Effect of cyclic fatty acid monomers on fat absorption and transport depends on their positioning within the ingested triacylglycerols

Journal of Lipid Research

Volumn 38, Issue 8, 1997, Pages 1666-1679

  Martin, Jean Charles ^a   Caselli, Claude ^b   Broquet, Stéphanie ^a,b   Juanéda, Pierre ^a   Nour, Mohammed ^a   Sébédio, Jean Louis ^a   Bernard, André ^b  

^a CEMAGREF   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Intestinal lipoproteins; Intestinal metabolism; Pancreatic lipase; Triacylglycerol structure

Indexed keywords

LINSEED OIL; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE;

ACYLATION; ANIMAL MODEL; ARTICLE; BIOAVAILABILITY; CONTROLLED STUDY; ELECTROPHYSIOLOGY; ENZYME ACTIVITY; FAT INTAKE; FATTY ACID METABOLISM; FATTY ACID TRANSPORT; HYDROLYSIS; INGESTION; LIPID ABSORPTION; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; CHYLOMICRONS; DIETARY FATS; FATTY ACIDS; HYDROLYSIS; INTESTINAL ABSORPTION; LIPASE; LIPOPROTEINS; LYMPH; MALE; MICROSCOPY, ELECTRON; RATS; RATS, WISTAR; TRIGLYCERIDES;

