Rumenic acid (BioDeep_00000400564)
Main id: BioDeep_00000628736
代谢物信息卡片
化学式: C18H32O2 (280.2402172)
中文名称: 9(Z),11(E)-十八碳二烯酸
谱图信息:
最多检出来源 () 0%
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
Bovinic acid is a conjugated linoleic acid, present in human adipose tissue; the amount of bovinic acid in humans is significantly related to milk fat intake. Conjugated linoleic acids (CLAs) are a group of naturally occurring fatty acids present mainly in fats from ruminants. Milk contains over 20 isomers of CLA but the predominant one is cis-9,trans-11-CLA (bovinic acid). Biomedical studies with animal models have shown that this isomer has anticarcinogenic and anti-atherogenic activities. Bovinic acid is produced as an intermediate in the rumen biohydrogenation of linoleic acid but not of linolenic acid. However, it is only a transient intermediate, and the major source of milk fat CLA is from endogenous synthesis. (PMID 10393134, 15736916) [HMDB]
同义名列表
3 个代谢物同义名
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:32798
- KEGG: C04056
- PubChem: 5280644
- ChEMBL: CHEMBL4303722
- foodb: FDB021827
- CAS: 2540-56-9
- MoNA: MetaboBASE1026
- MoNA: MetaboBASE1025
- MoNA: MetaboBASE1024
- MoNA: MetaboBASE1023
- PubChem: 6756
- LipidMAPS: LMFA01030118
- 3DMET: B00672
- NIKKAJI: J604.211B
- RefMet: Rumenic acid
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)
1 个相关的物种来源信息
- 267567 - Skeletonema marinoi: 10.1038/S41396-018-0094-0
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
- P G Toral, G Hervás, P Frutos. Effect of lipid supplementation on the endogenous synthesis of milk cis-9,trans-11 conjugated linoleic acid in dairy sheep and goats: A tracer assay with 13C-vaccenic acid.
Journal of dairy science.
2022 Jan; 105(1):255-268. doi:
10.3168/jds.2021-20728
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Nutrients.
2021 Feb; 13(2):. doi:
10.3390/nu13020663
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Prostaglandins & other lipid mediators.
2021 02; 152(?):106495. doi:
10.1016/j.prostaglandins.2020.106495
. [PMID: 33045366] - Ali Jalilian, Taghi Golmohammadi, Reza Meshkani, Mehdi Koushki, Neda Eivazi, Reyhaneh Babaei Khorzoughi, Seyed Reza Hosseini Fard, Maliheh Paknejad. Evaluating the effect of a mixture of two main conjugated linoleic acid isomers on hepatic steatosis in HepG2 cellular model.
Molecular biology reports.
2021 Feb; 48(2):1359-1370. doi:
10.1007/s11033-021-06203-5
. [PMID: 33580458] - Etienne Guillocheau, Philippe Legrand, Vincent Rioux. Trans-palmitoleic acid (trans-9-C16:1, or trans-C16:1 n-7): Nutritional impacts, metabolism, origin, compositional data, analytical methods and chemical synthesis. A review.
Biochimie.
2020 Feb; 169(?):144-160. doi:
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Journal of animal physiology and animal nutrition.
2018 Aug; 102(4):962-976. doi:
10.1111/jpn.12902
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The Journal of nutritional biochemistry.
2018 08; 58(?):150-157. doi:
10.1016/j.jnutbio.2018.05.008
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Acta scientiarum polonorum. Technologia alimentaria.
2018 Jul; 17(3):199-209. doi:
10.17306/j.afs.0563
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Public health nutrition.
2017 Aug; 20(12):2145-2156. doi:
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Lipids.
2017 03; 52(3):223-233. doi:
10.1007/s11745-016-4221-2
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Acta poloniae pharmaceutica.
2017 Mar; 74(2):624-632. doi:
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Nutrients.
2016 Dec; 8(12):. doi:
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Meat science.
2016 Oct; 120(?):157-166. doi:
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Lipids.
2016 07; 51(7):807-19. doi:
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Animal : an international journal of animal bioscience.
2015 Dec; 9(12):2072-80. doi:
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Journal of dairy science.
2015 Sep; 98(9):6399-414. doi:
10.3168/jds.2015-9459
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Lipids.
