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Distribution of omega-3 and omega-6 fatty acids in the ether- and ester-linked phosphoglycerides from tissues of the rainbow trout, Salmo gairdneri.

1. Data presented here demonstrate that polyunsaturated fatty acids in the phospholipids of rainbow trout tissues are compartmentalized differently than in mammalian tissues. 2. We have determined the distribution of omega-3 (n-3) and omega-6 (n-6) fatty acids in the alkyl-, alk-1-enyl-, and diacyl- subclasses of phosphatidylcholines (PC), phosphatidyl-ethanolamines (PE), phosphatidylinositols (PI), and phosphatidylserines (PS) from gill, kidney and spleen of rainbow trout. 3. Alkyl-linked PC and alk-1-enyl-linked PE were the most abundant ether-containing phospholipids, amounting to 10-15% of each class; no ether-linked PI or PS was detected. 4. C20:4 n-6 was found in high concentrations only in PI; the n-3 fatty acids were found in highest concentration in the ether-linked phospholipids as compared with the diacyl subclasses and C20:5 n-3 was especially prevalent in 1-O-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamine and C22:6 n-3 was prevalent in PS.

Animals↗

The heptadecanoic fatty aldehyde--one of the main aldehydes of the far-eastern Bryozoa.

1. The relative content of 16:0, 17:0 and 18:0 fatty aldehydes in the lipids of eight species of the far-eastern Bryozoa was studied. 2. Heptadecanoic aldehyde is one of the main aldehydes in the seven species investigated comprising about 30% of the sum of these main bryozoan aldehydes. 3. We suggest the unusually high relative heptadecanoic aldehyde content in the lipids of Bryozoa may be helpful in settling some problems concerning their system.

Aldehydes↗

Peroxisome biogenesis disorders.

Defects in PEX genes impair peroxisome assembly and multiple metabolic pathways confined to this organelle, thus providing the biochemical and molecular bases of the peroxisome biogenesis disorders (PBD). PBD are divided into two types--Zellweger syndrome spectrum (ZSS) and rhizomelic chondrodysplasia punctata (RCDP). Biochemical studies performed in blood and urine are used to screen for the PBD. DNA testing is possible for all of the disorders, but is more challenging for the ZSS since 12 PEX genes are known to be associated with this spectrum of PBD. In contrast, PBD-RCDP is associated with defects in the PEX7 gene alone. Studies of the cellular and molecular defects in PBD patients have contributed significantly to our understanding of the role of each PEX gene in peroxisome assembly.

Amino Acid Sequence↗

Omega-3 fatty acids and antioxidants in neurological and psychiatric diseases: an overview.

RATIONALE: Omega-3 fatty acids are known to play a role in nervous system activity, cognitive development, memory-related learning, neuroplasticity of nerve membranes, synaptogenesis and synaptic transmission. The brain is considered abnormally sensitive to oxidative damage, and aging is considered one of the most significant risk factors for degenerative neurological disorders. Recently, clinical trials of several neurodegenerative diseases have increasingly targeted the evaluation of the effectiveness of various antioxidants. OBJECTIVES: The effects of omega-3 fatty acids and antioxidants on the anatomic and functional central nervous system development and their possible therapeutical use in some neurological and psychiatric pathologies are evaluated. RESULTS: A number of critical trials have confirmed the benefits of dietary supplementation with omega-3 fatty acids not only in several psychiatric conditions, but also in inflammatory and autoimmune and neurodegenerative diseases. Many evidences indicate that antioxidants are also essential in maintaining a correct neurophysiology. CONCLUSIONS: Omega-3 fatty acids could be useful in the prevention of different pathologies, such as cardiovascular, psychiatric, neurological, dermatological and rheumatological disorders. A number of studies suggest that antioxidants can prevent the oxidation of various macromolecules such as DNA, proteins, and lipids. The ideal use of antioxidants should be a prophylactic and continue treatment before aging.

Alzheimer Disease↗

Acid-catalyzed plasmenylcholine hydrolysis and its effect on bilayer permeability: a quantitative study.

This laboratory has previously shown (Anderson, V.C. and Thompson, D.H. (1992) Biochim. Biophys. Acta 1109, 33-42; Thompson, D.H., Gerasimov, O.V., Wheeler, J.J., Rui, Y. and Anderson, V.C. (1996) Biochim. Biophys. Acta 1279, 25-34), that plasmenylcholine (1-alk-1'-enyl-2-palmitoyl-sn-glycero-3-phosphocholine; PlsPamCho) liposomes release hydrophilic contents upon photooxidation or acid-catalyzed hydrolysis. We now report the kinetics and chemical mechanism of the acid-catalyzed reaction and its effect on calcein leakage rates. Hydrolysis of the plasmenylcholine vinyl ether linkage generates fatty aldehydes and 1-hydroxy-2-palmitoyl-sn-glycero-3-phosphocholine (lysolipid); HPLC and 1H-NMR experiments establish that the former is readily air-oxidized to fatty acids, while the latter undergoes rapid acid-catalyzed rearrangement to 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine. Lysolipid formation obeys first order kinetics, yielding observed pseudo-first order rate constants that are pH-dependent. Bimolecular hydrolysis rate constants, k(bi), have also been determined. Calcein release rates from plasmenylcholine liposomes are strongly dependent on both the dihydrocholesterol (DHC) content and the extent of PlsPamCho hydrolysis within the bilayer. DHC-free plasmenylcholine liposomes (38 degrees C, pH 2.5) require < 5% PlsPamCho hydrolysis to effect > 50% calcein release within 10 min. The presence of > or = 25 mol% DHC, however, greatly reduces the observed calcein release rate; nearly 30% PlsPamCho hydrolysis is required to effect 50% calcein release over a 70-min period in 6:4 PlsPamCho/DHC liposomes. Bacteriochlorophyll a-sensitized photooxidation of plasmenylcholine liposomes also produces fatty aldehyde and another intermediate, tentatively described as 1-formyl-2-palmitoyl-sn-glycero-3-phosphocholine, that hydrolyzes to form the 1-hydroxy lysolipid. These results have important implications for the quantitative description of lysolipid effects on membrane permeability and on the design of triggerable liposomes for drug delivery.

