studies revealed that replacement of the N-isobutyl group in the natural product by various alkyl, arylalkyl, or aryl groups is generally well tolerated, and derivatives could be identified that are slightly more potent anandamide reuptake inhibitors than guineensine itself. In contrast, modifications of the benzodioxolyl moiety led to decreased activity. Intriguingly, a change in the configuration of the C4=C5 double bond from E to Z was found to be very well tolerated, in spite of the associated change in the overall geometry of the molecule.

Investigating the Uptake of Arsenate by Chlamydomonas reinhardtii Cells and its Effect on their Lipid Profile using Single Cell ICP-MS and Easy Ambient Sonic-Spray Ionization-MS.

The complementary use of single cell atomic mass spectrometry (MS) and ambient molecular MS allowed for the in-depth study of arsenate uptake by Chlamydomonas reinhardtii cells and of the effect this toxic metalloid species has on their lipid profile. Compared to conventional inductively coupled plasma mass spectrometry (ICP-MS) analysis, in which case hundreds of thousands of cells are digested and then analyzed, it is demonstrated that single cell (SC) ICP-MS provides uptake data that are potentially of greater biological relevance. This includes the arsenic mass distribution within the cell population, which fits to a log-normal probability function, the most frequently contained arsenic mass within the cells (1.5-1.8 fg As per cell), and the mean arsenic uptake value (ranging from 2.7 to 4.1 fg As per cell for the three arsenate incubation concentrations, that is, 15, 22.5, and 30 μg As per mL) derived from the log-normal arsenic mass distribution within the cell population. The SC approach also allows for differentiating the arsenic present in and/or adsorbed on the cells, from the arsenic present in the extracellular solution, in a single analysis. In a similar fashion, ambient molecular MS in the form of desorption easy ambient sonic spray ionization (EASI) -MS was used to rapidly profile cell membrane lipids from cells spotted directly on a glass slide. EASI-MS analysis revealed that cells grown in the presence of increasing concentrations of arsenate exhibited changes in the degree of saturation of their membrane lipids, as was observed by the increasing intensity ratio of lipids with less unsaturated acyl chains to the same type of lipids with more unsaturated fatty acid chains. Thus, indicating "homeoviscous adaptation" of extraplastidial and thylakoid cell membranes, induced by the presence of arsenate.

Evaluating the effect of roasting on coffee lipids using a hybrid targeted-untargeted NMR approach in combination with MRI

An integrated targeted-untargeted 1H and 13C Nuclear Magnetic Resonance (NMR) analysis was applied to determine the impact of roasting on coffee lipids. For targeted analysis, both an internal standard (IS) method, as well as the ERETIC2 tool based on PULCON (Pulse Length-based Concentration determination), were used for quantitation. PULCON allows for quantitative analysis without sample contamination with an IS and was found to be in very good agreement with the traditional IS approach as indicated by a systematic Bland-Altman comparison study. For the untargeted analysis, NMR was coupled with multivariate statistical analysis (MVSA), namely Principal Component Analysis (PCA), Hierarchical Cluster Analysis (HCA), and Orthogonal Projection to Latent Structures Discriminant Analysis (OPLS-DA). 13C NMR spectra were acquired using a z-stored spin-echo sequence to achieve higher spectral quality, which is important for both targeted and untargeted analysis. Results showed that roasting has a clear effect on coffee lipids, with diterpenes, oxidation/hydrolysis products and unsaturated fatty acid chains being the most significant markers. In addition, the application of MRI indicated important morphological alterations in bean structure and lipid migration from the endosperm to the surface of the coffee bean.

