FA 22:5 (BioDeep_00000628823)

Main id: BioDeep_00000018220

Secondary id: BioDeep_00000229693

PANOMIX_OTCML-2023 natural product Volatile Flavor Compounds


代谢物信息卡片


(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid

化学式: C22H34O2 (330.2558664)
中文名称: 二十二碳五烯酸, 鲫鱼酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.27%

分子结构信息

SMILES: C(=C/C/C=C/C/C=C/C/C=C/CC)\C/C=C/CCCCCC(=O)O
InChI: InChI=1S/C22H34O2/c23-17(24)9-7-5-3-1-2-4-6-8-13-12-16-18(13)22-20-15-11-10-14(15)19(20)21(16)22/h13-16,18-22H,1-12H2,(H,23,24)

描述信息

The all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 7-, 10-, 13-, 16- and 19-positions.
Docosapentaenoic acid (22n-3) is a component of phospholipids found in all animal cell membranes.

同义名列表

26 个代谢物同义名

(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid; (7Z,10Z,13Z,16Z,19Z)-Docosapentaenoic acid; 7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid; Docosapentaenoic acid (22:5(n-3)); docosapentaenoic acid; C22:5n-3,6,9,12,15; Clupanodonic acid; Osbonds acid; FA 22:5; DPA; (4Z,8Z,12Z,15Z,19Z)-docosa-4,8,12,15,19-pentaenoic acid; Z,8Z,12Z,15Z,19Z-docosapentaenoic acid; Clupadonic acid; 4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid; 22:5(4Z,7Z,10Z,13Z,16Z); C22:5n-6,9,12,15,18; 2E,4E,6E,8E,10E-docosapentaenoic acid; C22:5n-12,14,16,18,20; 10-[5]-ladderane-decanoic acid; 7,10,13,16,19-docosapentaenoic acid; Docosa-4,8,12,15,19-pentaenoic acid; 4,8,12,15,19-docosapentaenoic acid; C22:5n-3,7,10,14,18; 4,7,10,13,16-docosapentaenoic acid; Docosapentaenoic acid (22n-3); (7Z,10Z,13Z,16Z,19Z)-Docosapentaenoic acid



数据库引用编号

34 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)

