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At least 19 recordsLinked to original sources
PubMed1985

Incorporation of some eicosanoic acids into endothelial cells--effect on platelet inhibitory activity and prostacyclin production.

Primary cultures of endothelial cells from human umbilical veins were grown until confluency. Then, dihomogammalinolenic acid (DHLA or 20:3n-6) and eicosapentaenoic acid (EPA or 20:5n-3), precursors of monoenoic and trienoic prostanoids, respectively, as well as 5,8,11-eicosatrienoic acid (20:3n-9), and isomer of DHLA, were incorporated into endothelial lipids. DHLA-rich endothelial cells had a decreased capacity of prostacyclin production. By contrast EPA- or 20:3n-9-rich endothelial cells were comparable to controls in this respect. DHLA and EPA were efficiently acylated into cell phospholipids and triglycerides at the opposite of 20:3n-9. It is suggested that both DHLA and EPA could alter the liberation of endogenous arachidonic acid for prostacyclin synthesis but this might be counterbalanced in EPA-rich endothelial cells by PGI3 production. We conclude that DHLA enrichment of endothelial cell lipids may impair the possible beneficial effect of the acid upon platelet functions whereas that of EPA would not be modified.

8,11,14-Eicosatrienoic Acid↗
PubMed1991

[Eicosanoic acid levels in children with atopic dermatitis].

Column chromatography followed by RIA was used to measure the blood plasma content of arachidonic acid metabolites (leukotrienes C4, B4, C4/D4/E4, prostaglandins F2 alpha, E2, 6-keto-prostaglandin F1 alpha, thromboxane B2) in 146 children aged 6 months to 14 years with atopic dermatitis. The data obtained were compared to the healthy children's parameters. The majority of the patients manifested activation of the system of arachidonic acid metabolism. The intensity of changes in the content of eicosanoids was found to depend on the clinical pattern and spreading of skin lesions.

6-Ketoprostaglandin F1 alpha↗
PubMed1993

Phospholipid and fatty acid compositions of Rhizobium leguminosarum biovar trifolii ANU843 in relation to flavone-activated pSym nod gene expression.

The phospholipid and associated fatty acid compositions of the bacterial symbiont of clover, Rhizobium leguminosarum biovar trifolii wild-type ANU843, was analyzed by two-dimensional silica thin-layer chromatography, fast atom bombardment-mass spectrometry, flame-ionization detection gas-liquid chromatography and combined gas-liquid chromatography/mass spectrometry. The phospholipid composition included phosphatidylethanolamine (15%), N-methylphosphatidylethanolamine (47%), N,N-dimethylphosphatidylethanolamine (9%), phosphatidylglycerol (19%), cardiolipin (5%) and phosphatidylcholine (2%). Fatty acid composition included predominantly cis-11-octadecenoic acid, lower levels of cis-9-hexadecenoic acid, hexadecanoic acid, 11-methyl-11-octadecenoic acid, octadecanoic acid, 11,12-methyleneoctadecanoic acid, eicosanoic acid and traces of branched, and di- and triunsaturated fatty acids. The influence of expression of the "nodulation" genes encoding symbiotic functions on the composition of these membrane lipids was examined in wild-type cells grown with or without the flavone inducer, 4',7-dihydroxyflavone and in mutated cells lacking the entire symbiotic plasmid where these genes reside, or containing single transposon insertions in selected nodulation genes. No significant changes in phospholipid or associated fatty acid compositions were detected by the above methods of analysis.

Fatty Acids↗
PubMed2001

Final report on the safety assessment of Corylus Avellana (Hazel) Seed Oil, Corylus Americana (Hazel) Seed Oil, Corylus Avellana (Hazel) Seed Extract, Corylus Americana (Hazel) Seed Extract, Corylus Avellana (Hazel) Leaf Extract, Corylus Americana (Hazel) Leaf Extract, and Corylus Rostrata (Hazel) Leaf Extract.