1H and 13C NMR investigation of oils extracted from exotic fruits

Exotic fruit seeds are waste of industrial preparation of foods and human consumption. The contents in terms of nutrients of oils extracted from exotic fruit seeds are not fully understood, and they remain object of study. We propose a practical, inexpensive, qualitative and quantitative approach based on the use of 1H and 13C NMR spectroscopy for the fatty acid chain profiling of these oils. The composition of eleven seed oils was investigated. The amounts of linoleic (from 3.5% in Rambutan to 84.6% in Feijoa), oleic (from 6.9% to 68.7% in Papaya), and saturated fatty acid chains (from 7.9% in Feijoa to 49.5% in Rambutan) were determined. The total contents of unsaturated fatty acid (MUFA and PUFA) chains in oils ranged from 37.5% in Mangosteen to 91.5% in Feijoa. The oils were characterized by saturated/unsaturated (SFA/PUFA) ratios ranging from 0.08 to 1.07, with values which were superior to that commonly reported for extra virgin olive oil. These ratios are potentially favorable for human health. The ANOVA test showed the model to be remarkably significant (p < 0.05). Spectral data agreed those reported in the literature for conventional methods. Although linolenic acid was not detected in all oils, their fatty acid chain profiles make them desirable in terms of nutrition and as alternative energy sources.

Potential of Olive Oil Extract (Olea europaea) For Affecting Lipid Profile, Lipid Oxidative and Fatty Liver on Hiperlipemic Rats (Rattus norvegicus)

Olive oil ( Olea europaea ) contains 55 to 83% oleic acid which is a single chain unsaturated fatty acid or mono-unsaturated fatty acid (MUFA), and 2% phenolic components in the form of hydroxytyrosol and tyrosol. This study aims to determine the potential of olive oil extract ( Olea europaea ) in reducing cholesterol and malondialdehyde levels, along with inhibiting fatty liver development in hiperlipemic rats. Sixteen rats were divided into four groups, the first group was healthy control group, the second group was positive control group, received a high-fat diet containing 100 mg of cholesterol powder, 25 mg of cholic acid powder and 1 mL of quail egg yolk for 28 days. Third and fourth treatment groups were received for 28 days, plus 0.828 g (1 mL) and 1.656 g (2 mL) of olive oil extract daily for 14 days, respectively. The measurement of total cholesterol used cholesterol test strips based on oxidation enzyme reaction cholesterol esterase and cholesterol oxidase that produce hydrogen peroxidation, then analyzed with biosensor refractophotometry. Measurement of malondialdehyde used thiobarbituric acid (TBA) test. Histological observation of fatty liver was assessed using a NAS (Non-alcoholic fatty liver disease score). The results showed that 1.656 g (2 mL) of olive oil extract per day decreased total cholesterol level up to 44.41 %, malondialdehyde level up to 61.75%, and NAS score up to 50%, compared with positive control. It was concluded that olive oil extract was decreasing total cholesterol level, as an anti-oxidant and prevent fatty liver development. Keywords: fatty liver, hyperlipidemia, malondialdehyde, Olea europaea .

Novel carboxylate-based glycolipids: TLR4 antagonism, MD-2 binding and self-assembly properties

New monosaccharide-based lipid A analogues were rationally designed through MD-2 docking studies. A panel of compounds with two carboxylate groups as phosphates bioisosteres, was synthesized with the same glucosamine-bis-succinyl core linked to different unsaturated and saturated fatty acid chains. The binding of the synthetic compounds to purified, functional recombinant human MD-2 was studied by four independent methods. All compounds bound to MD-2 with similar affinities and inhibited in a concentration-dependent manner the LPS-stimulated TLR4 signaling in human and murine cells, while being inactive as TLR4 agonists when provided alone. A compound of the panel was tested in vivo and was not able to inhibit the production of proinflammatory cytokines in animals. This lack of activity is probably due to strong binding to serum albumin, as suggested by cell experiments in the presence of the serum. The interesting self-assembly property in solution of this type of compounds was investigated by computational methods and microscopy, and formation of large vesicles was observed by cryo-TEM microscopy.

