Stearidonic acid (BioDeep_00000003492)

   

human metabolite Endogenous blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid

化学式: C18H28O2 (276.2089188)
中文名称: 芥酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.28%

Reviewed

Last reviewed on 2024-07-29.

Cite this Page

Stearidonic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/stearidonic_acid (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000003492). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CCCC/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O
InChI: InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-

描述信息

Steridonic acid, also known as (6z,9z,12z,15z)-octadecatetraenoic acid or stearidonate, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, steridonic acid is considered to be a fatty acid lipid molecule. Steridonic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Steridonic acid can be found in borage, which makes steridonic acid a potential biomarker for the consumption of this food product. Steridonic acid can be found primarily in blood and feces. In humans, steridonic acid is involved in the alpha linolenic acid and linoleic acid metabolism.
Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) PUFA. These oils appear to possess hypotriglyceridemic properties typically associated with fish oils.(PMID: 15173404). Stearidonic acid may be used as a precursor to increase the EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition in order to influence cellular responses and functions in desirable ways. (PMID: 15120716).

同义名列表

22 个代谢物同义名

(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid; (6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoate; all-cis-6,9,12,14-Octadecatetraenoic acid; (6Z,9Z,12Z,15Z)-Octadecatetraenoic acid; 6Z,9Z,12Z,15Z-octadecatetraenoic acid; (6Z,9Z,12Z,15Z)-Octadecatetraenoate; octadeca-6,9,12,15-tetraenoic acid; 6Z,9Z,12Z,15Z-Octadecatetraenoate; 6,9,12,15-octadecatetraenoic acid; 6,9,12,15-Octadecatetraenoate; FA(18:4(6Z,9Z,12Z,15Z)); Stearidonic acid C18:4; Stearidonic acid; Steridonic acid; C18:4n-3,6,9,12; Moroctic acid; Stearidonate; Morotic acid; FA(18:4n3); FA 18:4; SDA; Stearidonic acid



数据库引用编号

20 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

7 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(6)

PharmGKB(0)