These ingredients are all derived from hazelnut trees. The two seed oils are expressed from the nuts of the hazelnut tree of the particular species identified. Most current reported cosmetic uses are of the seed oils. The seed extracts are the extract of the nuts of the identified species tree. There is one current report of use of seed extract in cosmetics. The leaf extracts are the extract from the leaves of the particular species tree. There are no current reports of use of these extracts in cosmetics. Analysis of seed oil from one species identified Oleic Acid, Palmitoleic Acid, Linoleic Acid, Eicosaenoic Acid, Docosenoic Acid, Eicosanoic Acid, Palmitic Acid, Linolenic Acid, Stearic Acid, and Tetraeicosanoic Acid. Little information is available to characterize the extracts, however. The functions of most of these ingredients in cosmetics are not reported. In studies of hazelnuts from Spain and Egypt, aflatoxin was reported as a possible contaminant. Aflatoxins are considered carcinogenic in humans. Virtually no safety test data are available on these ingredients. Negative results in one comedogenicity study using a seed oil are reported. Cross-sensitivity to proteins in peanuts and those in hazelnuts are reported, but the presence or absence of protein in nut extract and plant extract from hazelnut trees is not known. Additional data were provided regarding concentration of use, method of extraction and contaminants, comedogenicity, and ultraviolet (UV) radiation absorption, but these data related to nut oil from only one species, and were not overall sufficient to resolve questions about irritation, sensitization, and photosensitization. Because of the absence of data, it is concluded that the available data are insufficient to support the safety of these ingredients in cosmetic products. Because of the limited information that characterizes any of these oils or extracts, data are needed on each (except that items 1, 2, and 3 below are not needed for Hazel [Corylus Avellana] Nut Oil). The additonal data needs include: (1) current concentration of use; (2) method of extraction/manufacture and quality control (i.e., chemical analyses); (3) contaminants and methods of extraction (especially pesticides and heavy metals); (4) dermal irritation and sensitization; (5) UV absorption; if there is significant absorption, then a photosensitization study will be needed; (6) 28-day dermal toxicity; (7) reproductive and developmental toxicity; and (8) two genotoxicity assays, one in a mammalian system; if positive, then a 2-year dermal carcinogenesis study using National Toxicology Program (NTP) methods may be needed.

Acne Vulgaris↗
PubMed2006

[Determination of fatty acids and organic acids in Ranunculus ternatus Thunb using GC-MS].

The determination of fatty acids and organic acids in Chinese medicinal plant Ranunculus ternatus Thunb using GC-MS was studied. The Ranunculus ternatus Thunb from Henan province was cut into less than 20 mesh pieces, then extracted by petroleum ether or ether in refluxing and esteried, and finally was determined using GC-MS. The results show that there are 23 kinds of organic compounds in the Chinese medicinal plant Ranunculus ternatus Thunb from Henan, among which 15 kinds of fatty acids were identified, including myristic acid, palmitic acid, stearic acid, oleic acid, linolenic acid, eicosanoic acid, docosanoic acid etc. The unsaturated fatty acids and oleic acid account for 58.19% and 35.68% of the total organic compounds respectively. The kinds of fatty acid in petroleum ether extract and ether extract are the same.

Alkanes↗
PubMed1990

[Chemical constituents of the seed oil of Astragalus complanatus R. Brown].

beta-sitosterol and fatty acids were obtained from the oil of seeds of Astragalus complanatus. The fatty acids were separated and their molecular weights determined by GC-MS. Fourteen of them were identified as heptenoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, octadecenoic acid, octadecanoic acid, octadecadienoic acid, linolenic acid, eicosanoic acid, eicosenoic acid and docosanoic acid, etc.

Drugs, Chinese Herbal↗
PubMed2000

[Studies on chemical constituents of Lagopsis supina (Steph.) Ik.-GaI].

OBJECTIVE: To study the chemical constituents of Lagopsis supina. METHOD: Compounds were separated by solvent extraction, column chromatography and TLC, and the structures were determined by chemical and spectral analyses. RESULTS: Six compounds were isolated from the ethanol extract of L. supina and identified as eicosanoic acid octadecyl ester, eicosanoic acid-16-methyl-15, 16-hetadecenyl ester, palmitic acid, beta-sitosterol, oleanolic acid and daucosterol. CONCLUSION: Except beta-sitosterol, all the compounds were isolated from this genus for the first time.

Lamiaceae↗
PubMed2005

Circulating adiponectin and plasma fatty acid profile.