EID: 0030773166     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. Sébédio, J-L., J-L. LeQuere, O. Morin, and A. Grandgirard. 1989. Heat treatment of vegetable oils. III. GC-MS characterization of cyclic fatty acid monomers in heated sunflower and linseed oils after total hydrogenation. J. Am. Oil Chem. Soc. 66: 704-709.
2. Dobson, G., W. W. Christie, and J-L. Sébédio. 1996. Monocyclic saturated fatty acids formed from oleic acid in heated sunflower oils. Chem. Phys. Lipids. 82: 101-110.
3. Christie, W. W., E. Y. Brechany, J-L. Sébédio, and J-L. LeQuere. 1993. Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic monoenoic acids formed in frying oils. Chem. Phys. Lipids. 66: 143-153.
4. Dobson, G., W. W. Christie, and J-L. Sébédio. 1996. Gas chromatographic properties of cyclic dienoic fatty acids formed in heated linseed oil. J. Chromatogr. 723: 349-354.
5. Mossoba, M., M. P. Yurawecz, J. A. G. Roach, H. S. Lin, R. E. MacDonald, B. D. Flickinge, and E. G. Perkins. 1995. Elucidation of cyclic fatty acid monomer structures. Cyclic and bicyclic ring sizes and double bond position and configuration. J. Am. Oil Chem. Soc. 72: 721-727.
6. Frankel, E. N., L. M. Smith, C. L. Hamblin, R. K. Creveling, and A. J. Clifford. 1984. Occurrence of cyclic fatty acid monomers in frying oils used for fast foods. J. Am. Oil Chem. Soc. 61: 87-90.
7. Sébédio, J-L., J. Kaitaranta, A. Grandgirard, and Y. Malkki. 1991. Quality assessment of industrial prefried french fries. J. Am. Oil Chem. Soc. 68: 299-302.
8. Saito, M., and T. Kaneda. 1976. Studies on the relationship between the nutritive value and the structure of polymerized oils. Jpn. J. Oil Chem. Soc. 25: 13-20.
9. Iwaoka, W. T., and E. G. Perkins. 1976. Nutritional effects of the cyclic monomers of methyl linolenate in the rat. Lipids. 11: 349-353.
10. Sébédio, J-L., and A. Grandgirard. 1989. Cyclic fatty acids: natural sources, formation during heat treatment, synthesis and biological properties. Prog. Lipid Res. 28: 303-336.
11. Sébédio, J-L., J. M. Chardigny, P. Juaneda, M. C. Giraud, M. Nour, W. W. Christie, and G. Dobson. 1995. Nutritional impact and selective incorporation of cyclic fatty acid monomers in rats during reproduction. In 21st World Congress of the International Society for Fat Research. 1995. P. J. Barnes, The Hague. 307-310.
12. Ribot, E., A. Grandgirard, J-L. Sébédio, A. Grynberg, and P. Athias. 1992. Incorporation of cyclic fatty acid monomers in lipids of rat heart cell cultures. Lipids. 27: 79-81.
13. Athias, P., E. Ribot, A. Grynberg, J-L. Sébédio, and A. Grandgirard. 1992. Effects of cyclic fatty acid monomers on the function of cultured rat cardiac myocytes in normoxia and hypoxia. Nutr. Res. 12: 737-745.
14. Potteau, B., M. Lhuissier, J. Leclerc, F. Custot, and R. Mezonne. 1970. Recherches sur la composition et les effets physioloques de l'huile de soja chauffée et de différentes fractions obtenues à partir de cette huile. Rev. Fr. Corps Gr. 17: 235-245.
15. Combe, N., M. J. Constantin, and B. Entressangles. 1981. Lymphatic absorption of nonvolatile oxidation products of heated oils in the rat. Lipids. 16: 8-14.
16. Tso, P. 1994. Intestinal lipid absorption. In Physiology of the Gastrointestinal Tract. L. R. Johnson, editor. Raven Press, New York. 1867-1907.
17. Carey, M. C., D. M. Small, and C. M. Bliss. 1983. Lipid digestion and absorption. Annu. Rev. Physiol. 45: 651-677.
18. Verger, R., M. Aoubala, F. Carriere, S. Ransac, L. Dupuis, J. DeCaro, F. Ferrato, I. Douchet, R. Laugier, and A. DeCaro. 1996. Regulation of lumen fat digestion: enzymatic aspect. Proc. Nutr. Soc. 55: 5-18.
19. Mattson, F. H., and R. A. Volpenheim. 1964. The digestion and absorption of triglycerides. J. Biol. Chem. 239: 2772-2777.
20. Yang, L. Y., and A. Kuksis. 1991. Apparent convergence (at 2-monoacylglycerol level) of phosphatidic acid and 2-monoacylglycerol pathways of synthesis of chylomicron triacylglycerol. J. Lipid Res. 32: 1173-1186.
21. Besnard, P., I. Niot, A. Bernard, and H. Carlier. 1996. Cellular and molecular aspects of fat metabolism in the small intestine. Proc. Nutr. Soc. 55: 19-37.
22. Christensen, M. S., C. E. Hoy, C. C. Becker, and T. G. Redgrave. 1995. Intestinal absorption and lymphatic transport or eicosapentaenoic (EPA), docosahexaenoic (DHA), and decanoic acids: dependence on intramolecular triacylglycerol structure. Am. J. Clin. Nutr. 61: 56-61.
23. Innis, S. M., R. Dyer, and C. M. Nelson. 1994. Evidence that palmitic acid is absorbed as sn-2 monoacylglycerol from human milk by breast-fed infants. Lipids. 29: 541-545.
