Elaidic Acid (BioDeep_00000410642)

Main id: BioDeep_00000400557

 

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


Oleic acid, from tall oil fatty acids

化学式: C18H34O2 (282.2559)
中文名称: 反油酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)O
InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+

描述信息

A 9-octadecenoic acid and the trans-isomer of oleic acid.
COVID info from PDB, Protein Data Bank
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
It is used as a food additive .
Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent.
Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent.

同义名列表

4 个代谢物同义名

Elaidic Acid; Oleic acid, from tall oil fatty acids; (9E)-Octadecenoic acid; Elaidic acid



数据库引用编号

32 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

18 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Takuya Iino, Ryuji Toh, Manabu Nagao, Masakazu Shinohara, Amane Harada, Katsuhiro Murakami, Yasuhiro Irino, Makoto Nishimori, Sachiko Yoshikawa, Yutaro Seto, Tatsuro Ishida, Ken-Ichi Hirata. Effects of Elaidic Acid on HDL Cholesterol Uptake Capacity. Nutrients. 2021 Sep; 13(9):. doi: 10.3390/nu13093112. [PMID: 34578988]
  • Shanjie Wang, Wei Tian, Yige Liu, Guangcan Yan, Shaohong Fang, Yafeng Wang, Bo Yu. Temporal trend of circulating trans-fatty acids and risk of long-term mortality in general population. Clinical nutrition (Edinburgh, Scotland). 2021 03; 40(3):1095-1101. doi: 10.1016/j.clnu.2020.07.010. [PMID: 32768317]
  • Kenichi Ishibashi, Yoshihiro Takeda, Lisa Nakata, Fumihiko Hakuno, Shin-Ichiro Takahashi, Gen-Ichi Atsumi. Elaidate, a trans fatty acid, suppresses insulin signaling for glucose uptake in a manner distinct from that of stearate. Biochimie. 2020 Oct; 177(?):98-107. doi: 10.1016/j.biochi.2020.07.021. [PMID: 32822725]
  • Prapassorn Poolchanuan, Panida Unagul, Sanit Thongnest, Suthep Wiyakrutta, Nattaya Ngamrojanavanich, Chulabhorn Mahidol, Somsak Ruchirawat, Prasat Kittakoop. An anticonvulsive drug, valproic acid (valproate), has effects on the biosynthesis of fatty acids and polyketides in microorganisms. Scientific reports. 2020 06; 10(1):9300. doi: 10.1038/s41598-020-66251-y. [PMID: 32518288]
  • Simon Lecoutre, Valérie Montel, Emmanuelle Vallez, Charlène Pourpe, Anne Delmont, Elodie Eury, Marie Verbanck, Anne Dickes-Coopman, Pierre Daubersies, Jean Lesage, Christine Laborie, Anne Tailleux, Bart Staels, Philippe Froguel, Christophe Breton, Didier Vieau. Transcription profiling in the liver of undernourished male rat offspring reveals altered lipid metabolism pathways and predisposition to hepatic steatosis. American journal of physiology. Endocrinology and metabolism. 2019 12; 317(6):E1094-E1107. doi: 10.1152/ajpendo.00291.2019. [PMID: 31638854]
  • Takanori Honda, Tomoyuki Ohara, Masakazu Shinohara, Jun Hata, Ryuji Toh, Daigo Yoshida, Mao Shibata, Tatsuro Ishida, Yoichiro Hirakawa, Yasuhiro Irino, Satoko Sakata, Kazuhiro Uchida, Takanari Kitazono, Shigenobu Kanba, Ken-Ichi Hirata, Toshiharu Ninomiya. Serum elaidic acid concentration and risk of dementia: The Hisayama Study. Neurology. 2019 11; 93(22):e2053-e2064. doi: 10.1212/wnl.0000000000008464. [PMID: 31645469]
  • Antwi-Boasiako Oteng, Anke Loregger, Michel van Weeghel, Noam Zelcer, Sander Kersten. Industrial Trans Fatty Acids Stimulate SREBP2-Mediated Cholesterogenesis and Promote Non-Alcoholic Fatty Liver Disease. Molecular nutrition & food research. 2019 10; 63(19):e1900385. doi: 10.1002/mnfr.201900385. [PMID: 31327168]
  • Toshihiko Oshita, Ryuji Toh, Masakazu Shinohara, Kenta Mori, Yasuhiro Irino, Manabu Nagao, Tetsuya Hara, Hiromasa Otake, Tatsuro Ishida, Ken-Ichi Hirata. Elevated Serum Elaidic Acid Predicts Risk of Repeat Revascularization After Percutaneous Coronary Intervention in Japan. Circulation journal : official journal of the Japanese Circulation Society. 2019 04; 83(5):1032-1038. doi: 10.1253/circj.cj-18-1175. [PMID: 30867359]
  • Buyun Liu, Yangbo Sun, Guifeng Xu, Yang Du, Avanthi S Ajjarapu, Linda G Snetselaar, Wei Bao. Association between plasma concentrations of elaidic acid, a major trans fatty acid, and depression in a nationally representative sample of U.S. adults. Journal of affective disorders. 2019 Apr; 249(?):301-306. doi: 10.1016/j.jad.2019.02.032. [PMID: 30797122]