9 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

  • Satoshi Hirako, Takahiro Hirabayashi, Junko Shibato, Ai Kimura, Michio Yamashita, Yuzuru Iizuka, Nobuhiro Wada, Naoko Kaibara, Fumiko Takenoya, Seiji Shioda. Docosapentaenoic acid-rich oil lowers plasma glucose and lipids in a mouse model of diabetes and mild obesity. Nutrition research (New York, N.Y.). 2023 Aug; 118(?):128-136. doi: 10.1016/j.nutres.2023.08.004. [PMID: 37660501]
  • Kenta Furutani, Ouyang Chen, Aidan McGinnis, Yuqing Wang, Charles N Serhan, Trond Vidar Hansen, Ru-Rong Ji. Novel proresolving lipid mediator mimetic 3-oxa-PD1n-3 docosapentaenoic acid reduces acute and chronic itch by modulating excitatory and inhibitory synaptic transmission and astroglial secretion of lipocalin-2 in mice. Pain. 2023 06; 164(6):1340-1354. doi: 10.1097/j.pain.0000000000002824. [PMID: 36378290]
  • 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]
  • Kevin C Maki, Harold E Bays, Christie M Ballantyne, James A Underberg, John J P Kastelein, Judith B Johnson, James J Ferguson. A Head-to-Head Comparison of a Free Fatty Acid Formulation of Omega-3 Pentaenoic Acids Versus Icosapent Ethyl in Adults With Hypertriglyceridemia: The ENHANCE-IT Study. Journal of the American Heart Association. 2022 03; 11(6):e024176. doi: 10.1161/jaha.121.024176. [PMID: 35232215]
  • Chang-Yu Wu, Tomoyo Okuda, Akinori Ando, Ayami Hatano, Hiroshi Kikukawa, Jun Ogawa. Isolation and characterization of the ω3-docosapentaenoic acid-producing microorganism Aurantiochytrium sp. T7. Journal of bioscience and bioengineering. 2022 Mar; 133(3):229-234. doi: 10.1016/j.jbiosc.2021.10.011. [PMID: 34893429]
  • Lifang Wang, Hack Sun Choi, Yan Su, Jung-Hyun Ju, Sun-Yeon Heo, Jong-Jae Yi, Back-Rock Oh, Yong-Suk Jang, Jeong-Woo Seo. The docosahexaenoic acid derivatives, diHEP-DPA and TH-DPA, synthesized via recombinant lipoxygenase, ameliorate disturbances in lipid metabolism and liver inflammation in high fat diet-fed mice. Life sciences. 2022 Feb; 291(?):120219. doi: 10.1016/j.lfs.2021.120219. [PMID: 35041834]
  • Srinivas Belide, Pushkar Shrestha, Yoko Kennedy, Antonio Leonforte, Malcolm D Devine, James R Petrie, Surinder P Singh, Xue-Rong Zhou. Engineering docosapentaenoic acid (DPA) and docosahexaenoic acid (DHA) in Brassica juncea. Plant biotechnology journal. 2022 01; 20(1):19-21. doi: 10.1111/pbi.13739. [PMID: 34694688]
  • Alicia Leikin-Frenkel, Aya Mohr-Sasson, Matan Anteby, Michal Kandel-Kfir, Ayelet Harari, Roni Rahav, Yehuda Kamari, Aviv Shaish, Dror Harats, Hofit Cohen, Israel Hendler. Blood fatty acid analysis reveals similar n-3 fatty acid composition in non-pregnant and pregnant women and their neonates in an Israeli pilot study. Prostaglandins, leukotrienes, and essential fatty acids. 2021 10; 173(?):102339. doi: 10.1016/j.plefa.2021.102339. [PMID: 34487973]
  • Jeffery L Heileson, Anthony J Anzalone, Aaron F Carbuhn, Andrew T Askow, Jason D Stone, Stephanie M Turner, Lyn M Hillyer, David W L Ma, Joel A Luedke, Andrew R Jagim, Jonathan M Oliver. The effect of omega-3 fatty acids on a biomarker of head trauma in NCAA football athletes: a multi-site, non-randomized study. Journal of the International Society of Sports Nutrition. 2021 Sep; 18(1):65. doi: 10.1186/s12970-021-00461-1. [PMID: 34579748]
  • Devaraj Parasannanavar, Indraja Gaddam, Tulja Bukya, Ahamed Ibrahim S, Suryam Reddy K, Santosh Kumar Banjara, Blessy P Priyanka Salvadi, Naveen Kumar B, Sylvia Fernandez Rao, J J Babu Geddam, Hemalatha Rajkumar. Omega-3 polyunsaturated fatty acid intake and plasma fatty acids of school going Indian children - a cross-sectional study. Prostaglandins, leukotrienes, and essential fatty acids. 2021 07; 170(?):102294. doi: 10.1016/j.plefa.2021.102294. [PMID: 34052598]
  • Samaneh Ghasemi Fard, David Cameron-Smith, Andrew J Sinclair. n - 3 Docosapentaenoic acid: the iceberg n - 3 fatty acid. Current opinion in clinical nutrition and metabolic care. 2021 03; 24(2):134-138. doi: 10.1097/mco.0000000000000722. [PMID: 33315722]
  • Michael A Crawford, Walter F Schmidt, C Leigh Broadhurst, Yiqun Wang. Lipids in the origin of intracellular detail and speciation in the Cambrian epoch and the significance of the last double bond of docosahexaenoic acid in cell signaling. Prostaglandins, leukotrienes, and essential fatty acids. 2021 03; 166(?):102230. doi: 10.1016/j.plefa.2020.102230. [PMID: 33588307]
  • Kei Hamazaki, Yutaka J Matsuoka, Taiki Yamaji, Norie Sawada, Masaru Mimura, Shoko Nozaki, Ryo Shikimoto, Shoichiro Tsugane. Plasma phospholipid n-3 polyunsaturated fatty acids and major depressive disorder in Japanese elderly: the Japan Public Health Center-based Prospective Study. Scientific reports. 2021 02; 11(1):4003. doi: 10.1038/s41598-021-83478-5. [PMID: 33597590]
