(9E,11E)-Octadecadienoic acid (BioDeep_00000028036)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


trans-9,trans-11 Conjugated linoleic acid

化学式: C18H32O2 (280.2402172)
中文名称: 9(E),11(E)-十八碳二烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 29.96%

分子结构信息

SMILES: CCCCCC/C=C/C=C/CCCCCCCC(O)=O
InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+

描述信息

Conjugated linoleic acid is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. Conjugated linoleic acid is present in the food namely in the red meat and dairy products which the contemporary dietary recommendations tend to limit. Those limitations should be compensated with dietary supplements. Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation and obesity. More recent human conjugated linoleic acid supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, in particular after supplementation with the trans-10,cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. As far as human studies are concerned, a specific dietary pattern has not been established. As a result differences among studies and also among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity may also be crucial. (PMID: 17053429, 17217167, 17554969, 16477173).
Conjugated linoleic acid (CLA) is a collective term for a mixture of positional and geometric isomers of linoleic acid (18:2) in which the two double bonds are conjugated. CLA has been suggested to have effects on human health, including effects on body composition, blood lipids, liver metabolism, insulin sensitivity and immune function, with mixed results.

同义名列表

50 个代谢物同义名

trans-9,trans-11 Conjugated linoleic acid; 9-trans,11-trans-Conjugated linoleic acid; trans-9, trans-11-octadecadienoic acid; 9-trans,11-trans-Conjugated linoleate; trans-11-trans-9-Octadecadienoic acid; 9-trans,11-trans-Octadecadienoic acid; trans,trans-9,11-Octadecadienoic acid; trans-9,trans-11-Octadecadienoic acid; (9E,11E)-octadeca-9,11-dienoic acid; (9E,11E)-9,11-Octadecadienoic acid; trans-9, trans-11-Octadecadienoate; 9-trans,11-trans-Octadecadienoate; Conjugated (9E,11E)-linoleic acid; trans,trans-9,11-Octadecadienoate; 9,11-Linoleic acid, (E,E)-isomer; (e,e)-9,11-Octadecadienoic acid; 9-trans,11-trans-Linoleic acid; delta9,11-Octadecadienoic acid; (9E,11E)-9,11-Octadecadienoate; Conjugated (9E,11E)-linoleate; 9,11-Conjugated linoleic acid; (9E,11E)-Octadecadienoic acid; 10E,12Z-octadecadienoic acid; 9E,11E-octadecadienoic acid; (e,e)-9,11-Octadecadienoate; delta9,11-Octadecadienoate; Octadeca-9,11-dienoic acid; Δ9,11-Octadecadienoic acid; (9E,11E)-Octadecadienoate; 9,11-Octadecadienoic acid; Conjugated linoleic acid; 10E,12Z-Octadecadienoate; 9E,11E-Octadecadienoate; (e,e)-Isolinoleic acid; 9,11-Isolinoleic acid; 9,11-Octadecadienoate; 9-trans, 11-trans-CLA; 9,11-Linoleic acid; (e,e)-Isolinoleate; Isolinoleic acid; FA(18:2(9E,11E)); Nouracid de 554; Ricinenic acid; Ricineic acid; Mangolds acid; Isolinoleate; 9t,11t-CLA; 9E,11E-CLA; Selin cla; CLA 80



数据库引用编号

10 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

1 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(0)

PharmGKB(0)