  • Farkas Sarnyai, Mária Berinkeiné Donkó, Judit Mátyási, Zsófia Gór-Nagy, Ildikó Marczi, Laura Simon-Szabó, Veronika Zámbó, Anna Somogyi, Tamás Csizmadia, Péter Lőw, Péter Szelényi, Éva Kereszturi, Blanka Tóth, Miklós Csala. Cellular toxicity of dietary trans fatty acids and its correlation with ceramide and diglyceride accumulation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Feb; 124(?):324-335. doi: 10.1016/j.fct.2018.12.022. [PMID: 30572061]
  • Véronique Chajès, Lorna J Gibson, Carine Biessy, Nadia Slimani, Gershim Asiki, Laure Dossus, Christopher P Wild, Robert Newton. Trends of serum phospholipid fatty acids over time in rural Uganda: evidence of nutritional transition?. The British journal of nutrition. 2019 01; 121(2):130-136. doi: 10.1017/s0007114518003227. [PMID: 30477593]
  • Qian Zhang, Yuwei Yang, Mingjun Hu, Haibo Li, Qi Zhong, Fen Huang. Relationship between plasma trans-fatty acid isomer concentrations and self-reported cardiovascular disease risk in US adults. International journal of food sciences and nutrition. 2018 Dec; 69(8):976-984. doi: 10.1080/09637486.2018.1428538. [PMID: 29376474]
  • Buyun Liu, Yangbo Sun, Linda G Snetselaar, Qi Sun, Quanhe Yang, Zefeng Zhang, Liegang Liu, Frank B Hu, Wei Bao. Association between plasma trans-fatty acid concentrations and diabetes in a nationally representative sample of US adults. Journal of diabetes. 2018 Aug; 10(8):653-664. doi: 10.1111/1753-0407.12652. [PMID: 29446544]
  • Samia Hadj Ahmed, Wafa Kharroubi, Nadia Kaoubaa, Amira Zarrouk, Fathi Batbout, Habib Gamra, Mohamed Fadhel Najjar, Gérard Lizard, Isabelle Hininger-Favier, Mohamed Hammami. Correlation of trans fatty acids with the severity of coronary artery disease lesions. Lipids in health and disease. 2018 Mar; 17(1):52. doi: 10.1186/s12944-018-0699-3. [PMID: 29544473]
  • Yomica L Powder-George, Faisal K Mohammed. GC-MS analysis of the bioactive phytoconstituents of various organic crude extracts from the seed kernels of Manilkara bidentata (balata) collected in Trinidad, W.I. Natural product research. 2018 Feb; 32(3):358-361. doi: 10.1080/14786419.2017.1354192. [PMID: 28714318]
  • C M Lezama-Dávila, A P Isaac-Márquez. Treating murine Kala-azar with a Mayan plant induces immunochemical changes. Parasite immunology. 2018 01; 40(1):. doi: 10.1111/pim.12495. [PMID: 28984989]
  • Kiyotaka Itcho, Yoko Yoshii, Haruya Ohno, Kenji Oki, Masakazu Shinohara, Yasuhiro Irino, Ryuji Toh, Tatsuro Ishida, Ken-Ichi Hirata, Masayasu Yoneda. Association between Serum Elaidic Acid Concentration and Insulin Resistance in Two Japanese Cohorts with Different Lifestyles. Journal of atherosclerosis and thrombosis. 2017 Dec; 24(12):1206-1214. doi: 10.5551/jat.39164. [PMID: 28484112]
  • Wei-Wei Ma, Lei Zhao, Lin-Hong Yuan, Huan-Ling Yu, Hui Wang, Xin-Yuan Gong, Feng Wei, Rong Xiao. Elaidic acid induces cell apoptosis through induction of ROS accumulation and endoplasmic reticulum stress in SH‑SY5Y cells. Molecular medicine reports. 2017 Dec; 16(6):9337-9346. doi: 10.3892/mmr.2017.7830. [PMID: 29152653]
  • Changwon Yang, Whasun Lim, Fuller W Bazer, Gwonhwa Song. Oleic acid stimulation of motility of human extravillous trophoblast cells is mediated by stearoyl-CoA desaturase-1 activity. Molecular human reproduction. 2017 11; 23(11):755-770. doi: 10.1093/molehr/gax051. [PMID: 29117333]
  • Meryam Debbabi, Amira Zarrouk, Maryem Bezine, Wiem Meddeb, Thomas Nury, Asmaa Badreddine, El Mostafa Karym, Randa Sghaier, Lionel Bretillon, Stéphane Guyot, Mohammad Samadi, Mustapha Cherkaoui-Malki, Boubker Nasser, Mondher Mejri, Sofien Ben-Hammou, Mohamed Hammami, Gérard Lizard. Comparison of the effects of major fatty acids present in the Mediterranean diet (oleic acid, docosahexaenoic acid) and in hydrogenated oils (elaidic acid) on 7-ketocholesterol-induced oxiapoptophagy in microglial BV-2 cells. Chemistry and physics of lipids. 2017 10; 207(Pt B):151-170. doi: 10.1016/j.chemphyslip.2017.04.002. [PMID: 28408132]