2015 Jul; 50(7):659-66. doi:
10.1007/s11745-015-4034-8
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Journal of animal science.
2015 Jun; 93(6):3179-88. doi:
10.2527/jas.2014-8708
. [PMID: 26115304] - Nathalie Nicod, Robert S Parker, Elena Giordano, Virginia Maestro, Alberto Davalos, Francesco Visioli. Isomer-specific effects of conjugated linoleic acid on HDL functionality associated with reverse cholesterol transport.
The Journal of nutritional biochemistry.
2015 Feb; 26(2):165-72. doi:
10.1016/j.jnutbio.2014.10.002
. [PMID: 25468613] - Edyta Maslak, Elzbieta Buczek, Antoni Szumny, Wojciech Szczepnski, Magdalena Franczyk-Zarow, Aneta Kopec, Stefan Chlopicki, Teresa Leszczynska, Renata B Kostogrys. Individual CLA Isomers, c9t11 and t10c12, Prevent Excess Liver Glycogen Storage and Inhibit Lipogenic Genes Expression Induced by High-Fructose Diet in Rats.
BioMed research international.
2015; 2015(?):535982. doi:
10.1155/2015/535982
. [PMID: 26090419] - Aida Maribel Chisaguano, Rosa Montes, Ana Isabel Castellote, Eva Morales, Jordi Júlvez, Jesús Vioque, Jordi Sunyer, Maria Carmen López-Sabater. Elaidic, vaccenic, and rumenic acid status during pregnancy: association with maternal plasmatic LC-PUFAs and atopic manifestations in infants.
Pediatric research.
2014 Nov; 76(5):470-6. doi:
10.1038/pr.2014.119
. [PMID: 25119335] - S Andrés, L Morán, N Aldai, M L Tejido, N Prieto, R Bodas, F J Giráldez. Effects of linseed and quercetin added to the diet of fattening lambs on the fatty acid profile and lipid antioxidant status of meat samples.
Meat science.
2014 Jun; 97(2):156-63. doi:
10.1016/j.meatsci.2014.02.001
. [PMID: 24583323] - P Vahmani, A H Fredeen, K E Glover. Effect of supplementation with fish oil or microalgae on fatty acid composition of milk from cows managed in confinement or pasture systems.
Journal of dairy science.
2013 Oct; 96(10):6660-70. doi:
10.3168/jds.2013-6914
. [PMID: 23958023] - Valentina Vasta, Dorra Aouadi, Daniela M R Brogna, Manuel Scerra, Giuseppe Luciano, Alessandro Priolo, Hichem Ben Salem. Effect of the dietary supplementation of essential oils from rosemary and artemisia on muscle fatty acids and volatile compound profiles in Barbarine lambs.
Meat science.
2013 Oct; 95(2):235-41. doi:
10.1016/j.meatsci.2012.12.021
. [PMID: 23747617] - Seong H Choi, Ki Y Chung, Bradley J Johnson, Gwang W Go, Kyoung H Kim, Chang W Choi, Stephen B Smith. Co-culture of bovine muscle satellite cells with preadipocytes increases PPARγ and C/EBPβ gene expression in differentiated myoblasts and increases GPR43 gene expression in adipocytes.
The Journal of nutritional biochemistry.
2013 Mar; 24(3):539-43. doi:
10.1016/j.jnutbio.2012.01.015
. [PMID: 22748806] - Clare M Reynolds, Sinead Toomey, Rachael McBride, Jolene McMonagle, Melissa J Morine, Orina Belton, Aidan P Moloney, Helen M Roche. Divergent effects of a CLA-enriched beef diet on metabolic health in ApoE-/- and ob/ob mice.
The Journal of nutritional biochemistry.
2013 Feb; 24(2):401-11. doi:
10.1016/j.jnutbio.2011.12.006
. [PMID: 22626767] - P G Toral, Y Chilliard, L Bernard. Short communication: in vivo deposition of [1-13C]vaccenic acid and the product of its Δ9-desaturation, [1-13C]rumenic acid, in the body tissues of lactating goats fed oils.
Journal of dairy science.
2012 Nov; 95(11):6755-9. doi:
10.3168/jds.2012-5620
. [PMID: 22959933] - A J Pordomingo, T P García, G Volpi Lagreca. Effect of feeding treatment during the backgrounding phase of beef production from pasture on: II. Longissimus muscle proximate composition, cholesterol and fatty acids.