Production of Fatty Acids during Alcoholic Wine Fermentation under Selected Temperature and Aeration Conditions

The synthesis of medium chain saturated fatty acids (MCFA, toxic to yeast cells) and long chain unsaturated fatty acids (LCUFA, required for yeast survival) during alcoholic wine fermentation was examined. The contents of MCFA and LCUFA during laboratory scale alcoholic fermentation of Carmenere using Saccharomyces cerevisiae yeast were tracked in 19 fermentations under selected temperature and aeration conditions. Fermentations were sampled daily and analyzed for fatty acids using a gas chromatograph with flame detector. Fatty acid synthesis was greatest under normal fermentation conditions (28°C, pH 3.5, aeration at the beginning of fermentation), and both MCFA and LCUFA were reduced at 24 and 32°C. Although fatty acid concentrations increased at the same fermentation stage, they never exceeded the production levels observed under normal fermentation. The MCFA/LCUFA ratio at 32°C was between 3.55 and 4.43, due to significantly increased MCFA production at this temperature; we recommend keeping fermentations below 28°C. Under anaerobic conditions, the MCFA/LCUFA ratio was very high compared to the other aeration strategies, showing that oxygen improves fermentation performance by limiting MCFA synthesis, which can cause stuck and sluggish fermentations. Aeration at the beginning and at the end of the exponential phase maintained the MCFA/LCUFA ratio below 1.0, indicating a greater production of LCUFA when oxygen is used during the fermentation.

Evaluation of the oxidation stability of jatropha biodiesel/diesel blends

One of the major technical issues facing biodiesel is its susceptibility to oxidation which is due to its content of unsaturated fatty acid chains, especially those with bis–allylic methylene moieties. In addition to the presence of air, various other factors influence the oxidation process of biodiesel including presence of light, elevated temperature, as well as extraneous materials such as metals which may be even present in the container material. The overall goal of this work is to evaluate the oxidation stability of Jatropha biodiesel/diesel blends. To achieve this goal, an acid–catalyzed pretreatment followed by a standard transesterification procedure with methanol and potassium methoxide catalyst was untaken to produce Jatropha methyl ester (JME) from Jatropha curcas L. oil (JO) with high acid value of 16.25 mg KOH/g. Analysis of the physicochemical properties has shown JME demonstrated potential as a good candidate for feedstock in biodiesel production because the studied physicochemical properties of JME adequately satisfied the relevant standards for biodiesel quality, with the exception of the kinematic viscosity at 40oC. Also, gas chromatography–mass spectrometry (GC–MS) analytical result showed that fatty acid composition of JO was quite similar to that of conventional oils. Especially, the evaluation of oxidation stability of Jatropha biodiesel/diesel blends was accomplished with respect to the change in the quality after oxidation by bubbling oxygen at elevated temperature as well as oxidation of blend fuels in contact with copper plate. The results demonstrated a strong correlation between biodiesel concentration and blend stability; i.e., the increase in biodiesel concentration results in the lower stability in both cases of the copper strip corrosion test and the accelerated oxidation.

The cytochrome P450BM-1 of Bacillus megaterium A14K is induced by 2,3,7,8-Tetrachlorinated dibenzo-p-dioxin: Biophysical, molecular and biochemical determinants

The current study describes biological changes in Bacillus megaterium A14K cells growing in the presence of 2,3,7,8-Tetrachlorinated dibenzo-p-dioxin (TCDD), the most potent congener of dioxins. The results indicate that the metabolizing of 2,3,7,8-TCDD by BmA14K was accompanied with a novel morphological and biophysical profile typified by the growth of single cells with high levels of biosurfactant production, surface hydrophobicity and cell membrane permeability. Moreover, the TCDD-grown bacteria exhibited a specific fatty acid profile characterized by low ratios of branched/straight chain fatty acids (BCFAs/SCFAs) and saturated/unsaturated fatty acids (SFAs/USFAs) with a specific “signature” due to the presence of branched chain unsaturated fatty acids (BCUFAs). This was synchronized with a significant induction of P450BM-1, an unsaturated fatty acid-metabolizing enzyme in B. megaterium. Subsequently, the profile of oxygenated fatty acids in the TCDD-grown bacteria was typified by the presence of 5,6-epoxy derived from unsaturated C15, C16 and C17 fatty acids, that were absent in control bacteria. A net increase was also detected in both hydroxylated and epoxidized fatty acids, especially those derived from C15:0 and C16:1, respectively, suggesting a specific TCDD-induced “signature” of oxygenated fatty acids in BmA14K. Overall, this study sheds light on the use of B. megaterium A14K as a promising bioindicator/biodegrader of dioxins.

