General Information of Metabolite (ID: MT078)
  Meta Name
Conjugated linoleic acid
  Unify Name
(9E,11E)-Octadecadienoic acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
9,11-Linoleic acid;CLA 80;Conjugated linoleic acid;delta9,11-Octadecadienoate;Nouracid de 554;Ricineic acid;Ricinenic acid;Selin cla;9,11-Linoleic acid, (E,E)-isomer;9,11-Isolinoleic acid;Octadeca-9,11-dienoic acid;9,11-Octadecadienoate;(9E,11E)-9,11-Octadecadienoic acid;(9E,11E)-Octadecadienoic acid;9,11-Conjugated linoleic acid;9-trans,11-trans-Linoleic acid;9-trans,11-trans-Octadecadienoic acid;9E,11E-Octadecadienoic acid;FA(18:2(9E,11E));delta9,11-Octadecadienoic acid;trans-11-trans-9-Octadecadienoic acid;trans-9,trans-11 Conjugated linoleic acid;trans-9,trans-11-Octadecadienoic acid;delta9,11-Octadecadienoic acid;9E,11E-Octadecadienoate;10E,12Z-Octadecadienoate;(E,E)-9,11-Octadecadienoic acid;(E,E)-Isolinoleic acid;9-trans, 11-trans-CLA;9-trans,11-trans-Conjugated linoleic acid;9E,11E-CLA;9t,11t-CLA;Conjugated (9E,11E)-linoleic acid;Isolinoleic acid;Mangold's acidtrans,trans-9,11-Octadecadienoic acid;trans-9, trans-11-Octadecadienoic acid;(9E,11E)-9,11-Octadecadienoate;(E,E)-9,11-Octadecadienoate;(E,E)-Isolinoleate;9-trans,11-trans-Conjugated linoleate;9-trans,11-trans-Octadecadienoate;Conjugated (9E,11E)-linoleate;Isolinoleate;trans,trans-9,11-Octadecadienoate;trans-9, trans-11-Octadecadienoate
  Molecule Type
Polyunsaturated fatty acid (PUFAs)
  Formula
C18H32O2
  Inchi Key
JBYXPOFIGCOSSB-XBLVEGMJSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
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 ).
  External Links   HMDB ID   HMDB0005047

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
DNA Methylation DNMT EM Info . . . [1], [2]
Histone Deacetylation SIRT1 EM Info . . . [1], [2]

The microbes that produce this metabolite
      Roseburia
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [1]
         Description
Roseburia is a genus of butyrate-producing, gram-positive anaerobic bacteria that inhabit the human colon.
      Clostridium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Clostridium is a genus of gram-positive, anaerobic bacteria from the family Bacillaceae.
      Bifidobacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Bifidobacteria is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract, vagina and mouth of mammals, including humans.
      Klebsiella
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Klebsiella is a genus of gram-negative, oxidase-negative, rod-shaped bacteria from the family Enterobacteriaceae
      Enterobacter
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Enterobacter is a genus of common gram-negative, facultatively anaerobic, rod-shaped, non-spore-forming bacteria of the family Enterobacteriaceae. It is the type genus of the order Enterobacterales.
      Citrobacter
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Citrobacter is a genus of gram-negative coliform bacteria in the family Enterobacteriaceae. The species C. amalonaticus, C. koseri, and C. freundii can use citrate as a sole carbon source. Citrobacter species are differentiated by their ability to convert tryptophan to indole, ferment lactose, and use malonate.
      Lactobacillus
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [1]
         Description
Lactobacillus is a genus of gram-positive, facultative anaerobic or microaerophilic, rod-shaped, non-spore-forming bacteria. They are a major part of the lactic acid bacteria group. In humans, they constitute a significant component of the microbiota at a number of body sites, such as the digestive system, urinary system, and genital system.

References
1 Gut Microbiota as Important Mediator Between Diet and DNA Methylation and Histone Modifications in the Host. Nutrients. 2020 Feb 25;12(3):597. doi: 10.3390/nu12030597.
2 Arachidonic and oleic acid exert distinct effects on the DNA methylome. Epigenetics. 2016 May 3;11(5):321-34. doi: 10.1080/15592294.2016.1161873. Epub 2016 Apr 18.
3 Valerian and valeric acid inhibit growth of breast cancer cells possibly by mediating epigenetic modifications. Sci Rep. 2021 Jan 28;11(1):2519. doi: 10.1038/s41598-021-81620-x.

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