81 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

  • 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]
  • F Xin, R Wang, Y Chang, Z Xie, Y Zhao, H Zhang, Y Song. Solid-state fermentation produces greater stearidonic acid levels in genetically engineered Mucor circinelloides. Letters in applied microbiology. 2022 Dec; 75(6):1617-1627. doi: 10.1111/lam.13829. [PMID: 36067029]
  • Changhwan Ju, Yu Jin Lee, Hui Su Yoon, Byung Hee Kim, In-Hwan Kim. Efficient Synthesis of Stearidonic Acid Enriched Triacylglycerol from Ahiflower Seed Oil via a Two-Step Enzyme Reaction. Journal of oleo science. 2022; 71(11):1679-1688. doi: 10.5650/jos.ess22215. [PMID: 36310055]
  • Ahmed S A El-Zenary, Khalid M Gaafar, Reham Abou-Elkhair, Robert G Elkin, John W Boney, Kevin J Harvatine. Comparison of Ahiflower oil containing stearidonic acid to a high-alpha-linolenic acid flaxseed oil at two levels on tissue omega-3 enrichment in broilers. Lipids. 2022 01; 57(1):57-68. doi: 10.1002/lipd.12329. [PMID: 34800048]
  • Robert G Elkin, Ahmed S A El-Zenary, Rebecca Bomberger, Kevin J Harvatine. Supplemental dietary oils rich in oleic acid or linoleic acid attenuate egg yolk and tissue n-3 polyunsaturated fatty acid contents in laying hens co-fed oils enriched in either stearidonic acid or α-linolenic acid. Prostaglandins, leukotrienes, and essential fatty acids. 2021 09; 172(?):102322. doi: 10.1016/j.plefa.2021.102322. [PMID: 34399187]
  • P Prasad, P Anjali, R V Sreedhar. Plant-based stearidonic acid as sustainable source of omega-3 fatty acid with functional outcomes on human health. Critical reviews in food science and nutrition. 2021; 61(10):1725-1737. doi: 10.1080/10408398.2020.1765137. [PMID: 32431176]
  • José Luis Guil-Guerrero, María José González-Fernández, Svetlana Lyashenko, Dmitri Fabrikov, Miguel Ángel Rincón-Cervera, Miguel Urrestarazu, Francisco Gómez-Mercado. γ-Linolenic and Stearidonic Acids from Boraginaceae of Diverse Mediterranean Origin. Chemistry & biodiversity. 2020 Dec; 17(12):e2000627. doi: 10.1002/cbdv.202000627. [PMID: 33045128]
  • Rafael R Segura Munoz, Truyen Quach, João C Gomes-Neto, Yibo Xian, Pamela A Pena, Steven Weier, Michael A Pellizzon, Hatem Kittana, Liz A Cody, Abby L Geis, Kari Heck, Robert J Schmaltz, Laure B Bindels, Edgar B Cahoon, Andrew K Benson, Tom Elmo Clemente, Amanda E Ramer-Tait. Stearidonic-Enriched Soybean Oil Modulates Obesity, Glucose Metabolism, and Fatty Acid Profiles Independently of Akkermansia muciniphila. Molecular nutrition & food research. 2020 09; 64(17):e2000162. doi: 10.1002/mnfr.202000162. [PMID: 32656952]
  • Dhruvesh Patel, Susan Goruk, Marnie Newell, Guanqun Chen, Caroline Richard, Catherine J Field. Feeding a Bioactive Oil Enriched in Stearidonic Acid during Early Life Influences Immune System Maturation in Neonatal Sprague-Dawley Rats. The Journal of nutrition. 2020 03; 150(3):606-615. doi: 10.1093/jn/nxz255. [PMID: 31722423]
  • Svetlana Lyashenko, María José González-Fernández, Francisco Gómez-Mercado, Svetlana Yunusova, Oleg Denisenko, José Luis Guil-Guerrero. Ribes taxa: A promising source of γ-linolenic acid-rich functional oils. Food chemistry. 2019 Dec; 301(?):125309. doi: 10.1016/j.foodchem.2019.125309. [PMID: 31398673]
  • Theresa Greupner, Elisabeth Koch, Laura Kutzner, Andreas Hahn, Nils Helge Schebb, Jan Philipp Schuchardt. Single-Dose SDA-Rich Echium Oil Increases Plasma EPA, DPAn3, and DHA Concentrations. Nutrients. 2019 Oct; 11(10):. doi: 10.3390/nu11102346. [PMID: 31581725]
  • A Novinscak, M Filion. Persistence of Pseudomonas fluorescens LBUM677 in the rhizosphere of corn gromwell (Buglossoides arvensis) under field conditions and its impact on seed oil and stearidonic acid bioaccumulation. Journal of applied microbiology. 2019 Jul; 127(1):208-218. doi: 10.1111/jam.14283. [PMID: 30985950]
  • Yuelian Li, Han Sun, Tao Wu, Yunlei Fu, Yongjin He, Xuemei Mao, Feng Chen. Storage carbon metabolism of Isochrysis zhangjiangensis under different light intensities and its application for co-production of fucoxanthin and stearidonic acid. Bioresource technology. 2019 Jun; 282(?):94-102. doi: 10.1016/j.biortech.2019.02.127. [PMID: 30852337]
