European Journal of Lipid Science and Technology

Cover image for Vol. 117 Issue 8

August 2015

Volume 117, Issue 8

Pages 1091–1302

  1. Cover Picture

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      Cover Picture: Eur. J. Lipid Sci. Technol. 8∕2015

      Article first published online: 6 AUG 2015 | DOI: 10.1002/ejlt.201570081

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      The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils

      Elizabeth S. Budilarto and Afaf Kamal-Eldin

      According to the new paradigm, lipid oxidation is described as a complex reaction catalyzed both by a combination of free radical reactions and heterogeneous phase modifications. Reactions take place in micelles that are destabilized by hydroperoxides and other amphiphilic molecules. Primary antioxidants scavenge free radicals and synergists stabilize the micelles and bring the primary antioxidants in close proximity with the free radicals. Micelles are stable during the induction period and when they collapse, the reaction enters the propagation phase with exponential formation of hydroperoxides. This understanding may enable tailoring of improved protection of oxidatively-prone lipids.

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      Editorial Board: Eur. J. Lipid Sci. Technol. 8∕2015

      Article first published online: 6 AUG 2015 | DOI: 10.1002/ejlt.201570082

  3. In this Issue

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      In this issue

      Article first published online: 6 AUG 2015 | DOI: 10.1002/ejlt.201570083

  4. Contents

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    3. Editorial Board
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      Contents: Eur. J. Lipid Sci. Technol. 8∕2015

      Article first published online: 6 AUG 2015 | DOI: 10.1002/ejlt.201570084

  5. Editorial

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  6. Review Article

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      The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils (pages 1095–1137)

      Elizabeth S. Budilarto and Afaf Kamal-Eldin

      Article first published online: 26 FEB 2015 | DOI: 10.1002/ejlt.201400200

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      The evolution of micellar size and number during and after the induction period of lipid oxidation. Amphiphilic compounds, including lipid hydroperoxides, contribute to micelle formation and act as prooxidants. Antioxidants and retarders stabilize micelles and prevent their breakdown.

  7. Research Articles

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    8. Research Articles
    9. Short Communications
    10. Data Report
    1. Protectin DX, a double lipoxygenase product from DHA, inhibits the production of both inflammatory cytokines and reactive oxygen species in human retinal pigment epithelium cells (pages 1138–1145)

      Yining Dai, Chan Zhao, Xiaofang Liang, Rongping Dai and Fangtian Dong

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejlt.201400423

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      DHA is highly concentrated in RPE and can be converted into the active oxygenate derivative protectin DX (PDX). Pretreatment with PDX significantly inhibited production of t-BH-induced reactive oxygen species (ROS) and increased capability of intracellular total antioxidant (T-AOC) and activity of superoxide dismutase (SOD) in RPE cells. Furthermore, PDX pretreatment greatly suppressed t-BH-induced excessive secretion of tumor necrosis factor-α (TNF-α) and vascular endothelial growth factor-A (VEGF-A). Interestingly, peroxisome proliferator-activated receptor-γ coactivator-1α (PGC-1α), a key regulator of enzymes that detoxify ROS, was shown to be up-regulated by PDX pretreatment, suggesting a possible mechanism underlying the antioxidant effects of PDX in RPE cells.

    2. Trans fatty acid retention and conversion rates of fatty acids in tissues depend on dietary fat in mice (pages 1146–1158)

      Juliana Saín, Marcela Aída González, Jimena Verónica Lavandera, María Victoria Scalerandi and Claudio Adrián Bernal

      Article first published online: 26 FEB 2015 | DOI: 10.1002/ejlt.201400287

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      The levels of trans fatty acids (TFA) in a particular tissue might be related to different variables including: type and level of the dietary TFA isomer; uptake, metabolization and release from the tissue, and interference with different dietary fatty acids.

    3. Regioselective synthesis of diacylglycerol rosmarinates and evaluation of their antioxidant activity in fibroblasts (pages 1159–1170)

      Erwann Durand, Christelle Bayrasy, Mickaël Laguerre, Nathalie Barouh, Jérôme Lecomte, Thierry Durand, Laurence Balas, Chantal Wrutniak-Cabello, Gérard Cabello and Pierre Villeneuve

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejlt.201400607

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      A series of new model of lipophilized phenolic compound (1,2-diacylglycerol rosmarinate, RDAG) were synthesized through a chemo-enzymatic synthesis. In terms of antioxidant activity assessed in fibroblasts, all synthesized RDAG exhibited higher ROS inhibition level than free rosmarinic acid. RDAG with two lauryl chains (RDAG12) displayed the best antioxidant ability of the series, with higher activity than vitamins E and C. These results confirm that linking an appropriate hydrophobic domain is a powerful strategy to synthesize effective antioxidants.

    4. Ionic liquids improve the selective synthesis of hydrophilic glyceryl ferulates by the enzymatic transesterification of ethyl ferulate with monostearin: Comparison with organic solvents (pages 1171–1178)

      Shangde Sun, Bingxue Hu, Fanfan Song and Yanlan Bi

      Article first published online: 13 FEB 2015 | DOI: 10.1002/ejlt.201400335

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      Enzymatic transesterification of ethyl ferulate (EF) with monostearin to produce hydrophilic glyceryl monoferulate (GMF)+glyceryl diferulate (GDF) and lipophilic feruloylated monoacylglycerols (FMAG)+feruloylated diacylglycerols (FDAG) in ionic liquids or organic solvents.