  • Chen Zhang, Miao-Miao Zhou, Tian-Tian Zhang, Pei-Xu Cong, Jie Xu, Chang-Hu Xue, Teruyoshi Yanagita, Zi-Hao Wei, Yu-Ming Wang. Effects of Dietary Supplementation with EPA-enriched Phosphatidylcholine and Phosphatidylethanolamine on Glycerophospholipid Profile in Cerebral Cortex of SAMP8 Mice fed with High-fat Diet. Journal of oleo science. 2021 Feb; 70(2):275-287. doi: 10.5650/jos.ess20212. [PMID: 33456004]
  • Yongliang Fan, Abdelaziz Adam Idriss Arbab, Huimin Zhang, Yi Yang, Xubin Lu, Ziyin Han, Zhangping Yang. MicroRNA-193a-5p Regulates the Synthesis of Polyunsaturated Fatty Acids by Targeting Fatty Acid Desaturase 1 (FADS1) in Bovine Mammary Epithelial Cells. Biomolecules. 2021 01; 11(2):. doi: 10.3390/biom11020157. [PMID: 33504005]
  • Xingjun Meng, Bo Zhu, Yan Liu, Lei Fang, Binbin Yin, Yanni Sun, Mengni Ma, Yuli Huang, Yuning Zhu, Yunlong Zhang. Unique Biomarker Characteristics in Gestational Diabetes Mellitus Identified by LC-MS-Based Metabolic Profiling. Journal of diabetes research. 2021; 2021(?):6689414. doi: 10.1155/2021/6689414. [PMID: 34212051]
  • Juan Lei, Yu Zhou, Huakan Zhao, Yu Chen, Guifang Yan, Lei Wu, Yanquan Xu, Jiangang Zhang, Xiao Zhang, Jingchun Wang, Dingshan Li, Yongsheng Li. Dabigatran activates inflammation resolution by promoting fibrinogen-like protein 2 shedding and RvD5n-3 DPA production. Theranostics. 2021; 11(9):4251-4261. doi: 10.7150/thno.50182. [PMID: 33754059]
  • Anandita Pal, Adam H Metherel, Lauren Fiabane, Nicole Buddenbaum, Richard P Bazinet, Saame Raza Shaikh. Do Eicosapentaenoic Acid and Docosahexaenoic Acid Have the Potential to Compete against Each Other?. Nutrients. 2020 Dec; 12(12):. doi: 10.3390/nu12123718. [PMID: 33276463]
  • Siting Li, Zhangli Hu, Xuewei Yang, Yan Li. Effect of Nitrogen Sources on Omega-3 Polyunsaturated Fatty Acid Biosynthesis and Gene Expression in Thraustochytriidae sp. Marine drugs. 2020 Dec; 18(12):. doi: 10.3390/md18120612. [PMID: 33271856]
  • Kerry Flannagan, Sheila Gahagan, Arun Das, Raquel Burrows, Betsy Lozoff, Eduardo Villamor. Serum polyunsaturated fatty acids in infancy are associated with body composition in adolescence. Pediatric obesity. 2020 11; 15(11):e12656. doi: 10.1111/ijpo.12656. [PMID: 32426929]
  • Esteban A Gomez, Romain A Colas, Patricia R Souza, Rebecca Hands, Myles J Lewis, Conrad Bessant, Costantino Pitzalis, Jesmond Dalli. Blood pro-resolving mediators are linked with synovial pathology and are predictive of DMARD responsiveness in rheumatoid arthritis. Nature communications. 2020 10; 11(1):5420. doi: 10.1038/s41467-020-19176-z. [PMID: 33110080]
  • Sebastian Dams, Sandra Holasek, Melina Tsiountsioura, Martin Edelsbrunner, Pavel Dietz, Harald Koefeler, Daniela-Eugenia Malliga, Ayse Gürbüz, Nathalie Meier-Allard, Brigitte Poncza, Sonja Lackner, Elke Schwarzenberger, Yvonne Jansenberger, Manfred Lamprecht. Effects of a plant-based fatty acid supplement and a powdered fruit, vegetable and berry juice concentrate on omega-3-indices and serum micronutrient concentrations in healthy subjects. International journal of food sciences and nutrition. 2020 Sep; 71(6):769-780. doi: 10.1080/09637486.2020.1725960. [PMID: 32064970]
  • Melinda S Schaller, Mian Chen, Romain A Colas, Thomas A Sorrentino, Ann A Lazar, S Marlene Grenon, Jesmond Dalli, Michael S Conte. Treatment With a Marine Oil Supplement Alters Lipid Mediators and Leukocyte Phenotype in Healthy Patients and Those With Peripheral Artery Disease. Journal of the American Heart Association. 2020 08; 9(15):e016113. doi: 10.1161/jaha.120.016113. [PMID: 32696697]
  • So-Ichiro Hirata, Takahiro Nagatake, Kento Sawane, Koji Hosomi, Tetsuya Honda, Sachiko Ono, Noriko Shibuya, Emiko Saito, Jun Adachi, Yuichi Abe, Junko Isoyama, Hidehiko Suzuki, Ayu Matsunaga, Takeshi Tomonaga, Hiroshi Kiyono, Kenji Kabashima, Makoto Arita, Jun Kunisawa. Maternal ω3 docosapentaenoic acid inhibits infant allergic dermatitis through TRAIL-expressing plasmacytoid dendritic cells in mice. Allergy. 2020 08; 75(8):1939-1955. doi: 10.1111/all.14217. [PMID: 32027039]
  • Xiao-Fei Guo, Wen-Feng Tong, Yue Ruan, Andrew J Sinclair, Duo Li. Different metabolism of EPA, DPA and DHA in humans: A double-blind cross-over study. Prostaglandins, leukotrienes, and essential fatty acids. 2020 07; 158(?):102033. doi: 10.1016/j.plefa.2019.102033. [PMID: 31740197]
  • Ge Liu, Robert A Gibson, Damien Callahan, Xiao-Fei Guo, Duo Li, Andrew J Sinclair. Pure omega 3 polyunsaturated fatty acids (EPA, DPA or DHA) are associated with increased plasma levels of 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid (CMPF) in a short-term study in women. Food & function. 2020 Mar; 11(3):2058-2066. doi: 10.1039/c9fo02440a. [PMID: 32142084]
  • Maria K Pangopoulos, Jens M N Nolsøe, Simen G Antonsen, Romain A Colas, Jesmond Dalli, Marius Aursnes, Yngve Stenstrøm, Trond Vidar Hansen. Enzymatic studies with 3-oxa n-3 DPA. Bioorganic chemistry. 2020 03; 96(?):103653. doi: 10.1016/j.bioorg.2020.103653. [PMID: 32062066]
