(9Z,11Z)-9,11-Octadecadienoic acid (BioDeep_00000844437)
代谢物信息卡片
(9Z,11Z)-9,11-Octadecadienoic acid
化学式: C18H32O2 (280.2402172)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCC=CC=CCCCCCCCC(=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-
相关代谢途径
Reactome(0)
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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)
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PharmGKB(0)
0 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
- 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. [PMID: 34763909] - Monique T Ngo Njembe, Barbara Pachikian, Irina Lobysheva, Nancy Van Overstraeten, Louis Dejonghe, Eleonore Verstraelen, Marine Buchet, Catherine Rasse, Cécile Gardin, Eric Mignolet, Jean-Luc Balligand, Yvan Larondelle. A Three-Month Consumption of Eggs Enriched with ω-3, ω-5 and ω-7 Polyunsaturated Fatty Acids Significantly Decreases the Waist Circumference of Subjects at Risk of Developing Metabolic Syndrome: A Double-Blind Randomized Controlled Trial.
Nutrients.
2021 Feb; 13(2):. doi:
10.3390/nu13020663. [PMID: 33670720] - Tomasz Lepionka, Małgorzata Białek, Marian Czauderna, Agnieszka Białek. Pomegranate seed oil and bitter melon extract supplemented in diet influence the lipid profile and intensity of peroxidation in livers of SPRD rats exposed to a chemical carcinogen.
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:
10.1016/j.biochi.2019.12.004. [PMID: 31837411] - A Białek, M Białek, T Lepionka, K Kaszperuk, T Banaszkiewicz, A Tokarz. The effect of pomegranate seed oil and grapeseed oil on cis-9, trans-11 CLA (rumenic acid), n-3 and n-6 fatty acids deposition in selected tissues of chickens.
Journal of animal physiology and animal nutrition.
2018 Aug; 102(4):962-976. doi:
10.1111/jpn.12902. [PMID: 29682807] - Fei Koon Chan, Chin Hsu, Tsai-Chung Li, Wen-Hung Chen, Kuo-Tang Tseng, Pei-Min Chao. Bitter melon seed oil increases mitochondrial content in gastrocnemius muscle and improves running endurance in sedentary C57BL/6J mice.
The Journal of nutritional biochemistry.
2018 08; 58(?):150-157. doi:
10.1016/j.jnutbio.2018.05.008. [PMID: 29957359] - Teresa Banaszkiewicz, Agnieszka Białek, Andrzej Tokarz, Karol Kaszperuk. Effect of dietary grape and pomegranate seed oil on the post-slaughter value and physicochemical properties of muscles of broiler chickens.
Acta scientiarum polonorum. Technologia alimentaria.
2018 Jul; 17(3):199-209. doi:
10.17306/j.afs.0563. [PMID: 30269459] - Ana Paula Simões-Wüst, Carolina Moltó-Puigmartí, Eugene Hjm Jansen, Martien Cjm van Dongen, Pieter C Dagnelie, Carel Thijs. Organic food consumption during pregnancy and its association with health-related characteristics: the KOALA Birth Cohort Study.
Public health nutrition.
2017 Aug; 20(12):2145-2156. doi:
10.1017/s1368980017001215. [PMID: 28625206] - Grace E Berryhill, Susan G Miszewski, Josephine F Trott, Jana Kraft, Adam L Lock, Russell C Hovey. Trans-Fatty Acid-Stimulated Mammary Gland Growth in Ovariectomized Mice is Fatty Acid Type and Isomer Specific.
Lipids.
2017 03; 52(3):223-233. doi:
10.1007/s11745-016-4221-2. [PMID: 28074319] - Agnieszka Bialek, Malgorzata Czerwonka, Malgorzata Bialek, Tomasz Lepionka, Karol Kaszperuk, Teresa Banaszkiewicz, Andrzej Tokarz. INFLUENCE OF POMEGRANATE SEED OIL AND GRAPE SEED OIL ON CHOLESTEROL CONTENT AND FATTY ACIDS PROFILE IN LIVERS OF CHICKENS.
Acta poloniae pharmaceutica.
2017 Mar; 74(2):624-632. doi:
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Nutrients.
2016 Dec; 8(12):. doi:
10.3390/nu8120805. [PMID: 27973445] - S Jaturasitha, N Chaiwang, A Kayan, M Kreuzer. Nutritional strategies to improve the lipid composition of meat, with emphasis on Thailand and Asia.
Meat science.
2016 Oct; 120(?):157-166. doi:
10.1016/j.meatsci.2016.04.014. [PMID: 27127010] - Shane M Huebner, Jake M Olson, James P Campbell, Jeffrey W Bishop, Peter M Crump, Mark E Cook. Low Dietary c9t11-Conjugated Linoleic Acid Intake from Dairy Fat or Supplements Reduces Inflammation in Collagen-Induced Arthritis.
Lipids.
2016 07; 51(7):807-19. doi:
10.1007/s11745-016-4163-8. [PMID: 27270404] - W Polviset, J T Schonewille, H Everts, C Wachirapakorn, C Yuangklang, E Claeys, S De Smet. Effect of whole cottonseed v. sunflower seed on the fatty acid profile of subcutaneous fat, longissimus dorsi and blood of Thai Native and Holstein bulls.
Animal : an international journal of animal bioscience.
2015 Dec; 9(12):2072-80. doi:
10.1017/s1751731115001627. [PMID: 26289959] - R Khiaosa-Ard, M Kreuzer, F Leiber. Apparent recovery of C18 polyunsaturated fatty acids from feed in cow milk: a meta-analysis of the importance of dietary fatty acids and feeding regimens in diets without fat supplementation.
Journal of dairy science.