  • Yoshinori Nagasawa, Toshiro Shinke, Ryuji Toh, Tatsuro Ishida, Hiromasa Otake, Tomofumi Takaya, Daisuke Sugiyama, Takayosi Toba, Masaru Kuroda, Hachidai Takahashi, Daisuke Terashita, Natsuko Tahara, Yuto Shinkura, Kenzo Uzu, Daiji Kashiwagi, Koji Kuroda, Yuichiro Nagano, Hiroyuki Yamamoto, Kenichi Yanaka, Yoshiro Tsukiyama, Ken-Ichi Hirata. The impact of serum trans fatty acids concentration on plaque vulnerability in patients with coronary artery disease: Assessment via optical coherence tomography. Atherosclerosis. 2017 10; 265(?):312-317. doi: 10.1016/j.atherosclerosis.2017.06.922. [PMID: 28697847]
  • Haibo Li, Qian Zhang, Jiangen Song, Anshi Wang, Yunfei Zou, Lei Ding, Yufeng Wen. Plasma trans-fatty acids levels and mortality: a cohort study based on 1999-2000 National Health and Nutrition Examination Survey (NHANES). Lipids in health and disease. 2017 Sep; 16(1):176. doi: 10.1186/s12944-017-0567-6. [PMID: 28915883]
  • Ana Paula Simões-Wüst, Carolina Moltó-Puigmartí, Eugene Hjm Jansen, Martien Cjm van Dongen, Pieter C Dagnelie, Carel Thijs. Organic food consumption during pregnancy and its association with health-related characteristics: the KOALA Birth Cohort Study. Public health nutrition. 2017 Aug; 20(12):2145-2156. doi: 10.1017/s1368980017001215. [PMID: 28625206]
  • Yoshiro Wada, Shumi Yoshida-Yamamoto, Yoshinao Wada, Masahiro Nakayama, Nobuaki Mitsuda, Hiroyuki Kitajima. Trans fatty acid accumulation in the human placenta. Journal of mass spectrometry : JMS. 2017 03; 52(3):139-143. doi: 10.1002/jms.3910. [PMID: 28124800]
  • S Haj Ahmed, W Kharroubi, A Zarrouk, F Brahmi, T Nury, G Lizard, M Hammami. Protective effects of bezafibrate against elaidic acid-induced accumulation of lipid droplets in monocytic cells. Current research in translational medicine. 2017 Jan; 65(1):20-30. doi: 10.1016/j.retram.2016.08.001. [PMID: 28340693]
  • Yao Pan, Benxin Liu, Zeyuan Deng, Yawei Fan, Jing Li, Hongyan Li. Lipid Rafts Promote trans Fatty Acid-Induced Inflammation in Human Umbilical Vein Endothelial Cells. Lipids. 2017 01; 52(1):27-35. doi: 10.1007/s11745-016-4213-2. [PMID: 27853933]
  • Debanjan Tewari, Amal Kanti Bera. Modulation of the voltage-dependent anion channel of mitochondria by elaidic acid. Biochemical and biophysical research communications. 2016 08; 477(3):490-4. doi: 10.1016/j.bbrc.2016.06.067. [PMID: 27318085]
  • Kenichi Ishibashi, Kana Nehashi, Toshiyuki Oshima, Naoki Ohkura, Gen-Ichi Atsumi. Differentiation with elaidate tends to impair insulin-dependent glucose uptake and GLUT4 translocation in 3T3-L1 adipocytes. International journal of food sciences and nutrition. 2016; 67(2):99-110. doi: 10.3109/09637486.2016.1144721. [PMID: 26883301]
  • Marine S Da Silva, Pierre Julien, Louis Pérusse, Marie-Claude Vohl, Iwona Rudkowska. Natural Rumen-Derived trans Fatty Acids Are Associated with Metabolic Markers of Cardiac Health. Lipids. 2015 Sep; 50(9):873-82. doi: 10.1007/s11745-015-4055-3. [PMID: 26210489]
  • Rachael Dangarembizi, Eliton Chivandi, Sumaya Dawood, Kennedy Honey Erlwanger, Mazuru Gundidza, Michael Libala Magwa, Perkins Muredzi, Amidou Samie. Report-The fatty acid composition and physicochemical properties of the underutilised Cassia abbreviata seed oil. Pakistan journal of pharmaceutical sciences. 2015 May; 28(3):1005-8. doi: ". [PMID: 26004707]
  • Haribalan Perumalsamy, Myung Jin Jang, Jun-Ran Kim, Murugan Kadarkarai, Young-Joon Ahn. Larvicidal activity and possible mode of action of four flavonoids and two fatty acids identified in Millettia pinnata seed toward three mosquito species. Parasites & vectors. 2015 Apr; 8(?):237. doi: 10.1186/s13071-015-0848-8. [PMID: 25928224]
  • Dominika Jamioł-Milc, Ewa Stachowska, Tomasz Janus, Anna Barcz, Dariusz Chlubek. [Trans fatty acids (elaidic and vaccenic) in the human milk]. Pomeranian journal of life sciences. 2015; 61(1):58-63. doi: . [PMID: 27116857]
  • Dominika Jamioł-Milc, Ewa Stachowska, Tomasz Janus, Anna Barcz, Dariusz Chlubek. Elaidic acid and vaccenic acid in the plasma of pregnant women and umbilical blood plasma. Pomeranian journal of life sciences. 2015; 61(1):51-7. doi: 10.21164/pomjlifesci.52. [PMID: 27116856]