Meat science.
2012 Apr; 90(4):947-55. doi:
10.1016/j.meatsci.2011.11.038
. [PMID: 22193038] - Xiaojie Hu, Yanmei Li, Chunhua Li, Yuanqing Fu, Fang Cai, Qi Chen, Duo Li. Combination of fucoxanthin and conjugated linoleic acid attenuates body weight gain and improves lipid metabolism in high-fat diet-induced obese rats.
Archives of biochemistry and biophysics.
2012 Mar; 519(1):59-65. doi:
10.1016/j.abb.2012.01.011
. [PMID: 22289788] - Madhu Suman Rana, A Tyagi, Sk Asraf Hossain, A K Tyagi. Effect of tanniniferous Terminalia chebula extract on rumen biohydrogenation, ∆(9)-desaturase activity, CLA content and fatty acid composition in longissimus dorsi muscle of kids.
Meat science.
2012 Mar; 90(3):558-63. doi:
10.1016/j.meatsci.2011.09.016
. [PMID: 22019314] - José M Pestana, Ana S H Costa, Susana P Alves, Susana V Martins, Cristina M Alfaia, Rui J B Bessa, José A M Prates. Seasonal changes and muscle type effect on the nutritional quality of intramuscular fat in Mirandesa-PDO veal.
Meat science.
2012 Mar; 90(3):819-27. doi:
10.1016/j.meatsci.2011.11.023
. [PMID: 22133588] - Anne-Catherine Schneider, Pauline Beguin, Sophie Bourez, James W Perfield, Eric Mignolet, Cathy Debier, Yves-Jacques Schneider, Yvan Larondelle. Conversion of t11t13 CLA into c9t11 CLA in Caco-2 cells and inhibition by sterculic oil.
PloS one.
2012; 7(3):e32824. doi:
10.1371/journal.pone.0032824
. [PMID: 22427892] - Christian Degen, Josef Ecker, Stefanie Piegholdt, Gerhard Liebisch, Gerd Schmitz, Gerhard Jahreis. Metabolic and growth inhibitory effects of conjugated fatty acids in the cell line HT-29 with special regard to the conversion of t11,t13-CLA.
Biochimica et biophysica acta.
2011 Dec; 1811(12):1070-80. doi:
10.1016/j.bbalip.2011.08.005
. [PMID: 21889998] - M A G Quaresma, Susana P Alves, I Trigo-Rodrigues, R Pereira-Silva, N Santos, J P C Lemos, A S Barreto, R J B Bessa. Nutritional evaluation of the lipid fraction of feral wild boar (Sus scrofa scrofa) meat.
Meat science.
2011 Dec; 89(4):457-61. doi:
10.1016/j.meatsci.2011.05.005
. [PMID: 21658850] - Elena Giordano, Sebastiano Banni, Loredana Quadro. A single dose of c9,t11 or t10,c12 conjugated linoleic acid isomers perturbs vitamin A metabolism in mice.
Nutrition research (New York, N.Y.).
2011 Nov; 31(11):855-62. doi:
10.1016/j.nutres.2011.09.013
. [PMID: 22118757] - T R Whitney, C J Lupton, S B Smith. Redberry juniper as a roughage source in lamb feedlot rations: wool and carcass characteristics, meat fatty acid profiles, and sensory panel traits.
Meat science.
2011 Oct; 89(2):160-5. doi:
10.1016/j.meatsci.2011.04.010
. [PMID: 21570776] - Arturo Anadon, Maria Rosa Martinez-Larranaga, Maria Aranzazu Martinez, Irma Ares, Eva Ramos, Pilar Gomez-Cortes, Manuela Juarez, Miguel Angel de la Fuente. A 4-week repeated oral dose toxicity study of dairy fat naturally enriched in vaccenic, rumenic and α-linolenic acids in rats.
Journal of agricultural and food chemistry.
2011 Jul; 59(14):8036-46. doi:
10.1021/jf201251g
. [PMID: 21678997] - Shan Jiang, Han Chen, Zhigang Wang, Jean-Jack Riethoven, Yuannan Xia, Jess Miner, Michael Fromm. Activated AMPK and prostaglandins are involved in the response to conjugated linoleic acid and are sufficient to cause lipid reductions in adipocytes.
