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Journal of Lipid Research Jun 1995Fatty acid composition of anterior pituitary cell membranes of rats deprived of essential fatty acids (EFA) and of rats receiving a standard diet was determined during...
Fatty acid composition of anterior pituitary cell membranes of rats deprived of essential fatty acids (EFA) and of rats receiving a standard diet was determined during postnatal development and in adults. Pregnant rats were fed an EFA-deficient diet and the offspring were fed the same diet after weaning. In parallel, effects of the diet on growth and on growth hormone (GH) responsiveness to GHRH stimulation were determined in control animals. Membrane content of arachidonic acid (20:4n-6) and of its elongation product adrenic acid (22:4n-6) increased regularly from day 2 to day 12 after birth. EFA-deficiency resulted on day 2 in increased oleic acid and in substitution of arachidonic and adrenic acids by corresponding elongation-desaturation products of oleic acid: eicosatrienoic (20:3n-9) and docosatrienoic (22:3n-9) acids. At the age of 24 days, n-9 series fatty acid reached the same level as in adult animals. Two-day-old EFA-deficient rats paradoxically exhibited a higher level of 20:4n-6 as compared to control rats. EFA-deficiency also decreased growth rate and GH pituitary responses to GHRH during the prepubertal period. These results suggest that changes in the lipid structure and in pituitary secretion properties elicited by EFA-deficiency depend upon the stage of development.
Topics: Animals; Arachidonic Acid; Cell Membrane; Erucic Acids; Fatty Acids; Fatty Acids, Essential; Fatty Acids, Unsaturated; Female; Growth Hormone; Growth Hormone-Releasing Hormone; Pituitary Gland, Anterior; Pregnancy; Prenatal Exposure Delayed Effects; Rats; Rats, Wistar
PubMed: 7666016
DOI: No ID Found -
Journal of Natural Products Dec 1994The diunsaturated fatty acids 5,9-heneicosadienoic acid, 5,9-docosadienoic acid and 5,9-tricosadienoic acid, the brominated fatty acids 6-bromo- 5,9-heneicosadienoic...
The diunsaturated fatty acids 5,9-heneicosadienoic acid, 5,9-docosadienoic acid and 5,9-tricosadienoic acid, the brominated fatty acids 6-bromo- 5,9-heneicosadienoic acid and 6-bromo-5,9-docosadienoic acid, and the polyunsaturated fatty acids 5,9,13-eicosatrienoic acid and 5,9,13-docosatrienoic acid, were identified for the first time in nature in the phospholipids (mainly phosphatidylethanolamine and phosphatidylserine) of the anemone Stoichactis helianthus. Structural elucidation was accomplished by means of mass spectrometry and chemical transformations such as pyrrolidide and dimethyldisulfide derivatization. Other delta 5,9 fatty acids such as 5,9-hexadecadienoic acid, 5,9-octadecadienoic acid, and 5,9-eicosadienoic acid were also identified in the anemone. Our results indicate that delta 5,9 phospholipid fatty acids are not unique to sponges, as previously recognized, but can be found in other marine invertebrates such as an anemone. 24-Methylated sterols predominated in the sterol composition of the anemone investigated.
Topics: Aldehydes; Animals; Fatty Acids; Mass Spectrometry; Phospholipids; Puerto Rico; Sea Anemones
PubMed: 7714536
DOI: 10.1021/np50114a011 -
The Journal of Biological Chemistry Dec 1993Six previously unidentified leukotriene (LT) B4 metabolites formed during incubation of LTB4 with human keratinocytes in primary culture indicate the importance of the...