BACKGROUND: The amount and type of fat in the diet influence the development of obesity and related inflammatory activity. Knowledge of the possible influence of dietary habits on circulating adiponectin, a molecule with putative antiinflammatory properties, may be helpful in preventing atherosclerosis and type 2 diabetes. METHODS: The association between dietary fat, as inferred from plasma fatty acid composition (gas-liquid chromatography), and circulating adiponectin (RIA) was evaluated in 116 healthy individuals. RESULTS: The proportion of saturated fatty acids in plasma was significantly associated with circulating adiponectin concentration (r = -0.24; P = 0.01). Specifically, percentage of palmitic acid (C16:0) was significantly associated with lower adiponectin concentration (r = -0.28; P = 0.002), particularly among women (r = -0.37; P = 0.02) and nonsmokers (r = -0.30; P = 0.007). Percentage of myristic acid (C14:0) was also significantly associated with lower adiponectin among nonsmokers (r = -0.26; P = 0.02) and women (r = -0.39; P = 0.01). The other fatty acids were not significantly associated with adiponectin except for eicosanoic acid (C20:1 omega-9), which was significantly and positively associated with adiponectin in all individuals (r = 0.23; P = 0.01). This latter association was most significant in smokers (r = 0.43; P = 0.007). In a multivariate regression analysis to predict circulating adiponectin, after controlling for age, body mass index, waist-to-hip ratio, and the individual remaining fatty acids, the percentages of palmitic (P = 0.005) and eicosanoic acid (P = 0.03) contributed independently (6% and 3%, respectively) to adiponectin variance. Among nonsmokers, the percentages of palmitic acid (P = 0.01) and omega-3 fatty acids contributed 8% and 7%, respectively, to adiponectin variance. Among smokers, the percentage of eicosanoic acid (P = 0.03) contributed to 10% of adiponectin variance, independently of body mass index, age, waist-to hip ratio, and the remaining individual fatty acids. CONCLUSIONS: Saturated and omega-3 fatty acids of dietary origin (as inferred from plasma fatty acid concentration) are associated with circulating adiponectin concentrations in healthy humans. The proportion of eicosanoic acid also appears to be positively associated with circulating adiponectin. The knowledge of how these interactions occur may be helpful in the planning of dietary measures aimed at the modulation of inflammatory activity.

Adiponectin↗
PubMed1997

Production of 3R-hydroxy-polyenoic fatty acids by the yeast Dipodascopsis uninucleata.

Various fatty acids were fed to the yeast Dipodascopsis uninucleata UOFS Y 128, and the extracted samples were analyzed for the accumulation of 3-hydroxy metabolites with the help of electron impact gas chromatography-mass spectrometry. Fatty acids containing of 5Z,8Z-diene system (5Z,8Z,11Z-eicosatrienoic, 5Z,8Z,11Z,14Z-eicosatetraenoic, and 5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acids) yielded the corresponding 3-hydroxy-all-Z-eicosapolyenoic acids. Moreover, linoleic acid (9Z,12Z-octadecadienoic acid) and 11Z,14Z,17Z-eicosatrienoic acid were converted to the 3-hydorxylated metabolites of shorter chain length, e,g., 3-hydroxy-5Z,8Z-tetradecadienoic acid and 3-hydroxy-5Z,8Z,11Z-tetradecatrienoic acid, respectively. In contrast, no accumulation of a 3-hydroxy metabolite was observed with oleic acid (9Z-octadecenoic acid), linolelaidic acid (9E,12E-octadecadienoic acid), gamma-linolenic acid (6Z,9Z,12Z-octadecatrienoic acid), and eicosanoic acid as substrate. These findings pinpoint that the 3-hydroxylation of a fatty acid in Dipodascopsis uninucleata requires a 5Z,8Z-diene system either directly or following initial incomplete beta-oxidation. Following analysis of the enantiomer composition, the arachidonic acid metabolite was identified as 3R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, which rules out a normal beta-oxidation as biosynthetic route to this new class of oxylipins.

Arachidonic Acids↗
PubMed1994

Bio-anticlastogenic effects of unsaturated fatty acids included in fish oil--docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid--in cultured Chinese hamster cells.

Bio-anticlastogenic effects of unsaturated fatty acids--cis-4,7,10,13,16,19-docosahexaenoic acid (DHA), cis-7,10,13,16,19-docosapentaenoic acid (DPA), and cis-5,8,11,14,17-eicosapentaenoic acid (EPA)--on chemically induced chromosome aberrations were studied in cultured Chinese hamster cells. The induction of chromosome aberrations by the crosslinking agents mitomycin C (MMC) and cisplatin (DDP), the SN-1 type alkylating agents N-ethyl-N'-nitro-N-nitrosoguanidine (ENNG), methyl nitrosourea (MNU), and ethyl nitrosourea (ENU), and the SN-2 type alkylating agent ethyl methanesulfonate (EMS), but not by the SN-1 type alkylating agent N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) and the SN-2 type alkylating agent methyl methanesulfonate (MMS), was suppressed by post-treatment with DHA, DPA, and EPA. Since there was no opportunity to inactivate mutagens by desmutagenic mechanisms under the post-treatment schedule used, the results demonstrate the bio-anticlastogenicity of unsaturated fatty acids. Suppression by the unsaturated fatty acids was observed when cells were treated during the G2 phase, suggesting that G2 events were responsible for the bio-anticlastogenic effects. Two saturated fatty acids with the same number of carbons as the studied unsaturated fatty acids--docosanoic acid and eicosanoic acid--did not affect chromosome aberration induction, suggesting the necessity of unsaturation for fatty acid bio-anticlastogenicity.