  • Md Ahsanul Kabir Khan, Junhuan Yang, Syed Ammar Hussain, Huaiyuan Zhang, Victoriano Garre, Yuanda Song. Genetic Modification of Mucor circinelloides to Construct Stearidonic Acid Producing Cell Factory. International journal of molecular sciences. 2019 Apr; 20(7):. doi: 10.3390/ijms20071683. [PMID: 30987311]
  • Kyeong-Ryeol Lee, Kyung-Hwan Kim, Jung Bong Kim, Seung-Bum Hong, Inhwa Jeon, Hyun Uk Kim, Myung Hee Lee, Jae Kwang Kim. High accumulation of γ-linolenic acid and Stearidonic acid in transgenic Perilla (Perilla frutescens var. frutescens) seeds. BMC plant biology. 2019 Apr; 19(1):120. doi: 10.1186/s12870-019-1713-2. [PMID: 30935415]
  • Kate J Bowen, Chesney K Richter, Ann C Skulas-Ray, Dariush Mozaffarian, Penny M Kris-Etherton. Projected Long-Chain n-3 Fatty Acid Intake Post-Replacement of Vegetables Oils with Stearidonic Acid-Modified Varieties: Results from a National Health and Nutrition Examination Survey 2003-2008 Analysis. Lipids. 2018 10; 53(10):961-970. doi: 10.1002/lipd.12105. [PMID: 30536415]
  • Carlos Cardoso, Joana Paiva Martinho, Paula A Lopes, Susana Martins, Jorge Correia, Cláudia Afonso, Francisco J Alarcón, María J González-Fernández, Rui M Pinto, José A Prates, Narcisa M Bandarra, José L Guil-Guerrero. Stearidonic acid combined with alpha-linolenic acid improves lipemic and neurological markers in a rat model subject to a hypercaloric diet. Prostaglandins, leukotrienes, and essential fatty acids. 2018 08; 135(?):137-146. doi: 10.1016/j.plefa.2018.07.010. [PMID: 30103925]
  • A Novinscak, M Filion. Enhancing total lipid and stearidonic acid yields in Buglossoides arvensis through PGPR inoculation. Journal of applied microbiology. 2018 Jul; 125(1):203-215. doi: 10.1111/jam.13749. [PMID: 29495107]
  • Pierluigi Delmonte, Andrea Milani, Shivani Bhangley. Structural Determination and Occurrence in Ahiflower Oil of Stearidonic Acid Trans Fatty Acids. Lipids. 2018 02; 53(2):255-266. doi: 10.1002/lipd.12009. [PMID: 29537611]
  • Luis Vázquez, Elena Ortego, Marta Corzo-Martínez, Guillermo Reglero, Carlos F Torres. Stearidonic Acid Concentration by Urea Complexation from Echium Oil. Journal of oleo science. 2018; 67(9):1091-1099. doi: 10.5650/jos.ess18025. [PMID: 30175765]
  • Yueru Li, Yinghui Rong, Lisui Bao, Ben Nie, Guang Ren, Chen Zheng, Rajesh Amin, Robert D Arnold, Ramesh B Jeganathan, Kevin W Huggins. Suppression of adipocyte differentiation and lipid accumulation by stearidonic acid (SDA) in 3T3-L1 cells. Lipids in health and disease. 2017 Sep; 16(1):181. doi: 10.1186/s12944-017-0574-7. [PMID: 28946872]
  • R V Sreedhar, P Prasad, L Prasanna Anjaneya Reddy, Ram Rajasekharan, Malathi Srinivasan. Unravelling a stearidonic acid-rich triacylglycerol biosynthetic pathway in the developing seeds of Buglossoides arvensis: A transcriptomic landscape. Scientific reports. 2017 09; 7(1):10473. doi: 10.1038/s41598-017-09882-y. [PMID: 28874672]
  • Jeehye Sung, Heemang Jeon, In-Hwan Kim, Heon Sang Jeong, Junsoo Lee. Anti-Inflammatory Effects of Stearidonic Acid Mediated by Suppression of NF-κB and MAP-Kinase Pathways in Macrophages. Lipids. 2017 09; 52(9):781-787. doi: 10.1007/s11745-017-4278-6. [PMID: 28744771]
  • Natalie Lefort, Rémi LeBlanc, Marc E Surette. Dietary Buglossoides Arvensis Oil Increases Circulating n-3 Polyunsaturated Fatty Acids in a Dose-Dependent Manner and Enhances Lipopolysaccharide-Stimulated Whole Blood Interleukin-10-A Randomized Placebo-Controlled Trial. Nutrients. 2017 Mar; 9(3):. doi: 10.3390/nu9030261. [PMID: 28287415]
  • Hyunwoo Park, Steven Weier, Fareha Razvi, Pamela A Peña, Neil A Sims, Jennica Lowell, Cory Hungate, Karma Kissinger, Gavin Key, Paul Fraser, Johnathan A Napier, Edgar B Cahoon, Tom E Clemente. Towards the development of a sustainable soya bean-based feedstock for aquaculture. Plant biotechnology journal. 2017 02; 15(2):227-236. doi: 10.1111/pbi.12608. [PMID: 27496594]
  • 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]
  • Mahinda Y Abeywardena, Michael Adams, Julie Dallimore, Soressa M Kitessa. Rise in DPA Following SDA-Rich Dietary Echium Oil Less Effective in Affording Anti-Arrhythmic Actions Compared to High DHA Levels Achieved with Fish Oil in Sprague-Dawley Rats. Nutrients. 2016 Jan; 8(1):. doi: 10.3390/nu8010014. [PMID: 26742064]
