FA 18:1 (BioDeep_00000009097)

 

Secondary id: BioDeep_00000003249, BioDeep_00000169696, BioDeep_00000264844, BioDeep_00000400559, BioDeep_00000593468, BioDeep_00000869031, BioDeep_00001883978

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


7-(2-octylcyclopropyl)heptanoic acid

化学式: C18H34O2 (282.2558664)
中文名称: 反式-11-十八烯酸, 反式十八烷酸, (C16-18、C18-不饱和)脂肪酸, 石油硬脂酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.33%

分子结构信息

SMILES: C(/C=C/CCCCCC)CCCCCCCCC(=O)O
InChI: InChI=1S/C18H34O2/c19-18-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-17-20-18/h1-17H2

描述信息

trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.
trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

同义名列表

111 个代谢物同义名

18-Octadecanolide; FA 18:1; 13-cyclopentyltridecanoic acid; Cyclopentanetridecanoic acid; 7-(2-octylcyclopropyl)heptanoic acid; Dihydromalvalic acid; 10-Octadecenoic acid; 15-methyl-4-heptadecenoic acid; 17:1(4)(15Me); 14Z-octadecenoic acid; 18:1(14Z); C18:1n-4; 14E-octadecenoic acid; 18:1(14E); 13E-octadecenoic acid; 18:1(13E); C18:1n-5; 5Z-octadecenoic acid; C18:1n-13; 4Z-octadecenoic acid; C18:1n-14; 3Z-octadecenoic acid; C18:1n-15; 17-octadecenoic acid; C18:1n-1; 16Z-octadecenoic acid; C18:1n-2; 15Z-octadecenoic acid; C18:1n-3; 13Z-octadecenoic acid; trans-16-octadecenoic acid; 16E-octadecenoic acid; trans-15-octadecenoic acid; 15E-octadecenoic acid; trans-12-octadecenoic acid; 12E-octadecenoic acid; trans-12-elaidic acid; C18:1n-6; cis-12-octadecenoic acid; 12Z-octadecenoic acid; cis-12-oleic acid; trans-11-octadecenoic acid; 11E-octadecenoic acid; trans-Vaccenic acid; Vaccensaure; C18:1n-7; cis-11-octadecenoic acid; 11Z-octadecenoic acid; cis-vaccenic acid; Asclepic acid; trans-10-Octadecenoic acid; linseed oil fatty acids; 10E-octadecenoic acid; 10(E)-OME; C18:1n-8; cis-10-Octadecenoic acid; 10Z-octadecenoic acid; cis-10-oleic acid; Isooleic acid; trans-9-octadecenoic acid; 9E-octadecenoic acid; trans-Elaidic acid; trans-Oleic acid; Elaidinic acid; 9-elaidic acid; C18:1n-9; trans-8-octadecenoic acid; trans-8-elaidic acid; 8E-octadecenoic acid; C18:1n-10; cis-8-octadecenoic acid; 8Z-octadecenoic acid; cis-8-oleic acid; trans-7-octadecenoic acid; 7E-octadecenoic acid; C18:1n-11; cis-7-octadecenoic acid; 7Z-octadecenoic acid; trans-6-octadecenoic acid; (6E)-6-Octadecenoic acid; 6E-octadecenoic acid; Petroselaidic acid; C18:1n-12; trans-5-octadecenoic acid; 5E-octadecylenic acid; 5E-octadecenoic acid; Thalictric acid; 4-octadecylenic acid; 4-octadecenoic acid; 3-octadecylenic acid; 3-octadecenoic acid; trans-2-octadecenoic acid; 2Z-octadecenoic acid; trans-2-oleic acid; C18:1n-16; cis-2-octadecenoic acid; 16-methyl-6Z-heptadecenoic acid; Isooctadecenoic acid; isocis-6-oleic acid; 16-methyl-8Z-heptadecenoic acid; isocis-8-oleic acid; 7-methyl-12-heptadecenoic acid; 17:1(12)(7Me); 9-methyl-6-heptadecenoic acid; 17:1(6)(9Me); 16-methyl-4-heptadecenoic acid; 17:1(4)(16Me); 2-methyl-16-heptadecenoic acid; omega-Cycloheptylundecanoic acid; 11-Cycloheptylundecanoic acid; (11E)-Octadecenoic acid