    5. Synthesis and characterization of novel trialdehyde, tribenzylamine, and triamine from triolein (pages 1179–1184)

      Jian Yang, Jin Yue, Baoping Zha and Yanyun Zhao

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejlt.201400625

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      The polyamine could be utilized as potential bio-monomers to produce polymers, such as polyurea and polyamide. In this study, a novel tribenzylamine, and triamine were synthesized from triolein, a major component of rapeseed oil. The developed synthetic methodology could be employed on other unsaturated triacyglycerols and plant oils.

    6. Kinetics of the epoxidation of soybean oil with H2O2 catalyzed by phosphotungstic heteropoly acid in the presence of polyethylene glycol (pages 1185–1191)

      Weiwei Cheng, Guoqin Liu, Xuede Wang, Xinqi Liu and Lu Jing

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejlt.201400614

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      The activation energy of the soybean oil epoxidation reaction with H2O2 catalyzed by phosphotungstic heteropoly acid (PHA) in the presence of polyethylene glycol (PEG) was lower than that of PEG alone, accounting for the results showing that the epoxy group band of the former (PHA + PEG) appeared quicker than the latter (PHA) in IR spectra.

    7. Ionic liquid-assisted subcritical water promotes the extraction of lipids from wet microalgae Scenedesmus sp (pages 1192–1198)

      Xiaolin Chen, Linfeng Hu, Ronge Xing, Song Liu, Huahua Yu, Yukun Qin, Kecheng Li, Rongfeng Li and Pengcheng Li

      Article first published online: 10 FEB 2015 | DOI: 10.1002/ejlt.201400189

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      A new, environmentally friendly method of extracting lipids from the wet Scenedesmus sp. is described, in which the effect of various experimental parameters including ionic liquid species, the concentration of ionic liquids, and temperature on the extraction efficiency were evaluated. By this method, lipids can be extracted from wet microalgae easily and efficiently. The lipid yield under the optimal conditions was close to the extraction result of Bligh & Dyer's method and the TAG concentration was higher than that of the Bligh & Dyer's method. Analysis of the fatty acid composition showed that the extracted lipids were a good source of crude oil for future biodiesel production.

    8. Monitoring the oxidative stability and volatiles in blanched, roasted and fried almonds under normal and accelerated storage conditions by DSC, thermogravimetric analysis and ATR-FTIR (pages 1199–1213)

      Arantzazu Valdés, Ana Beltrán, Ioannis Karabagias, Anastasia Badeka, Michael G. Kontominas and María Carmen Garrigós

      Article first published online: 24 FEB 2015 | DOI: 10.1002/ejlt.201400384

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      The effect of different cooking processes (blanching, roasting and frying) on the oxidative stability of almonds under normal storage and accelerated oxidation conditions were investigated. Fatty acid composition, primary and secondary oxidation products, thermal parameters, volatiles and lipid degradation were assessed. Results indicate that processing and technological strategies should be used for almond production in order to obtain better oxidative stability and to assure preservation of their overall nutritional profile.

    9. New parameters for evaluating the quality of commercial krill oil capsules from the aspect of lipid oxidation and non-enzymatic browning reactions (pages 1214–1224)

      Fung Sieng Henna Lu, Inge Bruheim and Charlotte Jacobsen

      Article first published online: 11 MAR 2015 | DOI: 10.1002/ejlt.201400512

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      The quality of commercial krill oil capsules could be differentiated through parameters such as chemical compositions (bioactive compounds), hydrophobic pyrroles, and volatile profiles (volatiles derived from lipid oxidation and non-enzymatic browning reactions). The data of chemical composition of krill oil were correlated well with those from volatile measurement and new insights into lipid oxidation and non-enzymatic browning reactions in krill oil were obtained.

    10. Antioxidant activity and phytochemical content of cold-pressed rapeseed oil obtained from roasted seeds (pages 1225–1237)

      Aleksander Siger, Aleksandra Kaczmarek and Magdalena Rudzińska

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejlt.201400378

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      An analytic comparison was made of cold-pressed rapeseed oil produced from unroasted seeds and cold-pressed oil produced from seeds that had previously undergone roasting at temperatures of 140, 160, and 180°C for 5, 10, and 15 min. It was determined whether the duration and temperature of roasting have any qualitative and quantitative effects on the contents of the native antioxidants (tocopherol, PC-8, phenolic compounds, canolol, and phytosterols) found in rapeseed oil. In the oil from the unroasted seeds, the canolol content was 11.54 μg/g oil. It was shown that increases both in temperature and in duration of seed roasting result in a statistically significant increase in the canolol content of cold-pressed oils. For the seed roasted at 180°C for 15 min, this increase was fiftyfold (609.94 μg canolol/g oil). The same roasting conditions also led to a twofold increase in the antioxidant activity of the oil.