  • Manja Dittrich, Gerhard Jahreis, Kristin Bothor, Carina Drechsel, Michael Kiehntopf, Matthias Blüher, Christine Dawczynski. Benefits of foods supplemented with vegetable oils rich in α-linolenic, stearidonic or docosahexaenoic acid in hypertriglyceridemic subjects: a double-blind, randomized, controlled trail. European journal of nutrition. 2015 Sep; 54(6):881-93. doi: 10.1007/s00394-014-0764-2. [PMID: 25216712]
  • Melissa L Bainbridge, Adam L Lock, Jana Kraft. Lipid-Encapsulated Echium Oil (Echium plantagineum) Increases the Content of Stearidonic Acid in Plasma Lipid Fractions and Milk Fat of Dairy Cows. Journal of agricultural and food chemistry. 2015 May; 63(19):4827-35. doi: 10.1021/acs.jafc.5b00857. [PMID: 25904162]
  • Satyanarayana R Pondugula, Glennie Ferniany, Farah Ashraf, Kodye L Abbott, Bruce F Smith, Elaine S Coleman, Mahmoud Mansour, R Curtis Bird, Annette N Smith, Chandrabose Karthikeyan, Piyush Trivedi, Amit K Tiwari. Stearidonic acid, a plant-based dietary fatty acid, enhances the chemosensitivity of canine lymphoid tumor cells. Biochemical and biophysical research communications. 2015 May; 460(4):1002-7. doi: 10.1016/j.bbrc.2015.03.141. [PMID: 25847597]
  • Samuel Cirés, Carlos Alvarez-Roa, Kirsten Heimann. First use of the WAVE™ disposable rocking bioreactor for enhanced bioproduct synthesis by N2 -fixing cyanobacteria. Biotechnology and bioengineering. 2015 Mar; 112(3):621-6. doi: 10.1002/bit.25455. [PMID: 25219374]
  • D J M Pieters, R P Mensink. Effects of stearidonic acid on serum triacylglycerol concentrations in overweight and obese subjects: a randomized controlled trial. European journal of clinical nutrition. 2015 Jan; 69(1):121-6. doi: 10.1038/ejcn.2014.193. [PMID: 25226826]
  • K Subedi, H-M Yu, M Newell, R J Weselake, D Meesapyodsuk, X Qiu, S Shah, C J Field. Stearidonic acid-enriched flax oil reduces the growth of human breast cancer in vitro and in vivo. Breast cancer research and treatment. 2015 Jan; 149(1):17-29. doi: 10.1007/s10549-014-3212-3. [PMID: 25417173]
  • 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]
  • Ji Yeon Baik, Nam Ho Kim, Se-Wook Oh, In-Hwan Kim. Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography. Journal of oleo science. 2015; 64(7):729-36. doi: 10.5650/jos.ess14252. [PMID: 25994555]
  • Soressa M Kitessa, Mahinda Abeywardena, Chakra Wijesundera, Peter D Nichols. DHA-containing oilseed: a timely solution for the sustainability issues surrounding fish oil sources of the health-benefitting long-chain omega-3 oils. Nutrients. 2014 May; 6(5):2035-58. doi: 10.3390/nu6052035. [PMID: 24858407]
  • Yiheng Yan, Jason Candreva, Hai Shi, Evan Ernst, Robert Martienssen, Jorg Schwender, John Shanklin. Survey of the total fatty acid and triacylglycerol composition and content of 30 duckweed species and cloning of a Δ6-desaturase responsible for the production of γ-linolenic and stearidonic acids in Lemna gibba. BMC plant biology. 2013 Dec; 13(?):201. doi: 10.1186/1471-2229-13-201. [PMID: 24308551]
  • John M Casey, William J Banz, Elaine S Krul, Dustie N Butteiger, Daniel A Goldstein, Jeremy E Davis. Effect of stearidonic acid-enriched soybean oil on fatty acid profile and metabolic parameters in lean and obese Zucker rats. Lipids in health and disease. 2013 Oct; 12(?):147. doi: 10.1186/1476-511x-12-147. [PMID: 24139088]
  • Jonathan P Arm, Joshua A Boyce, Lin Wang, Heng Chhay, Muhammad Zahid, Vaishali Patil, Usha Govindarajulu, Priscilla Ivester, Kelly L Weaver, Susan Sergeant, Elliot Israel, Floyd H Chilton. Impact of botanical oils on polyunsaturated fatty acid metabolism and leukotriene generation in mild asthmatics. Lipids in health and disease. 2013 Oct; 12(?):141. doi: 10.1186/1476-511x-12-141. [PMID: 24088297]
  • Mauro Do Nascimento, Maria de Los Angeles Dublan, Juan Cesar Federico Ortiz-Marquez, Leonardo Curatti. High lipid productivity of an Ankistrodesmus-Rhizobium artificial consortium. Bioresource technology. 2013 Oct; 146(?):400-407. doi: 10.1016/j.biortech.2013.07.085. [PMID: 23948276]
