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Dealkylation of various 14-alkylsterols by the nematodeCaenorhabditis elegans

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Lipids

Abstract

The metabolism of 4 dietary 24-alkylsterols was investigated in the free-living nematodeCaenorhabditis elegans. The major unesterified sterols ofC. elegans in media supplemented with either campesterol, 22-dihydrobrassicasterol or stigmasterol included cholesta-5,7-dienol, cholesterol, cholest-7-enol, and 4α-methylcholest-8(14)-enol. Dietary stigmastanol yielded cholest-7-enol, cholestanol, cholest-8(14)-enol, and 4α-methylcholest-8(14)-enol as major unesterified sterols. Esterified sterols comprised less than 22% of the total sterol. Removal of a C-24 ethyl substituent of sterols was neither hindered by the presence of a Δ22-bond in the sterol side chain nor was it depedent on unsaturation in ring B of the steroid nucleus.C. elegans reduced a Δ22-bond during its metabolism of stigmasterol; it did not introduce a Δ22-bond during stigmastanol metabolism.C. elegans was capable of removing a C-24 methyl substituent regardless of its stereochemical orientation. Metabolic processes involving the steroid ring system of cholesterol (C-7 dehydrogenation, Δ5-bond, 4α-methylation, Δ8(14)-isomerization inC. elegans were not hindered by the presence of a 24-methyl group; various 24-methylsterol metabolites from campesterol were detected, mostly 24-methylcholesta-5,7-dienol. In contrast, no 24-ethylsterol metabolites from the dietary ethylsterols were found. More dietary 24-methylsterol remained unmetabolized than did dietary 24-ethylsterol. A 24α-ethyl group and a 24β-methyl group were dealkylated to a greater extent byC. elegans than was a 24α-methyl group, perhaps reflecting the substrate specificity of the dealkylation enzyme system, or suggesting different enzymes altogether.

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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 & 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. James A. Svoboda
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Lozano, R., Lusby, W.R., Chitwood, D.J. et al. Dealkylation of various 14-alkylsterols by the nematodeCaenorhabditis elegans . Lipids 20, 102–107 (1985). https://doi.org/10.1007/BF02534215

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  • DOI: https://doi.org/10.1007/BF02534215

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