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Physiology and Molecular Biology of... May 2022Parinaric and α-eleostearic acids are unusual conjugated fatty acids. Unusual fatty acids, in general, are known to have roles in defense response; however, the role of...
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Parinaric and α-eleostearic acids are unusual conjugated fatty acids. Unusual fatty acids, in general, are known to have roles in defense response; however, the role of parinaric acid in is not known, nor is it known whether it occurs in different species of or its closest monotypic relative, (L.) Wight & Arn. The aim of the study was to (a) characterize the fatty acid composition of 21 species of and and (b) determine whether parinaric and α-eleostearic acids are present in these taxa and, if so, (c) whether there is interspecific and intraspecific variation in parinaric acid content. Fatty acid profiling was done using gas chromatography and mass spectrometry (GC-MS). To uncover taxonomic patterns of variation in fatty acids, principal component analysis and hierarchical cluster analysis were performed. The major fatty acids in were found to be palmitic (5.57-20.85%), stearic (2.86-21.61%), oleic (2.79-28.99%), linoleic (C18:2Δ, 2.04-26.64%), α-linolenic (C18:3∆; 11.07-53.99%), and four forms of parinaric acid (5.93-70.21%). Genus contains two unusual conjugated fatty acids- parinaric and α-eleostearic, however these are absent in closely related This study reports the presence of four different forms of parinaric acid in for the first time. Some species (, and ) were found to contain very high levels (> 50%) of parinaric acid and they might be useful for various biomedical and industrial applications. Apparently, the presence of parinaric acid is a characteristic of Significant variations were found in the amount and forms of parinaric acid. We propose the potential application of parinaric acid and α-eleostearic acid as chemotaxonomic markers for
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The online version contains supplementary material available at 10.1007/s12298-022-01194-4.
PubMed: 35722517
DOI: 10.1007/s12298-022-01194-4 -
The FEBS Journal Feb 2015We report the transmembrane voltage-induced lateral reorganization of highly-ordered lipid microdomains in the plasma membrane of living Saccharomyces cerevisiae. Using...
We report the transmembrane voltage-induced lateral reorganization of highly-ordered lipid microdomains in the plasma membrane of living Saccharomyces cerevisiae. Using trans-parinaric acid (all-trans-9,11,13,15-octadecatetraenoic acid) as a probe of lipid order and different methods of membrane depolarization, we found that depolarization always invokes a significant reduction in the amount of gel-like microdomains in the membrane. Different depolarization mechanisms, including the application of ionophores, cell depolarization by an external electric field, depolarization by proton/hexose co-transport facilitated by HUP1 protein and a reduction of membrane potential caused by compromised respiration efficiency, yielded the same results independently of the yeast strain used. The data suggest that the voltage-induced reorganization of lateral membrane structure could play significant role in fast cellular response to acute stress conditions, as well as in other membrane microdomain-related regulatory mechanisms.
Topics: Cell Membrane; Membrane Microdomains; Membrane Potentials; Saccharomyces cerevisiae; Saccharomyces cerevisiae Proteins
PubMed: 25410771
DOI: 10.1111/febs.13156 -
Turkish Journal of Chemistry 2022In the present work, triacylglycerol and fatty acid compositions of . and . seed oils were determined using reverse phase high performance liquid chromatography with...
In the present work, triacylglycerol and fatty acid compositions of . and . seed oils were determined using reverse phase high performance liquid chromatography with both refractive index and spectrophotometric detections. The presence of conjugated octadecatetraenoic moieties was confirmed by UV and IR spectroscopy. Triacylglycerol (TAG) compositions were performed using an incremental approach and confirmed by the results of MS and electronic spectra. The quantitative analysis of TAG was achieved by careful calibration, introducing correction factors for the sensitivity of each compound. The results showed that both seed oils contain the same 23 TAGs. The mole fraction of 15 TAGs containing conjugated moieties was more significant than 88% (for .) and 81% (for .). Seed oils of and contain 43.44% and 36.12% mole of conjugated octadecatetraenoic fatty acids, respectively. These conjugated fatty acids were determined to be α-parinaric (C18:4) and β-parinaric (C18:4), in which isomer β-parinaric represents 23.21% and 26.27% of conjugated octadecatetraenoic acids for and seed oils, respectively. In addition, the mole fraction of -linolenic acid in both seed oils was also abundant at 24.5% and 28.2% for and . Therefore, .and seed oils are potential sources of polyunsaturated fatty acids, especially conjugated octadecatetraenoic acids.
PubMed: 37538780
DOI: 10.55730/1300-0527.3440 -
Journal of Oleo Science 2024Conjugated fatty acids have anticancer effects. Therefore, the establishment of a synthetic method for conjugated fatty acids is important for overcoming cancer. Here,...