  • Véronique Chajès, Carine Biessy, Pietro Ferrari, Isabelle Romieu, Heinz Freisling, Inge Huybrechts, Augustin Scalbert, Bas Bueno de Mesquita, Dora Romaguera, Marc J Gunter, Paolo Vineis, Camilla Plambeck Hansen, Marianne Uhre Jakobsen, Françoise Clavel-Chapelon, Guy Fagherazzi, Marie-Christine Boutron-Ruault, Verana Katzke, Jasmine Neamat-Allah, Heiner Boeing, Ursula Bachlechner, Antonia Trichopoulou, Androniki Naska, Philippos Orfanos, Valeria Pala, Giovanna Masala, Amalia Mattiello, Guri Skeie, Elisabete Weiderpass, Antonio Agudo, Jose Maria Huerta, Eva Ardanaz, Maria Jose Sánchez, Miren Dorronsoro, Jose Ramon Quirós, Ingegerd Johansson, Anna Winkvist, Emily Sonested, Tim Key, Kay-Tee Khaw, Nicolas J Wareham, Petra H M Peeters, Nadia Slimani. Plasma elaidic acid level as biomarker of industrial trans fatty acids and risk of weight change: report from the EPIC study. PloS one. 2015; 10(2):e0118206. doi: 10.1371/journal.pone.0118206. [PMID: 25675445]
  • Kenta Mori, Tatsuro Ishida, Tomoyuki Yasuda, Minoru Hasokawa, Tomoko Monguchi, Maki Sasaki, Kensuke Kondo, Hideto Nakajima, Masakazu Shinohara, Toshiro Shinke, Yasuhiro Irino, Ryuji Toh, Kunihiro Nishimura, Ken-Ichi Hirata. Serum Trans-Fatty Acid Concentration Is Elevated in Young Patients With Coronary Artery Disease in Japan. Circulation journal : official journal of the Japanese Circulation Society. 2015; 79(9):2017-25. doi: 10.1253/circj.cj-14-0750. [PMID: 26166015]
  • Aida Maribel Chisaguano, Rosa Montes, Ana Isabel Castellote, Eva Morales, Jordi Júlvez, Jesús Vioque, Jordi Sunyer, Maria Carmen López-Sabater. Elaidic, vaccenic, and rumenic acid status during pregnancy: association with maternal plasmatic LC-PUFAs and atopic manifestations in infants. Pediatric research. 2014 Nov; 76(5):470-6. doi: 10.1038/pr.2014.119. [PMID: 25119335]
  • Ki-Hoon Park, Jong-Min Kim, Kyung-Hyun Cho. Elaidic acid (EA) generates dysfunctional high-density lipoproteins and consumption of EA exacerbates hyperlipidemia and fatty liver change in zebrafish. Molecular nutrition & food research. 2014 Jul; 58(7):1537-45. doi: 10.1002/mnfr.201300955. [PMID: 24863413]
  • Fei Shao, David A Ford. Elaidic acid increases hepatic lipogenesis by mediating sterol regulatory element binding protein-1c activity in HuH-7 cells. Lipids. 2014 May; 49(5):403-13. doi: 10.1007/s11745-014-3883-x. [PMID: 24481861]
  • Huan Rao, Li-Xin Ma, Ting-Ting Xu, Jing Li, Ze-Yuan Deng, Ya-Wei Fan, Hong-Yan Li. Lipid rafts and Fas/FasL pathway may involve in elaidic acid-induced apoptosis of human umbilical vein endothelial cells. Journal of agricultural and food chemistry. 2014 Jan; 62(3):798-807. doi: 10.1021/jf404834e. [PMID: 24364735]
  • Janelle R Zacherl, Stephanie J Mihalik, Donald H Chace, Tyson C Christensen, Lisa J Robinson, Harry C Blair. Elaidate, an 18-carbon trans-monoenoic fatty acid, inhibits β-oxidation in human peripheral blood macrophages. Journal of cellular biochemistry. 2014 Jan; 115(1):62-70. doi: 10.1002/jcb.24633. [PMID: 23904193]
  • Hanene Ghazghazi, Chedia Aouadhi, Leila Riahi, Abderrazak Maaroufi, Brahim Hasnaoui. Fatty acids composition of Tunisian Ziziphus lotus L. (Desf.) fruits and variation in biological activities between leaf and fruit extracts. Natural product research. 2014; 28(14):1106-10. doi: 10.1080/14786419.2014.913244. [PMID: 24805194]
  • Lone Vendel Nielsen, Toke P Krogager, Clifford Young, Carla Ferreri, Chryssostomos Chatgilialoglu, Ole Nørregaard Jensen, Jan J Enghild. Effects of elaidic acid on lipid metabolism in HepG2 cells, investigated by an integrated approach of lipidomics, transcriptomics and proteomics. PloS one. 2013; 8(9):e74283. doi: 10.1371/journal.pone.0074283. [PMID: 24058537]
  • Anan Yaghmur, Barbara Sartori, Michael Rappolt. Self-assembled nanostructures of fully hydrated monoelaidin-elaidic acid and monoelaidin-oleic acid systems. Langmuir : the ACS journal of surfaces and colloids. 2012 Jul; 28(26):10105-19. doi: 10.1021/la3019716. [PMID: 22690845]
  • Kevin A Harvey, Candace L Walker, Zhidong Xu, Phillip Whitley, Rafat A Siddiqui. Trans fatty acids: induction of a pro-inflammatory phenotype in endothelial cells. Lipids. 2012 Jul; 47(7):647-57. doi: 10.1007/s11745-012-3681-2. [PMID: 22684911]