  • Shawna L Lemke, Kevin C Maki, Glenna Hughes, Mary L Taylor, Elaine S Krul, Daniel A Goldstein, Hong Su, Tia M Rains, Ratna Mukherjea. Consumption of stearidonic acid-rich oil in foods increases red blood cell eicosapentaenoic acid. Journal of the Academy of Nutrition and Dietetics. 2013 Aug; 113(8):1044-56. doi: 10.1016/j.jand.2013.04.020. [PMID: 23885702]
  • K Kavanagh, D M Flynn, K A Jenkins, M D Wilson, F H Chilton. Stearidonic and γ-linolenic acids in echium oil improves glucose disposal in insulin resistant monkeys. Prostaglandins, leukotrienes, and essential fatty acids. 2013 Jul; 89(1):39-45. doi: 10.1016/j.plefa.2013.04.003. [PMID: 23664597]
  • Chisa Matsumoto, Nirupa R Matthan, Jemma B Wilk, Alice H Lichtenstein, J Michael Gaziano, Luc Djoussé. Erythrocyte stearidonic acid and other n-3 fatty acids and CHD in the Physicians' Health Study. The British journal of nutrition. 2013 Jun; 109(11):2044-9. doi: 10.1017/s0007114512004060. [PMID: 23098619]
  • Marc E Surette. Dietary omega-3 PUFA and health: stearidonic acid-containing seed oils as effective and sustainable alternatives to traditional marine oils. Molecular nutrition & food research. 2013 May; 57(5):748-59. doi: 10.1002/mnfr.201200706. [PMID: 23417895]
  • Miguel Ángel Rincón Cervera, Elena Venegas Venegas, Rebeca Ramos Bueno, Ignacio Rodríguez García, José Luis Guil-Guerrero. Acyl migration evaluation in monoacylglycerols from Echium plantagineum seed oil and Marinol. Journal of bioscience and bioengineering. 2013 May; 115(5):518-22. doi: 10.1016/j.jbiosc.2012.11.023. [PMID: 23287502]
  • Patrícia Borges Botelho, Karina da Rocha Mariano, Marcelo Macedo Rogero, Inar Alves de Castro. Effect of Echium oil compared with marine oils on lipid profile and inhibition of hepatic steatosis in LDLr knockout mice. Lipids in health and disease. 2013 Mar; 12(?):38. doi: 10.1186/1476-511x-12-38. [PMID: 23510369]
  • Terue Kawabata, Kazumi Shimoda, Sayaka Horiguchi, Marina Domon, Chie Hagiwara, Miho Takiyama, Yasuo Kagawa. Influences of stearidonic acid-enriched soybean oil on the blood and organ biochemical parameters in rats. Prostaglandins, leukotrienes, and essential fatty acids. 2013 Feb; 88(2):179-84. doi: 10.1016/j.plefa.2012.11.004. [PMID: 23219237]
  • Celia G Walker, Susan A Jebb, Philip C Calder. Stearidonic acid as a supplemental source of ω-3 polyunsaturated fatty acids to enhance status for improved human health. Nutrition (Burbank, Los Angeles County, Calif.). 2013 Feb; 29(2):363-9. doi: 10.1016/j.nut.2012.06.003. [PMID: 23102888]
  • Garima Pande, Casimir C Akoh, Robert L Shewfelt. Production of trans-free margarine with stearidonic acid soybean and high-stearate soybean oils-based structured lipid. Journal of food science. 2012 Nov; 77(11):C1203-10. doi: 10.1111/j.1750-3841.2012.02935.x. [PMID: 23094958]
  • Vuyisile S Thibane, Ruan Ells, Arno Hugo, Jacobus Albertyn, Walter J Janse van Rensburg, Pieter W J Van Wyk, Johan L F Kock, Carolina H Pohl. Polyunsaturated fatty acids cause apoptosis in C. albicans and C. dubliniensis biofilms. Biochimica et biophysica acta. 2012 Oct; 1820(10):1463-8. doi: 10.1016/j.bbagen.2012.05.004. [PMID: 22609876]
  • Fatmahan Atalar, Selcuk Gormez, Baris Caynak, Gokce Akan, Gamze Tanriverdi, Sema Bilgic-Gazioglu, Demet Gunay, Cihan Duran, Belhhan Akpinar, Ugur Ozbek, Ahmet Sevim Buyukdevrim, Zeliha Yazici. The role of mediastinal adipose tissue 11β-hydroxysteroid d ehydrogenase type 1 and glucocorticoid expression in the development of coronary atherosclerosis in obese patients with ischemic heart disease. Cardiovascular diabetology. 2012 Sep; 11(?):115. doi: 10.1186/1475-2840-11-115. [PMID: 23009206]
  • Soressa M Kitessa, Paul Young, Greg Nattrass, Graham Gardner, Kelly Pearce, David W Pethick. When balanced for precursor fatty acid supply echium oil is not superior to linseed oil in enriching lamb tissues with long-chain n-3 PUFA. The British journal of nutrition. 2012 Jul; 108(1):71-9. doi: 10.1017/s0007114511005411. [PMID: 22011528]
  • Tomáš Řezanka, Jaromír Lukavský, Lucie Siristova, Karel Sigler. Regioisomer separation and identification of triacylglycerols containing vaccenic and oleic acids, and α- and γ-linolenic acids, in thermophilic cyanobacteria Mastigocladus laminosus and Tolypothrix sp. Phytochemistry. 2012 Jun; 78(?):147-55. doi: 10.1016/j.phytochem.2012.02.028. [PMID: 22445652]
