Lipids (LIPIDS)

Publications in this journal

• Article: Citations: The Rules They Didn’t Teach You

  Eric J. Murphy
  Lipids 05/2012; 46(4):307-309.
• Article: Unusual lipid composition of a Bacillus sp. Isolated from Lake Pomorie in Bulgaria

  Nstor M. Carballeira, Aikomari Guzmn, Jordan T. Nechev, Kantcho Lahtchev, Albena Ivanova, Kamen Stefanov
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  ABSTRACT: The lipid composition of a Bacillus sp., isolated from Lake Pomorie in Bulgaria, was unusual and consisted of 26 different fatty acids between C12 and C26, with anteiso C15−C17 saturated fatty acids predominating. The furan fatty acid, 10,13-epoxy-11-methyloctadeca-10,12-dienoic acid, was also identified, a new finding for this genus. The hydrocarbons consisted of 30 different monounsaturated hydrocarbons, between C25 and C30, with the iso-iso, iso-anteiso, anteiso-anteiso, iso-normal, and anteiso-normal methyl branching for odd-numbered chains, and the iso-iso, iso-anteiso, iso-normal, and anteiso-normal methyl branching for even-numbered chains. The double bond positions in these hydrocarbons were determined by dimethyl disulfide derivatization followed by GC-MS, and the double-bond cis configuration was confirmed by infrared spectroscopy. Some previously unknown hydrocarbons in bacteria, such as (Z)-3,21-dimethyl-9-tricosene, (Z)-3,21-dimethyl-10-tricosene, (Z)-2,24-dimethyl-11-pentacosene, and (Z)-2,25-dimethyl-13-hexacosene were identified. Sterols were detected and were based on the sitosterol nucleus.
  Lipids 04/2012; 35(12):1371-1376.
• Article: Metabolities of dietary triacylglycerol and diacylglycerol during the digestion process in rats

  Noriko Osaki, Shinichi Meguro, Noriyuki Yajima, Noboru Matsuo, Ichiro Tokimitsu, Hiroyuki Shimasaki
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  ABSTRACT: The present study investigated the metabolic fate of dietary TAG and DAG and also their digestion products in the stomach and small intestine. A diet containing 10% TAG or DAG oil, enriched in 1,3-DAG, was fed to Wistar rats ad libitum for 9 d. After 18 h of fasting, each diet was re-fed ad libitum for 1 h. The weights of the contents of the stomach and small intestine were measured, and the acylglycerol and FFA levels were analyzed by GC at 0, 1, and 4 h after the 1-h re-feeding. The amounts of re-fed diet ingested and the gastric and small intestinal content were not different between the two diet groups. In the TAG diet group, the main products were TAG and DAG, especially 1(3),2-DAG. In addition, 1,3-DAG and 1(3)-MAG were present in the stomach, and the 1,3-DAG levels increased over time after the re-feeding period. In the DAG diet group, the main products in the stomach were DAG, MAG, FFA, and TAG. There were significantly greater amounts of 1,3-DAG, 1(3)-MAG, and FFA in the DAG diet group in the stomach compared with the TAG diet group. The amount of FFA in the stomach relative to the amount of ingested TAG plus DAG in the DAG diet group was higher than that in the TAG diet group. Acylglycerol and FFA levels were considerably lower in the small intestine than in the stomach. These results indicate that, in the stomach, where acyl migration might occur, the digestion products were already different between TAG and DAG oil ingestion, and that DAG might be more readily digested by lingual lipase compared with TAG. Furthermore, almost all of the dietary lipid was absorbed, irrespective of the structure of the acylglycerol present in the small intestine.
  Lipids 04/2012; 40(3):281-286.
• Article: Synthesis and biological activity of new lodoacetamide derivatives on mutants of squalene-hopene cyclase