Six previously unidentified leukotriene (LT) B4 metabolites formed during incubation of LTB4 with human keratinocytes in primary culture indicate the importance of the 12-hydroxyeicosanoid dehydrogenase pathway in LTB4 metabolism. The ultraviolet absorption spectra obtained for all keratinocyte metabolites revealed the presence of a conjugated diene structural moiety rather than the conjugated triene structure of LTB4. Metabolites were characterized using fast atom bombardment-mass spectrometry, gas chromatography-mass spectrometry of the pentafluorobenzyl ester, trimethylsilyl ether derivatives and specific degradation reactions. The previously identified 10,11-dihydro-LTB4 and 10,11-dihydro-12-epi-LTB4 were observed as well as 20-OH-10,11-dihydro-LTB4, consistent with the reductase pathway of LTB4 metabolism. This pathway involves initial formation of 12-oxo-LTB4 catalyzed by 12-hydroxyeicosanoid dehydrogenase followed by reduction by delta 10-reductase. The most lipophilic metabolite of LTB4 was identified as 10-hydroxy-4,6,12-octadecatrienoic acid which could result from beta-oxidation reactions of LTB4 following reduction of the 10,11-double bond. One of the most abundant metabolites was characterized as 3,7,14-trihydroxy-8,10,16- docosatrienoic acid which could result from fatty acid elongation following reduction of the 10,11-double bond. Additional abundant LTB4 metabolites were identified that result from glutathione conjugation of 12-oxo-LTB4. These were characterized using fast atom bombardment-mass spectrometry and by chemical degradation using hypochlorous acid as well as transpeptidases. These metabolites were identified as 5,12-dihydroxy-6-glutathionyl-7,9,14-eicosatrienoic acid (c-LTB3), 5,12-dihydroxy-6-cysteinyl-glycyl-7,9,14-eicosatrienoic acid (d-LTB3) and 5,12-dihydroxy-6-cysteinyl-7,9,14-eicosatrienoic acid (e-LTB3). We propose that these metabolites result from a 1,8 Michael-type addition of glutathione to the 12-oxo-LTB4 intermediate.
Topics: Biotransformation; Cells, Cultured; Glutathione; Humans; Infant, Newborn; Keratinocytes; Leukotriene B4; Male; Mass Spectrometry; Skin; Spectrometry, Mass, Fast Atom Bombardment
PubMed: 8244977
DOI: No ID Found -
Lancet (London, England) Oct 1992It has not been established whether nutrition in early infancy affects subsequent neurodevelopment and function. If there is an effect, it seems probable that the...
It has not been established whether nutrition in early infancy affects subsequent neurodevelopment and function. If there is an effect, it seems probable that the essential fatty acids and their metabolites, the major constituents of brain structure, will be the most susceptible to dietary influence. We determined the phospholipid fatty-acid composition of cerebral cortex grey matter obtained from 20 term and 2 preterm infants who had died of "cot deaths" and related results to the milk diet the infants had received. Tissues were analysed by gas chromatography. The mean weight percentage of docosahexaenoic acid was significantly greater (p less than 0.02) in 5 breast-milk-fed infants (9.7%) than in 5 age-comparable formula-milk-fed infants (7.6%). In these formula-fed babies, the overall percentage of long-chain polyunsaturated fatty acids was maintained by increased incorporation of the major n-6 series fatty acids. In 1 formula-fed preterm infant, in whom the lowest concentration of cortical docosahexaenoic acid was found, the compensatory effect was only partial with both n-9 series eicosatrienoic acid or Mead acid and docosatrienoic acid also detected in the phospholipid. Supplementation of formula milks for term infants with docosahexaenoic acid and those for preterm infants with both docosahexaenoic and arachidonic acid could prove beneficial to subsequent neurodevelopment.
Topics: Age Factors; Animals; Arachidonic Acids; Cerebral Cortex; Dietary Fats; Docosahexaenoic Acids; Fatty Acids, Monounsaturated; Fatty Acids, Unsaturated; Female; Humans; Infant; Infant Food; Infant, Newborn; Male; Milk; Milk, Human; Palmitic Acids; Phospholipids
PubMed: 1357244
DOI: 10.1016/0140-6736(92)92684-8 -
Journal of Chromatography Dec 1991Free and total fatty acids in the blood serum of patients with hyperlipoproteinemia have been analysed as their methyl esters by capillary gas chromatography using an...