  • Toke Peter Krogager, Lone Vendel Nielsen, Steffen Bak, Clifford Young, Carla Ferreri, Ole Nørregaard Jensen, Peter Højrup, Vladimiros Thoma, Ida B Thøgersen, Jan J Enghild. Identification of a potential biomarker panel for the intake of the common dietary trans fat elaidic acid (trans∆9-C18:1). Journal of proteomics. 2012 May; 75(9):2685-96. doi: 10.1016/j.jprot.2012.03.023. [PMID: 22483997]
  • Natalie Fournier, Nesrine Attia, Delphine Rousseau-Ralliard, Benoît Vedie, Frédéric Destaillats, Alain Grynberg, Jean-Louis Paul. Deleterious impact of elaidic fatty acid on ABCA1-mediated cholesterol efflux from mouse and human macrophages. Biochimica et biophysica acta. 2012 Feb; 1821(2):303-12. doi: 10.1016/j.bbalip.2011.10.005. [PMID: 22074701]
  • Véronique Chajès, Carine Biessy, Graham Byrnes, Geneviève Deharveng, Mitra Saadatian-Elahi, Mazda Jenab, Petra H M Peeters, Marga Ocké, H Bas Bueno-de-Mesquita, Ingegerd Johansson, Göran Hallmans, Jonas Manjer, Elisabet Wirfält, Paula Jakszyn, Carlos A González, Jose-Maria Huerta, Carmen Martinez, Pilar Amiano, Laudina Rodriguez Suárez, Eva Ardanaz, Anne Tjønneland, Jytte Halkjaer, Kim Overvad, Marianne Uhre Jakobsen, Franco Berrino, Valeria Pala, Domenico Palli, Rosario Tumino, Paolo Vineis, Maria Santucci de Magistris, Elisabeth A Spencer, Francesca L Crowe, Sheila Bingham, Kay-Tee Khaw, Jakob Linseisen, Sabine Rohrmann, Heiner Boeing, Ute Nöethlings, Karina Standahl Olsen, Guri Skeie, Eiliv Lund, Antonia Trichopoulou, Dimosthenis Zilis, Erifili Oustoglou, Françoise Clavel-Chapelon, Elio Riboli, Nadia Slimani. Ecological-level associations between highly processed food intakes and plasma phospholipid elaidic acid concentrations: results from a cross-sectional study within the European prospective investigation into cancer and nutrition (EPIC). Nutrition and cancer. 2011 Nov; 63(8):1235-50. doi: 10.1080/01635581.2011.617530. [PMID: 22043987]
  • Zhen-Yu Du, Pascal Degrace, Joseph Gresti, Olivier Loreau, Pierre Clouet. Vaccenic and elaidic acid equally esterify into triacylglycerols, but differently into phospholipids of fed rat liver cells. Lipids. 2011 Jul; 46(7):647-57. doi: 10.1007/s11745-011-3569-6. [PMID: 21614647]
  • Megan R Ruth, Ye Wang, Howe-Ming Yu, Susan Goruk, Martin J Reaney, Spencer D Proctor, Donna F Vine, Catherine J Field. Vaccenic and elaidic acid modify plasma and splenocyte membrane phospholipids and mitogen-stimulated cytokine production in obese insulin resistant JCR: LA-cp rats. Nutrients. 2010 02; 2(2):181-97. doi: 10.3390/nu2020181. [PMID: 22254015]
  • Smita P Soni, Jesse A Ward, Stephanie E Sen, Scott E Feller, Stephen R Wassall. Effect of trans unsaturation on molecular organization in a phospholipid membrane. Biochemistry. 2009 Nov; 48(46):11097-107. doi: 10.1021/bi901179r. [PMID: 19817487]
  • Sean W P Koppe, Marc Elias, Richard H Moseley, Richard M Green. Trans fat feeding results in higher serum alanine aminotransferase and increased insulin resistance compared with a standard murine high-fat diet. American journal of physiology. Gastrointestinal and liver physiology. 2009 Aug; 297(2):G378-84. doi: 10.1152/ajpgi.90543.2008. [PMID: 19541924]
  • Suzanne E Dorfman, Didier Laurent, John S Gounarides, Xue Li, Tara L Mullarkey, Erik C Rocheford, Farid Sari-Sarraf, Erica A Hirsch, Thomas E Hughes, S Renee Commerford. Metabolic implications of dietary trans-fatty acids. Obesity (Silver Spring, Md.). 2009 Jun; 17(6):1200-7. doi: 10.1038/oby.2008.662. [PMID: 19584878]
  • Véronique Chajès, Anne C M Thiébaut, Maxime Rotival, Estelle Gauthier, Virginie Maillard, Marie-Christine Boutron-Ruault, Virginie Joulin, Gilbert M Lenoir, Françoise Clavel-Chapelon. Association between serum trans-monounsaturated fatty acids and breast cancer risk in the E3N-EPIC Study. American journal of epidemiology. 2008 Jun; 167(11):1312-20. doi: 10.1093/aje/kwn069. [PMID: 18390841]
