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Sulfur-substituted and α-methylated fatty acids as peroxisome proliferator-activated receptor activators

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Lipids

Abstract

FA with varying chain lengths and an α-methyl group and/or a sulfur in the β-position were tested as peroxisome proliferator-activated receptor (PPAR)α,-δ(β), and-γ ligands by transient transfection in COS-1 cells using chimeric receptor expression plasmids, containing cDNAs encoding the ligand-binding domain of PPARα,-δ, and-γ. For PPARα, an increasing activation was found with increasing chain length of the sulfur-substituted FA up to C14-S acetic acid (tetradecylthioacetic acid=TTA). The derivatives were poor, and nonsignificant, activators of PPARδ. For PPARγ, activation increased with increasing chain length up to C16-S acetic acid. A methyl group was introduced in the α-position of palmitic acid, TTA, EPA, DHA, cis9,trans11CLA, and trans10,cis12 CLA. An increased activation of PPARα was obtained for the α-methyl derivatives compared with the unmethylated FA. This increase also resulted in increased expression of the two PPARα target genes acyl-CoA oxidase and liver FA-binding protein for α-methyl TTA, α-methyl EPA, and α-methyl DHA. Decreased or altered metabolism of these derivatives in the cells cannot be excluded. In conclusion, saturated FA with sulfur in the β-position and increasing carbon chain length from C9−S acetic acid to C14−S acetic acid have increasing effects as activators of PPARα and-γ in transfection assays. Furthermore, α-methyl FA derivatives of a saturated natural FA (palmitic acid), a sulfur-substituted FA (TTA), and PUFA (EPA, DHA, c9,t11 CLA, and t10,c12 CLA) are stronger PPARα activators than the unmethylated compounds.

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Abbreviations

AcA:

acetic acid

ACO:

acyl-CoA oxidase 1

BRL 49653:

rosiglitazone

HRMS:

high-resolution MS

LBD:

ligand-binding domain

L-FABP:

liver-specific fatty acid-binding protein

PPAR:

peroxisome proliferator-activated receptor

RXR:

retinoid X receptor

TTA:

tetradecylthioacetic acid (C14−S acetic acid)

USAS:

upstream activating sequence

WY-14,643:

pirinixic acid, also know as 4-chloro-6-(2,3-xylidino)-2-pyrimidinylthioacetic acid

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Authors and Affiliations

  1. Institute of Basic Medical Sciences, Department Chemistry, University of Oslo, Norway

    Anne Kristin Holmeide & Lars Skattebøl

  2. Institute of Basic Medical Sciences, Department Nutrition, University of Oslo, Norway

    Linda Granlund & Hilde Irene Nebb

  3. Institute of Basic Medical Sciences, Department of Biochemistry, University of Oslo, P.O. Box 1112, Blindern, 0317, Oslo, Norway

    Laila N. Larsen & Jon Bremer

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  1. Laila N. Larsen
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  2. Linda Granlund
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Correspondence to Laila N. Larsen.

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Larsen, L.N., Granlund, L., Holmeide, A.K. et al. Sulfur-substituted and α-methylated fatty acids as peroxisome proliferator-activated receptor activators. Lipids 40, 49–57 (2005). https://doi.org/10.1007/s11745-005-1359-3

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