  • Hua Liang Liu, Zhi Jie Yin, Li Xiao, Yi Nong Xu, Le Qing Qu. Identification and evaluation of ω-3 fatty acid desaturase genes for hyperfortifying α-linolenic acid in transgenic rice seed. Journal of experimental botany. 2012 May; 63(8):3279-87. doi: 10.1093/jxb/ers051. [PMID: 22378946]
  • William J Banz, Jeremy E Davis, Richard W Clough, Joseph L Cheatwood. Stearidonic acid: is there a role in the prevention and management of type 2 diabetes mellitus?. The Journal of nutrition. 2012 Mar; 142(3):635S-640S. doi: 10.3945/jn.111.146829. [PMID: 22279133]
  • Jay Whelan, Julia Gouffon, Yi Zhao. Effects of dietary stearidonic acid on biomarkers of lipid metabolism. The Journal of nutrition. 2012 Mar; 142(3):630S-634S. doi: 10.3945/jn.111.149138. [PMID: 22279143]
  • William S Harris. Stearidonic acid-enhanced soybean oil: a plant-based source of (n-3) fatty acids for foods. The Journal of nutrition. 2012 Mar; 142(3):600S-604S. doi: 10.3945/jn.111.146613. [PMID: 22279144]
  • Eric A Decker, Casimir C Akoh, Richard S Wilkes. Incorporation of (n-3) fatty acids in foods: challenges and opportunities. The Journal of nutrition. 2012 Mar; 142(3):610S-613S. doi: 10.3945/jn.111.149328. [PMID: 22279141]
  • Richard J Deckelbaum, Philip C Calder, William S Harris, Casimir C Akoh, Kevin C Maki, Jay Whelan, William J Banz, Eileen Kennedy. Conclusions and recommendations from the symposium, Heart Healthy Omega-3s for Food: Stearidonic Acid (SDA) as a Sustainable Choice. The Journal of nutrition. 2012 Mar; 142(3):641S-643S. doi: 10.3945/jn.111.149831. [PMID: 22323767]
  • Richard J Deckelbaum, Claudia Torrejon. The omega-3 fatty acid nutritional landscape: health benefits and sources. The Journal of nutrition. 2012 Mar; 142(3):587S-591S. doi: 10.3945/jn.111.148080. [PMID: 22323763]
  • Lolita M Forrest, Elena Boudyguina, Martha D Wilson, John S Parks. Echium oil reduces atherosclerosis in apoB100-only LDLrKO mice. Atherosclerosis. 2012 Jan; 220(1):118-21. doi: 10.1016/j.atherosclerosis.2011.10.025. [PMID: 22100249]
  • LingLin Wan, Juan Han, Min Sang, AiFen Li, Hong Wu, ShunJi Yin, ChengWu Zhang. De novo transcriptomic analysis of an oleaginous microalga: pathway description and gene discovery for production of next-generation biofuels. PloS one. 2012; 7(4):e35142. doi: 10.1371/journal.pone.0035142. [PMID: 22536352]
  • Philipp Widmann, Karin Nuernberg, Christa Kuehn, Rosemarie Weikard. Association of an ACSL1 gene variant with polyunsaturated fatty acids in bovine skeletal muscle. BMC genetics. 2011 Nov; 12(?):96. doi: 10.1186/1471-2156-12-96. [PMID: 22078495]
  • Sarah A Teichert, Casimir C Akoh. Characterization of stearidonic acid soybean oil enriched with palmitic acid produced by solvent-free enzymatic interesterification. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9588-95. doi: 10.1021/jf201992k. [PMID: 21830790]
  • Lee D Roberts, Andrew J Murray, David Menassa, Tom Ashmore, Andrew W Nicholls, Julian L Griffin. The contrasting roles of PPARδ and PPARγ in regulating the metabolic switch between oxidation and storage of fats in white adipose tissue. Genome biology. 2011 Aug; 12(8):R75. doi: 10.1186/gb-2011-12-8-r75. [PMID: 21843327]
  • Ramez Alhazzaa, Andrew R Bridle, Peter D Nichols, Chris G Carter. Up-regulated desaturase and elongase gene expression promoted accumulation of polyunsaturated fatty acid (PUFA) but not long-chain PUFA in Lates calcarifer, a tropical euryhaline fish, fed a stearidonic acid- and γ-linoleic acid-enriched diet. Journal of agricultural and food chemistry. 2011 Aug; 59(15):8423-34. doi: 10.1021/jf201871w. [PMID: 21707030]
  • Lena Burri, Bodil Bjørndal, Hege Wergedahl, Kjetil Berge, Pavol Bohov, Asbjørn Svardal, Rolf K Berge. Tetradecylthioacetic acid increases hepatic mitochondrial β-oxidation and alters fatty acid composition in a mouse model of chronic inflammation. Lipids. 2011 Aug; 46(8):679-89. doi: 10.1007/s11745-011-3536-2. [PMID: 21479675]
  • Mohamed B Codabaccus, Andrew R Bridle, Peter D Nichols, Chris G Carter. Effect of feeding Atlantic salmon (Salmo salar L.) a diet enriched with stearidonic acid from parr to smolt on growth and n-3 long-chain PUFA biosynthesis. The British journal of nutrition. 2011 Jun; 105(12):1772-82. doi: 10.1017/s0007114510005714. [PMID: 21303572]