Conjugated fatty acids have anticancer effects. Therefore, the establishment of a synthetic method for conjugated fatty acids is important for overcoming cancer. Here, we attempted to synthesize conjugated fatty acids using enzymes extracted from seaweeds containing these fatty acids. Lipids from 12 species of seaweeds from the seas around Japan were analyzed, and Padina arborescens Holmes was found to contain conjugated fatty acids. Then, we synthesized parinaric acid, a conjugated tetraenoic acid, from α-linolenic acid using the enzyme of P. arborescens. This method is expected to have a variety of potential applications for overcoming cancer.
Topics: alpha-Linolenic Acid; Seaweed; Fatty Acids, Unsaturated; Antineoplastic Agents
PubMed: 38692896
DOI: 10.5650/jos.ess23209 -
Biophysical Journal Apr 2022Lactosylceramide (LacCer) in the plasma membranes of immune cells is an important lipid for signaling in innate immunity through the formation of LacCer-rich domains...
Lactosylceramide (LacCer) in the plasma membranes of immune cells is an important lipid for signaling in innate immunity through the formation of LacCer-rich domains together with cholesterol (Cho). However, the properties of the LacCer domains formed in multicomponent membranes remain unclear. In this study, we examined the properties of the LacCer domains formed in Cho-containing 1-palmitoyl-2-oleoyl phosphatidylcholine (POPC) membranes by deuterium solid-state NMR and fluorescence lifetimes. The potent affinity of LacCer-LacCer (homophilic interaction) is known to induce a thermally stable gel phase in the unitary LacCer bilayer. In LacCer/Cho binary membranes, Cho gradually destabilized the LacCer gel phase to form the liquid-ordered phase by its potent order effect. In the LacCer/POPC binary systems without Cho, the H NMR spectra of 10',10'-d-LacCer and 18',18',18'-d-LacCer probes revealed that LacCer was poorly miscible with POPC in the membranes and formed stable gel phases without being distributed in the liquid crystalline domain. The lamellar structure of the LacCer/POPC membrane was gradually disrupted at around 60°C, whereas the addition of Cho increased the thermal stability of the lamellarity. Furthermore, the area of the LacCer gel phase and its chain order were decreased in the LacCer/POPC/Cho ternary membranes, whereas the liquid-ordered domain, which was observed in the LacCer/Cho binary membrane, was not observed. Cho surrounding the LacCer gel domain liberated LacCer and facilitated forming the submicron to nano-scale small domains in the liquid crystalline domain of the LacCer/POPC/Cho membranes, as revealed by the fluorescence lifetimes of trans-parinaric acid and trans-parinaric acid-LacCer. Our findings on the membrane properties of the LacCer domains, particularly in the presence of Cho, would help elucidate the properties of the LacCer domains in biological membranes.
Topics: Antigens, CD; Cholesterol; Lactosylceramides; Lipid Bilayers; Phosphatidylcholines; Phospholipids
PubMed: 35218738
DOI: 10.1016/j.bpj.2022.02.037 -
PloS One 2013Rice white tip nematode, Aphelenchoides besseyi, is a kind of plant parasitic nematodes that cause serious losses in rice and many other crops. Fatty acid and retinoid...
Rice white tip nematode, Aphelenchoides besseyi, is a kind of plant parasitic nematodes that cause serious losses in rice and many other crops. Fatty acid and retinoid binding protein (FAR) is a specific protein in nematodes and is related to development, reproduction, infection to the host, and disruption of plant defense reactions, so the inhibition of FAR function is the potential approach to control A. besseyi. The full-length of Ab-far-1 cDNA is 805 bp, including 546 bp of ORF that encodes 181 amino acids. Software analysis revealed that the Ab-FAR-1 was rich in α-helix structure, contained a predicted consensus casein kinase II phosphorylation site and a hydrophobic secretory signal peptide, but did not have glycosylation sites. The Ab-FAR-1 had 52% homology to Gp-FAR-1 protein. The Ab-FAR-1 and Gp-FAR-1 were grouped in the same branch according to the phylogenetic tree. Fluorescence-based ligand binding analysis confirmed that the recombinant Ab-FAR-1 (rAb-FAR-1) bound with the fluorescent analogues 11-((5-dimethylaminonaphthalene-1-sulfonyl) amino) undecannoic acid (DAUDA), cis-parinaric acid and retinol, but the oleic acid would compete with the binding site. Quantitative PCR (qPCR) was used to assess the expression level of Ab-far-1 at different development stages of A. besseyi, the highest expression was found in the females, followed by eggs, juveniles and males. Using in situ hybridization technique, Ab-far-1 mRNA was present in the hypodermis of juveniles and adults, the ovaries of females and the testes of males. When A. besseyi was treated with Ab-far-1 dsRNA for 48 h, the silencing efficiency of Ab-far-1 was the best and the number of nematodes on the carrot was the least. Thus FAR plays important roles in the development and reproduction of nematodes. This study is useful and helpful to figure out a new way to control the plant parasitic nematodes.
