Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Fatty acid double bond orientation alters interaction with L-cell fibroblasts


Relatively little is known of fatty acid specificity in cellular fatty acid uptake. In this study L-cells, a fibroblastic cell line with very low levels of endogenous cytosolic fatty acid binding protein, were used to examine the role of cis and trans unsaturation on fatty acid uptake. The fluorescent fatty acids, trans-parinaric acid and cis-parinaric acid, were used as analogs of straight-chain saturated, and kinked-chain unsaturated fatty acids, respectively, in order to evaluate the fatty acid specificity of the uptake system. Parinaric acid is poorly metabolizable; greater than 97% was unesterified while 3H-oleic acid was almost totally metabolized after 30 min uptake. Cis- and trans-parinaric acid uptake was saturable and dependent on the concentration of fatty acid. However, the initial rate and maximal amount of trans-parinaric acid taken up by the L-cells was greater than for cis-parinaric acid under the same conditions. The affinity of L-cell uptake for trans-parinaric acid (Km = 0.12 uM) was 35-fold higher than that for cis-parinaric acid (Km = 4.17 uM) . Based on competition studies with oleic and stearic acids, it was concluded that the cis- and trans-parinaric acid were taken up by the same L-cell fatty acid uptake system. The results suggest that the L-cell fatty acid uptake system has selectivity for straight chain rather than kinked chain unsaturated fatty acids.

This is a preview of subscription content, log in to check access.


Cis-parinaric acid:

9Z, 11E, 13E, 15Z-octatetraenoic acid

trans-parinaric acid:

9E, I IE, 13E, 15E-octatetraenoic acid


ethylene glycol-bis(beta-amlno-ethyl ether) N,N,N′,N′-tetratacetic acid


bovine serum albumin


phosphate buffered saline


  1. 1.

    Kaikaus RM, Bass NM, Ockner RK: Functions of fatty acid binding protein. Experientia 46: 617–630, 1990

  2. 2.

    Stremmel W: Fatty acid uptake by isolated rat heart myocytes represents a carrier mediated transport process. J Clin Invest 81: 844–852, 1988

  3. 3.

    Abel-aleem S, Badr M, Frangakis C: Stimulation of polyunsaturated fatty acid oxidation in myocytes by regulating its cellular uptake. Life Sciences 49: 185–191, 1991

  4. 4.

    Doi O, Doi F, Schroeder F, Alberts AW, Vagelos PR: Manipulation of fatty acid composition of membrane phospholipid and its effects on cell growth in mouse LM cells. Biochim Biophys Acta 509: 239–250, 1978

  5. 5.

    Schroeder F, Holland JF, Doi O: Physical properties of murine fibroblasts with altered acyl chain unsaturation. Arch Biochem Biophys 194: 431–438, 1979

  6. 6.

    Schroeder F, Perlmutter J, Glaser M, Vagelos PR: Isolation and characterization of subcellular membranes with altered phospholipid composition from cultured fibroblasts. J Biol Chem 251: 5015–5026, 1976

  7. 7.

    Alberts AW Ferguson K, Hennessy S, Vagelos PR: Regulation of lipid synthesis in cultured animal cells: J Biol Chem 249: 5241–5249, 1974

  8. 8.

    Stremmel W Berk PD: Hepatocellular influx of 14C-oleate reflects membrane transport rather than intracellular metabolism or binding. Proc Natl Acad Sci USA 83: 3086–3090, 1986

  9. 9.

    Abumrad NA, Perry PR, Whitesell RR: Stimulation by epinephrine of the membrane transport of long chain fatty acid in the adipocyte. J Biol Chem 260: 9969–9971, 1985

  10. 10.

    Jefferson JR, Slotte JP, Nemecz G, Pastuszyn A, Scallen TJ, Schroeder F: Intracellular sterol distribution in transfected mouse L-cell fibroblasts expressing rat liver fatty acid binding protein. J Biol Chem 266: 5486–5496, 1991

  11. 11.

    Jefferson JR, Powell DM, Rymaszewski Z, Kukowska-Latallo J, Lowe JB, Schroeder F: Altered membrane structure in transfected mouse L-cell fibroblasts expressing rat liver fatty acid binding protein. J Biol Chem 265: 11062–11068, 1990

  12. 12.

    Kahn CR, Gopalakrishnan TV, Weiss M: Transfer of heritable properties by cell hybridization. Specificity and the role of selective pressure. Somatic Cell Genetics 7: 547–565, 1981

  13. 13.

    Demediuk P, Anderson DK, Horrocks LA, Means ED: Mechanical damage to murine neuronal-enriched cultures during harvesting: Effects on free fatty acids, diglycerides, (Na+,K+)-ATPase, and lipid peroxidation. In Vitro Cell.Develop.siol. 21: 569–574, 1985

  14. 14.

    Hara A, Radin NS: Lipid extraction of tissues with a low toxicity solvent. Anal.Biochem. 90: 420–426, 1978

  15. 15.

    Bradford MM: A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding. Anal.Biochem. 72: 248–254, 1976

  16. 16.

    Dugan LL, Demidiuk P, Pendley II CE, Horrocks LA: Separation of phospholipids by high pressure liquid chromatography: all major classes including ethanolamine and choline plasmalogens, and most minor classes, including lysophosphatidylethanolamine. J Chromatogr 378: 317–327, 1986

  17. 17.

    Murphy EJ, Stephens R, Jurkowitz MS, Horrocks LA: Acidic hydrolysis of plasmalogens followed by high performance liquid chromatography. Lipids 28: 565–568

  18. 18.