Acids↗

Platelet-activating factor in normal rat uterus.

Platelet-activating factor (PAF) was found in normal rat uterus and identified as 1-0-hexadecyl/octadecenyl-2-acetyl-sn-glycero-3-phosphocholine. PAF was purified by several successive chromatographic procedures. It showed platelet aggregating activity, which was inhibited by CV 3988, and had no effect on platelets desensitized with 1-0-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine. The tert-butyldimethyl-silylderivative of 1-0-alkyl-2-acetyl-sn-glycerol, which was obtained by hydrolysis of uterine PAF with phospholipase C, was analyzed by gas chromatography-mass spectrometry. One rat uterus contained approximately 21.3 ng of 1-0-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine. This is the first report of the occurrence of a significant amount of PAF in a normal animal tissue.

Animals↗

Conformational studies of a novel cationic glycolipid, glyceroplasmalopsychosine, from bovine brain by NMR spectroscopy.

A novel glycosphingolipid containing a long chain aldehyde conjugated to galactose and glycerol, Gro1(3)-O-CH((CH(2))(n)CH(3))-O-6Galbeta-sphingosine (glyceroplasmalopsychosine) has been studied by NMR spectroscopy (Hikita et al. J. Biol. Chem. 2001, 276, 23084-23091). We further report here on the conformation showing the galactose and the glycerol at the end of two parallel hydrophobic chains, i.e. the sphingosine and the fatty aldehyde. This is proposed based on the interproton distances derived from ROESY experiments and 3 J (H,H) coupling constants. The absence of any intraresidual NOEs between protons in the glycerol residue suggested that the C-C-2 and C-C-3 bonds in the glycerol may be rotating freely, supporting the proposed conformation in which the unique terminal glycerol is in an environment with a minimal steric hindrance. The present study proposes a conformation of glyceroplasmalopsychosine greatly different from the two conventional plasmalopsychosines possessing a fatty aldehyde chain oriented in an opposite direction to the sphingosine.

Animals↗

Glycerophospholipids in brain: their metabolism, incorporation into membranes, functions, and involvement in neurological disorders.

Neural membranes contain several classes of glycerophospholipids which turnover at different rates with respect to their structure and localization in different cells and membranes. The glycerophospholipid composition of neural membranes greatly alters their functional efficacy. The length of glycerophospholipid acyl chain and the degree of saturation are important determinants of many membrane characteristics including the formation of lateral domains that are rich in polyunsaturated fatty acids. Receptor-mediated degradation of glycerophospholipids by phospholipases A(l), A(2), C, and D results in generation of second messengers such as arachidonic acid, eicosanoids, platelet activating factor and diacylglycerol. Thus, neural membrane phospholipids are a reservoir for second messengers. They are also involved in apoptosis, modulation of activities of transporters, and membrane-bound enzymes. Marked alterations in neural membrane glycerophospholipid composition have been reported to occur in neurological disorders. These alterations result in changes in membrane fluidity and permeability. These processes along with the accumulation of lipid peroxides and compromised energy metabolism may be responsible for the neurodegeneration observed in neurological disorders.

Animals↗

Lipid peroxidation in presence of ebselen.

Lipid peroxidation is initiated by cell damage. After homogenisation of porcine heart tissue in aqueous solution we observed the same lipid peroxidation products as detected after heart infarction. We used this observation to study the influence of ebselen (2-phenyl-1,2-benzoisoselenazol-3-(2H)-one) on the generation of oxidatively derived monohydroxy fatty acids and alpha-hydroxyaldehydes, typical lipid peroxidation (LPO) products. Heart tissue was homogenised before and after enzyme destruction and with addition of ebselen. The obtained LPO products were analysed by GC/MS after appropriate derivatisation and quantified by using internal standards. The amount of monohydroxy fatty acids and alpha-hydroxyaldehydes increased considerably in the porcine heart homogenates in which the enzymes were kept active. Addition of ebselen caused an additional significant increase of hydroxy fatty acids, while the increase of aldehydic compounds was less. These results confirm the glutathione peroxidase-like activity of ebselen but demonstrate also that it does not prevent lipid peroxidation.

Acetamides↗