Free and total fatty acids in the blood serum of patients with hyperlipoproteinemia have been analysed as their methyl esters by capillary gas chromatography using an FFAP column. In one-step reactions the free fatty acids in serum react with methanol-acetyl chloride (50:1, v/v) at 25 degrees C, the total fatty acids (free plus esterified) are transesterified with methanol-toluene-acetyl chloride (8:2:1, v/v) at 100 degrees C. The quantification of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) is based on an internal standard (13,16,19-docosatrienoic acid) and on calibration standards. Under normal diet the concentrations of EPA and DHA are as follows (mean +/- S.D., n = 27): free EPA, 0.2 +/- 0.1 mg/dl; free DHA, 0.6 +/- 0.2 mg/dl; total EPA, 3.6 +/- 2.1 mg/dl; total DHA 11.4 +/- 3.1 mg/dl. Under a fish oil intake of 9 g per day, free and total EPA concentrations rise by ca. five- to six-fold, and free and total DHA concentrations by ca. two-fold.
Topics: Chromatography, Gas; Docosahexaenoic Acids; Eicosapentaenoic Acid; Esters; Fish Oils; Humans; Hyperlipoproteinemias; Placebos
PubMed: 1840144
DOI: 10.1016/0378-4347(91)80468-r -
Biochimica Et Biophysica Acta Oct 1991The lipolysis of rat chylomicron polyenoic fatty acid esters with bovine milk lipoprotein lipase and human hepatic lipase was examined in vitro. Chylomicrons obtained...
The lipolysis of rat chylomicron polyenoic fatty acid esters with bovine milk lipoprotein lipase and human hepatic lipase was examined in vitro. Chylomicrons obtained after feeding fish oil or soy bean oil emulsions were used as substrates. The lipolysis was followed by gas chromatography or by using chylomicrons containing radioactive fatty acids. Lipoprotein lipase hydrolyzed eicosapentaenoic (20:5) and arachidonic acid (20:4) esters at a slower rate than the C14-C18 acid esters. More 20:5 and 20:4 thus accumulated in remaining tri- and diacylglycerols. Eicosatrienoic, docosatrienoic and docosahexanoic acids exhibited an intermediate lipolysis pattern. When added together with lipoprotein lipase, hepatic lipase increased the rate of lipolysis of 20:5 and 20:4 esters of both tri- and diacylglycerols. Addition of NaCl (final concentration 1 M) during the course of lipolysis inhibited lipoprotein lipase as well as the enhancing effect of hepatic lipase on triacylglycerol lipolysis. Hepatic lipase however, hydrolyzed diacylglycerol that had already been formed. Chylomicron 20:4 and 20:5 esters thus exhibit a relative resistance to lipoprotein lipase. It is suggested that the tri- and diacylglycerol species containing these fatty acids may accumulate at the surface of the remnant particles and act as substrate for hepatic lipase during a concerted action of this enzyme and lipoprotein lipase.
Topics: Animals; Chylomicrons; Fatty Acids; Fish Oils; Glycerides; In Vitro Techniques; Lipase; Lipolysis; Lipoprotein Lipase; Liver; Male; Rats; Rats, Inbred Strains
PubMed: 1954225
DOI: 10.1016/0304-4165(91)90274-k -
Lipids Sep 1988An essential fatty acid (EFA) deficiency-like profile of fatty acids has been observed in HF-1 human skin fibroblasts cultured at clonal densities in MCDB 110 and 0.4%...