  • Vincent J T van Ginneken, Johannes P F G Helsper, Willem de Visser, Herman van Keulen, Willem A Brandenburg. Polyunsaturated fatty acids in various macroalgal species from North Atlantic and tropical seas. Lipids in health and disease. 2011 Jun; 10(?):104. doi: 10.1186/1476-511x-10-104. [PMID: 21696609]
  • Brian S Rett, Jay Whelan. Increasing dietary linoleic acid does not increase tissue arachidonic acid content in adults consuming Western-type diets: a systematic review. Nutrition & metabolism. 2011 Jun; 8(?):36. doi: 10.1186/1743-7075-8-36. [PMID: 21663641]
  • Elena Cequier-Sánchez, Covadonga Rodríguez, Roberto Dorta-Guerra, Angel G Ravelo, Rafael Zárate. Echium acanthocarpum hairy root cultures, a suitable system for polyunsaturated fatty acid studies and production. BMC biotechnology. 2011 Apr; 11(?):42. doi: 10.1186/1472-6750-11-42. [PMID: 21524311]
  • Afaf K El-Ansary, Abir G Ben Bacha, Layla Y Al-Ayahdi. Plasma fatty acids as diagnostic markers in autistic patients from Saudi Arabia. Lipids in health and disease. 2011 Apr; 10(?):62. doi: 10.1186/1476-511x-10-62. [PMID: 21510882]
  • S Johansson, A E Wold, A-S Sandberg. Low breast milk levels of long-chain n-3 fatty acids in allergic women, despite frequent fish intake. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology. 2011 Apr; 41(4):505-15. doi: 10.1111/j.1365-2222.2010.03678.x. [PMID: 21338426]
  • Lena Burri, Kjetil Berge, Karin Wibrand, Rolf K Berge, Jamie L Barger. Differential effects of krill oil and fish oil on the hepatic transcriptome in mice. Frontiers in genetics. 2011; 2(?):45. doi: 10.3389/fgene.2011.00045. [PMID: 22303341]
  • 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]
  • S M Ghoreishi, E Mardani, H S Ghaziaskar. Separation of γ-linolenic and other polyunsaturated fatty acids from Boraginaceae via supercritical CO2. Journal of separation science. 2011 Jan; 34(2):233-40. doi: 10.1002/jssc.201000716. [PMID: 21246730]
  • Alberto Amaretti, Stefano Raimondi, Maurizio Sala, Lucia Roncaglia, Marzia De Lucia, Alan Leonardi, Maddalena Rossi. Single cell oils of the cold-adapted oleaginous yeast Rhodotorula glacialis DBVPG 4785. Microbial cell factories. 2010 Sep; 9(?):73. doi: 10.1186/1475-2859-9-73. [PMID: 20863365]
  • 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]
  • Peter D Nichols, James Petrie, Surinder Singh. Long-chain omega-3 oils-an update on sustainable sources. Nutrients. 2010 06; 2(6):572-85. doi: 10.3390/nu2060572. [PMID: 22254042]
  • James R Petrie, Pushkar Shrestha, Qing Liu, Maged P Mansour, Craig C Wood, Xue-Rong Zhou, Peter D Nichols, Allan G Green, Surinder P Singh. Rapid expression of transgenes driven by seed-specific constructs in leaf tissue: DHA production. Plant methods. 2010 Mar; 6(?):8. doi: 10.1186/1746-4811-6-8. [PMID: 20222981]
  • Stephen L Pahl, David M Lewis, Feng Chen, Keith D King. Heterotrophic growth and nutritional aspects of the diatom Cyclotella cryptica (Bacillariophyceae): Effect of some environmental factors. Journal of bioscience and bioengineering. 2010 Mar; 109(3):235-9. doi: 10.1016/j.jbiosc.2009.08.480. [PMID: 20159570]
  • Philip C Calder. Omega-3 fatty acids and inflammatory processes. Nutrients. 2010 Mar; 2(3):355-374. doi: 10.3390/nu2030355. [PMID: 22254027]
  • 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]
  • Anant S Bharadwaj, Steven D Hart, Billie J Brown, Yong Li, Bruce A Watkins, Paul B Brown. Dietary source of stearidonic acid promotes higher muscle DHA concentrations than linolenic acid in hybrid striped bass. Lipids. 2010 Jan; 45(1):21-7. doi: 10.1007/s11745-009-3372-9. [PMID: 20049582]
  • Noemí Ruiz-López, Richard P Haslam, Mónica Venegas-Calerón, Tony R Larson, Ian A Graham, Johnathan A Napier, Olga Sayanova. The synthesis and accumulation of stearidonic acid in transgenic plants: a novel source of 'heart-healthy' omega-3 fatty acids. Plant biotechnology journal. 2009 Sep; 7(7):704-16. doi: 10.1111/j.1467-7652.2009.00436.x. [PMID: 19702757]