  Maurizio Ceruti, Gianni Balliano, Flavio Rocco, Alexander Jenhart, Georg E. Schulz, Francesco Castelli, Paola Milla
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  ABSTRACT: New iodoacetamide derivatives, containing a dodecyl or a squalenyl moiety, were synthesized. The effect of these new thiol-reacting molecules was studied on two mutants of Alicyclobacillus acidocaldarius squalene-hopene cyclase constructed especially for this purpose. In the quintuple mutant, all five cysteine residues of the enzyme are substituted with serine; in the sextuple mutant, this quintuple substitution is accompanied by the substitution of aspartate D376, located at the enzyme’s active site, with a cysteine. N-Dodecyliodoacetamide had little activity toward either mutant, whereas N-squalenyliodoacetamide showed a stronger effect on the sextuple than on the quintuple mutant, as expected.
  Lipids 04/2012; 40(7):729-735.
• Article: Effect of palm oil carotene on breat cancer tumorigenicity in nude mice

  Kalanithi Nesaretnam, Ammu Radhakrishnan, Kanga Rani Selvaduray, Karin Reimann, Jayalakshmi Pailoor, Ghazali Razak, Mina Mustafa Mahmood, Jasbir Singh Dahliwal
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  ABSTRACT: Biological therapies are new additions to breast cancer treatment. Among biological compounds, β-carotene has been reported to have immune modulatory effects, in particular, enhancement of natural killer cell activity and tumor necrosis factor-alpha production by macrophages. The objective of this study was to investigate the effect of palm carotene supplementation on the tumorigenicity of MCF-7 human breast cancer cells injected into athymic nude mice and to explore the mechanism by which palm carotenes suppress tumorigenesis. Forty-eight 4-wk-old mice were injected with 1×106 MCF-7 cells into their mammary fat pad. The experimental group was supplemented with palm carotene whereas the control group was not. Significant differences were observed in tumor incidence (P<0.001) and tumor surface area and metastasis to lung (P<0.005) between the two groups. Natural killer (NK) cells and B-lymphocytes in the peripheral blood of carotene-supplemented mice were significantly increased (P<0.05 and P<0.001, respectively) compared with controls. These results suggest that palm oil carotene is able to modulate the immune system by increasing peripheral blood NK cells and B-lymphocytes and suppress the growth of MCF-7 human breast cancer cells.
  Lipids 04/2012; 37(6):557-560.
• Article: Cyclodehydration reactions of methyl 9,10-; 10,12-; and 9,12-dioxostearates with 1,2-diaminoethane under ultrasonic irradiation

  Marcel S. F. Lie Ken Jie, Maureen M. L. Lau, Prabhavathi Kalluri
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  ABSTRACT: Reaction of methyl 9,10-dioxostearate (1) and 9,12-dioxostearate (2) with 1,2-diaminoethane under concomitant ultrasonic irradiation (10–15 min, 60°C) in water furnished the corresponding 2,3-dihydropyrazine (4, 79%) and 1,2,3,4-tetrahydro-1,4-diazocine (5, 70%) derivatives, respectively. Reaction of methyl 10,12-dioxostearate (3) with 1,2-diaminoethane was successful only when glacial acetic acid was used instead of water under ultrasonic irradiation (4×10 min, 70°C) to give a 2,3-dihydro-1H-1,4-diazepine (6, 95%) derivative. The structures of these novel six-membered (4), seven-membered (6), and eight-membered (5) N-heterocyclic fatty ester derivatives were confirmed by a combination of infrared, nuclear magnetic resonance spectroscopic and mass spectral analyses.
  Lipids 04/2012; 36(2):201-205.
• Article: Overestimates of oleic and linoleic acid contents in materials containing trans fatty acids and analyzed with short packed gas chromatographic columns

  Dietz Precht, Joachim Molkentin, Mark A. McGuire, Michelle K. McGuire, Robert G. Jensen
  Lipids 04/2012; 36(2):213-217.
• Article: Properties of a fluorescent bezafibrate derivative (DNS-X). A new tool to study peroxisome proliferation and fatty acid β-oxidation