  • Xingyu Zhu, Shuangfei Li, Liangxu Liu, Siting Li, Yanqing Luo, Chuhan Lv, Boyu Wang, Christopher H K Cheng, Huapu Chen, Xuewei Yang. Genome Sequencing and Analysis of Thraustochytriidae sp. SZU445 Provides Novel Insights into the Polyunsaturated Fatty Acid Biosynthesis Pathway. Marine drugs. 2020 Feb; 18(2):. doi: 10.3390/md18020118. [PMID: 32085426]
  • Lauren A Roach, Kenneth G Russell, Kelly Lambert, Jane L Holt, Barbara J Meyer. Polyunsaturated fatty acid food frequency questionnaire validation in people with end stage renal disease on dialysis. Nutrition & dietetics: the journal of the Dietitians Association of Australia. 2020 02; 77(1):131-138. doi: 10.1111/1747-0080.12483. [PMID: 30338904]
  • Qiu-Lan Ma, Cansheng Zhu, Marco Morselli, Trent Su, Matteo Pelligrini, Zhengqi Lu, Mychica Jones, Paul Denver, Daniel Castro, Xuelin Gu, Frances Relampagos, Kaitlin Caoili, Bruce Teter, Sally A Frautschy, Gregory M Cole. The Novel Omega-6 Fatty Acid Docosapentaenoic Acid Positively Modulates Brain Innate Immune Response for Resolving Neuroinflammation at Early and Late Stages of Humanized APOE-Based Alzheimer's Disease Models. Frontiers in immunology. 2020; 11(?):558036. doi: 10.3389/fimmu.2020.558036. [PMID: 33178186]
  • Pablo Perez-Martinez, Niki Katsiki, Dimitri P Mikhailidis. The Role of n-3 Fatty Acids in Cardiovascular Disease: Back to the Future. Angiology. 2020 01; 71(1):10-16. doi: 10.1177/0003319719842005. [PMID: 30966756]
  • Hiroaki Saito, Hisashi Ioka. Lipids and Fatty Acids of Sea Hares Aplysia kurodai and Aplysia juliana: High Levels of Icosapentaenoic and n-3 Docosapentaenoic Acids. Journal of oleo science. 2019 Dec; 68(12):1199-1213. doi: 10.5650/jos.ess19137. [PMID: 31735747]
  • Nhien Nguyen, Michelle Dow, Blake Woodside, J Bruce German, Oswald Quehenberger, Pei-An Betty Shih. Food-Intake Normalization of Dysregulated Fatty Acids in Women with Anorexia Nervosa. Nutrients. 2019 Sep; 11(9):. doi: 10.3390/nu11092208. [PMID: 31540208]
  • D Carreño, P G Toral, E Pinloche, A Belenguer, D R Yáñez-Ruiz, G Hervás, N R McEwan, C J Newbold, P Frutos. Rumen bacterial community responses to DPA, EPA and DHA in cattle and sheep: A comparative in vitro study. Scientific reports. 2019 08; 9(1):11857. doi: 10.1038/s41598-019-48294-y. [PMID: 31413283]
  • Zhenxiao Zheng, Zhiyuan Dai, Yalun Cao, Qing Shen, Yiqi Zhang. Docosapentaenoic acid (DPA, 22:5n-3) ameliorates inflammation in an ulcerative colitis model. Food & function. 2019 Jul; 10(7):4199-4209. doi: 10.1039/c8fo02338g. [PMID: 31250861]
  • Gaetan Drouin, Vincent Rioux, Philippe Legrand. The n-3 docosapentaenoic acid (DPA): A new player in the n-3 long chain polyunsaturated fatty acid family. Biochimie. 2019 Apr; 159(?):36-48. doi: 10.1016/j.biochi.2019.01.022. [PMID: 30716358]
  • Chesney K Richter, Karl Stessy Bisselou, Tara M Nordgren, Lynette Smith, Adams Kusi Appiah, Nicholas Hein, Ann Anderson-Berry, Penny Kris-Etherton, Corrine Hanson, Ann C Skulas-Ray. n-3 Docosapentaenoic Acid Intake and Relationship with Plasma Long-Chain n-3 Fatty Acid Concentrations in the United States: NHANES 2003-2014. Lipids. 2019 04; 54(4):221-230. doi: 10.1002/lipd.12146. [PMID: 31025717]
  • Anne M van der Does, Marieke Heijink, Oleg A Mayboroda, Louise J Persson, Marianne Aanerud, Per Bakke, Tomas M Eagan, Pieter S Hiemstra, Martin Giera. Dynamic differences in dietary polyunsaturated fatty acid metabolism in sputum of COPD patients and controls. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2019 03; 1864(3):224-233. doi: 10.1016/j.bbalip.2018.11.012. [PMID: 30528790]
  • Alok Patel, Leonidas Matsakas, Kateřina Hrůzová, Ulrika Rova, Paul Christakopoulos. Biosynthesis of Nutraceutical Fatty Acids by the Oleaginous Marine Microalgae Phaeodactylum tricornutum Utilizing Hydrolysates from Organosolv-Pretreated Birch and Spruce Biomass. Marine drugs. 2019 Feb; 17(2):. doi: 10.3390/md17020119. [PMID: 30781416]
  • Jørn Eivind Tungen, Lisa Gerstmann, Anders Vik, Roberta De Matteis, Romain Alexandre Colas, Jesmond Dalli, Nan Chiang, Charles Nicholas Serhan, Markus Kalesse, Trond Vidar Hansen. Resolving Inflammation: Synthesis, Configurational Assignment, and Biological Evaluations of RvD1n-3 DPA. Chemistry (Weinheim an der Bergstrasse, Germany). 2019 Jan; 25(6):1476-1480. doi: 10.1002/chem.201806029. [PMID: 30511787]
  • Aysegul Hanikoglu, Ertan Kucuksayan, Ferhat Hanikoglu, Tomris Ozben, Georgia Menounou, Anna Sansone, Chrys Chatgilialoglu, Giuseppe Di Bella, Carla Ferreri. Effects of Somatostatin and Vitamin C on the Fatty Acid Profile of Breast Cancer Cell Membranes. Anti-cancer agents in medicinal chemistry. 2019; 19(15):1899-1909. doi: 10.2174/1871520619666190930130732. [PMID: 31566138]
  • Gaetan Drouin, Daniel Catheline, Etienne Guillocheau, Pierre Gueret, Charlotte Baudry, Pascale Le Ruyet, Vincent Rioux, Philippe Legrand. Comparative effects of dietary n-3 docosapentaenoic acid (DPA), DHA and EPA on plasma lipid parameters, oxidative status and fatty acid tissue composition. The Journal of nutritional biochemistry. 2019 01; 63(?):186-196. doi: 10.1016/j.jnutbio.2018.09.029. [PMID: 30412907]