    Schroeder F, Holland JF, Vagelos PR: Use of beta-parinaric acid, a novel fluorimetric probe to determine characteristic temperatures of membranes and membrane lipids from cultured animal cells. J Biol Chem 251: 6747–6756, 1976

  19. 19.

    Schroeder F, Jefferson JR, Powell D, Incerpi S, Woodford JK, Colles S, Myers-Payne S, Emge T, Hubbell T, Moncecchi D, Prows D, Heyliger CE: Expression of rat L-FABP in mouse fibroblasts: role in fat absorption. Molec Cell Biochem 101: 73–83, 1993

  20. 20.

    Schroeder F: Hormonal effects on fatty acid binding and physical properties of rat liver plasma membranes. J Memb Biol 68: 1–10, 1982

  21. 21.

    Schroeder F: Lipid domains in plasma membranes from rat liver. Eur. J. Biochem. 132: 509–516, 1983

  22. 22.

    Prows DR, Murphy EJ, Schroeder F: Intestinal- and liver-fatty acid binding proteins differentially affect fatty acid uptake and esterification in L-cells. Lipids, in press, 1995

  23. 23.

    Nemecz G, Hubbell T, Jefferson JR, Lowe JB, Schroeder F: Interaction of fatty acids with recombinant rat intestinal and liver fatty acid binding proteins. Arch Biochem Biophys 286: 300–309, 1991

  24. 24.

    Nemecz G, Jefferson JR, Schroeder F: Polyene fatty acid interactions with recombinant rat intestinal and liver fatty acid binding proteins. JBiol Chem 266: 17112–17123, 1991

  25. 25.

    Paulussen RJA, Veerkamp JH: Intracellular fatty acid binding proteins: Characteristics and functions. In: H.J. Hilderson, (ed.). Subcellular Biochemistry Vol. 16 ‘Intracellular transfer of lipid molecules’ Plenum Press, Inc., NY 1990, pp. 175–226

  26. 26.

    Keler T, Barker CS, Sorof S: Specific growth stimulation by linoleic acid in hepatoma cells transfected with the target protein of a liver carcinogen. Proc Natl Acad Sci USA 89: 4830–4834, 1992

  27. 27.

    Sweetser DV, Birkenmeier EH, Klisak IJ, Zollman S, Sparkes RS, Mohandas T, Lusis AS, Gordon JI: The human and rodent intestinal fatty acid binding protein genes: a comparative analysis of their structure, expression and linkage relationships. J Biol Chem 262: 16060–16071, 1987

  28. 28.

    Trotter P, Storch J: Fatty acid uptake and metabolism in human intestinal cell line (Caco-2): comparison of apical and basolateral incubation. J Lipid Res 32: 293–304, 1991

  29. 29.

    Mallordy A, Besnard P, Carlier H: Research of and in vitro model to study the expression of fatty acid binding proteins in the small intestine. Mol Cell Biochem 123: 85–92, 1993

  30. 30.

    Schoentgen F, Pignede G, Bonnano LM, Jolles P: Fatty acid binding protein from bovine brain: amino acid sequence and some properties. Eur J Biochem 185: 35–40, 1989

  31. 31.

    Feng L, Hattten ME, Heintz N: Brain lipid binding protein (BLBP): a novel signaling system in developing mammalian central nervous system. Neuron 12: 895–908, 1994

  32. 32.

    Sarzani R, Claffey KP, Chobanian AV, Brecher P: Hypertension induces tissue specific gene suppression of a fatty acid binding protein in rat aorta. Proc Natl Acad. Sci USA 85: 7777–7781, 1988

  33. 33.

    Lee L, Wiggert B: Isolation and characterization of an unsaturated fatty acid binding protein from developing chick neural retina. J Neurochem 42: 47–53, 1984

  34. 34.

    Siegenthaler G, Hotz R, Chatellard-Gruaz D, Jaconi S, Saurat J-H: Characterization and expression of a novel human fatty acid binding protein: the epidermal type (E-FAsP). Biochem Biophys Res Commun 190: 482–486, 1993

  35. 35.

    Stremmel W, Strohmeyer G, Berk PD: Hepatocellular uptake of oleate is energy dependent, sodium dependent, sodium linked and inhibited by an antibody to a hepatocyte plasma membrane fatty acid binding protein: Proc Natl Acad Sci USA 83: 3584–3588, 1986

  36. 36.

    Abumrad NA, Park JH, Park CR: Permeation of long chain fatty acid into adipocytes. J Biol Chem 259: 8945–8953, 1984

  37. 37.

    Heyliger CE, Powell DM, Skau KA: Effect of hydralazine on myocardial plasma membrane fatty acid binding protein (PM-FABP) during diabetes. Mol Cell Biochem, 148: 39–44, 1995

  38. 38.

    Billheimer intracellular cholesterol esterification. In: M. Esfahani, J. Swaney (eds). Advances in Cholesterol Research. The Telford Press, Caldwell, NJ 1990, pp 7–45

Download references

Author information

Correspondence to Friedhelm Schroeder.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Heyliger, C.E., Kheshgi, T.J., Murphy, E.J. et al. Fatty acid double bond orientation alters interaction with L-cell fibroblasts. Mol Cell Biochem 155, 113–119 (1996).

Download citation

Key words

  • L-cells
  • oleic acid
  • cis-parinaric acid
  • trans-parinaric acid
  • fatty acid
  • transport
  • fluorescence