  Jean-Pierre Berlot, Thomas Lutz, Mutaspha Cherkaoui Malki, Val rie Nicolas-Frances, Brigitte Jannin, Norbert Latruffe
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  ABSTRACT: The first peroxisome proliferator-activated receptor (PPAR) was cloned in 1990 by Issemann and Green. Many studies have reported the importance of this receptor in the control of gene expression of enzymes involved in lipid metabolic pathways including mitochondrial and peroxisomal fatty acid β-oxidation, lipoprotein structure [apolipoprotein (apo) A2, apo Clll], and fatty acid synthase. By using radiolabeled molecules, it was shown that peroxisome proliferators bind and activate PPAR. As an alternative method, we developed a fluorescent dansyl (1-dimethyl-aminonaphthalene-5-sulfonyl) derivative peroxisome proliferator from bezafibrate (DNS-X), a hypolipidemic agent that exhibits an in vitro peroxisome proliferative activity on rat Fao-hepatic derived cultured cells. However, until now, the effect of this new compound on the liver of animals and subcellular localization was unknown. In addition to in vivo rat studies, we present a more efficient large-scale technique of DNS-X purification. Treating rats (DNS-X in the diet at 0.3% w/w) for 6 d leads to a hepatomegaly and a marked increase in liver peroxisomal palmitoyl-CoA oxidase activity. We also developed a method to localize and quantify DNS-X in tissues or cell compartment organelles. The primarily cytosolic distribution of DNS-X was confirmed by direct visualization using fluorescence microscopy of cultured Fao cells. Finally, transfection assay demonstrated that DNS-X enhanced the PPARα activity as well as other peroxisome proliferators do.
  Lipids 04/2012; 35(12):1397-1404.
• Article: Michael T. Arts, Michael T. Brett, Martin J. Kainz (eds): Lipids in aquatic ecosystems

  Néstor M. Carballeira
  Lipids 04/2012; 44(9):775-776.
• Article: Vinyl sulfide derivatives of truncated oxidosqualene as selective inhibitors of oxidosqualene and squalene-hopene cyclases

  Maurizio Ceruti, Gianni Balliano, Flavio Rocco, Paola Milla, Silvia Arpicco, Luigi Cattel, Franca Viola
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  ABSTRACT: Various vinyl sulfide and ketene dithioacetal derivatives of truncated 2,3-oxidosqualene were developed. These compounds, having the reactive functions at positions C-2, C-15 and C-19 of the squalene skeleton, were studied as inhibitors of pig liver and Saccharomyces cerevisiae oxidosqualene cyclases (OSC) (EC 5.4.99.7) and of Alicyclobacillus acidocaldarius squalene hopene cyclase (SHC) (EC 5.4.99.-). They contain one or two sulfur atoms in α-skeletal position to carbons considered to be cationic during enzymatic cyclization of the substrate and should strongly interact with enzyme nucleophiles of the active site. Most of the new compounds are inhibitors of the OSC and of SHC, with various degrees of selectivity. The methylthiovinyl derivative, having the reactive group at position 19, was the most potent and selective inhibitor of the series toward S. cerevisiae OSC, with a concentration inhibiting 50% of the activity of 50 nM, while toward the animal enzyme it was 20 times less potent. These results could offer new insight for the design of antifungal drugs.
  Lipids 04/2012; 36(6):629-636.
• Article: Effect of sesamin on mitochondrial and peroxisomal β-oxidation of arachidonic and eicosapentaenoic acids in rat liver