  • Quang Vu Nguyen, Hung Van Le, Don Viet Nguyen, Bunmi S Malau-Aduli, Peter D Nichols, Aduli E O Malau-Aduli. Enhancement of dairy sheep cheese eating quality with increased n-3 long-chain polyunsaturated fatty acids. Journal of dairy science. 2019 Jan; 102(1):211-222. doi: 10.3168/jds.2018-15215. [PMID: 30391173]
  • Natalie M Hohos, Kirstin J Cho, Delaney C Swindle, Amanda A Allshouse, Michael C Rudolph, Malgorzata E Skaznik-Wikiel. Fat-1 Transgene Is Associated With Improved Reproductive Outcomes. Endocrinology. 2018 12; 159(12):3981-3992. doi: 10.1210/en.2018-00723. [PMID: 30403782]
  • Xianrong Shao, Gizem Bor, Sabah Al-Hosayni, Stefan Salentinig, Anan Yaghmur. Structural characterization of self-assemblies of new omega-3 lipids: docosahexaenoic acid and docosapentaenoic acid monoglycerides. Physical chemistry chemical physics : PCCP. 2018 Oct; 20(37):23928-23941. doi: 10.1039/c8cp04256j. [PMID: 30209464]
  • Gaetan Drouin, Etienne Guillocheau, Daniel Catheline, Charlotte Baudry, Pascale Le Ruyet, Vincent Rioux, Philippe Legrand. Impact of n-3 Docosapentaenoic Acid Supplementation on Fatty Acid Composition in Rat Differs Depending upon Tissues and Is Influenced by the Presence of Dairy Lipids in the Diet. Journal of agricultural and food chemistry. 2018 Sep; 66(38):9976-9988. doi: 10.1021/acs.jafc.8b03069. [PMID: 30056717]
  • Xiao-Fei Guo, Andrew J Sinclair, Gunveen Kaur, Duo Li. Differential effects of EPA, DPA and DHA on cardio-metabolic risk factors in high-fat diet fed mice. Prostaglandins, leukotrienes, and essential fatty acids. 2018 09; 136(?):47-55. doi: 10.1016/j.plefa.2017.09.011. [PMID: 29113747]
  • Kimberly Pistorius, Patricia R Souza, Roberta De Matteis, Shani Austin-Williams, Karoline G Primdahl, Anders Vik, Francesca Mazzacuva, Romain A Colas, Raquel M Marques, Trond V Hansen, Jesmond Dalli. PDn-3 DPA Pathway Regulates Human Monocyte Differentiation and Macrophage Function. Cell chemical biology. 2018 06; 25(6):749-760.e9. doi: 10.1016/j.chembiol.2018.04.017. [PMID: 29805036]
  • Xiaoling Leng, Jacob J Kinnun, Andres T Cavazos, Samuel W Canner, Saame Raza Shaikh, Scott E Feller, Stephen R Wassall. All n-3 PUFA are not the same: MD simulations reveal differences in membrane organization for EPA, DHA and DPA. Biochimica et biophysica acta. Biomembranes. 2018 May; 1860(5):1125-1134. doi: 10.1016/j.bbamem.2018.01.002. [PMID: 29305832]
  • Romain A Colas, Patricia R Souza, Mary E Walker, Maudrian Burton, Zbigniew Zasłona, Annie M Curtis, Raquel M Marques, Jesmond Dalli. Impaired Production and Diurnal Regulation of Vascular RvDn-3 DPA Increase Systemic Inflammation and Cardiovascular Disease. Circulation research. 2018 03; 122(6):855-863. doi: 10.1161/circresaha.117.312472. [PMID: 29437834]
  • P C Calder. Very long-chain n-3 fatty acids and human health: fact, fiction and the future. The Proceedings of the Nutrition Society. 2018 02; 77(1):52-72. doi: 10.1017/s0029665117003950. [PMID: 29039280]
  • Xiao-Yuan Dai Perrard, Zeqin Lian, George Bobotas, Mary R Dicklin, Kevin C Maki, Huaizhu Wu. Effects of n-3 fatty acid treatment on monocyte phenotypes in humans with hypertriglyceridemia. Journal of clinical lipidology. 2017 Nov; 11(6):1361-1371. doi: 10.1016/j.jacl.2017.08.011. [PMID: 28942094]
  • Karoline Gangestad Primdahl, Jørn Eivind Tungen, Patricia Regina Soares De Souza, Romain Alexandre Colas, Jesmond Dalli, Trond Vidar Hansen, Anders Vik. Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PDn-3 DPA. Organic & biomolecular chemistry. 2017 Oct; 15(40):8606-8613. doi: 10.1039/c7ob02113e. [PMID: 28980694]
  • Jiung-Pang Huang, Mei-Ling Cheng, Cheng-Yu Hung, Chao-Hung Wang, Po-Shiuan Hsieh, Ming-Shi Shiao, Jan-Kan Chen, Dai-Er Li, Li-Man Hung. Docosapentaenoic acid and docosahexaenoic acid are positively associated with insulin sensitivity in rats fed high-fat and high-fructose diets. Journal of diabetes. 2017 Oct; 9(10):936-946. doi: 10.1111/1753-0407.12505. [PMID: 27860326]
  • Yanzhu Tian, Ami Katsuki, Donato Romanazzi, Matthew R Miller, Serean L Adams, Kazuo Miyashita, Masashi Hosokawa. Docosapentaenoic Acid (22:5n-3) Downregulates mRNA Expression of Pro-inflammatory Factors in LPS-activated Murine Macrophage Like RAW264.7 Cells. Journal of oleo science. 2017 Oct; 66(10):1149-1156. doi: 10.5650/jos.ess17111. [PMID: 28924088]
  • Rennan Feng, Chao Luo, Chunlong Li, Shanshan Du, Akinkunmi Paul Okekunle, Yanchuan Li, Yang Chen, Tianqi Zi, Yucun Niu. Free fatty acids profile among lean, overweight and obese non-alcoholic fatty liver disease patients: a case - control study. Lipids in health and disease. 2017 Sep; 16(1):165. doi: 10.1186/s12944-017-0551-1. [PMID: 28870233]