Isochrysis affinis galbana ve Phaeodactylum tricornutum Kültürlerinde Kuru Madde Tahminlerinin Karşılaştırılması

Isochrysis affinis galbana tek hücreli denizel bir mikroalg türü olup yüksek miktarda uzun zincirli doymamış yağ asitleri (PUFA) içermesinden dolayı akuakültürde özellikle bivalvia larvalarının beslenmesinde canlı yem kaynağı olarak kullanılmaktadır. Phaeodactylum tricornutum ise oval ve fusiform hücre şekilleri olan tek hücreli pennat bir diyatom türüdür. Phaeodactylum tricornutum %30-45 arasında uzun zincirli doymamış yağ asitlerini (PUFA) içermekte ve bu oranın da %20-40‘ını eikosapentaenoik asit (EPA) oluşturmaktadır. Esansiyel yağ asitlerinden eikosapentaenoik asit'in önemli potansiyel kaynağı olarak düşünülen mikroalgler insan gıdası olarak ve akuakültürde hayvan beslenmesinde kullanılmaktadır. Çalışmada, Isochrysis affinis galbana ve Phaeodactylum tricornutum kültürlerine ait kuru madde miktarlarının çoklu regresyon analizi yöntemi kullanılarak tahmin edilmesi amaçlanmıştır. Türler, F/2 besi ortamında %20 aşılama oranı ile kontrol grubu ve %50 oranında azotun eksiltildiği besi ortamı kullanılarak, laboratuvar ortamında kültüre alınmıştır. Deneme süresince optik yoğunluk, kuru madde ve klorofil a günlük olarak ölçülmüştür. Türlere ait kontrol grubu ve %50 oranında azotun eksiltildiği gruplarda optik yoğunluk ve klorofil a kullanılarak matematiksel bir model oluşturulmuştur. Bu modellerin önem testleri yapılıp, R2 ve HKO bulunmuştur.

Medium chain unsaturated fatty acid ethyl esters inhibit persister formation of Escherichia coli via antitoxin HipB.

Persisters represent a small bacterial population that is dormant and that survives under antibiotic treatment without experiencing genetic adaptation. Persisters are also considered one of the major reasons for recalcitrant chronic bacterial infections. Although several mechanisms of persister formation have been proposed, it is not clear how cells enter the dormant state in the presence of antibiotics or how persister cell formation can be effectively controlled. A fatty acid compound, cis-2-decenoic acid, was reported to decrease persister formation as well as revert the dormant cells to a metabolically active state. We reasoned that some fatty acid compounds may be effective in controlling bacterial persistence because they are known to benefit host immune systems. This study investigated persister cell formation by pathogens that were exposed to nine fatty acid compounds during antibiotic treatment. We found that three medium chain unsaturated fatty acid ethyl esters (ethyl trans-2-decenoate, ethyl trans-2-octenoate, and ethyl cis-4-decenoate) decreased the level of Escherichia coli persister formation up to 110-fold when cells were exposed to ciprofloxacin or ampicillin antibiotics. RNA sequencing analysis and gene deletion persister studies elucidated that these fatty acids inhibit bacterial persistence by regulating antitoxin HipB. A similar persister cell reduction was observed for pathogenic E. coli EDL933, Pseudomonas aeruginosa PAO1, and Serratia marcescens ICU2-4 strains. This study demonstrates that fatty acid ethyl esters can be used to disrupt bacterial dormancy to combat persistent infectious diseases.