24. Aoyama, T., K. Fukui, K. Taniguchi, S. Nagaoka, T. Yamamoto, and Y. Hashimoto. 1996. Absorption and metabolism of lipids in rats depend on fatty acid isomeric position. J. Nutr. 126: 225-231.
25. Pufal, D. A., P. T. Quinlan, and A. M. Salter. 1995. Effect of dietary triacylglycerol structure on lipoprotein metabolism: a comparison of the effects of dioleoylpalmitoylglycerol in which palmitate is esterified to the 2- or 1(3)-position of the glycerol. Biochim. Biophys. Acta. 1258: 41-48.
26. Caselli, C., H. Carlier, and J. Bezard. 1979. Size of lipoprotein particles in the intestinal lymph of rats fed on corn oil, peanut oil, rapeseed oil or canbra oil. Nutr. Metab. 23: 73-87.
27. Degrace, P., C. Caselli, J. M. Rayo, and A. Bernard. 1996. Intestinal lymph absorption of butter, corn oil, cod liver oil, menhaden oil, and eicosapentaenoic and docosahexaenoic acid ethyl esters in rats. Lipids. 31: 405-414.
28. Sébédio, J-L., J-L. LeQuere, E. Semon, O. Morin, J. Prevost, and A. Grandgirard. 1987. Heat treatment of vegetable oils. II. GC-MS and GC-FTIR spectra of some isolated cyclic fatty acid monomers. J. Am. Oil Chem. Soc. 64: 1324-1333.
29. Kodali, D. R., D. Atkinson, T. G. Redgrave, and D. M. Small. 1987. Structure and polymorphism of 18-carbon fatty acyl triacylglycerols: effect of unsaturation and substitution in the 2-position. J. Lipid Res. 28: 403-131.
30. Loev, B., and M. M. Goodman. 1967. Dry column chromatography: a preparative chromatographic technique with the resolution of thin-layer chromatography. Chem. Ind. 2026-2032.
31. Bentley, P. H., and W. Mac Crae. 1970. An efficient synthesis of symmetrical 1,3 diglycerides. J. Org. Chem. 35: 2082-2083.
32. Golding, B. T., and P. V. Ioannou. 1977. Rapid syntheses of 3-O-benzyl-sn-glycerol and 2-O-benzyl-sn-glycerol. Synthesis. 6: 423-424.
33. Kodali, D. R., and R. I. Duclos. 1992. Debenzylation and detritylation by bromodimethylborane: synthesis of mono-acid or mixed-acid 1,2- or 2,3-diacyl-sn-glycerols. Chem. Phys. Lipids. 61: 169-173.
34. Guindon, Y., C. Yoakim, and H. E. Morton. 1984. Dimethylboron bromide and diphenylboron bromide: cleavage of acetals and ketals. J. Org. Chem. 49: 3912-3919.
35. Myher, J. J., and A. Kuksis. 1979. Stereospecific analysis of triacylglycerols via racemic phosphatidylcholines and phospholipase C. Can. J. Biochem. 57: 117-124.
36. Martin, J. C., P. Bougnoux, J. M. Antoine, M. Lanson, and C. Couet. 1993. Triacylglycerol structure of human colostrum and mature milk. Lipids. 28: 637-643.
37. Henderson, R. J., I. C. Burkow, and R. M. Millar. 1993. Hydrolysis of fish oils containing polymers of triacylglycerols by pancreatic lipase in vitro. Lipids. 28: 313-319.
38. Morrison, W. R., and L. M. Smith. 1964. Preparation of fatty acid methyl esters and dimethylacetals from lipids with boron fluoride-methanol. J. Lipid Res. 5: 600-608.
39. Kuksis, A., J. J. Myher, and K. Geher. 1993. Quantitation of plasma lipids by gas-liquid chromatography on high temperature polarizable capillary columns. J. Lipid Res. 34: 1029-1038.
40. Tso, P., A. Balint, and W. J. Simmonds. 1977. Role of biliary lecithin in lymphatic transport of fat. Gastroenterology. 73: 1362-1367.
41. Mansbach, C. M., and R. F. Dowell. 1992. Uptake and metabolism of circulating fatty acids by rat intestine. J. Lipid Res. 23: 1009-1019.
42. VanKuiken, B., and W. D. Behnke. 1994. The activation of porcine pancreatic lipase by cis-unsaturated fatty acids. Biochim. Biophys. Acta, 1214: 148-160.
43. Yang, L. Y., A. Kuksis, and A. Myher. 1989. Lumenal hydrolysis of menhaden and rapeseed oils and their fatty acid methyl and ethyl esters in the rat. Biochem. Cell Biol. 67: 192-204.
44. Ockner, R. K., and J. A. Manning. 1976. Role of FABP in esterification of absorbed long chain fatty acid in rat intestine. J. Clin. Invest. 58: 631-641.
45. Prows, D. R., E. J. Murphy, and F. Schroeder. 1995. Intestinal and liver fatty acid binding proteins differentially affect fatty acid uptake and esterification in L-cells. Lipids. 30: 907-910.
46. Christie, W. W. 1994. Silver ion and chiral chromatography in the analysis of triacylglycerols. Prog. Lipid Res. 33: 9-18.
47. Innis, S. M., R. D. Dyer, P. T. Quinlan, and D. Diersen-Schade. 1996. Dietary triacylglycerol structure and saturated fat alter plasma and tissue fatty acids in piglets. Lipids. 31: 497-505.
48. Field, F.J., and S. N. Mathur. 1995. Intestinal lipoprotein synthesis and secretion. Prog. Lipid Res. 34: 185-198.
49. Scow, R. O., E. J. Blanchette-Mackie, and L. C. Smith. 1980. Transport of lipid across capillary endothelium. Fed. Proc. 39: 2610-2617.