  • Don V Nguyen, Van H Le, Quang V Nguyen, Bunmi S Malau-Aduli, Peter D Nichols, Aduli E O Malau-Aduli. Omega-3 Long-Chain Fatty Acids in the Heart, Kidney, Liver and Plasma Metabolite Profiles of Australian Prime Lambs Supplemented with Pelleted Canola and Flaxseed Oils. Nutrients. 2017 Aug; 9(8):. doi: 10.3390/nu9080893. [PMID: 28817082]
  • Juliana Dos Santos Vaz, Dayana Rodrigues Farias, Amanda Rodrigues Amorim Adegboye, Antonio Egidio Nardi, Gilberto Kac. Omega-3 supplementation from pregnancy to postpartum to prevent depressive symptoms: a randomized placebo-controlled trial. BMC pregnancy and childbirth. 2017 Jun; 17(1):180. doi: 10.1186/s12884-017-1365-x. [PMID: 28599630]
  • Slavica Ranković, Tamara Popović, Jasmina Debeljak Martačić, Snježana Petrović, Mirko Tomić, Đurđica Ignjatović, Gordana Tovilović-Kovačević, Maria Glibetić. Liver phospholipids fatty acids composition in response to different types of diets in rats of both sexes. Lipids in health and disease. 2017 May; 16(1):94. doi: 10.1186/s12944-017-0483-9. [PMID: 28526084]
  • Ivar A Eide, Anders Åsberg, My Svensson, Thor Ueland, Tom E Mollnes, Anders Hartmann, Kristian S Bjerve, Annika Michelsen, Pål Aukrust, Jeppe H Christensen, Erik B Schmidt, Trond Jenssen. Plasma Levels of Marine n-3 Fatty Acids Are Inversely Correlated With Proinflammatory Markers sTNFR1 and IL-6 in Renal Transplant Recipients. Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation. 2017 05; 27(3):161-168. doi: 10.1053/j.jrn.2016.09.008. [PMID: 27838193]
  • T J P Pinto, A A F Vilela, D R Farias, J Lepsch, G M Cunha, J S Vaz, P Factor-Litvak, G Kac. Serum n-3 polyunsaturated fatty acids are inversely associated with longitudinal changes in depressive symptoms during pregnancy. Epidemiology and psychiatric sciences. 2017 Apr; 26(2):157-168. doi: 10.1017/s204579601500116x. [PMID: 27026507]
  • 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]
  • Yanzhu Tian, Donato Romanazzi, Kazuo Miyashita, Masashi Hosokawa. Bioconversion of Docosapentaenoic Acid in Human Cell Lines, Caco-2, HepG2, and THP-1. Journal of oleo science. 2016 Dec; 65(12):1017-1022. doi: 10.5650/jos.ess16128. [PMID: 27829615]
  • James F Markworth, Gunveen Kaur, Eliza G Miller, Amy E Larsen, Andrew J Sinclair, Krishna Rao Maddipati, David Cameron-Smith. Divergent shifts in lipid mediator profile following supplementation with n-3 docosapentaenoic acid and eicosapentaenoic acid. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2016 11; 30(11):3714-3725. doi: 10.1096/fj.201600360r. [PMID: 27461565]
  • Kyoko Miura, Maria Celia B Hughes, Jacobus Pj Ungerer, Adèle C Green. Plasma eicosapentaenoic acid is negatively associated with all-cause mortality among men and women in a population-based prospective study. Nutrition research (New York, N.Y.). 2016 11; 36(11):1202-1209. doi: 10.1016/j.nutres.2016.09.006. [PMID: 27865614]
  • Karoline G Primdahl, Marius Aursnes, Mary E Walker, Romain A Colas, Charles N Serhan, Jesmond Dalli, Trond V Hansen, Anders Vik. Synthesis of 13(R)-Hydroxy-7Z,10Z,13R,14E,16Z,19Z Docosapentaenoic Acid (13R-HDPA) and Its Biosynthetic Conversion to the 13-Series Resolvins. Journal of natural products. 2016 10; 79(10):2693-2702. doi: 10.1021/acs.jnatprod.6b00634. [PMID: 27704804]
  • Karsten-H Weylandt. Docosapentaenoic acid derived metabolites and mediators - The new world of lipid mediator medicine in a nutshell. European journal of pharmacology. 2016 Aug; 785(?):108-115. doi: 10.1016/j.ejphar.2015.11.002. [PMID: 26546723]
  • R Daneshmand, S Kurl, T-P Tuomainen, J K Virtanen. Associations of serum n-3 and n-6 polyunsaturated fatty acids with plasma natriuretic peptides. European journal of clinical nutrition. 2016 08; 70(8):963-9. doi: 10.1038/ejcn.2016.58. [PMID: 27071511]
  • T A D'Ascoli, J Mursu, S Voutilainen, J Kauhanen, T-P Tuomainen, J K Virtanen. Association between serum long-chain omega-3 polyunsaturated fatty acids and cognitive performance in elderly men and women: The Kuopio Ischaemic Heart Disease Risk Factor Study. European journal of clinical nutrition. 2016 08; 70(8):970-5. doi: 10.1038/ejcn.2016.59. [PMID: 27071510]
  • Liana C Del Gobbo, Fumiaki Imamura, Stella Aslibekyan, Matti Marklund, Jyrki K Virtanen, Maria Wennberg, Mohammad Y Yakoob, Stephanie E Chiuve, Luicito Dela Cruz, Alexis C Frazier-Wood, Amanda M Fretts, Eliseo Guallar, Chisa Matsumoto, Kiesha Prem, Tosh Tanaka, Jason H Y Wu, Xia Zhou, Catherine Helmer, Erik Ingelsson, Jian-Min Yuan, Pascale Barberger-Gateau, Hannia Campos, Paulo H M Chaves, Luc Djoussé, Graham G Giles, Jose Gómez-Aracena, Allison M Hodge, Frank B Hu, Jan-Håkan Jansson, Ingegerd Johansson, Kay-Tee Khaw, Woon-Puay Koh, Rozenn N Lemaitre, Lars Lind, Robert N Luben, Eric B Rimm, Ulf Risérus, Cecilia Samieri, Paul W Franks, David S Siscovick, Meir Stampfer, Lyn M Steffen, Brian T Steffen, Michael Y Tsai, Rob M van Dam, Sari Voutilainen, Walter C Willett, Mark Woodward, Dariush Mozaffarian. ω-3 Polyunsaturated Fatty Acid Biomarkers and Coronary Heart Disease: Pooling Project of 19 Cohort Studies. JAMA internal medicine. 2016 08; 176(8):1155-66. doi: 10.1001/jamainternmed.2016.2925. [PMID: 27357102]