  • Peter Andrew Megdal, Neal A Craft, Garry J Handelman. A simplified method to distinguish farmed (Salmo salar) from wild salmon: fatty acid ratios versus astaxanthin chiral isomers. Lipids. 2009 Jun; 44(6):569-76. doi: 10.1007/s11745-009-3294-6. [PMID: 19452184]
  • Soressa M Kitessa, Paul Young. Echium oil is better than rapeseed oil in enriching poultry meat with n-3 polyunsaturated fatty acids, including eicosapentaenoic acid and docosapentaenoic acid. The British journal of nutrition. 2009 Mar; 101(5):709-15. doi: 10.1017/s0007114508030742. [PMID: 18616838]
  • Marie Zarevúcka, Zdeněk Wimmer. Plant products for pharmacology: application of enzymes in their transformations. International journal of molecular sciences. 2008 Dec; 9(12):2447-2473. doi: 10.3390/ijms9122447. [PMID: 19330086]
  • Matthew R Miller, Peter D Nichols, Chris G Carter. n-3 Oil sources for use in aquaculture--alternatives to the unsustainable harvest of wild fish. Nutrition research reviews. 2008 Dec; 21(2):85-96. doi: 10.1017/s0954422408102414. [PMID: 19087364]
  • Ping Zhang, Elena Boudyguina, Martha D Wilson, Abraham K Gebre, John S Parks. Echium oil reduces plasma lipids and hepatic lipogenic gene expression in apoB100-only LDL receptor knockout mice. The Journal of nutritional biochemistry. 2008 Oct; 19(10):655-63. doi: 10.1016/j.jnutbio.2007.08.005. [PMID: 18155507]
  • William S Harris, Shawna L Lemke, Susan N Hansen, Daniel A Goldstein, Maureen A DiRienzo, Hong Su, Margaret A Nemeth, Mary L Taylor, Gulam Ahmed, Cherian George. Stearidonic acid-enriched soybean oil increased the omega-3 index, an emerging cardiovascular risk marker. Lipids. 2008 Sep; 43(9):805-11. doi: 10.1007/s11745-008-3215-0. [PMID: 18683001]
  • Floyd H Chilton, Lawrence L Rudel, John S Parks, Jonathan P Arm, Michael C Seeds. Mechanisms by which botanical lipids affect inflammatory disorders. The American journal of clinical nutrition. 2008 Feb; 87(2):498S-503S. doi: 10.1093/ajcn/87.2.498s. [PMID: 18258646]
  • Ralf Schubert, Richard Kitz, Christopher Beermann, Markus Andreas Rose, Patrick Carolus Baer, Stefan Zielen, Hansjosef Boehles. Influence of low-dose polyunsaturated fatty acids supplementation on the inflammatory response of healthy adults. Nutrition (Burbank, Los Angeles County, Calif.). 2007 Oct; 23(10):724-30. doi: 10.1016/j.nut.2007.06.012. [PMID: 17664057]
  • William S Harris, Maureen A DiRienzo, Scott A Sands, Cherian George, Philip G Jones, Alex K Eapen. Stearidonic acid increases the red blood cell and heart eicosapentaenoic acid content in dogs. Lipids. 2007 Apr; 42(4):325-33. doi: 10.1007/s11745-007-3036-6. [PMID: 17406927]
  • Bernhard Hennig, Adrienne S Ettinger, Ronald J Jandacek, Sung Koo, Craig McClain, Harold Seifried, Allen Silverstone, Bruce Watkins, William A Suk. Using nutrition for intervention and prevention against environmental chemical toxicity and associated diseases. Environmental health perspectives. 2007 Apr; 115(4):493-5. doi: 10.1289/ehp.9549. [PMID: 17450213]
  • Matthew R Miller, Peter D Nichols, Chris G Carter. Replacement of dietary fish oil for Atlantic salmon parr (Salmo salar L.) with a stearidonic acid containing oil has no effect on omega-3 long-chain polyunsaturated fatty acid concentrations. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2007 Feb; 146(2):197-206. doi: 10.1016/j.cbpb.2006.10.099. [PMID: 17134928]
  • Andrzej Stolyhwo, Jolanta Mol. Changes in the content of gamma-linolenic C18:3 (n-6) and stearidonic C18:4 (n-3) acids in developing seeds of viper's bugloss Echium vulgare L. Acta biochimica Polonica. 2007; 54(4):741-6. doi: . [PMID: 18066400]
  • Olga Sayanova, Richard Haslam, Mónica Venegas-Calerón, Johnathan A Napier. Identification of Primula "front-end" desaturases with distinct n-6 or n-3 substrate preferences. Planta. 2006 Nov; 224(6):1269-77. doi: 10.1007/s00425-006-0306-0. [PMID: 16773377]
  • Douglas R Tocher, James R Dick, Philip MacGlaughlin, J Gordon Bell. Effect of diets enriched in Delta6 desaturated fatty acids (18:3n-6 and 18:4n-3), on growth, fatty acid composition and highly unsaturated fatty acid synthesis in two populations of Arctic charr (Salvelinus alpinus L.). Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2006 Jun; 144(2):245-53. doi: 10.1016/j.cbpb.2006.03.001. [PMID: 16630735]