Conversion of t11t13 CLA into C9t11 CLA in CACO-2 cells and inhibition by sterculic oil

PLoS ONE

Volumn 7, Issue 3, 2012, Pages

  Schneider, Anne Catherine ^a   Beguin, Pauline ^a   Bourez, Sophie ^a   Perfield, James W ^b   Mignolet, Eric ^a   Debier, Cathy ^a   Schneider, Yves Jacques ^a   Larondelle, Yvan ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED LINOLEIC ACID; OIL; STERCULIC OIL; UNCLASSIFIED DRUG; 9,11 LINOLEIC ACID; 9,11-LINOLEIC ACID; ACYL COENZYME A DESATURASE; FATTY ACID; VEGETABLE OIL;

ARTICLE; BIOTRANSFORMATION; CELL STRAIN CACO 2; CELLULAR DISTRIBUTION; CONTROLLED STUDY; ENZYME ACTIVITY; FATTY ACID DESATURATION; FATTY ACID METABOLISM; HUMAN; HUMAN CELL; INCUBATION TIME; METABOLITE; ANALYSIS OF VARIANCE; BIOSYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; GAS CHROMATOGRAPHY; METABOLISM; SOLID PHASE EXTRACTION; STERCULIA;

MAMMALIA;

ANALYSIS OF VARIANCE; CACO-2 CELLS; CHROMATOGRAPHY, GAS; FATTY ACIDS; HUMANS; LINOLEIC ACIDS, CONJUGATED; PLANT OILS; SOLID PHASE EXTRACTION; STEAROYL-COA DESATURASE; STERCULIA;

EID: 84858018660     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0032824     Document Type: Article

References (44)