  Rumi Umeda-Sawada, Megumi Ogawa, Mayumi Nakamura, Osamu Igarashi
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  ABSTRACT: The effects of dietary sesamin on the hepatic metabolism of arachidonic (AA) and eicosapentaenoic (EPA) acids, were investigated with respect to their β-oxidation and secretion as triacylglycerol (TG). For 2 wk, rats were fed three types of dietary oils: (i) corn oil (control) group; (ii) FPA group: FPA ethyl esters/rapeseed oil=2∶3; (iii) AA group: AA ethyl esters/palm oil/perilla oil=2∶2∶1, with or without 0.5% (w/w) of sesamin. Dietary sesamin significantly increased the activities of hepatic mitochondrial and peroxisomal fatty acid oxidation enzymes (mitochondrial carnitine acyltransferase I, acyl-CoA dehydrogenase, and peroxisomal acyl-CoA oxidase). Dietary FPA increased mitochondrial carnitine acyltransferase I and peroxisomal acyl-CoA oxidase. Dietary AA, however, had an effect on peroxisomal acyl-CoA oxidase only. In whole liver and the TG fraction, EPA and AA concentrations were significantly increased by dietary EPA and AA, respectively, and were decreased by dietary sesamin. In hepatic mitochondria and peroxisomes, EPA concentration was increased by dietary EPA, but AA was not changed by dietary AA. The addition of dietary sesamin to the EPA-supplemented diet significantly decreased the EPA concentration compared to concentrations found with consumption of dietary EPA alone. These results suggest that sesamin increased β-oxidation enzyme activities and reduced hepatic EPA and AA concentrations by degradation. The stimulating effect of sesamin on β-oxidation, however, was more significant in the EPA group than in the AA group. Hepatic AA concentration was altered by the joint effect of sesamin through esterification into TG and the stimulation of β-oxidation.
  Lipids 04/2012; 36(5):483-489.
• Article: Quantitative determination of 13C-labeled and endogenous β-carotene, lutein, and vitamin A in human plasma

  Mark A. Kelm, Vincent P. Flanagan, Robert J. Pawlosky, Janet A. Novotny, Beverly A. Clevidence, Steven J. Britz
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  ABSTRACT: Quantitative procedures employing liquid-chromatography/particle beam mass spectrometry (LC/PB-MS) and gas chromatography-mass spectrometry (GC-MS) were applied to the determination of the endogenous and 13C-labeled β-carotene, lutein, and retinol in plasma of a subject who consumed kale (Brassica oleracea) that had been grown in a 13CO2-enriched atmosphere. All compounds were analyzed in the negative chemical ionization (NCI) mode using methane as the moderating reagent gas. β-Carotene and lutein were analyzed using LC/PB-MS applying reversed-phase high-performance liquid chromatography (HPLC) separation procedures to resolve the analytes. The concentrations of the β-carotene isotopomers in the plasma over a several-week period were determined using 2H8-β-carotene as an internal standard. The total plasma concentrations of all trans-lutein were quantified by HPLC analysis with a photodiode array detector using β-apo-8′-carotenal as an internal standard, and the ratio of the 13C∶12C isotopomers of lutein was determined by PB-MS. The retinol isotopomers were collected from individual HPLC fractions of the plasma extract and then analyzed as the trimethylsilyl ethers by GC-MS in the NCI mode. The 13C-and 12C-retinol isotopomers were quantified using 2H4-retinol as an internal standard. These methods demonstrate the application of highly sensitive procedures empolying NCI MS for the quantitative determination of carotenoids and vitamin A for the purpose of conducting metabolism studies of phytonutrients.
  Lipids 04/2012; 36(11):1277-1282.
• Article: Cu2+-induced low density lipoprotein peroxidation is dependent on the initial O2 concentration: An O2 consumption study