数据库引用编号

146 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

136 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。



文献列表

  • Ahmed Hajib, Said El Harkaoui, Hasnae Choukri, Aya Khouchlaa, Sarra Aourabi, Naoual El Menyiy, Abdelhakim Bouyahya, Bertrand Matthaeus. Apiaceae Family an Important Source of Petroselinic Fatty Acid: Abundance, Biosynthesis, Chemistry, and Biological Proprieties. Biomolecules. 2023 11; 13(11):. doi: 10.3390/biom13111675. [PMID: 38002357]
  • Genlai Dong, Shijie Xu, Shuobo Shi. De Novo Biosynthesis of Free Vaccenic Acid with a Low Content of Oleic Acid in Saccharomyces cerevisiae. Journal of agricultural and food chemistry. 2023 Nov; 71(43):16204-16211. doi: 10.1021/acs.jafc.3c04793. [PMID: 37856078]
  • 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]
  • P G Toral, G Hervás, P Frutos. Effect of lipid supplementation on the endogenous synthesis of milk cis-9,trans-11 conjugated linoleic acid in dairy sheep and goats: A tracer assay with 13C-vaccenic acid. Journal of dairy science. 2022 Jan; 105(1):255-268. doi: 10.3168/jds.2021-20728. [PMID: 34763909]
  • 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]
  • N L Weir, B T Steffen, W Guan, L M Johnson, L Djousse, K J Mukamal, M Y Tsai. Circulating omega-7 fatty acids are differentially related to metabolic dysfunction and incident type II diabetes: The Multi-Ethnic Study of Atherosclerosis (MESA). Diabetes & metabolism. 2020 09; 46(4):319-325. doi: 10.1016/j.diabet.2019.10.005. [PMID: 31706030]
  • Zheng Yang, Changsheng Li, Qingli Jia, Cuizhu Zhao, David C Taylor, Dawei Li, Meng Zhang. Transcriptome Analysis Reveals Candidate Genes for Petroselinic Acid Biosynthesis in Fruits of Coriandrum sativum L. Journal of agricultural and food chemistry. 2020 May; 68(19):5507-5520. doi: 10.1021/acs.jafc.0c01487. [PMID: 32320606]
  • Ilse G Pranger, Eva Corpeleijn, Frits A J Muskiet, Ido P Kema, Cécile Singh-Povel, Stephan J L Bakker. Circulating fatty acids as biomarkers of dairy fat intake: data from the lifelines biobank and cohort study. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2019 Jun; 24(4):360-372. doi: 10.1080/1354750x.2019.1583770. [PMID: 30773031]
  • 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]
  • 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]
  • Tomasz Olszowski, Izabela Gutowska, Irena Baranowska-Bosiacka, Agnieszka Łukomska, Arleta Drozd, Dariusz Chlubek. Cadmium Alters the Concentration of Fatty Acids in THP-1 Macrophages. Biological trace element research. 2018 Mar; 182(1):29-36. doi: 10.1007/s12011-017-1071-6. [PMID: 28600650]
  • 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]
  • Helen K Woodfield, Drew Sturtevant, Ljudmilla Borisjuk, Eberhard Munz, Irina A Guschina, Kent Chapman, John L Harwood. Spatial and Temporal Mapping of Key Lipid Species in Brassica napus Seeds. Plant physiology. 2017 04; 173(4):1998-2009. doi: 10.1104/pp.16.01705. [PMID: 28188274]
  • Juergen K R Wanner, Do N Dai, Le T Huong, Nguyen V Hung, Erich Schmidt, Leopold Jirovetz. Fatty Acid Methyl Ester Composition of Some Turkish Apiaceae Seed Oils: New Sources for Petroselinic Acid. Natural product communications. 2016 Nov; 11(11):1697-1700. doi: ". [PMID: 30475510]
  • S Jaturasitha, N Chaiwang, A Kayan, M Kreuzer. Nutritional strategies to improve the lipid composition of meat, with emphasis on Thailand and Asia. Meat science. 2016 Oct; 120(?):157-166. doi: 10.1016/j.meatsci.2016.04.014. [PMID: 27127010]
  • Evelien Uitterhaegen, Klicia A Sampaio, Elisabeth I P Delbeke, Wim De Greyt, Muriel Cerny, Philippe Evon, Othmane Merah, Thierry Talou, Christian V Stevens. Characterization of French Coriander Oil as Source of Petroselinic Acid. Molecules (Basel, Switzerland). 2016 Sep; 21(9):. doi: 10.3390/molecules21091202. [PMID: 27617992]
  • W Schlörmann, M Birringer, A Lochner, S Lorkowski, I Richter, C Rohrer, M Glei. In vitro fermentation of nuts results in the formation of butyrate and c9,t11 conjugated linoleic acid as chemopreventive metabolites. European journal of nutrition. 2016 Sep; 55(6):2063-73. doi: 10.1007/s00394-015-1020-0. [PMID: 26286349]