Topics: Animals; Binding, Competitive; Cloning, Molecular; Dansyl Compounds; Fatty Acid-Binding Proteins; Fatty Acids; Fatty Acids, Unsaturated; Female; Fluorescent Dyes; Gene Knockdown Techniques; Helminth Proteins; Male; Oleic Acid; Organ Specificity; Oryza; Ovum; Phylogeny; Plant Diseases; Protein Binding; RNA Interference; Retinol-Binding Proteins; Sequence Analysis, Protein; Tylenchida; Vitamin A
PubMed: 23755297
DOI: 10.1371/journal.pone.0066011 -
PLoS Neglected Tropical Diseases Oct 2018Parasitic nematodes produce an unusual class of fatty acid and retinol (FAR)-binding proteins that may scavenge host fatty acids and retinoids. Two FARs from Brugia...
Parasitic nematodes produce an unusual class of fatty acid and retinol (FAR)-binding proteins that may scavenge host fatty acids and retinoids. Two FARs from Brugia malayi (Bm-FAR-1 and Bm-FAR-2) were expressed as recombinant proteins, and their ligand binding, structural characteristics, and immunogenicities examined. Circular dichroism showed that rBm-FAR-1 and rBm-FAR-2 are similarly rich in α-helix structure. Unexpectedly, however, their lipid binding activities were found to be readily differentiated. Both FARs bound retinol and cis-parinaric acid similarly, but, while rBm-FAR-1 induced a dramatic increase in fluorescence emission and blue shift in peak emission by the fluorophore-tagged fatty acid (dansyl-undecanoic acid), rBm-FAR-2 did not. Recombinant forms of the related proteins from Onchocerca volvulus, rOv-FAR-1 and rOv-FAR-2, were found to be similarly distinguishable. This is the first FAR-2 protein from parasitic nematodes that is being characterized. The relative protein abundance of Bm-FAR-1 was higher than Bm-FAR-2 in the lysates of different developmental stages of B. malayi. Both FAR proteins were targets of strong IgG1, IgG3 and IgE antibody in infected individuals and individuals who were classified as endemic normal or putatively immune. In a B. malayi infection model in gerbils, immunization with rBm-FAR-1 and rBm-FAR-2 formulated in a water-in-oil-emulsion (®Montanide-720) or alum elicited high titers of antigen-specific IgG, but only gerbils immunized with rBm-FAR-1 formulated with the former produced a statistically significant reduction in adult worms (68%) following challenge with B. malayi infective larvae. These results suggest that FAR proteins may play important roles in the survival of filarial nematodes in the host, and represent potential candidates for vaccine development against lymphatic filariasis and related filarial infections.
Topics: Adjuvants, Immunologic; Animals; Antibodies, Helminth; Antigens, Helminth; Brugia malayi; Circular Dichroism; Disease Models, Animal; Fatty Acid-Binding Proteins; Female; Filariasis; Gerbillinae; Humans; Immunoglobulin E; Immunoglobulin G; Male; Parasite Load; Protein Binding; Protein Structure, Secondary; Retinol-Binding Proteins; Treatment Outcome; Vaccines, Synthetic; Vitamin A
PubMed: 30296268
DOI: 10.1371/journal.pntd.0006772 -
Biochimica Et Biophysica Acta Dec 1997cis-Parinaric acid (PnAc), a fluorescent, polyunsaturated fatty acid, was used to measure lipid peroxidation during simulated ischemia and reperfusion in cultured...
cis-Parinaric acid (PnAc), a fluorescent, polyunsaturated fatty acid, was used to measure lipid peroxidation during simulated ischemia and reperfusion in cultured neonatal rat cardiomyocytes. PnAc was used both as free fatty acid, inserted in the membranes following cultivation of the cells, as well as constituent of the cellular complex lipids by metabolically integrating the fatty acid during growth. In the insertion experiments a pre-incubation with DL-aminocarnitine, an inhibitor of beta-oxidation, was necessary to prevent loss of fluorescent signal. Such a pre-incubation resulted in an enrichment of PnAc in the sarcolemma: In pre-treated cells 57 +/- 1.3% of total inserted PnAc is present in the sarcolemma compared to 27 +/- 5.7% in cells containing the integrated probe. Both methods to introduce PnAc into the cells were compared with respect to their sensitivity for an externally applied oxidative stress and thereafter lipid peroxidation during simulated ischemia and reperfusion was assayed. Going from normoxic to ischemic conditions lipid peroxidation did not increase and remained at a low level. When the ischemic cells were subsequently subjected to reperfusion (reintroduction of both oxygen and glucose), large scale lipid peroxidation was obvious. When, on the other hand, oxygen alone was reintroduced (reoxygenation) no increased lipid peroxidation was observed. These observations led to the conclusion that ischemia does not lead to an enhanced lipid peroxidation and that resumption of metabolic activity during reperfusion is necessary to induce lipid peroxidation.