Effect of gender on breast and thigh turkey meat quality

ABSTRACT1. The influence of gender on chemical composition, physicochemical parameters, fatty acid profile, amino acid and mineral composition of turkey breast and thigh meat was studied in order to assess nutrient requirements.2. Chemical composition showed that only intramuscular fat in breast meat was significantly affected by gender (p < 0.05). The results showed a higher percentage of intramuscular fat in male samples, almost double the amount found in females (0.73% vs. 0.38%).3.For meat colour parameters, only a* showed different results between sexes, with male samples (breast: p < 0.01; thigh: p < 0.001) having the highest values.4. Fatty acid profiles showed that medium chain unsaturated fatty acids were the most abundant. The significant differences (p < 0.05) found in both breast and thigh muscle could be linked to a difference in metabolism between males and females.5.There were higher levels of C16:1n-7 in females (breast: p < 0.001; thigh: p < 0.01) compared with male muscle sample (5.05 vs. 2.67 g/100 g in breast and 4.95 vs. 3.27 g/100 g in thigh). Nutritional indices (n-6/n-3 and thrombogenic index) were more favourable in female samples demonstrating that female turkeys had better fatty acid profile than the others.6. Turkey meat is an important source of dietary amino acids, and female samples had the highest contents both of essential and non-essential amino acids. Furthermore, gender had a numeric effect (p > 0.05) on amino acid composition.7. Mineral composition showed that Na, Zn and Fe were the minerals most affected by turkey gender.

Mutation in MON2, Which Encodes a Protein Implicated in Vesicular Transport, Affects Response to Exogenous Fatty Acids in Yeast

Metabolism of exogenous fatty acids requires cells to take up, traffic, and molecularly respond to fed fatty acids. Our lab has determined that a mutation in mon2 results in defective growth on the fatty acid 10‐undecenoic acid. Like wild type cells, mon2Δ mutants are capable of normal response to the feeding of long chain unsaturated fatty acids (UFAs) by reducing transcription of OLE1, (which encodes the Δ9 desaturase), and by reducing the accumulation of endogenously produced UFAs. However, wild type cells when fed 10‐undecenoic acid will continue to express OLE1 and increase their content of endogenously produced UFAs. In contrast, mon2Δ mutants do not differentially respond to the two fatty acids. Staining with a BODIPY‐labeled fluorescent fatty acid analog indicates that there is a difference in localization/amount of the supplied fatty acid in mon2Δ cells compared to wild type cells. Thus, it appears that the mon2 mutation decreases the cell's ability to differentiate between fatty acids, perhaps due to mislocalization of the fed fatty acid or regulatory proteins.Support or Funding InformationThis work was supported by a Jacob Nyenhuis Faculty Award (VM), NSF‐REU (AG, MS, BG) and a Summer Scholar award from the Dean for Natural and Applied Science (RD).This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal.

Discovery of Hydrolysis-Resistant Isoindoline N-Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration.

N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.

Characterization of triacylglycerols in unfermented cocoa beans by HPLC-ESI mass spectrometry

The nutritional value of cocoa butter is mainly determined by the composition of triacylglycerols (TAGs). In this paper we have developed a non-aqueous reversed-phase liquid chromatographic method, using ethanol as the mobile phase, coupled to electrospray ionization (ESI) tandem mass spectrometry to identify TAGs in raw cocoa beans from six different origins. Tandem mass spectrometry was adopted to facilitate the identification of TAGs using unique diacylglycerol product ions and neutral losses. Additionally, two-dimensional m/z retention time maps aided the identification of entire homologous series of TAGs. A total of 83 different TAGs were identified in unfermented cocoa beans, 58 of which were not previously reported in cocoa. Thirty-one of these compounds represent a new class of TAGs characterized by the presence of one to three hydroxyl groups on the unsaturated fatty acid chain. To date, this represents the largest number of TAGs identified in cocoa.