    11. Blending Local olive oils with Arbequina or Picual oils produces high quality, distinctive EVOOs (pages 1238–1247)

      Patricia Reboredo-Rodríguez, Carmen González-Barreiro, Beatriz Cancho-Grande, Giuseppe Fregapane, María Desamparados Salvador and Jesus Simal-Gándara

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejlt.201400357

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      Galician virgin olive oil producers want to promote the production and marketing of high quality extra virgin olive oils with peculiar sensory and health characteristics. To reach this goal, it is of great interest to recover old autochthonous Local olive varieties, which may bring added value to the most common Galician olive oils elaborated from Arbequina and Picual cultivars. Results obtained in this study showed that the previous knowledge of quality-related indices, fatty acid composition, as well as minor composition, such as phenolic and volatile profiles of monovarietal EVOOs, could be a good strategy to produce high quality extra virgin olive oils à la carte.

    12. Policosanol variation in olive oil as a result of variety, ripening, and storage (pages 1248–1260)

      Marina Lukić, Igor Lukić, Barbara Sladonja and Vlasta Piližota

      Article first published online: 26 FEB 2015 | DOI: 10.1002/ejlt.201400483

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      Policosanol alcohol variation as a result of variety, ripening degree, and storage temperature was investigated. The use of policosanol variation as a chemical indicator and discriminator according to these factors was tested.

    13. Influence of genotype on the fatty acids composition of virgin olive oils from advanced selections obtained by crosses between Arbequina, Picual, and Frantoio cultivars along the ripening process (pages 1261–1270)

      Verónica Sánchez de Medina, Mónica Calderón-Santiago, Milad El Riachy, Feliciano Priego-Capote and María Dolores Luque de Castro

      Article first published online: 4 MAR 2015 | DOI: 10.1002/ejlt.201400488

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      (ejlt201400488-gra-0001) Dark green to yellow or yellowish–green skin (RI 0–1); (ejlt201400488-gra-0002) yellowish with reddish spots (RI 2); (ejlt201400488-gra-0003) reddish or light violet to black (RI 3–4).

    14. Machining effects of different mechanical crushers on pit particle size and oil drop distribution in olive paste (pages 1271–1279)

      Alessandro Leone, Roberto Romaniello, Riccardo Zagaria, Erika Sabella, Luigi De Bellis and Antonia Tamborrino

      Article first published online: 4 MAR 2015 | DOI: 10.1002/ejlt.201400485

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      Different crushing machines produce different pit and oil drop fragmentation, and the trends confirm that increased pit fragmentation corresponds to increased droplet fragmentation. The data expressed in this research could be used to construct a guideline for the design and sizing of crushing machines with the goal of achieving a balance between pulp fragmentation, pit breakage and oil drop fragmentation.

  8. Short Communications

    1. Top of page
    2. Cover Picture
    3. Editorial Board
    4. In this Issue
    5. Contents
    6. Editorial
    7. Review Article
    8. Research Articles
    9. Short Communications
    10. Data Report
    1. Evaluation of contamination associated with current blood spot technology for determining the fatty acid status of individuals (pages 1280–1286)

      Ge Liu, Beverly Sara Mühlhäusler and Robert Alan Gibson

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejlt.201400470

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      Attempts to validate blood spot technology for determining the fatty acid status of individuals found that contaminants various sources may reduce the accuracy of fatty acid analysis results of blood spot samples. This study evaluates levels of contaminants in different collection papers to develop a method which would minimize the contaminant problem.

    2. Fatty acid profile of seashore mallow (Kosteletzkya pentacarpos) seed oil and properties of the methyl esters (pages 1287–1294)

      Gerhard Knothe and Bryan R. Moser

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejlt.201400612

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      The seed oils of Kosteletzkya species contain malvalic acid and other acids with cyclic moieties.

    3. Monitoring odour of heated extra-virgin olive oils from Arbequina and Manzanilla cultivars using an electronic nose (pages 1295–1300)

      Valeria Messina, Ana Sancho and Noemi Walsöe de Reca

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejlt.201400651

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      An odour index was performed using a metal oxide sensors signal. Linear regressions were performed with emissions of several volatile compounds, assessing content and odour index to predict appearance of undesired odour in extra-virgin olive oil.

  9. Data Report

    1. Top of page
    2. Cover Picture
    3. Editorial Board
    4. In this Issue
    5. Contents
    6. Editorial
    7. Review Article
    8. Research Articles
    9. Short Communications
    10. Data Report
    1. Fatty acid composition, tocopherol, and sterol contents of sumac (Rhus coriaria L.) fruit oils (pages 1301–1302)

      Bertrand Matthaus and Mehmet Musa Özcan

      Article first published online: 26 FEB 2015 | DOI: 10.1002/ejlt.201400547

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      The major fatty acids found in sumac oil were palmitic, oleic and linoleic acids. γ-Tocopherol is the predominant component in sumac fruit oil, followed by γ-tocotriol. The composition of sterols in sumac oil is dominated by β-sitosterol, which accounted for about 75–80% of the total sterols in the oil.

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