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Inhibition of C28 and C29 phytosterol metabolism by N, N-dimethyldodecanamine in the nematodecaenorhabditis elegans

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Lipids

Abstract

Effects on the metabolism of campesterol and stigmasterol inCaenorhabditis elegans were investigated using N,N-dimethyldodecanamine, a known inhibitor of growth, reproduction and the Δ24-sterol reductase of this nematode. 7-Dehydrocholesterol was the predominant sterol (51%) ofC. elegans grown in stigmasterol-supplemented media, whereas addition of 25 ppm amine resulted in a large decrease in the relative percentage of 7-dehydrocholesterol (23%) and the accumulation of a substantial proportion (33%) of Δ24-sterols (e.g., cholesta-5,7,24-trienol) and Δ22,24-sterols (e.g., cholesta-5,7,22, 24-tetraenol) but yielded no Δ22-sterols. Dealkylation of stigmasterol byC. elegans proceeded in the presence of the Δ22-bond; reduction of the Δ22-bond occurred prior to Δ24-reduction. Addition of 25 ppm amine to campesterol-supplemented media altered the sterol composition ofC. elegans by increasing the percentage of unmetabolized dietary campesterol from 39 to 60%, decreasing the percentage of 7-dehydrocholesterol from 26 to 12%, and causing the accumulation of several Δ24-sterols (6%).C. elegans also was shown to be capable of dealkylating a Δ24(28)-sterol as it converted 24-methyl-enecholesterol to mostly 7-dehydrocholesterol. The proposed role of 24-methylenecholesterol as an intermediate between campesterol and 7-dehydrocholesterol was supported by the results.

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Authors and Affiliations

  1. Department of Botany, University of Maryland, 20742, College Park, MD

    Ruben Lozano

  2. Insect Physiology Laboratory, ARS, USDA, Bldg. 467, BARC-East, 20705, Beltsville, MD

    William R. Lusby, David J. Chitwood, Malcolm J. Thompson & James A. Svoboda

Authors
  1. Ruben Lozano
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  2. William R. Lusby
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  3. David J. Chitwood
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  4. Malcolm J. Thompson
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  5. James A. Svoboda
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Lozano, R., Lusby, W.R., Chitwood, D.J. et al. Inhibition of C28 and C29 phytosterol metabolism by N, N-dimethyldodecanamine in the nematodecaenorhabditis elegans . Lipids 20, 158–166 (1985). https://doi.org/10.1007/BF02534248

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  • DOI: https://doi.org/10.1007/BF02534248

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