  John K. Lodge, Maret G. Traber, Peter J. Sadler
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  ABSTRACT: Atherosclerotic plaques form in the arterial intima, where low density lipoprotein (LDL) is thought to be oxidatively modified at sites which may contain catalytic amounts of copper in the presence of low O2 tension. We have investigated O2 consumption during LDL peroxidation induced by Cu2+ ions in vitro and found two phases: a lag phase followed by a phase of rapid O2 consumption. The length of the lag phase was dependent on Cu2+ and on initial O2 concentrations; increasing either decreased the lag time; however, LDL concentration had no effect. LDL-induced Cu2+ reduction, however, was not affected by low initial O2 concentrations, suggesting that O2 is not required for LDL-mediated reduction of Cu2+. Following the lag phase O2 consumption was dependent upon LDL or initial O2 concentrations; Cu2+ concentrations had little effect, suggesting that the propagation phase is more dependent on the presence of LDL lipids and O2 as substrates for the reaction. In summary, LDL peroxidation takes place in the presence of Cu2+ at low O2 tension; however, the reaction is dependent upon initial O2 concentrations; increases shorten the lag phase and accelerate O2 consumption.
  Lipids 04/2012; 35(10):1087-1092.
• Article: Lipids of gelatinous antarctic zooplankton: Cnidaria and Ctenophora

  Matthew M. Nelson, Charles F. Phleger, Ben D. Mooney, Peter D. Nichols
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  ABSTRACT: Antarctic gelatinous zooplankton, including Cnidaria (Calycopsis borchgrevinki, Diphyes antarctica, Stygiomedusa gigantea, Atolla wyvillei, Dimophyes arctica) and Ctenophora (Beroe cucumis, B. forskalii, Pleurobrachia pileus, Bolinopsis infundibulum) were collected near Elephant Island, South Shetland Islands, during January and February 1997 and 1998. Total lipid was low in all zooplankton (0.1–5 mg g−1 wet mass) and included primarily polar lipids (59–96% of total lipid). Triacylglycerols were 0–26% of total lipids, and wax esters were 0–11% in all species. Cholesterol was the major sterol in all Cnidaria (50–63% of total sterols) whereas in most ctenophores it was lower at 26–45%. These cholesterol levels are consistent with a combined carnivorous and phytoplanktivorous diet in the ctenophores, with the carnivorous diet more dominant in the Cnidaria. Other sterols included primarily trans-dehydrocholesterol, desmosterol, 24-methylcholest-5,22E-dien-3β-ol, 24-nordehydrocholesterol, and 24-methylenecholesterol. Total stanols were 0–6% in all zooplankton. Eicosapentaenoic acid and docosahexaenoic acid were the major polyunsaturated fatty acids (PUFA) in all samples (7–25% of total fatty acids) except for A. wyvillei in which docosapentaenoic acid was 10% of total fatty acids. The PUFA 18∶5n−3 was not detected in 1997 samples, but constituted 0.2–0.8% in most 1998 samples. Monounsaturated fatty acids included primarily 18∶1n−9c, 16∶1n−7c, and 18∶1n−7c. The principal saturated fatty acids in all samples were 16∶0, 18∶0, and 14∶0. These data are the first for many of these zooplankton species and the first sterol data for most species. The use of the signature lipid approach has enabled examination of aspects of trophodynamics not obtainable by conventional techniques.
  Lipids 04/2012; 35(5):551-559.
• Article: Modulation of arachidonate and docosahexaenoate in Morone chrysops larval tissues and the effect on growth and survival