2 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

  • Birsen Aydın, Cansu Güler Şahin, Vedat Şekeroğlu, Zülal Atlı Şekeroğlu. Conjugated linoleic acid protects brain mitochondrial function in acrolein induced male rats. Toxicology mechanisms and methods. 2021 Nov; 31(9):674-679. doi: 10.1080/15376516.2021.1952673. [PMID: 34238125]
  • A M Abdelatty, O A M Badr, S A Mohamed, M S Khattab, Sh M Dessouki, O A A Farid, A A Elolimy, O G Sakr, M A Elhady, G Mehesen, M Bionaz. Long term conjugated linoleic acid supplementation modestly improved growth performance but induced testicular tissue apoptosis and reduced sperm quality in male rabbit. PloS one. 2020; 15(1):e0226070. doi: 10.1371/journal.pone.0226070. [PMID: 31923252]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • A Abolghasemi, E Dirandeh, Z Ansari Pirsaraei, B Shohreh. Dietary conjugated linoleic acid supplementation alters the expression of genes involved in the endocannabinoid system in the bovine endometrium and increases plasma progesterone concentrations. Theriogenology. 2016 Oct; 86(6):1453-1459. doi: 10.1016/j.theriogenology.2016.05.003. [PMID: 27262886]
  • Suleyman Bulut, Ebru Bodur, Ridvan Colak, Husrev Turnagol. Effects of conjugated linoleic acid supplementation and exercise on post-heparin lipoprotein lipase, butyrylcholinesterase, blood lipid profile and glucose metabolism in young men. Chemico-biological interactions. 2013 Mar; 203(1):323-9. doi: 10.1016/j.cbi.2012.09.022. [PMID: 23073171]
  • Arion Kennedy, Angel Overman, Kathleen Lapoint, Robin Hopkins, Tiffany West, Chia-Chi Chuang, Kristina Martinez, Doris Bell, Michael McIntosh. Conjugated linoleic acid-mediated inflammation and insulin resistance in human adipocytes are attenuated by resveratrol. Journal of lipid research. 2009 Feb; 50(2):225-32. doi: 10.1194/jlr.m800258-jlr200. [PMID: 18776171]
  • Robert Ringseis, Nadja Schulz, Daniela Saal, Klaus Eder. Troglitazone but not conjugated linoleic acid reduces gene expression and activity of matrix-metalloproteinases-2 and -9 in PMA-differentiated THP-1 macrophages. The Journal of nutritional biochemistry. 2008 Sep; 19(9):594-603. doi: 10.1016/j.jnutbio.2007.08.003. [PMID: 18155510]
  • Li-Fen Liu, Aparna Purushotham, Angela A Wendel, Martha A Belury. Combined effects of rosiglitazone and conjugated linoleic acid on adiposity, insulin sensitivity, and hepatic steatosis in high-fat-fed mice. American journal of physiology. Gastrointestinal and liver physiology. 2007 Jun; 292(6):G1671-82. doi: 10.1152/ajpgi.00523.2006. [PMID: 17322064]
  • S D Proctor, S E Kelly, K L Stanhope, P J Havel, J C Russell. Synergistic effects of conjugated linoleic acid and chromium picolinate improve vascular function and renal pathophysiology in the insulin-resistant JCR:LA-cp rat. Diabetes, obesity & metabolism. 2007 Jan; 9(1):87-95. doi: 10.1111/j.1463-1326.2006.00578.x. [PMID: 17199723]
  • Khelifa Arab, Adrien Rossary, Laurent Soulère, Jean-Paul Steghens. Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. The British journal of nutrition. 2006 Nov; 96(5):811-9. doi: 10.1017/bjn20061910. [PMID: 17092368]
  • Arunabh Bhattacharya, M Mizanur Rahman, Roger McCarter, Marianne O'Shea, Gabriel Fernandes. Conjugated linoleic acid and chromium lower body weight and visceral fat mass in high-fat-diet-fed mice. Lipids. 2006 May; 41(5):437-44. doi: 10.1007/s11745-006-5117-3. [PMID: 16933788]
  • Craig D Albright, Erich Klem, Anish A Shah, Patricia Gallagher. Breast cancer cell-targeted oxidative stress: enhancement of cancer cell uptake of conjugated linoleic acid, activation of p53, and inhibition of proliferation. Experimental and molecular pathology. 2005 Oct; 79(2):118-25. doi: 10.1016/j.yexmp.2005.05.005. [PMID: 15992797]
  • Karine Valeille, Jacqueline Férézou, Ghislaine Amsler, Annie Quignard-Boulangé, Michel Parquet, Daniel Gripois, Victoria Dorovska-Taran, Jean-Charles Martin. A cis-9,trans-11-conjugated linoleic acid-rich oil reduces the outcome of atherogenic process in hyperlipidemic hamster. American journal of physiology. Heart and circulatory physiology. 2005 Aug; 289(2):H652-9. doi: 10.1152/ajpheart.00130.2005. [PMID: 15778275]
  • Yumiko Yasui, Masashi Hosokawa, Takehiko Sahara, Rikako Suzuki, Satoru Ohgiya, Hiroyuki Kohno, Takuji Tanaka, Kazuo Miyashita. Bitter gourd seed fatty acid rich in 9c,11t,13t-conjugated linolenic acid induces apoptosis and up-regulates the GADD45, p53 and PPARgamma in human colon cancer Caco-2 cells. Prostaglandins, leukotrienes, and essential fatty acids. 2005 Aug; 73(2):113-9. doi: 10.1016/j.plefa.2005.04.013. [PMID: 15961301]
  • Alan A Sneddon, Hsin-Chieh Wu, Andrew Farquharson, Ian Grant, John R Arthur, Dino Rotondo, Sun-Nam Choe, Klaus W J Wahle. Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants. Atherosclerosis. 2003 Nov; 171(1):57-65. doi: 10.1016/j.atherosclerosis.2003.08.008. [PMID: 14642406]