  • Miriam Jacome-Sosa, Claudia Vacca, Rabban Mangat, Abdoulaye Diane, Randy C Nelson, Martin J Reaney, Jianheng Shen, Jonathan M Curtis, Donna F Vine, Catherine J Field, Miki Igarashi, Daniele Piomelli, Sebastiano Banni, Spencer D Proctor. Vaccenic acid suppresses intestinal inflammation by increasing anandamide and related N-acylethanolamines in the JCR:LA-cp rat. Journal of lipid research. 2016 Apr; 57(4):638-49. doi: 10.1194/jlr.m066308. [PMID: 26891736]
  • Xiaofeng Wang, Joel Gupta, Matthew Kerslake, Gina Rayat, Spencer D Proctor, Catherine B Chan. Trans-11 vaccenic acid improves insulin secretion in models of type 2 diabetes in vivo and in vitro. Molecular nutrition & food research. 2016 Apr; 60(4):846-57. doi: 10.1002/mnfr.201500783. [PMID: 27061233]
  • Sarah K Gebauer, Frédéric Destaillats, Fabiola Dionisi, Ronald M Krauss, David J Baer. Vaccenic acid and trans fatty acid isomers from partially hydrogenated oil both adversely affect LDL cholesterol: a double-blind, randomized controlled trial. The American journal of clinical nutrition. 2015 Dec; 102(6):1339-46. doi: 10.3945/ajcn.115.116129. [PMID: 26561632]
  • Luís Miguel Rodríguez-Alcalá, Irma Ares, Javier Fontecha, Manuela Juarez, Victor Castellano, María Rosa Martínez-Larrañaga, Arturo Anadón, María Aránzazu Martínez. Oral Absorption and Disposition of alpha-Linolenic, Rumenic and Vaccenic Acids After Administration as a Naturally Enriched Goat Dairy Fat to Rats. Lipids. 2015 Jul; 50(7):659-66. doi: 10.1007/s11745-015-4034-8. [PMID: 26044769]
  • 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]
  • Hui Tao, Guangjun Chang, Tianle Xu, Huajian Zhao, Kai Zhang, Xiangzhen Shen. Feeding a High Concentrate Diet Down-Regulates Expression of ACACA, LPL and SCD and Modifies Milk Composition in Lactating Goats. PloS one. 2015; 10(6):e0130525. doi: 10.1371/journal.pone.0130525. [PMID: 26086219]
  • 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]
  • Young-Ah Moon, Courtney R Ochoa, Matthew A Mitsche, Robert E Hammer, Jay D Horton. Deletion of ELOVL6 blocks the synthesis of oleic acid but does not prevent the development of fatty liver or insulin resistance. Journal of lipid research. 2014 Dec; 55(12):2597-605. doi: 10.1194/jlr.m054353. [PMID: 25281760]
  • 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]
  • M Miriam Jacome-Sosa, Faye Borthwick, Rabban Mangat, Richard Uwiera, Martin J Reaney, Jianheng Shen, Ariel D Quiroga, René L Jacobs, Richard Lehner, Spencer D Proctor, Randal C Nelson. Diets enriched in trans-11 vaccenic acid alleviate ectopic lipid accumulation in a rat model of NAFLD and metabolic syndrome. The Journal of nutritional biochemistry. 2014 Jul; 25(7):692-701. doi: 10.1016/j.jnutbio.2014.02.011. [PMID: 24775093]
  • Roman A Sidorov, Anatoly V Zhukov, Vasily P Pchelkin, Andrei G Vereshchagin, Vladimir D Tsydendambaev. Dynamics of fatty-acid composition of neutral acylglycerols in maturing euonymus fruits. Chemistry & biodiversity. 2014 Apr; 11(4):581-92. doi: 10.1002/cbdv.201300305. [PMID: 24706628]
  • A Ishlak, A A AbuGhazaleh, M Günal. Short communication: Effect of blackberry and pomegranate oils on vaccenic acid formation in a single-flow continuous culture fermentation system. Journal of dairy science. 2014 Feb; 97(2):1067-71. doi: 10.3168/jds.2013-6860. [PMID: 24342694]
  • Vincent Rioux, Frédérique Pédrono, Hélène Blanchard, Cécile Duby, Nathalie Boulier-Monthéan, Laurence Bernard, Erwan Beauchamp, Daniel Catheline, Philippe Legrand. Trans-vaccenate is Δ13-desaturated by FADS3 in rodents. Journal of lipid research. 2013 Dec; 54(12):3438-52. doi: 10.1194/jlr.m042572. [PMID: 24070791]
  • Najla Gooda Sahib, Farooq Anwar, Anwarul-Hassan Gilani, Azizah Abdul Hamid, Nazamid Saari, Khalid M Alkharfy. Coriander (Coriandrum sativum L.): a potential source of high-value components for functional foods and nutraceuticals--a review. Phytotherapy research : PTR. 2013 Oct; 27(10):1439-56. doi: 10.1002/ptr.4897. [PMID: 23281145]
