Skip to main content

Phytanic and Pristanic Acid Are Naturally Occuring Ligands

  • Conference paper
Peroxisomal Disorders and Regulation of Genes

Abstract

Phytanic acid (3,7,11,15 tetramethylhexadecanoic acid) is an isoprenoid-derived 3-methyl fatty acid, which is solely derived from external sources. This branched-chain fatty acid originates from the phytol side chain of chlorophyll. Microorganisms, which are present in the rumen of ruminants, are thought to release phytol from chlorophyll, after which phytol is converted into phytanic acid (Patton and Benson, 1966). Because humans are not capable of phytol release from chlorophyll (Baxter, 1968), all phytanic acid enters the human body via the diet. Especially ruminant fats, fish and dairy products are rich sources of phytanic acid. Phytanic acid is metabolized into pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) through a-oxidation. Degradation of pristanic acid starts with three cycles of P-oxidation in the peroxisome, followed by further ß-oxidation in the mitochondrion (Verhoeven et al, 1998). Like phytanic acid, pristanic acid is present in lipids from many sources (Hansen, 1980).

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Baxter, J.H., 1968, Absorption of chlorophyll phytol in normal man and in patients with Refsum’s disease. J. Lipid Res. 9: 636–641.

    PubMed  CAS  Google Scholar 

  • Clairmont, A. and Sies, H., 1997, Evidence for a posttranscriptional effect of retinoic acid on connexin43 gene expression via the 3’-untranslated region. FEBS lett. 419: 268–270.

    Article  PubMed  CAS  Google Scholar 

  • de Urquiza, A.M., Liu, S., Sjoberg, M., Zetterstrom, R.H., Griffiths, W., Sjovall, J., Perlmann, T., 2000, Docosahexaenoic acid, a ligand for the retinoid X receptor in mouse brain. Science 290: 2140–2144.

    Article  PubMed  CAS  Google Scholar 

  • Ellinghaus, P., Wolfrum, C, Assmann, G., Spener, F. and Seedorf, U., 1999, Phytanic acid activates the peroxisome proliferator-activated receptor alpha (PPAR alpha) in sterol carrier-protein 2-/ sterol carrier protein x-deficient mice. J. Biol Chem. 274: 2766–2772.

    Article  PubMed  CAS  Google Scholar 

  • Glass, C.K., Rose, D.W. and Rosenfeld, M.G., 1997, Nuclear receptor coactivators. Curr.Opin.Cell Biol. 9: 222–232.

    Article  PubMed  CAS  Google Scholar 

  • Green, S., 1995, PPAR: a mediator of peroxisome proliferation action. Mutat. Res. 333 : 101–109.

    Article  PubMed  CAS  Google Scholar 

  • Hansen, R.P., 1980, Phytol: its metabolic products and their distribution. A review. New Zealand J. Sci 23: 259–275.

    CAS  Google Scholar 

  • Heyman, R.A., Mangelsdorf, D.J., Dyck, J.A., Stein, R.B., Eichele, G., Evans, R.M. and Thaller, C, 1992, 9-cis retinoic acid is a high affinity ligand for the retinoid X receptor. Cell 68: 397–406.

    Article  PubMed  CAS  Google Scholar 

  • Kitareewan, S., Burka, L.T., Tomer, K.B., Parker, CE., Deterding, L.J., Stevens, R.D., Forman, B.M., Mais, D.E., Heyman, R.A., McMorris, T. and Weinberger, C, 1996, Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR. Mol. Biol. Cell 7: 1153–1166.

    PubMed  CAS  Google Scholar 

  • Kliewer, S.A., Umesono, K., Noonan, D.J., Heyman, R.A., and Evans, R.M., 1992, Convergence of 9-cis retinoic acid and peroxisome proliferator signalling pathways through heterodimer formation of their receptors. Nature 358: 771–774.

    Article  PubMed  CAS  Google Scholar 

  • Krey, G., Keller, A., Mahfoudi, A. and Wahli, W., 1995, PPARs: nuclear hormone receptors controlling peroxisomal fatty acid ß-oxidation. In Functions and biogenesis of peroxisomes in relation to human disease (R.J.A. Wanders, R.B.H. Schutgens and H.F. Tabak, eds) Elsevier, Amsterdam, pp 167–200.

    Google Scholar 

  • Krey, G., Braissant, O., L’Horset, F., Kalkhoven, E., Perroud, M., Parker, M.G., and Wahli. W., 1997, Fatty acids, eicosanoids, and hypolipidemic agents identified as ligands of peroxisome proliferator-activated receptors by coactivator-dependent receptor ligand assay. Mol Endocrinol. 11: 779–791.