2015 Sep; 98(9):6399-414. doi:
10.3168/jds.2015-9459. [PMID: 26142845] - Luís Miguel Rodríguez-Alcalá, Irma Ares, Javier Fontecha, Manuela Juarez, Victor Castellano, María Rosa Martínez-Larrañaga, Arturo Anadón, María Aránzazu Martínez. Oral Absorption and Disposition of alpha-Linolenic, Rumenic and Vaccenic Acids After Administration as a Naturally Enriched Goat Dairy Fat to Rats.
Lipids.
2015 Jul; 50(7):659-66. doi:
10.1007/s11745-015-4034-8. [PMID: 26044769] - M Lanza, M Scerra, M Bognanno, A Buccioni, C Cilione, L Biondi, A Priolo, G Luciano. Fatty acid metabolism in lambs fed citrus pulp.
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. [PMID: 20965713] - Carolina Ramírez-Santana, Cristina Castellote, Margarida Castell, Carolina Moltó-Puigmartí, Montserrat Rivero, Francisco J Pérez-Cano, Angels Franch. Enhancement of antibody synthesis in rats by feeding cis-9,trans-11 conjugated linoleic acid during early life.
The Journal of nutritional biochemistry.
2011 May; 22(5):495-501. doi:
10.1016/j.jnutbio.2010.04.005. [PMID: 20688497] - Audrey M Neyrinck, Sam Possemiers, Céline Druart, Tom Van de Wiele, Fabienne De Backer, Patrice D Cani, Yvan Larondelle, Nathalie M Delzenne. Prebiotic effects of wheat arabinoxylan related to the increase in bifidobacteria, Roseburia and Bacteroides/Prevotella in diet-induced obese mice.
PloS one.
2011; 6(6):e20944. doi:
10.1371/journal.pone.0020944. [PMID: 21695273] - Jia-jie Zhai, Zhao-liang Liu, Jie-mei Li, Jian-ping Chen, Lin Jiang, Dong-mei Wang, Jin Yuan, Jian-Gang Shen, De-Po Yang, Jia-Qi Chen. Different mechanisms of cis-9,trans-11- and trans-10,cis-12- conjugated linoleic acid affecting lipid metabolism in 3T3-L1 cells.
The Journal of nutritional biochemistry.
2010 Nov; 21(11):1099-105. doi:
10.1016/j.jnutbio.2009.09.007. [PMID: 20138494] - Josef Ecker, Gerhard Liebisch, Max Scherer, Gerd Schmitz. Differential effects of conjugated linoleic acid isomers on macrophage glycerophospholipid metabolism.
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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Microbiology (Reading, England).
2009 Jan; 155(Pt 1):285-294. doi:
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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:
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The British journal of nutrition.
2008 Jan; 99(1):49-58. doi:
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The British journal of nutrition.
2007 Dec; 98(6):1152-8. doi:
10.1017/s0007114507772677. [PMID: 17559699] - R John Wallace, Nest McKain, Kevin J Shingfield, Estelle Devillard. Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria.
Journal of lipid research.
2007 Oct; 48(10):2247-54. doi:
10.1194/jlr.m700271-jlr200. [PMID: 17644775] - Anne Mullen, Fiona Moloney, Anne P Nugent, Lorna Doyle, Kevin D Cashman, Helen M Roche. Conjugated linoleic acid supplementation reduces peripheral blood mononuclear cell interleukin-2 production in healthy middle-aged males.
The Journal of nutritional biochemistry.
2007 Oct; 18(10):658-66. doi:
10.1016/j.jnutbio.2006.12.008. [PMID: 17368881] - Tsuyoshi Tsuzuki, Ikuo Ikeda. Slow absorption of conjugated linoleic acid in rat intestines, and similar absorption rates of 9c,11t-conjugated linoleic acid and 10t,12c-conjugated linoleic acid.
Bioscience, biotechnology, and biochemistry.
2007 Aug; 71(8):2034-40. doi:
10.1271/bbb.70238. [PMID: 17690459] - Martial LeDoux, Laurent Laloux, Jean-Jacques Fontaine, Yvon A Carpentier, Jean-Michel Chardigny, Jean-Louis Sébédio. Rumenic acid significantly reduces plasma levels of LDL and small dense LDL cholesterol in hamsters fed a cholesterol- and lipid-enriched semi-purified diet.
Lipids.
2007 Mar; 42(2):135-41. doi:
10.1007/s11745-007-3023-y. [PMID: 17393219] - Dominique Bauchart, Alexandre Roy, Stephanie Lorenz, Jean-Michel Chardigny, Anne Ferlay, Dominique Gruffat, Jean-Louis Sébédio, Yves Chilliard, Denys Durand. Butters varying in trans 18:1 and cis-9,trans-11 conjugated linoleic acid modify plasma lipoproteins in the hypercholesterolemic rabbit.
Lipids.
2007 Mar; 42(2):123-33. doi:
10.1007/s11745-006-3018-0. [PMID: 17393218] - Guidong Huang, Xianfeng Zhong, Yusheng Cao, Yan Chen. Antiproliferative effects of conjugated linoleic acid on human colon adenocarcinoma cell line Caco-2.
Asia Pacific journal of clinical nutrition.
2007; 16 Suppl 1(?):432-6. doi:
NULL. [PMID: 17392145] - Fumiaki Beppu, Masashi Hosokawa, Leo Tanaka, Hiroyuki Kohno, Takuji Tanaka, Kazuo Miyashita. Potent inhibitory effect of trans9, trans11 isomer of conjugated linoleic acid on the growth of human colon cancer cells.
The Journal of nutritional biochemistry.
2006 Dec; 17(12):830-6. doi:
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American journal of physiology. Heart and circulatory physiology.
2005 Aug; 289(2):H652-9. doi:
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The British journal of nutrition.
2004 Feb; 91(2):191-9. doi:
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