The Journal of nutritional biochemistry.
2011 Jul; 22(7):656-64. doi:
10.1016/j.jnutbio.2010.05.005
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The Journal of nutritional biochemistry.
2011 May; 22(5):495-501. doi:
10.1016/j.jnutbio.2010.04.005
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PloS one.
2011; 6(6):e20944. doi:
10.1371/journal.pone.0020944
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The Journal of nutritional biochemistry.
2010 Nov; 21(11):1099-105. doi:
10.1016/j.jnutbio.2009.09.007
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Journal of lipid research.
2010 Sep; 51(9):2686-94. doi:
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The British journal of nutrition.
2010 Aug; 104(3):346-54. doi:
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Journal of health, population, and nutrition.
2010 Apr; 28(2):159-66. doi:
10.3329/jhpn.v28i2.4886
. [PMID: 20411679] - Jae In Jung, Han Jin Cho, Jongdai Kim, Dae Young Kwon, Jung Han Yoon Park. trans-10,cis-12 conjugated linoleic acid inhibits insulin-like growth factor-I receptor signaling in TSU-Pr1 human bladder cancer cells.
Journal of medicinal food.
2010 Feb; 13(1):13-9. doi:
10.1089/jmf.2009.1201
. [PMID: 20136431] - Anke Jaudszus, Peter Moeckel, Eckard Hamelmann, Gerhard Jahreis. Trans-10,cis-12-CLA-caused lipodystrophy is associated with profound changes of fatty acid profiles of liver, white adipose tissue and erythrocytes in mice: possible link to tissue-specific alterations of fatty acid desaturation.
Annals of nutrition & metabolism.
2010; 57(2):103-11. doi:
10.1159/000319877
. [PMID: 20924169] - Berenice Ortiz, Lesley Wassef, Elena Shabrova, Lina Cordeddu, Sebastiano Banni, Loredana Quadro. Hepatic retinol secretion and storage are altered by dietary CLA: common and distinct actions of CLA c9,t11 and t10,c12 isomers.
Journal of lipid research.
2009 Nov; 50(11):2278-89. doi:
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Journal of dairy science.
2009 Aug; 92(8):3874-93. doi:
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. [PMID: 19620671] - Freda M McIntosh, Kevin J Shingfield, Estelle Devillard, Wendy R Russell, R John Wallace. Mechanism of conjugated linoleic acid and vaccenic acid formation in human faecal suspensions and pure cultures of intestinal bacteria.
Microbiology (Reading, England).
2009 Jan; 155(Pt 1):285-294. doi:
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. [PMID: 19118369] - Margaret H Cooper, Jessica R Miller, Patricia L Mitchell, Deborah L Currie, Roger S McLeod. Conjugated linoleic acid isomers have no effect on atherosclerosis and adverse effects on lipoprotein and liver lipid metabolism in apoE-/- mice fed a high-cholesterol diet.
Atherosclerosis.
2008 Oct; 200(2):294-302. doi:
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Lipids in health and disease.
2008 Sep; 7(?):34. doi:
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Biochemistry.
2008 Sep; 47(36):9618-26. doi:
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Lipids in health and disease.
2008 Aug; 7(?):31. doi:
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The British journal of nutrition.
2008 Jul; 100(1):112-9. doi:
10.1017/s0007114507886326
. [PMID: 18167173] - Magdalena Franczyk-Zarów, Renata B Kostogrys, Beata Szymczyk, Jacek Jawień, Mariusz Gajda, Tadeusz Cichocki, Leszek Wojnar, Stefan Chlopicki, Paweł M Pisulewski. Functional effects of eggs, naturally enriched with conjugated linoleic acid, on the blood lipid profile, development of atherosclerosis and composition of atherosclerotic plaque in apolipoprotein E and low-density lipoprotein receptor double-knockout mice (apoE/LDLR-/-).
The British journal of nutrition.
2008 Jan; 99(1):49-58. doi:
10.1017/s0007114507793893
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The British journal of nutrition.
2007 Dec; 98(6):1152-8. doi:
10.1017/s0007114507772677
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Journal of lipid research.
2007 Oct; 48(10):2247-54. doi:
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The Journal of nutritional biochemistry.
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