Stearidonic acid (BioDeep_00000003492)

   

human metabolite Endogenous blood metabolite


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 2024-11-03) (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

21 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



数据库引用编号

17 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)

20 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]
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  • 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]
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  • 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]
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  • 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]
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