  • P Vahmani, A H Fredeen, K E Glover. Effect of supplementation with fish oil or microalgae on fatty acid composition of milk from cows managed in confinement or pasture systems. Journal of dairy science. 2013 Oct; 96(10):6660-70. doi: 10.3168/jds.2013-6914. [PMID: 23958023]
  • Valentina Vasta, Dorra Aouadi, Daniela M R Brogna, Manuel Scerra, Giuseppe Luciano, Alessandro Priolo, Hichem Ben Salem. Effect of the dietary supplementation of essential oils from rosemary and artemisia on muscle fatty acids and volatile compound profiles in Barbarine lambs. Meat science. 2013 Oct; 95(2):235-41. doi: 10.1016/j.meatsci.2012.12.021. [PMID: 23747617]
  • M S Herrera-Meza, M R Mendoza-López, O García-Barradas, M G Sanchez-Otero, E R Silva-Hernández, J O Angulo, R M Oliart-Ros. Dietary anhydrous milk fat naturally enriched with conjugated linoleic acid and vaccenic acid modify cardiovascular risk biomarkers in spontaneously hypertensive rats. International journal of food sciences and nutrition. 2013 Aug; 64(5):575-86. doi: 10.3109/09637486.2013.763908. [PMID: 23360131]
  • Suresh K Mohankumar, Danielle Hanke, Linda Siemens, Alexander Cattini, Jennifer Enns, Jianheng Shen, Martin Reaney, Peter Zahradka, Carla G Taylor. Dietary supplementation of trans-11-vaccenic acid reduces adipocyte size but neither aggravates nor attenuates obesity-mediated metabolic abnormalities in fa/fa Zucker rats. The British journal of nutrition. 2013 May; 109(9):1628-36. doi: 10.1017/s000711451200339x. [PMID: 22914200]
  • Sasmita Tripathy, Donald B Jump. Elovl5 regulates the mTORC2-Akt-FOXO1 pathway by controlling hepatic cis-vaccenic acid synthesis in diet-induced obese mice. Journal of lipid research. 2013 Jan; 54(1):71-84. doi: 10.1194/jlr.m028787. [PMID: 23099444]
  • Arshya Hashim, M Salman Khan, Mohd Sajid Khan, Mohd Hassan Baig, Saheem Ahmad. Antioxidant and α -amylase inhibitory property of phyllanthus virgatus L.: an in vitro and molecular interaction study. BioMed research international. 2013; 2013(?):729393. doi: 10.1155/2013/729393. [PMID: 23957001]
  • P G Toral, Y Chilliard, L Bernard. Short communication: in vivo deposition of [1-13C]vaccenic acid and the product of its Δ9-desaturation, [1-13C]rumenic acid, in the body tissues of lactating goats fed oils. Journal of dairy science. 2012 Nov; 95(11):6755-9. doi: 10.3168/jds.2012-5620. [PMID: 22959933]
  • Anke Jaudszus, Gerhard Jahreis, Wiebke Schlörmann, Janine Fischer, Ronny Kramer, Christian Degen, Carsten Rohrer, Alexander Roth, Holger Gabriel, Dagmar Barz, Michael Gruen. Vaccenic acid-mediated reduction in cytokine production is independent of c9,t11-CLA in human peripheral blood mononuclear cells. Biochimica et biophysica acta. 2012 Oct; 1821(10):1316-22. doi: 10.1016/j.bbalip.2012.06.010. [PMID: 22750019]
  • Michael A Zulyniak, Jessica C Ralston, Amy J Tucker, Kathy A MacKay, Lyn M Hillyer, Paul D McNicholas, Terry E Graham, Lindsay E Robinson, Alison M Duncan, David W L Ma, David M Mutch. Vaccenic acid in serum triglycerides is associated with markers of insulin resistance in men. Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme. 2012 Oct; 37(5):1003-7. doi: 10.1139/h2012-081. [PMID: 22720879]
  • Ye Wang, Maria M Jacome-Sosa, Megan R Ruth, Yan Lu, Jianheng Shen, Martin J Reaney, Shannon L Scott, Michael E R Dugan, Hope D Anderson, Catherine J Field, Spencer D Proctor, Donna F Vine. The intestinal bioavailability of vaccenic acid and activation of peroxisome proliferator-activated receptor-α and -γ in a rodent model of dyslipidemia and the metabolic syndrome. Molecular nutrition & food research. 2012 Aug; 56(8):1234-46. doi: 10.1002/mnfr.201100517. [PMID: 22714958]
  • Madhu Suman Rana, A Tyagi, Sk Asraf Hossain, A K Tyagi. Effect of tanniniferous Terminalia chebula extract on rumen biohydrogenation, ∆(9)-desaturase activity, CLA content and fatty acid composition in longissimus dorsi muscle of kids. Meat science. 2012 Mar; 90(3):558-63. doi: 10.1016/j.meatsci.2011.09.016. [PMID: 22019314]