    Article  PubMed  CAS  Google Scholar 

  • Lemotte, P.K., Keidel, S. and Apfel, CM., 1996, Phytanic acid is a retinoid X receptor ligand. Eur. J. Biochem. 236: 328–333.

    Article  PubMed  CAS  Google Scholar 

  • Patton, S and Benson, A.A., 1966, Phytol metabolism in the bovine. Biochim. Biophys. Acta 125: 22–32.

    Article  PubMed  CAS  Google Scholar 

  • Radominska-Pandya, A. and Chen, G., 2002, Photoaffinity labeling of human retinoid X receptor beta (RXRbeta) with 9-cis-retinoic acid: identification of phytanic acid, docosahexaenoic acid, and lithocholic acid as ligands for RXRbeta. Biochemistry 41: 4883–4890.

    Article  PubMed  CAS  Google Scholar 

  • Schluter, A., Yubero, P., Giralt, M. and Villarroya, F., 2002, The chlorophyll-derived metabolite phytanic acid induces white adipocyte differentiation. Int. J. Obes. Relat. Metab. Disord. 26: 1277–1280.

    Article  CAS  Google Scholar 

  • Van den Branden, C, Vamecq, J., Wybo, I. and Roels, F., 1986, Phytol and peroxisome proliferation. Pediatr. Res. 20:411–415.

    Article  PubMed  CAS  Google Scholar 

  • Vanhooren, J.C., Fransen, M., de Bethune, B., Baumgart, E., Baes, M., Torrekens, S., Van Leuven, F., Mannaerts, G.P. and Van Veldhoven, P.P., 1996, Rat pristanoyl-CoA oxidase. cDNA cloning and recognition of its C- terminal (SQL) by the peroxisomal-targeting signal 1 receptor. Eur. J.Biochem. 239: 302–309.

    Article  PubMed  CAS  Google Scholar 

  • Verhoeven, N.M., Roe, D.S., Kok, R.M., Wanders, R.J.A., Jakobs, C. and Roe, C.R., 1998, Phytanic acid and pristanic acid are oxidized by sequential peroxisomal and mitochondrial reactions in cultured fibroblasts. J. Lipid Res. 39: 66–74.

    PubMed  CAS  Google Scholar 

  • Wolfram, C, Ellinghaus, P., Fobker, M., Seedorf, U., Assmann, G., Börchers, T. and Spener, F., 1999, Phytanic acid is ligand and transcriptional activator of murine liver fatty acid binding protein. J. Lipid Res. 40: 708–714.

    Google Scholar 

  • Woodyatt, N.J., Lambe, K.G., Myers, K.A., Tugwood, J.D. and Roberts, R.A. (1999), The peroxisome proliferator (PP) response element upstream of the human acyl CoA oxidase gene is inactive among a sample human population: significance for species differences in response to PPs. Carcinogenesis 20: 369–372.

    Article  PubMed  CAS  Google Scholar 

  • Zomer, A.W.M., van der Burg, B., Jansen, G.A., Wanders, R.J.A., Poll-The, B.T. and van der Saag, P.T., 2000a, Pristanic acid and phytanic acid: naturrally occurring ligands for the nuclear receptor peroxisome proliferator-activated receptor a. J. Lipid Res. 41: 1801–1807.

    CAS  Google Scholar 

  • Zomer, A.W.M., Jansen, G.A., van der Burg, B., Verhoeven, N.M., Jakobs, C, van der Saag, P.T. Wanders, R.J.A. and Poll-The, B.T., 2000b, Phytanoyl-CoA hydroxylase activity is induced by phytanic acid. Eur. J. Biochem. 267: 4063–4067.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2003 Springer Science+Business Media New York

About this paper

Cite this paper

Zomer, A.W., Van Der Saag, P.T., Poll-The, B.T. (2003). Phytanic and Pristanic Acid Are Naturally Occuring Ligands. In: Roels, F., Baes, M., De Bie, S. (eds) Peroxisomal Disorders and Regulation of Genes. Advances in Experimental Medicine and Biology, vol 544. Springer, Boston, MA. https://doi.org/10.1007/978-1-4419-9072-3_32

Download citation

  • DOI: https://doi.org/10.1007/978-1-4419-9072-3_32

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-4782-8

  • Online ISBN: 978-1-4419-9072-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics