adrenic acid (BioDeep_00001884459)

   

natural product


代谢物信息卡片


Docosa-7,10,13,16-tetraenoic acid

化学式: C22H36O2 (332.2715)
中文名称: 廿二碳四烯酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O
InChI: InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)

描述信息

同义名列表

3 个代谢物同义名

Docosa-7,10,13,16-tetraenoic acid; adrenic acid; Adrenic acid



数据库引用编号

8 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)

8 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
Cytoplasm 4 ACSL4, FGF19, GPX1, PLA2G12A
Endoplasmic reticulum membrane 7 ACSL4, CD4, ELOVL2, ELOVL5, FADS1, FADS2, SCD
Nucleus 1 PPARA
cytosol 3 ACOX1, GPX1, IL1B
dendrite 2 ELOVL2, ELOVL5
nucleoplasm 1 PPARA
Cell membrane 3 ACSL4, CD4, CD8A
Multi-pass membrane protein 5 ELOVL2, ELOVL5, FADS1, FADS2, SCD
cell surface 1 F3
Golgi membrane 1 INS
neuronal cell body 2 ELOVL2, ELOVL5
Cytoplasm, cytosol 1 IL1B
Lysosome 1 IL1B
plasma membrane 6 ACSL4, CD4, CD8A, F2, F3, FADS2
terminal bouton 1 GHRH
Membrane 8 ACOX1, ACSL4, ELOVL2, ELOVL5, F3, FADS1, FADS2, SCD
extracellular exosome 3 ACSL4, F2, SOD2
endoplasmic reticulum 4 ACSL4, ELOVL2, ELOVL5, SCD
extracellular space 7 F2, F3, FGF19, GHRH, IL1B, IL6, INS
mitochondrion 4 ACSL4, FADS1, GPX1, SOD2
intracellular membrane-bounded organelle 1 FADS1
Microsome membrane 1 ACSL4
Single-pass type I membrane protein 3 CD4, CD8A, F3
Secreted 5 F2, IL1B, IL6, INS, PLA2G12A
extracellular region 8 CD8A, F2, FGF19, GHRH, IL1B, IL6, INS, PLA2G12A
Mitochondrion outer membrane 1 ACSL4
mitochondrial outer membrane 1 ACSL4
[Isoform 1]: Membrane 1 F3
[Isoform 2]: Secreted 2 CD8A, F3
Mitochondrion matrix 1 SOD2
mitochondrial matrix 2 GPX1, SOD2
external side of plasma membrane 3 CD4, CD8A, F3
perikaryon 1 GHRH
nucleolus 1 SCD
Early endosome 1 CD4
Membrane raft 1 CD4
mitochondrial nucleoid 1 SOD2
Peroxisome 1 ACOX1
peroxisomal matrix 1 ACOX1
peroxisomal membrane 2 ACOX1, ACSL4
collagen-containing extracellular matrix 2 F2, F3
secretory granule 1 IL1B
receptor complex 1 CD8A
chromatin 1 PPARA
blood microparticle 1 F2
endosome lumen 1 INS
Lipid droplet 1 ACSL4
mitochondria-associated endoplasmic reticulum membrane contact site 1 ACSL4
[Isoform 1]: Endoplasmic reticulum membrane 1 FADS1
Cell projection, dendrite 2 ELOVL2, ELOVL5
Peroxisome membrane 1 ACSL4
plasma membrane raft 1 CD8A
secretory granule lumen 1 INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 4 CD4, F2, IL6, INS
transport vesicle 1 INS
Single-pass type III membrane protein 1 ACSL4
Secreted, extracellular exosome 1 IL1B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 CD4
[Isoform 1]: Cell membrane 1 CD8A
[Isoform 2]: Endoplasmic reticulum membrane 1 FADS1
T cell receptor complex 2 CD4, CD8A
interleukin-6 receptor complex 1 IL6
serine-type peptidase complex 1 F3
dendritic tree 2 ELOVL2, ELOVL5


文献列表

  • Chia-Hsiu Wu, Wen-Li Hsu, Ching-Chung Tsai, How-Ran Chao, Ching-Ying Wu, Yi-Hsuan Chen, Yun-Ru Lai, Chu-Huang Chen, Ming-Hsien Tsai. 7,10,13,16-Docosatetraenoic acid impairs neurobehavioral development by increasing reactive oxidative species production in Caenorhabditis elegans. Life sciences. 2023 Apr; 319(?):121500. doi: 10.1016/j.lfs.2023.121500. [PMID: 36796717]
  • Yan Wang, Xingyue Chen, Wenli Fan, Xujia Zhang, Siyuan Zhan, Tao Zhong, Jiazhong Guo, Jiaxue Cao, Li Li, Hongping Zhang, Linjie Wang. Integrated application of metabolomics and RNA-seq reveals thermogenic regulation in goat brown adipose tissues. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2021 09; 35(9):e21868. doi: 10.1096/fj.202100493rr. [PMID: 34449920]
  • Ji-Yoon Lee, Miso Nam, Hye Young Son, Kwangbeom Hyun, Seo Young Jang, Jong Woo Kim, Min Wook Kim, Youngae Jung, Eunji Jang, Seon-Jin Yoon, Jungeun Kim, Jihye Kim, Jinho Seo, Jeong-Ki Min, Kyoung-Jin Oh, Baek-Soo Han, Won Kon Kim, Kwang-Hee Bae, Jaewhan Song, Jaehoon Kim, Yong-Min Huh, Geum-Sook Hwang, Eun-Woo Lee, Sang Chul Lee. Polyunsaturated fatty acid biosynthesis pathway determines ferroptosis sensitivity in gastric cancer. Proceedings of the National Academy of Sciences of the United States of America. 2020 12; 117(51):32433-32442. doi: 10.1073/pnas.2006828117. [PMID: 33288688]
  • Cadiele Oliana Reichert, Fábio Alessandro de Freitas, Juliana Sampaio-Silva, Leonardo Rokita-Rosa, Priscila de Lima Barros, Debora Levy, Sérgio Paulo Bydlowski. Ferroptosis Mechanisms Involved in Neurodegenerative Diseases. International journal of molecular sciences. 2020 Nov; 21(22):. doi: 10.3390/ijms21228765. [PMID: 33233496]
  • Mary Xylaki, Ioanna Boumpoureka, Maroula G Kokotou, Theodoros Marras, Georgia Papadimitriou, Ismini Kloukina, Victoria Magrioti, George Kokotos, Kostas Vekrellis, Evangelia Emmanouilidou. Changes in the cellular fatty acid profile drive the proteasomal degradation of α-synuclein and enhance neuronal survival. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2020 11; 34(11):15123-15145. doi: 10.1096/fj.202001344r. [PMID: 32931072]
  • Souha Hammouda, Imen Ghzaiel, Wided Khamlaoui, Sonia Hammami, Samia Younes Mhenni, Slim Samet, Mohamed Hammami, Amira Zarrouk. Genetic variants in FADS1 and ELOVL2 increase level of arachidonic acid and the risk of Alzheimer's disease in the Tunisian population. Prostaglandins, leukotrienes, and essential fatty acids. 2020 09; 160(?):102159. doi: 10.1016/j.plefa.2020.102159. [PMID: 32682282]
  • Ángel Sánchez-Illana, Vidhi Shah, José David Piñeiro-Ramos, Juliann M Di Fiore, Guillermo Quintás, Thomas M Raffay, Peter M MacFarlane, Richard J Martin, Julia Kuligowski. Adrenic acid non-enzymatic peroxidation products in biofluids of moderate preterm infants. Free radical biology & medicine. 2019 10; 142(?):107-112. doi: 10.1016/j.freeradbiomed.2019.02.024. [PMID: 30818053]
  • Anna Marco-Ramell, Sara Tulipani, Magali Palau-Rodriguez, Raul Gonzalez-Dominguez, Antonio Miñarro, Olga Jauregui, Alex Sanchez-Pla, Manuel Macias-Gonzalez, Fernando Cardona, Francisco J Tinahones, Cristina Andres-Lacueva. Untargeted Profiling of Concordant/Discordant Phenotypes of High Insulin Resistance and Obesity To Predict the Risk of Developing Diabetes. Journal of proteome research. 2018 07; 17(7):2307-2317. doi: 10.1021/acs.jproteome.7b00855. [PMID: 29905079]
  • Izabela Kania-Korwel, Xianai Wu, Kai Wang, Hans-Joachim Lehmler. Identification of lipidomic markers of chronic 3,3',4,4',5-pentachlorobiphenyl (PCB 126) exposure in the male rat liver. Toxicology. 2017 09; 390(?):124-134. doi: 10.1016/j.tox.2017.09.005. [PMID: 28890136]
  • Saut Horas H Nababan, Shin Nishiumi, Yuki Kawano, Takashi Kobayashi, Masaru Yoshida, Takeshi Azuma. Adrenic acid as an inflammation enhancer in non-alcoholic fatty liver disease. Archives of biochemistry and biophysics. 2017 06; 623-624(?):64-75. doi: 10.1016/j.abb.2017.04.009. [PMID: 28456640]
  • Kin Sum Leung, Hok Fung Chan, Ho Hang Leung, Jean-Marie Galano, Camille Oger, Thierry Durand, Jetty Chung-Yung Lee. Short-time UVA exposure to human keratinocytes instigated polyunsaturated fatty acid without inducing lipid peroxidation. Free radical research. 2017 Mar; 51(3):269-280. doi: 10.1080/10715762.2017.1300885. [PMID: 28301979]
  • Valerian E Kagan, Gaowei Mao, Feng Qu, Jose Pedro Friedmann Angeli, Sebastian Doll, Claudette St Croix, Haider Hussain Dar, Bing Liu, Vladimir A Tyurin, Vladimir B Ritov, Alexandr A Kapralov, Andrew A Amoscato, Jianfei Jiang, Tamil Anthonymuthu, Dariush Mohammadyani, Qin Yang, Bettina Proneth, Judith Klein-Seetharaman, Simon Watkins, Ivet Bahar, Joel Greenberger, Rama K Mallampalli, Brent R Stockwell, Yulia Y Tyurina, Marcus Conrad, Hülya Bayır. Oxidized arachidonic and adrenic PEs navigate cells to ferroptosis. Nature chemical biology. 2017 Jan; 13(1):81-90. doi: 10.1038/nchembio.2238. [PMID: 27842066]
  • Kunio Yui, George Imataka, Yohei Kawasak, Hiroshi Yamada. Increased ω-3 polyunsaturated fatty acid/arachidonic acid ratios and upregulation of signaling mediator in individuals with autism spectrum disorders. Life sciences. 2016 Jan; 145(?):205-12. doi: 10.1016/j.lfs.2015.12.039. [PMID: 26724495]
  • Ming Long Sirius Chung, Jean-Marie Galano, Camille Oger, Thierry Durand, Jetty Chung-Yung Lee. Hyperoxia elevates adrenic acid peroxidation in marine fish and is associated with reproductive pheromone mediators. Marine drugs. 2015 Apr; 13(4):2215-32. doi: 10.3390/md13042215. [PMID: 25874920]
  • Jean-Marie Galano, Jetty Chung-Yung Lee, Cecile Gladine, Blandine Comte, Jean-Yves Le Guennec, Camille Oger, Thierry Durand. Non-enzymatic cyclic oxygenated metabolites of adrenic, docosahexaenoic, eicosapentaenoic and α-linolenic acids; bioactivities and potential use as biomarkers. Biochimica et biophysica acta. 2015 Apr; 1851(4):446-55. doi: 10.1016/j.bbalip.2014.11.004. [PMID: 25463478]
  • Aurélien de La Torre, Yiu Yiu Lee, Camille Oger, Per Torp Sangild, Thierry Durand, Jetty Chung-Yung Lee, Jean-Marie Galano. Synthesis, discovery, and quantitation of dihomo-isofurans: biomarkers for in vivo adrenic acid peroxidation. Angewandte Chemie (International ed. in English). 2014 Jun; 53(24):6249-52. doi: 10.1002/anie.201402440. [PMID: 24839059]
  • Juliana S Vaz, Gilberto Kac, Antonio E Nardi, Joseph R Hibbeln. Omega-6 fatty acids and greater likelihood of suicide risk and major depression in early pregnancy. Journal of affective disorders. 2014 Jan; 152-154(?):76-82. doi: 10.1016/j.jad.2013.04.045. [PMID: 23726775]
  • Thierry Durand, Claudio De Felice, Cinzia Signorini, Camille Oger, Valérie Bultel-Poncé, Alexandre Guy, Jean-Marie Galano, Silvia Leoncini, Lucia Ciccoli, Alessandra Pecorelli, Giuseppe Valacchi, Joussef Hayek. F(2)-Dihomo-isoprostanes and brain white matter damage in stage 1 Rett syndrome. Biochimie. 2013 Jan; 95(1):86-90. doi: 10.1016/j.biochi.2012.09.017. [PMID: 23009927]
  • Dahlia I Campbell, Christina R Ferreira, Livia S Eberlin, R Graham Cooks. Improved spatial resolution in the imaging of biological tissue using desorption electrospray ionization. Analytical and bioanalytical chemistry. 2012 Aug; 404(2):389-98. doi: 10.1007/s00216-012-6173-6. [PMID: 22706326]
  • E Patterson, R Wall, G F Fitzgerald, R P Ross, C Stanton. Health implications of high dietary omega-6 polyunsaturated Fatty acids. Journal of nutrition and metabolism. 2012; 2012(?):539426. doi: 10.1155/2012/539426. [PMID: 22570770]
  • Saki Kakutani, Yoshiyuki Ishikura, Norifumi Tateishi, Chika Horikawa, Hisanori Tokuda, Masanori Kontani, Hiroshi Kawashima, Yutaka Sakakibara, Yoshinobu Kiso, Hiroshi Shibata, Ikuo Morita. Supplementation of arachidonic acid-enriched oil increases arachidonic acid contents in plasma phospholipids, but does not increase their metabolites and clinical parameters in Japanese healthy elderly individuals: a randomized controlled study. Lipids in health and disease. 2011 Dec; 10(?):241. doi: 10.1186/1476-511x-10-241. [PMID: 22188761]
  • Cornelia Enzenbach, Janine Kröger, Vera Zietemann, Eugène H J M Jansen, Andreas Fritsche, Frank Döring, Heiner Boeing, Matthias B Schulze. Erythrocyte membrane phospholipid polyunsaturated fatty acids are related to plasma C-reactive protein and adiponectin in middle-aged German women and men. European journal of nutrition. 2011 Dec; 50(8):625-36. doi: 10.1007/s00394-011-0169-4. [PMID: 21301856]
  • Claudio De Felice, Cinzia Signorini, Thierry Durand, Camille Oger, Alexandre Guy, Valérie Bultel-Poncé, Jean-Marie Galano, Lucia Ciccoli, Silvia Leoncini, Maurizio D'Esposito, Stefania Filosa, Alessandra Pecorelli, Giuseppe Valacchi, Joussef Hayek. F2-dihomo-isoprostanes as potential early biomarkers of lipid oxidative damage in Rett syndrome. Journal of lipid research. 2011 Dec; 52(12):2287-2297. doi: 10.1194/jlr.p017798. [PMID: 21917727]
  • Junya Matsumoto, Yuki Sugiura, Dai Yuki, Takahiro Hayasaka, Naoko Goto-Inoue, Nobuhiro Zaima, Yasuto Kunii, Akira Wada, Qiaohui Yang, Keisuke Nishiura, Hiroyasu Akatsu, Akira Hori, Yoshio Hashizume, Takayuki Yamamoto, Keiko Ikemoto, Mitsutoshi Setou, Shin-ichi Niwa. Abnormal phospholipids distribution in the prefrontal cortex from a patient with schizophrenia revealed by matrix-assisted laser desorption/ionization imaging mass spectrometry. Analytical and bioanalytical chemistry. 2011 Jun; 400(7):1933-43. doi: 10.1007/s00216-011-4909-3. [PMID: 21461619]
  • Afaf K El-Ansary, Abir G Ben Bacha, Layla Y Al-Ayahdi. Impaired plasma phospholipids and relative amounts of essential polyunsaturated fatty acids in autistic patients from Saudi Arabia. Lipids in health and disease. 2011 Apr; 10(?):63. doi: 10.1186/1476-511x-10-63. [PMID: 21513514]
  • Irina Guschina, Steve Millership, Valerie O'Donnell, Natalia Ninkina, John Harwood, Vladimir Buchman. Lipid classes and fatty acid patterns are altered in the brain of γ-synuclein null mutant mice. Lipids. 2011 Feb; 46(2):121-30. doi: 10.1007/s11745-010-3486-0. [PMID: 20963507]
  • Miki Igarashi, Kaizong Ma, Fei Gao, Hyung-Wook Kim, Stanley I Rapoport, Jagadeesh S Rao. Disturbed choline plasmalogen and phospholipid fatty acid concentrations in Alzheimer's disease prefrontal cortex. Journal of Alzheimer's disease : JAD. 2011; 24(3):507-17. doi: 10.3233/jad-2011-101608. [PMID: 21297269]
  • Vuokko Aarnio, Marko Lehtonen, Markus Storvik, James C Callaway, Merja Lakso, Garry Wong. Caenorhabditis Elegans Mutants Predict Regulation of Fatty Acids and Endocannabinoids by the CYP-35A Gene Family. Frontiers in pharmacology. 2011; 2(?):12. doi: 10.3389/fphar.2011.00012. [PMID: 21687507]
  • James R Petrie, Surinder P Singh. Expanding the docosahexaenoic acid food web for sustainable production: engineering lower plant pathways into higher plants. AoB PLANTS. 2011; 2011(?):plr011. doi: 10.1093/aobpla/plr011. [PMID: 22476481]
  • Stephanie Van Biervliet, Jean-Pierre Van Biervliet, Eddy Robberecht, Armand Christophe. Fatty acid composition of serum phospholipids in cystic fibrosis (CF) patients with or without CF related liver disease. Clinical chemistry and laboratory medicine. 2010 Dec; 48(12):1751-5. doi: 10.1515/cclm.2010.336. [PMID: 20961201]
  • Aihua Liu, James Chang, Yanhua Lin, Zhengqing Shen, Paul S Bernstein. Long-chain and very long-chain polyunsaturated fatty acids in ocular aging and age-related macular degeneration. Journal of lipid research. 2010 Nov; 51(11):3217-29. doi: 10.1194/jlr.m007518. [PMID: 20688753]
  • Li Rong Shen, Chao Qiang Lai, Xiang Feng, Laurence D Parnell, Jian Bo Wan, Jing D Wang, Duo Li, Jose M Ordovas, Jing X Kang. Drosophila lacks C20 and C22 PUFAs. Journal of lipid research. 2010 Oct; 51(10):2985-92. doi: 10.1194/jlr.m008524. [PMID: 20656917]
  • Diana M Merino, David W L Ma, David M Mutch. Genetic variation in lipid desaturases and its impact on the development of human disease. Lipids in health and disease. 2010 Jun; 9(?):63. doi: 10.1186/1476-511x-9-63. [PMID: 20565855]
  • Songsri Kaewsuwan, Nantavan Bunyapraphatsara, David J Cove, Ralph S Quatrano, Pichit Chodok. High level production of adrenic acid in Physcomitrella patens using the algae Pavlova sp. Delta(5)-elongase gene. Bioresource technology. 2010 Jun; 101(11):4081-8. doi: 10.1016/j.biortech.2009.12.138. [PMID: 20106658]
  • Robert Kleemann, Marjan van Erk, Lars Verschuren, Anita M van den Hoek, Maud Koek, Peter Y Wielinga, Annie Jie, Linette Pellis, Ivana Bobeldijk-Pastorova, Thomas Kelder, Karin Toet, Suzan Wopereis, Nicole Cnubben, Chris Evelo, Ben van Ommen, Teake Kooistra. Time-resolved and tissue-specific systems analysis of the pathogenesis of insulin resistance. PloS one. 2010 Jan; 5(1):e8817. doi: 10.1371/journal.pone.0008817. [PMID: 20098690]
  • Aldona Pietrzak, Anna Michalak-Stoma, Grazyna Chodorowska, Jacek C Szepietowski. Lipid disturbances in psoriasis: an update. Mediators of inflammation. 2010; 2010(?):. doi: 10.1155/2010/535612. [PMID: 20706605]
  • Stefanie Ebert, Karin Weigelt, Yana Walczak, Wolfgang Drobnik, Richard Mauerer, David A Hume, Bernhard H F Weber, Thomas Langmann. Docosahexaenoic acid attenuates microglial activation and delays early retinal degeneration. Journal of neurochemistry. 2009 Sep; 110(6):1863-75. doi: 10.1111/j.1471-4159.2009.06286.x. [PMID: 19627444]
  • Nahed Hussein, Irina Fedorova, Toru Moriguchi, Kei Hamazaki, Hee-Yong Kim, Junji Hoshiba, Norman Salem. Artificial rearing of infant mice leads to n-3 fatty acid deficiency in cardiac, neural and peripheral tissues. Lipids. 2009 Aug; 44(8):685-702. doi: 10.1007/s11745-009-3318-2. [PMID: 19588181]
  • Eva Szabó, Tamás Marosvölgyi, Adrienne Kozári, Eva Erhardt, Gyula Soltész, Tamás Decsi. Long-chain polyunsaturated fatty acids in a diabetic teenager during and after nine repeated episodes of diabetic ketoacidosis. Pediatric diabetes. 2009 May; 10(3):209-12. doi: 10.1111/j.1399-5448.2008.00487.x. [PMID: 19076300]
  • L Jackson Roberts, Ginger L Milne. Isoprostanes. Journal of lipid research. 2009 Apr; 50 Suppl(?):S219-23. doi: 10.1194/jlr.r800037-jlr200. [PMID: 18957694]
  • Javad Nasrollahzadeh, Fereydoun Siassi, Mahmood Doosti, Mohammad Reza Eshraghian, Fazel Shokri, Mohammad Hossein Modarressi, Javad Mohammadi-Asl, Khosro Abdi, Arash Nikmanesh, Seyed Morteza Karimian. The influence of feeding linoleic, gamma-linolenic and docosahexaenoic acid rich oils on rat brain tumor fatty acids composition and fatty acid binding protein 7 mRNA expression. Lipids in health and disease. 2008 Nov; 7(?):45. doi: 10.1186/1476-511x-7-45. [PMID: 19014610]
  • Blair U Bradford, Thomas M O'Connell, Jun Han, Oksana Kosyk, Svitlana Shymonyak, Pamela K Ross, Jason Winnike, Hiroshi Kono, Ivan Rusyn. Metabolomic profiling of a modified alcohol liquid diet model for liver injury in the mouse uncovers new markers of disease. Toxicology and applied pharmacology. 2008 Oct; 232(2):236-43. doi: 10.1016/j.taap.2008.06.022. [PMID: 18674555]
  • Mike VanRollins, Randall L Woltjer, Huiyong Yin, Jason D Morrow, Thomas J Montine. F2-dihomo-isoprostanes arise from free radical attack on adrenic acid. Journal of lipid research. 2008 May; 49(5):995-1005. doi: 10.1194/jlr.m700503-jlr200. [PMID: 18250368]
  • Ben Speers-Roesch, Yuen K Ip, James S Ballantyne. Plasma non-esterified fatty acids of elasmobranchs: comparisons of temperate and tropical species and effects of environmental salinity. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2008 Feb; 149(2):209-16. doi: 10.1016/j.cbpa.2007.12.003. [PMID: 18203641]
  • Masataka Kusunoki, Kazuhiko Tsutsumi, Meiho Nakayama, Tsuyoshi Kurokawa, Takao Nakamura, Hitoshi Ogawa, Yoshitaka Fukuzawa, Munehiko Morishita, Tatsuro Koide, Tetsuro Miyata. Relationship between serum concentrations of saturated fatty acids and unsaturated fatty acids and the homeostasis model insulin resistance index in Japanese patients with type 2 diabetes mellitus. The journal of medical investigation : JMI. 2007 Aug; 54(3-4):243-7. doi: 10.2152/jmi.54.243. [PMID: 17878672]
  • R H M de Groot, G Hornstra, J Jolles. Exploratory study into the relation between plasma phospholipid fatty acid status and cognitive performance. Prostaglandins, leukotrienes, and essential fatty acids. 2007 Mar; 76(3):165-72. doi: 10.1016/j.plefa.2007.01.001. [PMID: 17317131]
  • Elizabeth A Thomas, Jeffrey K Yao. Clozapine specifically alters the arachidonic acid pathway in mice lacking apolipoprotein D. Schizophrenia research. 2007 Jan; 89(1-3):147-53. doi: 10.1016/j.schres.2006.08.011. [PMID: 17011169]
  • Andrew J Sinclair, Denovan Begg, Michael Mathai, Richard S Weisinger. Omega 3 fatty acids and the brain: review of studies in depression. Asia Pacific journal of clinical nutrition. 2007; 16 Suppl 1(?):391-7. doi: ". [PMID: 17392137]
  • Thomas A B Sanders, Kelly Gleason, Bruce Griffin, George J Miller. Influence of an algal triacylglycerol containing docosahexaenoic acid (22 : 6n-3) and docosapentaenoic acid (22 : 5n-6) on cardiovascular risk factors in healthy men and women. The British journal of nutrition. 2006 Mar; 95(3):525-31. doi: 10.1079/bjn20051658. [PMID: 16512939]
  • Yu Hong Lin, Norman Salem. In vivo conversion of 18- and 20-C essential fatty acids in rats using the multiple simultaneous stable isotope method. Journal of lipid research. 2005 Sep; 46(9):1962-73. doi: 10.1194/jlr.m500127-jlr200. [PMID: 15930514]
  • B A Thomas, Kebreab Ghebremeskel, Clara Lowy, Brigid Offley-Shore, Michael A Crawford. Plasma fatty acids of neonates born to mothers with and without gestational diabetes. Prostaglandins, leukotrienes, and essential fatty acids. 2005 May; 72(5):335-41. doi: 10.1016/j.plefa.2005.01.001. [PMID: 15850714]
  • Kebreab Ghebremeskel, Beverley Thomas, Clara Lowy, Yoeju Min, Michael A Crawford. Type 1 diabetes compromises plasma arachidonic and docosahexaenoic acids in newborn babies. Lipids. 2004 Apr; 39(4):335-42. doi: 10.1007/s11745-004-1237-z. [PMID: 15357021]
  • Rafael Mateo, W Nelson Beyer, James W Spann, David J Hoffman. Relation of fatty acid composition in lead-exposed mallards to fat mobilization, lipid peroxidation and alkaline phosphatase activity. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2003 Aug; 135(4):451-8. doi: 10.1016/s1532-0456(03)00148-0. [PMID: 12965190]
  • Stefanie D Krämer, Yannic B Schütz, Heidi Wunderli-Allenspach, N Joan Abbott, David J Begley. Lipids in blood-brain barrier models in vitro II: Influence of glial cells on lipid classes and lipid fatty acids. In vitro cellular & developmental biology. Animal. 2002 Nov; 38(10):566-71. doi: 10.1290/1543-706x(2002)38<566:libbmi>2.0.co;2. [PMID: 12762838]
  • Vasuki Wijendran, Peter Lawrence, Guan-Yeu Diau, G Boehm, P W Nathanielsz, J T Brenna. Significant utilization of dietary arachidonic acid is for brain adrenic acid in baboon neonates. Journal of lipid research. 2002 May; 43(5):762-7. doi: . [PMID: 11971947]
  • A Ikemoto, M Ohishi, Y Sato, N Hata, Y Misawa, Y Fujii, H Okuyama. Reversibility of n-3 fatty acid deficiency-induced alterations of learning behavior in the rat: level of n-6 fatty acids as another critical factor. Journal of lipid research. 2001 Oct; 42(10):1655-63. doi: 10.1016/s0022-2275(20)32220-3. [PMID: 11590222]
  • M Okita, T Sasagawa, Y Ohta, T Kaneyuki, K Suzuki. Effect of arachidonic acid-rich oil on lipids and arachidonate metabolites in ethanol- treated rats. Prostaglandins, leukotrienes, and essential fatty acids. 2001 Apr; 64(4-5):273-9. doi: 10.1054/plef.2001.0271. [PMID: 11418023]