  • O Vögler, A López-Bellan, R Alemany, S Tofé, M González, J Quevedo, V Pereg, F Barceló, P V Escriba. Structure-effect relation of C18 long-chain fatty acids in the reduction of body weight in rats. International journal of obesity (2005). 2008 Mar; 32(3):464-73. doi: 10.1038/sj.ijo.0803768. [PMID: 18059405]
  • Anders Björkbom, Bodil Ramstedt, J Peter Slotte. Phosphatidylcholine and sphingomyelin containing an elaidoyl fatty acid can form cholesterol-rich lateral domains in bilayer membranes. Biochimica et biophysica acta. 2007 Jul; 1768(7):1839-47. doi: 10.1016/j.bbamem.2007.04.009. [PMID: 17499576]
  • Yumi Kondoh, Teruo Kawada, Reiko Urade. Activation of caspase 3 in HepG2 cells by elaidic acid (t18:1). Biochimica et biophysica acta. 2007 Apr; 1771(4):500-5. doi: 10.1016/j.bbalip.2007.01.012. [PMID: 17321792]
  • Hong-Zhen Hu, Rui Xiao, Chunbo Wang, Na Gao, Craig K Colton, Jackie D Wood, Michael X Zhu. Potentiation of TRPV3 channel function by unsaturated fatty acids. Journal of cellular physiology. 2006 Jul; 208(1):201-12. doi: 10.1002/jcp.20648. [PMID: 16557504]
  • Hannu Jokela, Anne Kalela, Mari Lilja, Mia Salmi, Terho Lehtimäki, Tarja Kunnas, Klaus Teisala, Reijo Punnonen, Seppo T Nikkari. Sequentially combined estradiol valerate plus levonorgestrel therapy decreases 18:1 trans-fatty acid content of plasma lipids in healthy postmenopausal women. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2005 Dec; 21(6):360-5. doi: 10.1080/09513590500467361. [PMID: 16390785]
  • Nadège Cassagno, Antonio Palos-Pinto, Pierre Costet, Dominique Breilh, Michel Darmon, Annie M Bérard. Low amounts of trans 18:1 fatty acids elevate plasma triacylglycerols but not cholesterol and alter the cellular defence to oxidative stress in mice. The British journal of nutrition. 2005 Sep; 94(3):346-52. doi: 10.1079/bjn20051512. [PMID: 16176604]
  • Baukje de Roos, Ilse Duivenvoorden, Garry Rucklidge, Martin Reid, Karen Ross, Robert-Jan A N Lamers, Peter J Voshol, Louis M Havekes, Bas Teusink. Response of apolipoprotein E*3-Leiden transgenic mice to dietary fatty acids: combining liver proteomics with physiological data. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2005 May; 19(7):813-5. doi: 10.1096/fj.04-2974fje. [PMID: 15755870]
  • Susan Hazels Mitmesser, Timothy P Carr. Trans fatty acids alter the lipid composition and size of apoB-100-containing lipoproteins secreted by HepG2 cells. The Journal of nutritional biochemistry. 2005 Mar; 16(3):178-83. doi: 10.1016/j.jnutbio.2004.11.004. [PMID: 15741053]
  • Sérgio S Funari, Francisca Barceló, Pablo V Escribá. Effects of oleic acid and its congeners, elaidic and stearic acids, on the structural properties of phosphatidylethanolamine membranes. Journal of lipid research. 2003 Mar; 44(3):567-75. doi: 10.1194/jlr.m200356-jlr200. [PMID: 12562874]
  • Julie M Proell, Erin E Mosley, Gary L Powell, Thomas C Jenkins. Isomerization of stable isotopically labeled elaidic acid to cis and trans monoenes by ruminal microbes. Journal of lipid research. 2002 Dec; 43(12):2072-6. doi: 10.1194/jlr.m200284-jlr200. [PMID: 12454268]
  • Jennifer C Lovejoy, Steven R Smith, Catherine M Champagne, Marlene M Most, Michael Lefevre, James P DeLany, Yvonne M Denkins, Jennifer C Rood, Johannes Veldhuis, George A Bray. Effects of diets enriched in saturated (palmitic), monounsaturated (oleic), or trans (elaidic) fatty acids on insulin sensitivity and substrate oxidation in healthy adults. Diabetes care. 2002 Aug; 25(8):1283-8. doi: 10.2337/diacare.25.8.1283. [PMID: 12145222]
  • A Haastrup, C A Gadegbeku, D Zhang, Y V Mukhin, E L Greene, A A Jaffa, B M Egan. Lipids stimulate the production of 6-keto-prostaglandin f(1alpha) in human dorsal hand veins. Hypertension (Dallas, Tex. : 1979). 2001 Oct; 38(4):858-63. doi: 10.1161/hy1001.092615. [PMID: 11641299]
  • D S Roe, C Vianey-Saban, S Sharma, M T Zabot, C R Roe. Oxidation of unsaturated fatty acids by human fibroblasts with very-long-chain acyl-CoA dehydrogenase deficiency: aspects of substrate specificity and correlation with clinical phenotype. Clinica chimica acta; international journal of clinical chemistry. 2001 Oct; 312(1-2):55-67. doi: 10.1016/s0009-8981(01)00594-0. [PMID: 11580910]