1. MacDonald HB, (2000) Conjugated linoleic acid and disease prevention: a review of current knowledge. J Am Coll Nutr 19: 111S-118S.
2. Pariza MW, Park Y, Cook ME, (2000) Mechanisms of action of conjugated linoleic acid: evidence and speculation. Proc Soc Exp Biol Med 223: 8-13.
3. Bassaganya-Riera J, Hontecillas R, Beitz DC, (2002) Colonic anti-inflammatory mechanisms of conjugated linoleic acid. Clin Nutr 21: 451-459.
4. Badinga L, Greene ES, (2006) Physiological properties of conjugated linoleic acid and implications for human health. Nutr Clin Pract 21: 367-373.
5. Pariza MW, Hargraves WA, (1985) A beef-derived mutagenesis modulator inhibits initiation of mouse epidermal tumors by 7,12-dimethylbenz(a)anthracene. Carcinogenesis 6: 591-593.
6. Ip C, Chin SF, Scimeca JA, Pariza MW, (1991) Mammary cancer prevention by conjugated dienoic derivative of linoleic acid. Cancer Res 51: 6118-6124.
7. Belury MA, (2002) Inhibition of carcinogenesis by conjugated linoleic acid: potential mechanisms of action. J Nutr 132: 2995-2998.
8. Kim YS, Kim SJ, Oh TW, Byeon JI, Kim GS, et al. (2010) Differential inhibitory effects of conjugated linoleic acid isomers on mouse forestomach neoplasia induced by benzo(a)pyrene. J Agric Food Chem 58: 3177-3183.
9. Lampen A, Leifheit M, Voss J, Nau H, (2005) Molecular and cellular effects of cis-9, trans-11-conjugated linoleic acid in enterocytes: effects on proliferation, differentiation and gene expression. Biochim Biophys Acta 1735: 30-40.
10. Chen BQ, Yang YM, Gao YH, Liu JR, Xue YB, et al. (2003) Inhibitory effects of c9,t11-conjugated linoleic acid on invasion of human gastric carcinoma cell line SGC-7901. World J Gastroenterol 9: 1909-1914.
11. Huang G, Zhong X, Cao Y, Chen Y, (2007) Antiproliferative effects of conjugated linoleic acid on human colon adenocarcinoma cell line Caco-2. Asia Pac J Clin Nutr 16: 432-436.
12. McLeod RS, LeBlanc AM, Langille MA, Mitchell PL, Currie DL, (2004) Conjugated linoleic acids, atherosclerosis and hepatic very-low-density lipoprotein metabolism. Am J Clin Nutr 79: 1169S-1174S.
13. Kritchevsky D, Tepper SA, Wright S, Czarnecki SK, Wilson TA, et al. (2004) Conjugated linoleic acid isomer effects in atherosclerosis: growth and regression of lesions. Lipids 39: 611-616.
14. O'Shea M, Bassaganya-Riera J, Mohede ICM, (2004) Immunomodulatory properties of conjugated linoleic acid. Am J Clin Nutr 79: 1199S-1206S.
15. Reynolds CM, Loscher CE, Moloney AP, Roche HM, (2008) Cis-9, trans-11-conjugated linoleic acid but not its precursor trans-vaccenic acid attenuate inflammatory markers in the human colonic epithelial cell line Caco-2. Br J Nutr 100: 13-17.
16. Griinari JM, Corl BA, Lacy SH, Chouinard PY, Nurmela KV, et al. (2000) Conjugated linoleic acid is synthesized endogenously in lactating dairy cows by delta9-desaturase. J Nutr 130: 2285-2291.
17. Corl BA, Baumgard LH, Dwyer DA, Griinari JM, Philips BS, et al. (2001) The role of delta9-desaturase in the production of cis-9, trans-11 CLA. J Nutr Biochem 12: 622-630.
18. Kay JK, Mackle TR, Auldist MJ, Thomson NA, Bauman DE, (2004) Endogenous synthesis of cis-9, trans-11 conjugated linoleic acid in dairy cows fed fresh pasture. J Dairy Sci 87: 369-378.
19. Turpeinen AM, Mutanen M, Aro A, Salminen I, Basu S, et al. (2002) Bioconversion of vaccenic acid to conjugated linoleic acid in humans. Am J Clin Nutr 76: 504-510.
20. Santora JE, Palmquist DL, Roehrig KL, (2000) Trans-vaccenic acid is desaturated to conjugated linoleic acid in mice. J Nutr 130: 208-215.
21. Miller A, McGrath E, Stanton C, Devery R, (2003) Vaccenic acid (t11-18:1) is converted to c9,t11-CLA in MCF-7 and SW480 cancer cells. Lipids 38: 623-632.
22. Dang Van QC, Focant M, Mignolet E, Turu C, Froidmont E, et al. (2011) Influence of the diet structure on ruminal biohydrogenation and milk fatty acid composition of cows fed extruded linseed. Animal Feed Sci Technol 169: 1-10.
23. Loor JJ, Ueda K, Ferlay A, Chilliard Y, Doreau M, (2004) Biohydrogenation, duodenal flow, and intestinal digestibility of trans fatty acids and conjugated linoleic acids in response to dietary forage: concentrate ratio and linseed oil in dairy cows. J Dairy Sci 87: 2472-2485.
24. Doreau M, Laverroux S, Normand J, Chesneau G, Glasser F, (2009) Effect of linseed fed as rolled seeds, extruded seeds or oil on fatty acids rumen metabolism and intestinal digestibility in cows. Lipids 44: 53-62.
25. Degen C, Ecker J, Piegholdt S, Liebisch G, Schmitz G, et al. (2011) 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. Biochim Biophys Acta 1811: 1070-1080.
26. Hennessy AA, Ross RP, Devery R, Stanton C, (2011) The health promoting properties of the conjugated isomers of α-linolenic acid. Lipids 46: 105-119.
27. Takagi T, Itabashi Y, (1981) Occurrence of mixtures of geometrical isomers of conjugated octadecatrienoic acids in some seed oils: analysis by open-tubular gas liquid chromatography and high performance liquid chromatography. Lipids 16: 546-551.
28. Tsuzuki T, Tokuyama Y, Igarashi M, Nakagawa K, Ohsaki Y, et al. (2004) α-eleostearic acid (9Z11E13E-18:3) is quickly converted to conjugated linoleic acid (9Z11E-18:2) in rats. J Nutr 134: 2634-2639.
29. Tsuzuki T, Kawakami Y, Abe R, Nakagawa K, Koba K, et al. (2006) Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid. J Nutr 136: 2153-2159.
30. Yuan GF, Sinclair AJ, Zhou CQ, Li D, (2009) α-eleostearic acid is more effectively metabolized into conjugated linoleic acid than punicic acid in mice. J Sci Food Agric 89: 1006-1011.
31. Yuan GF, Sinclair AJ, Sun HY, Li D, (2009) Fatty acid composition in tissues of mice fed diets containing conjugated linolenic acid and conjugated linoleic acid. J Food Lipids 16: 148-163.
32. Yuan GF, Sinclair AJ, Xu C, Li D, (2009) Incorporation and metabolism of punicic acid in healthy young humans. Mol Nutr Food Res 53: 1336-1342.
33. Schneider AC, Mignolet E, Schneider YJ, Larondelle Y, (2011) Absorption of conjugated linolenic acids and biotransformation in c9t11 or t9t11 conjugated linoleic acids in Caco-2 cells. Br J Nutr in press.
34. Gomez FE, Bauman DE, Ntambi JM, Fox BG, (2003) Effects of sterculic acid on stearoyl-CoA desaturase in differentiating 3T3-L1 adipocytes. Biochem Biophys Res Commun 300: 316-326.
35. Khanal RC, Dhiman TR, (2004) Biosynthesis of conjugated linoleic acid (CLA): a review. Pakist J Nutr 3: 72-81.
36. Schneider YJ, (1989) Optimisation of hybridoma cell growth and monoclonal antibody secretion in a chemically defined, serum- and protein-free culture medium. J Immunol Methods 116: 65-77.
37. Halleux C, Schneider YJ, (1991) Iron absorption by intestinal epithelial cells: 1. CaCo2 cells cultivated in serum-free medium, on polyethyleneterephtalate microporous membranes, as an in vitro model. In vitro Cell Dev Biol 27A: 293-302.
38. Guil-Guerrero JL, Belarbi ElH, (2001) Purification process for cod liver oil polyunsaturated fatty acids. JAOCS 78: 477-484.
39. Bligh EG, Dyer WJ, (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37: 911-917.
40. Christie WW, (1982) A simple procedure for rapid transmethylation of glycerolipids and cholesteryl esters. J Lipid Res 23: 1072-1075.
41. Nakamura MT, Nara TY, (2004) Structure, function and dietary regulation of delta-6, delta-5 and delta-9 desaturases. Annu Rev Nutr 24: 345-376.
42. Renaville B, Mullen A, Moloney F, Larondelle Y, Schneider YJ, et al. (2006) Eicosapentaenoic acid and 3,10 dithia stearic acid inhibit desaturation of trans-vaccenic acid into cis-9, trans-11-conjugated linoleic acid through different pathways in Caco-2 and T84 cells. Br J Nutr 95: 688-695.
43. Moise AR, Isken A, Dominguez M, de Lera AR, von Lintig J, et al. (2007) Specificity of zebrafish retinol saturase: formation of all-trans-13,14-dihydroretinol and all-trans-7,8-dihydroretinol. Biochemistry 46: 1811-1820.
44. Moise AR, Kuksa V, Imanishi Y, Palczewski K, (2004) Identification of all-trans-retinol:all-trans-13,14-dihydroretinol saturase. J Biol Chem 279: 50230-50242.