Topics: Animals; Cells, Cultured; Fatty Acids, Unsaturated; Fluorescent Dyes; Lipid Peroxidation; Myocardial Ischemia; Myocardial Reperfusion; Myocardium; Oxygen; Rats
PubMed: 9408165
DOI: 10.1016/s0005-2736(97)00144-2 -
FEBS Letters Jun 2002Binding of the polyunsaturated cis-parinaric acid to bovine beta-lactoglobulin (BLG) was studied by circular dichroism (CD), electronic absorption spectroscopy and mass...
Binding of the polyunsaturated cis-parinaric acid to bovine beta-lactoglobulin (BLG) was studied by circular dichroism (CD), electronic absorption spectroscopy and mass spectrometry methods. Upon protein binding, the UV absorption band of parinaric acid is red shifted by ca. 5 nm, showing hypochromism and reduced vibrational fine structure, suggesting that the ligand binds as a monomer in non-planar geometry. In the CD spectra measured at pH 7.36 and 8.5 a strong, negative Cotton band appears centered at 310 nm (Delta epsilon = -25 M(-1) cm(-1)) corresponding to the long-wavelength absorption band of cis-parinaric acid. The source of this induced optical activity is the helical distortion of the polyene chromophore caused by the chiral protein environment. From CD spectral data the value of the association constant was calculated to be 4.7 x 10(5) M(-1) at pH 7.36. CD and mass spectrometry measurements showed that parinaric acid binds weakly to BLG in acidic solution, though small peaks at mass 18,559 and 18,645 can be obtained in the reconstructed electrospray mass spectrum; these correspond to the binding of parinaric acid in 1:1 stoichiometry to both monomer variants of BLG B and A. The hydrophobic interior cavity of BLG was assigned as the primary binding site of cis-parinaric acid.
Topics: Animals; Cattle; Circular Dichroism; Fatty Acids, Unsaturated; Lactoglobulins; Mass Spectrometry; Models, Molecular; Protein Binding; Spectrophotometry, Ultraviolet
PubMed: 12044875
DOI: 10.1016/s0014-5793(02)02771-0 -
The Journal of Biological Chemistry Sep 1991Binding and proximity relationships of fatty acids with recombinant rat liver fatty acid-binding protein (L-FABP) and intestinal fatty acid-binding protein (I-FABP) were...
Binding and proximity relationships of fatty acids with recombinant rat liver fatty acid-binding protein (L-FABP) and intestinal fatty acid-binding protein (I-FABP) were studied with absorption and fluorescence spectroscopy. Protein aromatic amino acids were examined in the absence and presence of bound fatty acid. Second derivative absorbance spectroscopy of the apo- and holoproteins suggested that fatty acid binding altered the conformation of L-FABP, but not of I-FABP. Fatty acid binding also blocked the accessibility of L-FABP tyrosine and I-FABP tryptophan to Stern-Volmer quenching by acrylamide, indicating that these amino acids were present in the fatty acid-binding pocket. Forster energy transfer from I-FABP tryptophan to bound cis-parinaric acid resulted in quenching of tryptophan lifetime and appearance of sensitized lifetime of bound cis-parinaric acid. The calculated donor-acceptor distances were 16.9 +/- 0.6 and 19.2 +/- 0.3 A for I-FABP and L-FABP, respectively. Absorbance spectral shifts and ratios of fluorescence excitation maxima indicated that the parinaric acid microenvironment in the fatty acid-binding site of I-FABP was much less polar than that of L-FABP. Parinaric acids displayed similar rotational correlation time and limiting anisotropy when bound to I-FABP and to L-FABP. These results are consistent with a close proximity of bound fatty acids to the tyrosine and tryptophan residues and with immobilization of the polyene fatty acids in the fatty acid-binding site(s) of L-FABP and I-FABP. The two proteins differ in that only L-FABP has two fatty acid-binding sites and appears to undergo significant conformational change upon fatty acid binding.
Topics: Acrylamides; Animals; Binding Sites; Carrier Proteins; Fatty Acid-Binding Protein 7; Fatty Acid-Binding Proteins; Fatty Acids; Fatty Acids, Unsaturated; Fluorescent Dyes; Intestinal Mucosa; Liver; Neoplasm Proteins; Nerve Tissue Proteins; Protein Conformation; Rats; Recombinant Proteins; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Tryptophan
PubMed: 1894608
DOI: No ID Found