  • M Martínez, I Mougan. Fatty acid composition of human brain phospholipids during normal development. Journal of neurochemistry. 1998 Dec; 71(6):2528-33. doi: 10.1046/j.1471-4159.1998.71062528.x. [PMID: 9832152]
  • M C Soares, M L Aléssio, C L Léger, M T Bluet-Pajot, H Clauser, A Enjalbert, C Kordon, D E Wandscheer. Effect of essential fatty acid deficiency on membrane fatty acid content and growth hormone stimulation of rat pituitaries during postnatal development. Journal of lipid research. 1995 Jun; 36(6):1401-6. doi: . [PMID: 7666016]
  • K E Orwig, S Leers-Sucheta, M F Moghaddam, Z D Jiang, W R Gerwick, F Stormshak. Unique metabolites of eicosapentaenoic acid interfere with corpus luteum function in the ewe. Prostaglandins. 1992 Dec; 44(6):519-30. doi: 10.1016/0090-6980(92)90022-l. [PMID: 1335585]
  • M L Alessio, D E Wandscheer, M C Soares, H Clauser, A Enjalbert, C Kordon, C L Léger. Effect of an essential fatty acid deficiency on the phospholipid composition in anterior pituitary membranes. Biochemical and biophysical research communications. 1992 Mar; 183(3):1047-55. doi: 10.1016/s0006-291x(05)80296-7. [PMID: 1567386]
  • J M Bourre, M Piciotti, O Dumont, G Pascal, G Durand. Dietary linoleic acid and polyunsaturated fatty acids in rat brain and other organs. Minimal requirements of linoleic acid. Lipids. 1990 Aug; 25(8):465-72. doi: 10.1007/bf02538090. [PMID: 2120529]
  • E Christensen, T A Hagve, B O Christophersen. The Zellweger syndrome: deficient chain-shortening of erucic acid (22:1 (n-9)) and adrenic acid (22:4 (n-6)) in cultured skin fibroblasts. Biochimica et biophysica acta. 1988 Mar; 959(2):134-42. doi: . [PMID: 3349094]
  • J C Bordet, M Guichardant, M Lagarde. Hydroperoxides produced by n-6 lipoxygenation of arachidonic and linoleic acids potentiate synthesis of prostacyclin related compounds. Biochimica et biophysica acta. 1988 Feb; 958(3):460-8. doi: 10.1016/0005-2760(88)90232-9. [PMID: 3124885]
  • Y Nakagawa, L A Horrocks. Different metabolic rates for arachidonoyl molecular species of ethanolamine glycerophospholipids in rat brain. Journal of lipid research. 1986 Jun; 27(6):629-36. doi: 10.1016/s0022-2275(20)38809-x. [PMID: 3746131]
  • W B Campbell, J R Falck, J R Okita, A R Johnson, K S Callahan. Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells. Biochimica et biophysica acta. 1985 Oct; 837(1):67-76. doi: 10.1016/0005-2760(85)90086-4. [PMID: 3931686]
  • H Sprecher, M VanRollins, F Sun, A Wyche, P Needleman. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. The Journal of biological chemistry. 1982 Apr; 257(7):3912-8. doi: . [PMID: 6801054]
  • V C Gavino, J S Miller, S O Ikharebha, G E Milo, D G Cornwell. Effect of polyunsaturated fatty acids and antioxidants on lipid peroxidation in tissue cultures. Journal of lipid research. 1981 Jul; 22(5):763-9. doi: . [PMID: 7288284]
  • V C Gavino, J S Miller, J M Dillman, G E Milo, D G Cornwell. Effect of exogenous adrenic acid on the proliferation and lipid metabolism of cells in tissue culture. Progress in lipid research. 1981; 20(?):323-5. doi: 10.1016/0163-7827(81)90064-3. [PMID: 7342096]