  Moti Harel, Eric Lund, Sonja Gavasso, Ryan Herbert, Allen R. Place
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  ABSTRACT: The extent to which extreme dietary levels of arachidonate (AA) and/pr docosahexaenoate (DHA) modulate lipid composition in the body tissues and consequently affect growth and survival in freshwater Morone larvae species was examined. White bass, M. chrysops, larvae (day 24–46) were fed Artemia nauplii enriched with algal oils containing varying proportions of AA and DHA (from 0 to over 20% the total fatty acids). Growth was significantly reduced (P<0.05) in larvae fed a DHA-deficient Artemia diet. Increases in dietary levels of AA also were associated with a significant growth reduction. However, the inhibitory effect of AA on larvae growth could be suppressed by the dietary addition of DHA (at a level of 21.6% of the total fatty acids in enrichment lipids). Larval brain+eyes tissue accumulated over 10 times more DHA than AA in its structural lipids (phosphatidylcholine, phosphatidylethanolamine) at any dietary ratio. In contrast, DHA accumulation, as compared to AA, in gill lipids declined considerably at higher than 10∶1 DHA/AA tissue ratios. DHA and eicosapentaenoic acid (EPA) contents in brain+eyes tissue were most sensitive to competition from dietary AA, being displaced from the tissue at rates of 0.36±0.07 mg DHA and 0.46±0.11 mg EPA per mg increase in tissue AA, and 0.55±0.14 mg AA per mg increase in tissue DHA. On the other hand, AA and EPA levels in gill tissue were most sensitive to dietary changes in DHA levels; AA was displaced at rates of 0.37±0.11 mg, whereas EPA increased at rates of 0.68±0.28 mg per mg increase in tissue DHA. Results suggest that balanced dietary DHA/AA ratios (that allow DHA/AA ratios of 2.5∶1 in brain+eyes tissue) promote a high larval growth rate, which also correlates with maximal regulatory response in tissue essential fatty acids.
  Lipids 04/2012; 35(11):1269-1280.
• Article: Hydrophilic Interaction Liquid Chromatography: ESI–MS/MS of Plasmalogen Phospholipids from Pectinatus Bacterium

  Tomáš Řezanka, Lucie Siristova, Dagmar Matoulková, Karel Sigler
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  ABSTRACT: Liquid chromatography–electrospray tandem mass spectrometry (LC/ESI–MS/MS) was used to analyze phospholipids from three species of the anaerobic beer-spoilage bacterial genus Pectinatus. Analysis of total lipids by HILIC (Hydrophilic Interaction Liquid Chromatography) column succeeded in separating diacyl- and plasmalogen phospholipids. Plasmalogens were then analyzed by means of the ESI–MS/MS and more than 220 molecular species of four classes of plasmalogens (PlsCho (choline plasmalogen), PlsEtn (ethanolamine plasmalogen), PlsGro (glycerol plasmalogen), and PlsSer (serine plasmalogen)) were identified. Major molecular species were c-p19:0/15:0 PlsEtn and PlsSer, which accounted for more than 4% of the total lipids. Keywords Pectinatus –Plasmalogens–Liquid chromatography–electrospray tandem mass spectrometry–HILIC column
  Lipids 04/2012; 46(8):765-780.
• Article: Total Synthesis and Antileishmanial Activity of the Natural Occurring Acetylenic Fatty Acids 6-Heptadecynoic Acid and 6-Icosynoic Acid

  Néstor M. Carballeira, Michelle M. Cartagena, Christopher Fernández Prada, Celia Fernández Rubio, Rafael Balaña-Fouce
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  ABSTRACT: The first total syntheses of the naturally occurring acetylenic fatty acids—6-heptadecynoic acid (59% overall yield) and 6-icosynoic acid (34% overall yield)—was accomplished in four steps. Using the same synthetic sequence the naturally occurring fatty acids (6Z)-heptadecenoic acid (46% overall yield) and (6Z)-icosenoic acid (27% overall yield) were also synthesized. The Δ6 acetylenic fatty acids displayed good antiprotozoal activity towards Leishmania donovani promastigotes (EC50=1–6µg/mL), but the 6-icosynoic acid was the most effective in the series. In addition, the (6Z)-icosenoic acid was a much better antiprotozoal compound (EC50=5–6µg/mL) than the (6Z)-heptadecenoic acid (EC50>25µg/mL). The saturated fatty acids n-heptadecanoic acid and n-eicosanoic acid were not effective towards L. donovani, indicating that the Δ6 unsaturation in these fatty acids is necessary for leishmanicidal activity. In addition, both the 6-icosynoic acid and the (6Z)-icosenoic acid were inhibitors of the Leishmania DNA topoisomerase IB enzyme (EC50’s=36–49µM), a possible intracellular target for these compounds. This is the first study assessing fatty acids as inhibitors of the Leishmania DNA topoisomerase IB enzyme.
  Lipids 04/2012; 44(10):953-961.