  • Emilie Lacroix, Amélie Charest, Audrey Cyr, Lisa Baril-Gravel, Yolaine Lebeuf, Paul Paquin, P Yvan Chouinard, Patrick Couture, Benoît Lamarche. Randomized controlled study of the effect of a butter naturally enriched in trans fatty acids on blood lipids in healthy women. The American journal of clinical nutrition. 2012 Feb; 95(2):318-25. doi: 10.3945/ajcn.111.023408. [PMID: 22205319]
  • 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]
  • Dongping Liu, Guiping Kong, Quan Cheng Chen, Guanghui Wang, Jie Li, Yang Xu, Ting lin, Yingpu Tian, Xiaokun Zhang, Xinsheng Yao, Gensheng Feng, Zhongxian Lu, Haifeng Chen. Fatty acids as natural specific inhibitors of the proto-oncogenic protein Shp2. Bioorganic & medicinal chemistry letters. 2011 Nov; 21(22):6833-7. doi: 10.1016/j.bmcl.2011.09.023. [PMID: 21962577]
  • Enrico Girardi, Esther Dawen Yu, Yali Li, Norihito Tarumoto, Bo Pei, Jing Wang, Petr Illarionov, Yuki Kinjo, Mitchell Kronenberg, Dirk M Zajonc. Unique interplay between sugar and lipid in determining the antigenic potency of bacterial antigens for NKT cells. PLoS biology. 2011 Nov; 9(11):e1001189. doi: 10.1371/journal.pbio.1001189. [PMID: 22069376]
  • Antonio Ruiz-Vela, Cristóbal Aguilar-Gallardo, Ana M Martínez-Arroyo, Mario Soriano-Navarro, Verónica Ruiz, Carlos Simón. Specific unsaturated fatty acids enforce the transdifferentiation of human cancer cells toward adipocyte-like cells. Stem cell reviews and reports. 2011 Nov; 7(4):898-909. doi: 10.1007/s12015-011-9253-7. [PMID: 21499706]
  • E Øie, T Ueland, C P Dahl, P Bohov, C Berge, A Yndestad, L Gullestad, P Aukrust, R K Berge. Fatty acid composition in chronic heart failure: low circulating levels of eicosatetraenoic acid and high levels of vaccenic acid are associated with disease severity and mortality. Journal of internal medicine. 2011 Sep; 270(3):263-72. doi: 10.1111/j.1365-2796.2011.02384.x. [PMID: 21466599]
  • Iness Bettaieb, Soumaya Bourgou, Jezia Sriti, Kamel Msaada, Ferid Limam, Brahim Marzouk. Essential oils and fatty acids composition of Tunisian and Indian cumin (Cuminum cyminum L.) seeds: a comparative study. Journal of the science of food and agriculture. 2011 Aug; 91(11):2100-7. doi: 10.1002/jsfa.4513. [PMID: 21681765]
  • Arturo Anadon, Maria Rosa Martinez-Larranaga, Maria Aranzazu Martinez, Irma Ares, Eva Ramos, Pilar Gomez-Cortes, Manuela Juarez, Miguel Angel de la Fuente. A 4-week repeated oral dose toxicity study of dairy fat naturally enriched in vaccenic, rumenic and α-linolenic acids in rats. Journal of agricultural and food chemistry. 2011 Jul; 59(14):8036-46. doi: 10.1021/jf201251g. [PMID: 21678997]
  • M L He, Y-H Chung, T A McAllister, K A Beauchemin, P S Mir, J L Aalhus, M E R Dugan. Inclusion of flaxseed in hay- and barley silage diets increases alpha-linolenic acid in cow plasma independent of forage type. Lipids. 2011 Jul; 46(7):577-85. doi: 10.1007/s11745-011-3534-4. [PMID: 21336984]
  • 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]
  • Laurence Bernard, Julien Mouriot, Jacques Rouel, Frédéric Glasser, Pierre Capitan, Estelle Pujos-Guillot, Jean-Michel Chardigny, Yves Chilliard. Effects of fish oil and starch added to a diet containing sunflower-seed oil on dairy goat performance, milk fatty acid composition and in vivo delta9-desaturation of [13C]vaccenic acid. The British journal of nutrition. 2010 Aug; 104(3):346-54. doi: 10.1017/s0007114510000486. [PMID: 20307350]
  • Shaobing O Zhang, Andrew C Box, Ningyi Xu, Johan Le Men, Jingyi Yu, Fengli Guo, Rhonda Trimble, Ho Yi Mak. Genetic and dietary regulation of lipid droplet expansion in Caenorhabditis elegans. Proceedings of the National Academy of Sciences of the United States of America. 2010 Mar; 107(10):4640-5. doi: 10.1073/pnas.0912308107. [PMID: 20176933]
  • 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]
  • Bochra Laribi, Karima Kouki, Abdelaziz Mougou, Brahim Marzouk. Fatty acid and essential oil composition of three Tunisian caraway (Carum carvi L.) seed ecotypes. Journal of the science of food and agriculture. 2010 Feb; 90(3):391-6. doi: 10.1002/jsfa.3827. [PMID: 20355058]
  • Dusan Jalc, Zora Váradyová, Andrea Lauková. Effect of inoculated corn silage enriched with sunflower oil on rumen fermentation and lipid metabolism in an artificial rumen (RUSITEC). Journal of the science of food and agriculture. 2010 Jan; 90(1):78-84. doi: 10.1002/jsfa.3783. [PMID: 20355015]