  • Behnam Tajik, Sudhir Kurl, Tomi-Pekka Tuomainen, Jyrki K Virtanen. The association of serum long-chain n-3 PUFA and hair mercury with exercise cardiac power in men. The British journal of nutrition. 2016 08; 116(3):487-95. doi: 10.1017/s0007114516002142. [PMID: 27255152]
  • Aleksandra Jelena Vidakovic, Susana Santos, Michelle A Williams, Liesbeth Duijts, Albert Hofman, Hans Demmelmair, Berthold Koletzko, Vincent W V Jaddoe, Romy Gaillard. Maternal plasma n-3 and n-6 polyunsaturated fatty acid concentrations during pregnancy and subcutaneous fat mass in infancy. Obesity (Silver Spring, Md.). 2016 08; 24(8):1759-66. doi: 10.1002/oby.21547. [PMID: 27356181]
  • Chad M Cook, Hogne Hallaråker, Per Christian Sæbø, Sheila M Innis, Kathleen M Kelley, Kristen D Sanoshy, Alvin Berger, Kevin C Maki. Bioavailability of long chain omega-3 polyunsaturated fatty acids from phospholipid-rich herring roe oil in men and women with mildly elevated triacylglycerols. Prostaglandins, leukotrienes, and essential fatty acids. 2016 08; 111(?):17-24. doi: 10.1016/j.plefa.2016.01.007. [PMID: 27151222]
  • Asenath N Nyantika, Tomi-Pekka Tuomainen, Jussi Kauhanen, Sari Voutilainen, Jyrki K Virtanen. Serum long-chain omega-3 polyunsaturated fatty acids and risk of orthostatic hypotension. Hypertension research : official journal of the Japanese Society of Hypertension. 2016 Jul; 39(7):543-7. doi: 10.1038/hr.2016.19. [PMID: 26911234]
  • C B Dias, L G Wood, M L Garg. Effects of dietary saturated and n-6 polyunsaturated fatty acids on the incorporation of long-chain n-3 polyunsaturated fatty acids into blood lipids. European journal of clinical nutrition. 2016 07; 70(7):812-8. doi: 10.1038/ejcn.2015.213. [PMID: 26757835]
  • Mitchell Harris, Jacob J Kinnun, Rasagna Kosaraju, Xiaoling Leng, Stephen R Wassall, Saame Raza Shaikh. Membrane Disordering by Eicosapentaenoic Acid in B Lymphomas Is Reduced by Elongation to Docosapentaenoic Acid as Revealed with Solid-State Nuclear Magnetic Resonance Spectroscopy of Model Membranes. The Journal of nutrition. 2016 07; 146(7):1283-9. doi: 10.3945/jn.116.231639. [PMID: 27306897]
  • Julie K Bassett, Allison M Hodge, Dallas R English, Robert J MacInnis, Graham G Giles. Plasma phospholipids fatty acids, dietary fatty acids, and breast cancer risk. Cancer causes & control : CCC. 2016 06; 27(6):759-73. doi: 10.1007/s10552-016-0753-2. [PMID: 27146840]
  • Amit Sharma, Md Abdul Hye Khan, Scott P Levick, Kin Sing Stephen Lee, Bruce D Hammock, John D Imig. Novel Omega-3 Fatty Acid Epoxygenase Metabolite Reduces Kidney Fibrosis. International journal of molecular sciences. 2016 May; 17(5):. doi: 10.3390/ijms17050751. [PMID: 27213332]
  • I S M van der Wurff, E C Bakker, G Hornstra, P A Kirschner, M Gielen, R W L Godschalk, S Kremers, M P Zeegers, R H M de Groot. Association between prenatal and current exposure to selected LCPUFAs and school performance at age 7. Prostaglandins, leukotrienes, and essential fatty acids. 2016 05; 108(?):22-9. doi: 10.1016/j.plefa.2016.03.005. [PMID: 27154361]
  • Matthew J Picklo, Eric J Murphy. A High-Fat, High-Oleic Diet, But Not a High-Fat, Saturated Diet, Reduces Hepatic α-Linolenic Acid and Eicosapentaenoic Acid Content in Mice. Lipids. 2016 05; 51(5):537-47. doi: 10.1007/s11745-015-4106-9. [PMID: 26694605]
  • Xuemei Xie, Xudong Wang, Gail J Mick, Janusz H Kabarowski, Landon Shay Wilson, Stephen Barnes, Gregory P Walcott, Xiaoping Luo, Kenneth McCormick. Effect of n-3 and n-6 Polyunsaturated Fatty Acids on Microsomal P450 Steroidogenic Enzyme Activities and In Vitro Cortisol Production in Adrenal Tissue From Yorkshire Boars. Endocrinology. 2016 Apr; 157(4):1512-21. doi: 10.1210/en.2015-1831. [PMID: 26889941]
  • V A Akmurzina, E E Petryairina, S V Saveliev, A A Selishcheva. [The profile of plasma non-esterified fatty acids in children with different terms of type 1 diabetes mellitus]. Biomeditsinskaia khimiia. 2016 Mar; 62(2):206-11. doi: 10.18097/pbmc20166202206. [PMID: 27143381]
  • Andrea L Edel, Amanda F Patenaude, Melanie N Richard, Elena Dibrov, J Alejandro Austria, Harold M Aukema, Grant N Pierce, Michel Aliani. The effect of flaxseed dose on circulating concentrations of alpha-linolenic acid and secoisolariciresinol diglucoside derived enterolignans in young, healthy adults. European journal of nutrition. 2016 Mar; 55(2):651-663. doi: 10.1007/s00394-015-0885-2. [PMID: 25808116]
  • Gunveen Kaur, Xiao-Fei Guo, Andrew J Sinclair. Short update on docosapentaenoic acid: a bioactive long-chain n-3 fatty acid. Current opinion in clinical nutrition and metabolic care. 2016 Mar; 19(2):88-91. doi: 10.1097/mco.0000000000000252. [PMID: 26808265]