Alkylating Agents↗
PubMed1998

Oriented growth of calcium oxalate monohydrate crystals beneath phospholipid monolayers.

Oriented calcium oxalate crystals have been grown beneath phospholipid monolayers at the air-solution interface from supersaturated calcium oxalate solutions. Mature calcium oxalate crystals grown beneath zwitterionic dipalmitoylphosphatidylcholine (DPPC) monolayers exhibit the characteristic morphology of calcium oxalate monohydrate (COM) crystals with the elongated (101) crystal face preferentially oriented parallel to the plane of the monolayer. Calcium oxalate crystals grown beneath negatively-charged dimyristoylphosphatidylserine (DMPS) monolayers also show a preferential orientation with respect to the monolayer; they do not, however, exhibit the characteristic COM morphology. Raman spectroscopy strongly suggests that the crystals grown beneath either DPPC or DMPS monolayers are the monohydrate phase of calcium oxalate; therefore, differences in crystal morphology are not due to differences in the crystalline phase. Dimyristoylphosphatidylethanolamine (DMPE), dimyristoylphosphatidic acid (DMPA), eicosanoic acid (C20), and eicosanol (C20-OH) monolayers have also been studied to help elucidate the mechanisms of interaction between the lipid monolayers and the calcium oxalate crystals. We discuss the roles of lattice matching, hydrogen bonding, stereochemistry and electrostatics on crystal orientation and morphology.

1,2-Dipalmitoylphosphatidylcholine↗
PubMed1971

Effects of Ca++ and prostaglandin E1 on vasopressin activation of renal adenyl cyclase.

Adenyl cyclase activity was assayed in crude homogenates of the renal cortex, medulla, and papilla of the golden hamster. The specific activity (moles C-AMP/unit of time per mg protein of tissue) of the enzyme under basal conditions, was greatest in papilla, somewhat lower in medulla, and least in cortex. On an absolute scale, the sensitivity to vasopressin was greater in the medullary and papillary than in the cortical homogenates. In addition, at concentrations of 0.1-1.0 mm, CaCl(2) inhibited the enzyme in the order papilla > medulla > cortex. These results imply the existence of distinct differences in the composition of the adenyl cyclase-receptor complex in various parts of the kidney. We proposed that Ca(++) inhibits the core enzyme directly since at the minimally inhibitory concentration (0.1 mm), CaCl(2) reduced to an equivalent extent (a) basal activity, (b) the response to graded doses of vasopressin (0.5 to 50.0 mU/ml) and (c) the response to maximal stimulatory concentrations of NaF (10 mm). Prostaglandin E(1) (PGE(1) = 10(-7)m) had no effect on either basal adenyl-cyclase activity or the response to 10 mm NaF in medullary and papillary homogenates. 7-Oxa-13-prostynoic acid (10(-4)m) similarly had no effect under basal conditions or on stimulation with NaF in medullary homogenates. Both fatty acids, however, inhibited the enzymic response to vasopressin, particularly at low concentrations of the peptide. The straight-chain fatty acid, 11-eicosanoic acid (10(-7)m), was inactive on basal activity or on the response to vasopressin. The possibility that PGE(1) modifies the coupling mechanism between the core enzyme and the hormone-specific receptor is discussed.

Adenylyl Cyclases↗
PubMed1989

[Chemical composition and biological quality of defatted hazelnut flour].