  • Heidi M Leskinen, Jukka-Pekka Suomela, Baoru Yang, Heikki P Kallio. Regioisomer compositions of vaccenic and oleic acid containing triacylglycerols in sea buckthorn (Hippophae rhamnoides) pulp oils: influence of origin and weather conditions. Journal of agricultural and food chemistry. 2010 Jan; 58(1):537-45. doi: 10.1021/jf902679v. [PMID: 19938856]
  • Chantal M C Bassett, Andrea L Edel, Amanda F Patenaude, Richelle S McCullough, David P Blackwood, P Yvan Chouinard, Paul Paquin, Benoît Lamarche, Grant N Pierce. Dietary vaccenic acid has antiatherogenic effects in LDLr-/- mice. The Journal of nutrition. 2010 Jan; 140(1):18-24. doi: 10.3945/jn.109.105163. [PMID: 19923390]
  • Xiuying Li, Yanhong Zhu, Tong Wu, Shuzhen Zhang, Peter Christie. Using a novel petroselinic Acid embedded cellulose acetate membrane to mimic plant partitioning and in vivo uptake of polycyclic aromatic hydrocarbons. Environmental science & technology. 2010 Jan; 44(1):297-301. doi: 10.1021/es902283x. [PMID: 19950922]
  • O Kuda, B Stankova, E Tvrzicka, M Hensler, T Jelenik, M Rossmeisl, P Flachs, J Kopecky. Prominent role of liver in elevated plasma palmitoleate levels in response to rosiglitazone in mice fed high-fat diet. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2009 Dec; 60(4):135-40. doi: NULL. [PMID: 20065507]
  • Ye Wang, M Miriam Jacome-Sosa, Megan R Ruth, Sue D Goruk, Martin J Reaney, David R Glimm, David C Wright, Donna F Vine, Catherine J Field, Spencer D Proctor. Trans-11 vaccenic acid reduces hepatic lipogenesis and chylomicron secretion in JCR:LA-cp rats. The Journal of nutrition. 2009 Nov; 139(11):2049-54. doi: 10.3945/jn.109.109488. [PMID: 19759243]
  • Heather J Blewett, Christopher A Gerdung, Megan R Ruth, Spencer D Proctor, Catherine J Field. Vaccenic acid favourably alters immune function in obese JCR:LA-cp rats. The British journal of nutrition. 2009 Aug; 102(4):526-36. doi: 10.1017/s0007114509231722. [PMID: 19216829]
  • Freda M McIntosh, Kevin J Shingfield, Estelle Devillard, Wendy R Russell, R John Wallace. Mechanism of conjugated linoleic acid and vaccenic acid formation in human faecal suspensions and pure cultures of intestinal bacteria. Microbiology (Reading, England). 2009 Jan; 155(Pt 1):285-294. doi: 10.1099/mic.0.022921-0. [PMID: 19118369]
  • Ye Wang, Jing Lu, Megan R Ruth, Sue D Goruk, Martin J Reaney, David R Glimm, Donna F Vine, Catherine J Field, Spencer D Proctor. Trans-11 vaccenic acid dietary supplementation induces hypolipidemic effects in JCR:LA-cp rats. The Journal of nutrition. 2008 Nov; 138(11):2117-22. doi: 10.3945/jn.108.091009. [PMID: 18936207]
  • Anna Haug, Per Sjøgren, Nina Hølland, Hanne Müller, Nils P Kjos, Ole Taugbøl, Nina Fjerdingby, Anne S Biong, Eirik Selmer-Olsen, Odd M Harstad. Effects of butter naturally enriched with conjugated linoleic acid and vaccenic acid on blood lipids and LDL particle size in growing pigs. Lipids in health and disease. 2008 Aug; 7(?):31. doi: 10.1186/1476-511x-7-31. [PMID: 18759970]
  • Eleni Tsiplakou, Georgios Zervas. The effect of dietary inclusion of olive tree leaves and grape marc on the content of conjugated linoleic acid and vaccenic acid in the milk of dairy sheep and goats. The Journal of dairy research. 2008 Aug; 75(3):270-8. doi: 10.1017/s0022029908003270. [PMID: 18513458]
  • Clare M Reynolds, Christine E Loscher, Aidan P Moloney, Helen M Roche. Cis-9, trans-11-conjugated linoleic acid but not its precursor trans-vaccenic acid attenuate inflammatory markers in the human colonic epithelial cell line Caco-2. The British journal of nutrition. 2008 Jul; 100(1):13-7. doi: 10.1017/s0007114508894329. [PMID: 18275620]
  • R K Kanwar, A K Macgibbon, P N Black, J R Kanwar, A Rowan, M Vale, G W Krissansen. Bovine milk fat enriched in conjugated linoleic and vaccenic acids attenuates allergic airway disease in mice. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology. 2008 Jan; 38(1):208-18. doi: 10.1111/j.1365-2222.2007.02868.x. [PMID: 18005183]