An essential fatty acid (EFA) deficiency-like profile of fatty acids has been observed in HF-1 human skin fibroblasts cultured at clonal densities in MCDB 110 and 0.4% fetal bovine serum (FBS). The profile was characterized by an accumulation of 16:1n-7, 18:1n-9, 20:3n-9 and 22:3n-9, a reduction of n-6 fatty acids and a reduction in total polyunsaturated fatty acids (PUFA). The fatty acid composition of sphingomyelin (SPH), phosphatidylcholine (PC), phosphatidylserine (PS), phosphatidylinositol (PI) and phosphatidylethanolamine (PE) was determined and, except for SPH, each displayed an EFA deficiency-like profile. The triene to tetraene ratio (20:3n-9/20:4n-6) ranged from 5.3 in PI to 0.9 in PE. In addition, the highest percentage of 20:3n-9 was present in the PI and the highest percentage of 22:3n-9, in PE. Other human fibroblasts (normal, transformed and at different population doubling number levels [PDL]) were grown under the same conditions and were found to display triene to tetraene ratios (20:3n-9/20:4n-6) in total cellular lipids ranging from 0.7 to 4.5. The accumulation of 20:3n-9 and 22:3n-9 is due primarily to the existence of a basal nutrient medium (MCDB 110) that allows for the rapid clonal growth of human fibroblasts at reduced serum levels (0.4%). This culture procedure can be exploited to further elucidate various aspects of lipid metabolism in human fibroblasts.
Topics: 8,11,14-Eicosatrienoic Acid; Cell Survival; Cells, Cultured; Fatty Acids, Essential; Fatty Acids, Unsaturated; Fibroblasts; Humans; Phospholipids
PubMed: 3185126
DOI: 10.1007/BF02536211 -
The Journal of Pharmacology and... Mar 1980Mice fed a saturated, Purina chow or unsaturated fat diet from birth have different synaptic membrane fatty acid compositions. The saturated diet decreased...
Mice fed a saturated, Purina chow or unsaturated fat diet from birth have different synaptic membrane fatty acid compositions. The saturated diet decreased docosahexaenoic [22:6 (n - 3)] and increased eicosatrienoic [20:3 (n - 9)], docosatrienoic [22:3 (n - 9)] and docosapentaenoic [22:5 (n - 6)] fatty acids compared to the Purina chow or unsaturated fat diet. The most notable alterations occurred in the synaptic membrane phosphatidylserine and phosphatidylethanolamine fractions. The saturated diet also caused a minor increase in oleic acid [18:1 (n - 9)i1. Animals fed the saturated diet showed a small, significant decrease in nitrous oxide ED50 (dose required to abolish the righting reflex in half the animals) but not in isoflurane ED50, compared to animals fed the Purina chow or unsaturated fat diet. Thus, large alterations in several synaptic membrane fatty acid components have little or no influence on anesthetic requirement.
Topics: Acetylcholinesterase; Anesthesia, Inhalation; Animals; Dietary Fats; Dose-Response Relationship, Drug; Fatty Acids; Female; Isoflurane; Membrane Lipids; Mice; Nitrous Oxide; Pregnancy; Sodium-Potassium-Exchanging ATPase; Synaptic Membranes
PubMed: 6244388
DOI: No ID Found -
Lipids Sep 1970
Topics: Adenoma; Adrenal Gland Neoplasms; Adrenal Glands; Adult; Aged; Animals; Arachidonic Acids; Cholesterol; Chromatography, Gas; Chromatography, Thin Layer; Esters; Fatty Acids; Humans; Hyperaldosteronism; Linoleic Acids; Lipids; Male; Middle Aged; Rats; Silver Nitrate
PubMed: 5457076
DOI: 10.1007/BF02531386 -
Biochimica Et Biophysica Acta Jul 1965
Topics: Animals; Chemical Phenomena; Chemistry; Chromatography, Thin Layer; Fatty Acids; In Vitro Techniques; Liver; Phosphatidylcholines; Phosphatidylethanolamines; Phospholipids; Rats
PubMed: 5848268
DOI: 10.1016/0005-2760(65)90110-4