  • Katrin Kuhnt, Stefanie Weiß, Michael Kiehntopf, Gerhard Jahreis. Consumption of echium oil increases EPA and DPA in blood fractions more efficiently compared to linseed oil in humans. Lipids in health and disease. 2016 Feb; 15(?):32. doi: 10.1186/s12944-016-0199-2. [PMID: 26892399]
  • Anne E Barden, Emilie Mas, Trevor A Mori. n-3 Fatty acid supplementation and proresolving mediators of inflammation. Current opinion in lipidology. 2016 Feb; 27(1):26-32. doi: 10.1097/mol.0000000000000262. [PMID: 26655290]
  • Rolf K Berge, Marie S Ramsvik, Pavol Bohov, Asbjørn Svardal, Jan E Nordrehaug, Espen Rostrup, Inge Bruheim, Bodil Bjørndal. Krill oil reduces plasma triacylglycerol level and improves related lipoprotein particle concentration, fatty acid composition and redox status in healthy young adults - a pilot study. Lipids in health and disease. 2015 Dec; 14(?):163. doi: 10.1186/s12944-015-0162-7. [PMID: 26666303]
  • Pavla Linhartova, Sabine Sampels. Combined incubation of cadmium, docosahexaenoic and eicosapentaenoic acid results in increased uptake of cadmium and elevated docosapentaenoic acid content in hepatocytes in vitro. Lipids in health and disease. 2015 Dec; 14(?):156. doi: 10.1186/s12944-015-0159-2. [PMID: 26627047]
  • Marcela Henríquez-Henríquez, Sandra Solari, Gisela Várgas, Luis Vásquez, Fidel Allende, Carla Castañón S, Marcela Tenorio, Teresa Quiroga Gutiérrez. ω-3 Long-Chain Polyunsaturated Fatty Acids and Fatty Acid Desaturase Activity Ratios as Eventual Endophenotypes for ADHD. Journal of attention disorders. 2015 Nov; 19(11):977-86. doi: 10.1177/1087054712461175. [PMID: 23100268]
  • Ann C Skulas-Ray, Michael R Flock, Chesney K Richter, William S Harris, Sheila G West, Penny M Kris-Etherton. Red Blood Cell Docosapentaenoic Acid (DPA n-3) is Inversely Associated with Triglycerides and C-reactive Protein (CRP) in Healthy Adults and Dose-Dependently Increases Following n-3 Fatty Acid Supplementation. Nutrients. 2015 Aug; 7(8):6390-404. doi: 10.3390/nu7085291. [PMID: 26247967]
  • Caroline Morin, Pierre U Blier, Samuel Fortin. Eicosapentaenoic acid and docosapentaenoic acid monoglycerides are more potent than docosahexaenoic acid monoglyceride to resolve inflammation in a rheumatoid arthritis model. Arthritis research & therapy. 2015 May; 17(?):142. doi: 10.1186/s13075-015-0653-y. [PMID: 26022389]
  • Shigemasa Tani, Atsuhiko Takahashi, Ken Nagao, Atsushi Hirayama. Association of Fish Consumption-Derived Ratio of Serum n-3 to n-6 Polyunsaturated Fatty Acids and Cardiovascular Risk With the Prevalence of Coronary Artery Disease. International heart journal. 2015 May; 56(3):260-8. doi: 10.1536/ihj.14-243. [PMID: 25902881]
  • A N Nyantika, T-P Tuomainen, J Kauhanen, S Voutilainen, J K Virtanen. Serum long-chain omega-3 polyunsaturated Fatty acids and future blood pressure in an ageing population. The journal of nutrition, health & aging. 2015 May; 19(5):498-503. doi: 10.1007/s12603-015-0463-6. [PMID: 25923477]
  • J K Pittaway, L T Chuang, K D K Ahuja, J M Beckett, R H Glew, M J Ball. Omega-3 dietary Fatty Acid status of healthy older adults in Tasmania, Australia: an observational study. The journal of nutrition, health & aging. 2015 May; 19(5):505-10. doi: 10.1007/s12603-015-0459-2. [PMID: 25923478]
  • András Tárnok, Tamás Marosvölgyi, Éva Szabó, Eszter Györei, Tamás Decsi. Low n-3 long-chain polyunsaturated fatty acids in newly diagnosed celiac disease in children with preexisting type 1 diabetes mellitus. Journal of pediatric gastroenterology and nutrition. 2015 Feb; 60(2):255-8. doi: 10.1097/mpg.0000000000000561. [PMID: 25207475]
  • Sun Hee Kim, Kyung Hee Roh, Jong-Sug Park, Kwang-Soo Kim, Hyun Uk Kim, Kyeong-Ryeol Lee, Han-Chul Kang, Jong-Bum Kim. Heterologous Reconstitution of Omega-3 Polyunsaturated Fatty Acids in Arabidopsis. BioMed research international. 2015; 2015(?):768478. doi: 10.1155/2015/768478. [PMID: 26339641]
  • Nisar A Shaikh, Jason Yantha, Sabah Shaikh, William Rowe, Maggie Laidlaw, Carla Cockerline, Abbas Ali, Bruce Holub, George Jackowski. Efficacy of a unique omega-3 formulation on the correction of nutritional deficiency and its effects on cardiovascular disease risk factors in a randomized controlled VASCAZEN(®) REVEAL Trial. Molecular and cellular biochemistry. 2014 Nov; 396(1-2):9-22. doi: 10.1007/s11010-014-2132-1. [PMID: 25185754]
  • Luc Djoussé, Andrew B Petrone, Natalie L Weir, Naomi Q Hanson, Robert J Glynn, Michael Y Tsai, J Michael Gaziano. Repeated versus single measurement of plasma omega-3 fatty acids and risk of heart failure. European journal of nutrition. 2014 Sep; 53(6):1403-8. doi: 10.1007/s00394-013-0642-3. [PMID: 24395612]
  • M-È Labonté, E Dewailly, M Lucas, P Couture, B Lamarche. Association of red blood cell n-3 polyunsaturated fatty acids with plasma inflammatory biomarkers among the Quebec Cree population. European journal of clinical nutrition. 2014 Sep; 68(9):1042-7. doi: 10.1038/ejcn.2014.125. [PMID: 25028086]