  • Xiangzhen Shen, Karin Nuernberg, Gerd Nuernberg, Ruqian Zhao, Nigel Scollan, Klaus Ender, Dirk Dannenberger. Vaccenic acid and cis-9,trans-11 CLA in the rumen and different tissues of pasture- and concentrate-fed beef cattle. Lipids. 2007 Dec; 42(12):1093-103. doi: 10.1007/s11745-007-3115-8. [PMID: 17912569]
  • A A AbuGhazaleh, L D Holmes. Diet supplementation with fish oil and sunflower oil to increase conjugated linoleic acid levels in milk fat of partially grazing dairy cows. Journal of dairy science. 2007 Jun; 90(6):2897-904. doi: 10.3168/jds.2006-684. [PMID: 17517729]
  • Kevin J Shingfield, Seppo Ahvenjärvi, Vesa Toivonen, Aila Vanhatalo, Pekka Huhtanen. Transfer of absorbed cis-9, trans-11 conjugated linoleic acid into milk is biologically more efficient than endogenous synthesis from absorbed vaccenic acid in lactating cows. The Journal of nutrition. 2007 May; 137(5):1154-60. doi: 10.1093/jn/137.5.1154. [PMID: 17449574]
  • Kyoko Shinzawa-Itoh, Hiroshi Aoyama, Kazumasa Muramoto, Hirohito Terada, Tsuyoshi Kurauchi, Yoshiki Tadehara, Akiko Yamasaki, Takashi Sugimura, Sadamu Kurono, Kazuo Tsujimoto, Tsunehiro Mizushima, Eiki Yamashita, Tomitake Tsukihara, Shinya Yoshikawa. Structures and physiological roles of 13 integral lipids of bovine heart cytochrome c oxidase. The EMBO journal. 2007 Mar; 26(6):1713-25. doi: 10.1038/sj.emboj.7601618. [PMID: 17332748]
  • Erin E Mosley, Michelle K McGuire, Janet E Williams, Mark A McGuire. Cis-9, trans-11 conjugated linoleic acid is synthesized from vaccenic acid in lactating women. The Journal of nutrition. 2006 Sep; 136(9):2297-301. doi: 10.1093/jn/136.9.2297. [PMID: 16920844]
  • Katrin Kuhnt, Jana Kraft, Peter Moeckel, Gerhard Jahreis. Trans-11-18 : 1 is effectively Delta9-desaturated compared with trans-12-18 : 1 in humans. The British journal of nutrition. 2006 Apr; 95(4):752-61. doi: 10.1079/bjn20051680. [PMID: 16571155]
  • Erin E Mosley, Bahman Shafii Dagger, Peter J Moate, Mark A McGuire. cis-9, trans-11 conjugated linoleic acid is synthesized directly from vaccenic acid in lactating dairy cattle. The Journal of nutrition. 2006 Mar; 136(3):570-5. doi: 10.1093/jn/136.3.570. [PMID: 16484526]
  • S Fukuda, Y Suzuki, M Murai, N Asanuma, T Hino. Augmentation of vaccenate production and suppression of vaccenate biohydrogenation in cultures of mixed ruminal microbes. Journal of dairy science. 2006 Mar; 89(3):1043-51. doi: 10.3168/jds.s0022-0302(06)72171-3. [PMID: 16507700]
  • Tine Tholstrup, Marianne Raff, Samar Basu, Pernille Nonboe, Kristen Sejrsen, Ellen M Straarup. Effects of butter high in ruminant trans and monounsaturated fatty acids on lipoproteins, incorporation of fatty acids into lipid classes, plasma C-reactive protein, oxidative stress, hemostatic variables, and insulin in healthy young men. The American journal of clinical nutrition. 2006 Feb; 83(2):237-43. doi: 10.1093/ajcn/83.2.237. [PMID: 16469980]
  • M Kunesová, R Braunerová, P Hlavatý, E Tvrzická, B Stanková, J Skrha, J Hilgertová, M Hill, J Kopecký, M Wagenknecht, V Hainer, M Matoulek, J Parízková, A Zák, S Svacina. The influence of n-3 polyunsaturated fatty acids and very low calorie diet during a short-term weight reducing regimen on weight loss and serum fatty acid composition in severely obese women. Physiological research. 2006; 55(1):63-72. doi: 10.33549/physiolres.930770. [PMID: 15857162]
  • S L Allred, T R Dhiman, C P Brennand, R C Khanal, D J McMahon, N D Luchini. Milk and cheese from cows fed calcium salts of palm and fish oil alone or in combination with soybean products. Journal of dairy science. 2006 Jan; 89(1):234-48. doi: 10.3168/jds.s0022-0302(06)72088-4. [PMID: 16357287]
  • Adam L Lock, Claire A M Horne, Dale E Bauman, Andrew M Salter. Butter naturally enriched in conjugated linoleic acid and vaccenic acid alters tissue fatty acids and improves the plasma lipoprotein profile in cholesterol-fed hamsters. The Journal of nutrition. 2005 Aug; 135(8):1934-9. doi: 10.1093/jn/135.8.1934. [PMID: 16046719]