The results of the chemical composition and biological quality of deffated hazel nut flour are shown. The samples analyzed contained significant amounts of proteins (19%) comparable to legume flour, higher than cereals and lower than deffated oleaginous flours. The oil extracted from the seed was analyzed and the average results obtained were the following: Refraction index, 1.47; saponification No. 184.8; iodine No. 85.0. The average composition of the fatty acids obtained by gas liquid chromatography was: Palmitic acid 2.3% Palmitoleic acid 37.0% Stearic acid 0.5% Oleic acid 39.5% Linoleic acid 6.9% Linolenic acid 1.1% Eicosanoic acid 2.3% Eicosaenoic acid 4.6% Docosenoic acid 3.4% Tetraeicosanoic acid 0.3% These results indicate a good-quality oil due to the low content of linolenic acid. The nutritive value of the deffated meal measured in the rats gave a net protein ratio (NPR) of 3.58, lower than the corresponding casein value (4.10). The true protein digestibility measured in the rat gave a value of 7.3%, compared to 95% for casein. The amounts of iron and phosphorous are comparatively lower than those reported for rape-seed meal and sunflower meal.

Animals↗
PubMed1993

[Studies on the chemical constituents of Desmodium styracifolium (Osbeck) Merr].

A new alkaloid, named desmodimine, C12H15NO4, gum, and a new natural product, named desmodilactone, C8H13NO3, mp 84-85 degrees C have been isolated from the aerial parts of Desmodium styracifolium (Osbeck) Merr. belonging Leguminosae. On the basis of spectral analysis their structures were deduced as formula I and II. In addition, lupenone (III), lupeol (IV), tritriacontane (V), stearic acid (VI), eicosanoic acid eicosyl ester (VIII) and beta-sitosterol (VII) were isolated for the first time from this plant.

Drugs, Chinese Herbal↗
PubMed1989

Eicosanoic fatty acid reduction in the tibiotarsus of biotin-deficient chicks.

Day-old male broiler chicks (Hubbard x Hubbard) were fed a purified diet containing biotin at 0 microgram/kg of diet (biotin-deficient) or 500 micrograms/kg of diet (biotin-adequate). Biotin-deficient (BD) chicks had decreased growth and feed efficiency and greater twisted leg and dermatitis symptoms than biotin-adequate (BA) chicks. Lipids in cortical bone of the tibiotarsi in BD chicks contained higher levels of linoleate, gamma-linolenate, and alpha-linolenate. Prostaglandin precursors, dihomo-gamma-linolenate (20:3 omega 6), arachidonate (20:4 omega 6), and eicosapentaenoate (20:5 omega 3) were all lower in BD chicks compared with BA chicks. Periosteal bone appositional and bone formation rates, and percent new bone formation were reduced in the tibiotarsi of BD chicks. Anatomically there were two different bone modeling patters at the mid-diaphysis. The cortex was thickest laterally in chicks fed the BA diet and thickest medially in chicks fed the BD diet. The quantitative differences in bone growth and the distinct bone modeling patterns, coupled with corresponding decreases in PG precursors, suggest that biotin deficiency may alter bone growth and modeling via a PG-dependent mechanism.

Animals↗
PubMed1995

Pre-incubation of synaptosomes with arachidonic acid potentiates inhibition of [3H]D-aspartate transport.

The ability of low micromolar concentrations of the polyunsaturated fatty acid, arachidonic acid (cis-5,8,11,14-eicosatetraenoic acid) to inhibit the high-affinity, sodium-dependent transport of [3H]D-aspartate into purified synaptosomes of rat brain has been examined. Pre-incubation of the synaptosomes with arachidonic acid for 10-60 min produced a marked potentiation of the response to 10 microM arachidonic acid compared to co-incubation, and the threshold for inhibition of [3H]D-aspartate transport occurred at a concentration of 1 microM. Minimal inhibition of transport was seen with the unsaturated fatty acids, cis-oleic (cis-9-octadecenoic acid) and cis-linolenic (cis-9,12,15-octadecatrienoic acid), nor with the 20-carbon saturated fatty acid, arachidic acid (n-eicosanoic acid). Inclusion of the cyclo-oxygenase inhibitor, nor-dihydroguaretic acid (NDGA), in the presence of 5 microM arachidonic acid did not alter the inhibition of [3H]D-aspartate transport between 0-10 min, but did enhance the response at longer pre-incubation times. Inhibition of [3H]D-aspartate transport by arachidonic acid persisted during addition of the calcium ionophore, A23187, whereas removal of calcium ions from the incubation medium potentiated the response to arachidonic acid. The results are discussed in terms of the physiological relevance of the inhibition of glutamate transport by arachidonic acid, and suggest that regulation of inhibition of the glutamate transporter by arachidonic acid may be achieved by changes in the extracellular, as well as the intracellular, concentration of calcium ions.

ATP-Binding Cassette Transporters↗