  • G W Meijer, A van Tol, T J van Berkel, J A Weststrate. Effect of dietary elaidic versus vaccenic acid on blood and liver lipids in the hamster. Atherosclerosis. 2001 Jul; 157(1):31-40. doi: 10.1016/s0021-9150(00)00661-4. [PMID: 11427201]
  • E Klein, N Weber. In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids. Journal of agricultural and food chemistry. 2001 Mar; 49(3):1224-7. doi: 10.1021/jf000725m. [PMID: 11312840]
  • G K Balendiran, F Schnutgen, G Scapin, T Borchers, N Xhong, K Lim, R Godbout, F Spener, J C Sacchettini. Crystal structure and thermodynamic analysis of human brain fatty acid-binding protein. The Journal of biological chemistry. 2000 Sep; 275(35):27045-54. doi: 10.1074/jbc.m003001200. [PMID: 10854433]
  • N Weber, E Klein, K Vosmann, K D Mukherjee. Antioxidants eliminate stereomutation and thioether formation during lipase-catalyzed thioesterification and transthioesterification for the preparation of uniform cis- and trans-unsaturated thioesters. Chemistry and physics of lipids. 2000 Apr; 105(2):215-23. doi: 10.1016/s0009-3084(00)00125-0. [PMID: 10823469]
  • R Borgdorf, S Warwel. Substrate selectivity of various lipases in the esterification of cis- and trans-9-octadecenoic acid. Applied microbiology and biotechnology. 1999 Apr; 51(4):480-5. doi: 10.1007/s002530051420. [PMID: 10341430]
  • G Lu, E L Greene, T Nagai, B M Egan. Reactive oxygen species are critical in the oleic acid-mediated mitogenic signaling pathway in vascular smooth muscle cells. Hypertension (Dallas, Tex. : 1979). 1998 Dec; 32(6):1003-10. doi: 10.1161/01.hyp.32.6.1003. [PMID: 9856964]
  • H M Vidgren, A M Louheranta, J J Agren, U S Schwab, M I Uusitupa. Divergent incorporation of dietary trans fatty acids in different serum lipid fractions. Lipids. 1998 Oct; 33(10):955-62. doi: 10.1007/s11745-998-0292-9. [PMID: 9832074]
  • T V Fungwe, B J Kudchodkar, A G Lacko, L Dory. Fatty acids modulate lecithin:cholesterol acyltransferase secretion independently of effects on triglyceride secretion in primary rat hepatocytes. The Journal of nutrition. 1998 Aug; 128(8):1270-5. doi: 10.1093/jn/128.8.1270. [PMID: 9687543]
  • M A Williams, I B King, T K Sorensen, R W Zingheim, B L Troyer, A M Zebelman, D A Luthy. Risk of preeclampsia in relation to elaidic acid (trans fatty acid) in maternal erythrocytes. Gynecologic and obstetric investigation. 1998 Aug; 46(2):84-7. doi: 10.1159/000010007. [PMID: 9701685]
  • D Schwarz, P Kisselev, W Pfeil, S Pisch, U Bornscheuer, R D Schmid. Evidence that nonbilayer phase propensity of the membrane is important for the side chain cleavage activity of cytochrome P450SCC. Biochemistry. 1997 Nov; 36(46):14262-70. doi: 10.1021/bi9714262. [PMID: 9369499]
  • T Koga, M Nonaka, J Y Gu, M Sugano. Linoleic and alpha-linolenic acids differently modify the effects of elaidic acid on polyunsaturated fatty acid metabolism and some immune indices in rats. The British journal of nutrition. 1997 Apr; 77(4):645-56. doi: 10.1079/bjn19970062. [PMID: 9155511]
  • J Thompson, N Winter, D Terwey, J Bratt, L Banaszak. The crystal structure of the liver fatty acid-binding protein. A complex with two bound oleates. The Journal of biological chemistry. 1997 Mar; 272(11):7140-50. doi: 10.1074/jbc.272.11.7140. [PMID: 9054409]
  • P Khosla, T Hajri, A Pronczuk, K C Hayes. Replacing dietary palmitic acid with elaidic acid (t-C18:1 delta9) depresses HDL and increases CETP activity in cebus monkeys. The Journal of nutrition. 1997 Mar; 127(3):531S-536S. doi: 10.1093/jn/127.3.531s. [PMID: 9082041]
  • K Sundram, A Ismail, K C Hayes, R Jeyamalar, R Pathmanathan. Trans (elaidic) fatty acids adversely affect the lipoprotein profile relative to specific saturated fatty acids in humans. The Journal of nutrition. 1997 Mar; 127(3):514S-520S. doi: 10.1093/jn/127.3.514s. [PMID: 9082038]
  • T Seppänen-Laakso, I Laakso, P Backlund, H Vanhanen, J Viikari. Elaidic and trans-vaccenic acids in plasma phospholipids as indicators of dietary intake of 18:1 trans-fatty acids. Journal of chromatography. B, Biomedical applications. 1996 Dec; 687(2):371-8. doi: 10.1016/s0378-4347(96)00256-3. [PMID: 9017460]