  • Graham C Burdge, Sabine Tricon, Rebecca Morgan, Kirsty E Kliem, Caroline Childs, Emma Jones, Jennifer J Russell, Robert F Grimble, Christine M Williams, Parveen Yaqoob, Philip C Calder. Incorporation of cis-9, trans-11 conjugated linoleic acid and vaccenic acid (trans-11 18 : 1) into plasma and leucocyte lipids in healthy men consuming dairy products naturally enriched in these fatty acids. The British journal of nutrition. 2005 Aug; 94(2):237-43. doi: 10.1079/bjn20051506. [PMID: 16115358]
  • Adam L Lock, Benjamin A Corl, David M Barbano, Dale E Bauman, Clement Ip. The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats. The Journal of nutrition. 2004 Oct; 134(10):2698-704. doi: 10.1093/jn/134.10.2698. [PMID: 15465769]
  • N Tsevegsuren, K Aitzetmuller, K Vosmann. Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid. Lipids. 2004 Jun; 39(6):571-6. doi: 10.1007/s11745-004-1265-8. [PMID: 15554157]
  • J K Kay, T R Mackle, M J Auldist, N A Thomson, D E Bauman. Endogenous synthesis of cis-9, trans-11 conjugated linoleic acid in dairy cows fed fresh pasture. Journal of dairy science. 2004 Feb; 87(2):369-78. doi: 10.3168/jds.s0022-0302(04)73176-8. [PMID: 14762080]
  • A A AbuGhazaleh, D J Schingoethe, A R Hippen, K F Kalscheur. Conjugated linoleic acid and vaccenic acid in rumen, plasma, and milk of cows fed fish oil and fats differing in saturation of 18 carbon fatty acids. Journal of dairy science. 2003 Nov; 86(11):3648-60. doi: 10.3168/jds.s0022-0302(03)73970-8. [PMID: 14672195]
  • Sébastien Guiet, Richard J Robins, Michele Lees, Isabelle Billault. Quantitative 2H NMR analysis of deuterium distribution in petroselinic acid isolated from parsley seed. Phytochemistry. 2003 Sep; 64(1):227-33. doi: 10.1016/s0031-9422(03)00278-4. [PMID: 12946421]
  • A T Ward, K M Wittenberg, H M Froebe, R Przybylski, L Malcolmson. Fresh forage and solin supplementation on conjugated linoleic acid levels in plasma and milk. Journal of dairy science. 2003 May; 86(5):1742-50. doi: 10.3168/jds.s0022-0302(03)73760-6. [PMID: 12778585]
  • Anu M Turpeinen, Marja Mutanen, Antti Aro, Irma Salminen, Samar Basu, Donald L Palmquist, J Mikko Griinari. Bioconversion of vaccenic acid to conjugated linoleic acid in humans. The American journal of clinical nutrition. 2002 Sep; 76(3):504-10. doi: 10.1093/ajcn/76.3.504. [PMID: 12197992]
  • Mi Chung Suh, David J Schultz, John B Ohlrogge. What limits production of unusual monoenoic fatty acids in transgenic plants?. Planta. 2002 Aug; 215(4):584-95. doi: 10.1007/s00425-002-0751-3. [PMID: 12172841]
  • G Carta, E Angioni, E Murru, M P Melis, S Spada, S Banni. Modulation of lipid metabolism and vitamin A by conjugated linoleic acid. Prostaglandins, leukotrienes, and essential fatty acids. 2002 Aug; 67(2-3):187-91. doi: 10.1054/plef.2002.0417. [PMID: 12324240]
  • Juan J Loor, Xiaobo Lin, Joseph H Herbein. Dietary trans-vaccenic acid (trans11-18:1) increases concentration of cis9,transll-conjugated linoleic acid (rumenic acid) in tissues of lactating mice and suckling pups. Reproduction, nutrition, development. 2002 Mar; 42(2):85-99. doi: 10.1051/rnd:2002009. [PMID: 12216963]
  • Giovanna Vlahov, Paul Kiprono Chepkwony, Paul K Ndalut. (13)C NMR characterization of triacylglycerols of Moringa oleifera seed oil: an "oleic-vaccenic acid" oil. Journal of agricultural and food chemistry. 2002 Feb; 50(5):970-5. doi: 10.1021/jf011054a. [PMID: 11853466]
  • Frederic Destaillats, Joseph Arul, James E Simon, Robert L Wolff, Paul Angers. Dibutyrate derivatization of monoacylglycerols for the resolution of regioisomers of oleic, petroselinic, and cis-vaccenic acids. Lipids. 2002 Jan; 37(1):111-6. doi: 10.1007/s11745-002-0870-x. [PMID: 11876258]
  • S Mekhedov, E B Cahoon, J Ohlrogge. An unusual seed-specific 3-ketoacyl-ACP synthase associated with the biosynthesis of petroselinic acid in coriander. Plant molecular biology. 2001 Nov; 47(4):507-18. doi: 10.1023/a:1011832611885. [PMID: 11669576]
  • 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]
  • P Avato, F P Fanizzi, I Rosito. The genus Thapsia as a source of petroselinic acid. Lipids. 2001 Aug; 36(8):845-50. doi: 10.1007/s11745-001-0794-5. [PMID: 11592737]