  • G F Watts, P Jackson, V Burke, B Lewis. Dietary fatty acids and progression of coronary artery disease in men. The American journal of clinical nutrition. 1996 Aug; 64(2):202-9. doi: 10.1093/ajcn/64.2.202. [PMID: 8694021]
  • O Holmqvist. Trans fatty acids in hardened vegetable oils. Atherosclerosis. 1996 Feb; 120(1-2):245-7. doi: 10.1016/0021-9150(95)05654-8. [PMID: 8645366]
  • R N Lewis, R N McElhaney. Acholeplasma laidlawii B membranes contain a lipid (glycerylphosphoryldiglucosyldiacylglycerol) which forms micelles rather than lamellar or reversed phases when dispersed in water. Biochemistry. 1995 Oct; 34(42):13818-24. doi: 10.1021/bi00042a013. [PMID: 7577975]
  • P J Foht, Q M Tran, R N Lewis, R N McElhaney. Quantitation of the phase preferences of the major lipids of the Acholeplasma laidlawii B membrane. Biochemistry. 1995 Oct; 34(42):13811-7. doi: 10.1021/bi00042a012. [PMID: 7577974]
  • R L Wolff. Structural importance of the cis-5 ethylenic bond in the endogenous desaturation product of dietary elaidic acid, cis-5,trans-9 18:2 acid, for the acylation of rat mitochondria phosphatidylinositol. Lipids. 1995 Oct; 30(10):893-8. doi: 10.1007/bf02537479. [PMID: 8538375]
  • K D Cromer, T C Jenkins, E J Thies. Replacing cis octadecenoic acid with trans isomers in media containing rat adipocytes stimulates lipolysis and inhibits glucose utilization. The Journal of nutrition. 1995 Sep; 125(9):2394-9. doi: 10.1093/jn/125.9.2394. [PMID: 7666258]
  • M Krugliak, E Deharo, G Shalmiev, M Sauvain, C Moretti, H Ginsburg. Antimalarial effects of C18 fatty acids on Plasmodium falciparum in culture and on Plasmodium vinckei petteri and Plasmodium yoelii nigeriensis in vivo. Experimental parasitology. 1995 Aug; 81(1):97-105. doi: 10.1006/expr.1995.1097. [PMID: 7628573]
  • T Decsi, B Koletzko. Do trans fatty acids impair linoleic acid metabolism in children?. Annals of nutrition & metabolism. 1995; 39(1):36-41. doi: 10.1159/000177840. [PMID: 7872654]
  • M Abbey, P J Nestel. Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet. Atherosclerosis. 1994 Mar; 106(1):99-107. doi: 10.1016/0021-9150(94)90086-8. [PMID: 8018112]
  • P Nestel, M Noakes, B Belling, R McArthur, P Clifton, E Janus, M Abbey. Plasma lipoprotein lipid and Lp[a] changes with substitution of elaidic acid for oleic acid in the diet. Journal of lipid research. 1992 Jul; 33(7):1029-36. doi: 10.1016/s0022-2275(20)41418-x. [PMID: 1431582]
  • B Koletzko. Trans fatty acids may impair biosynthesis of long-chain polyunsaturates and growth in man. Acta paediatrica (Oslo, Norway : 1992). 1992 Apr; 81(4):302-6. doi: 10.1111/j.1651-2227.1992.tb12230.x. [PMID: 1606388]
  • N C Johnston, H Goldfine. Replacement of the aliphatic chains of Clostridium acetobutylicum by exogenous fatty acids: regulation of phospholipid and glycolipid composition. Journal of bacteriology. 1992 Mar; 174(6):1848-53. doi: 10.1128/jb.174.6.1848-1853.1992. [PMID: 1548233]
  • M J Díaz-Guerra, M Junco, L Boscá. Oleic acid promotes changes in the subcellular distribution of protein kinase C in isolated hepatocytes. The Journal of biological chemistry. 1991 Dec; 266(35):23568-76. doi: 10.1016/s0021-9258(18)54321-0. [PMID: 1748635]
  • M J Steinbeck, J M Robinson, M J Karnovsky. Activation of the neutrophil NADPH-oxidase by free fatty acids requires the ionized carboxyl group and partitioning into membrane lipid. Journal of leukocyte biology. 1991 Apr; 49(4):360-8. doi: 10.1002/jlb.49.4.360. [PMID: 1848271]
  • R L Wolff, N A Combe, B Entressangles. [Time-course changes in the alkenyl and acyl chain composition of plasmalogens from the heart and kidneys of rats ingesting trielaidin]. Reproduction, nutrition, developpement. 1988; 28(3A):603-15. doi: . [PMID: 3406522]
  • A Bernard, B Echinard, H Carlier. Differential intestinal absorption of two fatty acid isomers: elaidic and oleic acids. The American journal of physiology. 1987 Dec; 253(6 Pt 1):G751-9. doi: 10.1152/ajpgi.1987.253.6.g751. [PMID: 3425717]
  • M D Rosenthal, M A Doloresco. The effects of trans fatty acids on fatty acyl delta 5 desaturation by human skin fibroblasts. Lipids. 1984 Nov; 19(11):869-74. doi: 10.1007/bf02534517. [PMID: 6521610]