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Identification of metabolites of phytosterols in rat feces using GC/MS

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  • Pharmacology, Toxicology & Pharmaceutics
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Abstract

β-Sitosterol, campesterol and stigmasterol have been known to the phytosterols the most frequently found in plants. Metabolism of phytosterols was investigated using rat feces and liver microsomes. Feces were collected after phytosterols (a well characterized mixture of β-sitosterol 40%, campesterol 30% and dihydrobrasicasterol) were administered orally (0.5 g/kg) to rats. Metabolites of phytosterols were identified using GC/MS. Three peaks were eluted at 12.47, 12.65, 12.87 min and had characteristic molecular ionsm/z 428, 430, 432, respectively. Three fecal metabolites were identified as androstadienedione, androstenedione, and androstanedione. No metabolites could be detected in the rat liver microsomal reaction mixture. The results suggest that the metabolites of phytosterols in rat feces are formed by oxidation at 3- position, saturation at 5- and 6- position, and 17- side chain cleavage in the rat large intestine.

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References

  • Aringer, L. and Eneroth, P., Studies on the formation of C7-oxygenated cholesterol and beta- sitosterol metabolites in cell-free preparations of rat liver.J. Lipid Res., 14, 563–572 (1973).

    PubMed  CAS  Google Scholar 

  • Aringer, L. and Eneroth, P., Formation and metabolism in vitro of 5,6-epoxides of cholesterol and beta-sitosterol.J. Lipid Res., 15, 389–398 (1974).

    PubMed  CAS  Google Scholar 

  • Baker, V. A., Hepburn, P. A., Kennedy, S. J., Jones, P. A., Lea, L. J., Sumpter, J. P. and Ashby, J., Safety evaluation of phytosterol esters. Part 1. Assessment of oestrogenicity using a combination of in vivo and in vitro assays.Food Chem. Toxicol., 37, 13–22 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Bartram, H. P., Gostner, A., Kelber, E., Dusel, G., Weimer, A., Scheppach, W. and Kasper, H., Effects of fish oil and fecal bacterial enzymes and steroid excretion in healthy volunteers: implications for colon cancer prevention.Nutrition and Cancer., 25, 71–78 (1996).

    PubMed  CAS  Google Scholar 

  • Bryant, M. B., Burkey, L.A., Cultural methods and some characteristics of the more numerous groups of bacterial in the bovine rumen.J. Diary Sci., 36, 205–17 (1953).

    Article  Google Scholar 

  • Djerassi, C., The manufacture of steroidal contraceptives: technical versus political aspects.Proc. R. Soc. Lond B Biol. Sci., 195, 175–186 (1976).

    Article  PubMed  CAS  Google Scholar 

  • El Samannoudy, F. A., Shareha, A. M., Ghannudi, S. A., Gillaly, G. A. and El Mougy, S. A., Adverse effects of phytoestrogens-7. Effect of beta-sitosterol treatment on follicular development, ovarian structure and uterus in the immature female sheep.Cell Mol. Biol., 26, 255–266 (1980).

    CAS  Google Scholar 

  • Elghamry, M. I. and Hansel, R., Activity and isolated phytoestrogen of shrub palmetto fruits (Serenoa repens Small), a new estrogenic plant.Experientia., 25, 828–829 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Eyssen, H. and Caenepeel, P. H., Metabolism of fats, bile acids and steroids. I.R. Rownland, Academic Press. London, 1988.

    Google Scholar 

  • Funken, G. S. and Johnsons, R. A., Chemical oxidations with microorganisms: Chap 6- Microbiological Baeyervilliger Oxidation. Dekker, New York, 1972.

    Google Scholar 

  • Guengerich, F. P., Martin, M. V., Beaune, P. H., Kremers, P., Wolff, T., and Waxman, D. J., Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism.J. Biol. Chem., 261, 5051–5060 (1986).

    PubMed  CAS  Google Scholar 

  • Kieslich, K., Production of drugs by microbial biosynthesis and biotransformation. Possibilities, limits and future developments (1st communication).Arzneimittelforschung., 36, 774–778 (1986).

    PubMed  CAS  Google Scholar 

  • Ling, W. H. and Jones, P. J., Dietary phytosterols: a review of metabolism, benefits and side effects.Life Sci., 57, 195–206 (1995).

    Article  PubMed  CAS  Google Scholar 

  • Lorwy, O. H., Rosebrough, N. J., Farr, A. L. and Randall, R. J., Protein measurement with the Folin phenol reagent.J. Biol. Chem., 193, 265–275 (1951).

    Google Scholar 

  • Malini, T. and Vanithakumari, G., Antifertility effects of betasitosterol in male albino rats.J. Ethnopharmacol., 35, 149–153 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Mattson, F. H., Grundy, S. M., and Crouse, J. R., Optimizing the effect of plant sterols on cholesterol absorption in man.Am. J. Clin. Nutr., 35, 697–700 (1982).

    PubMed  CAS  Google Scholar 

  • Mellanen, P., Petanen, T., Lehtimaki, J., Makela, S., Bylund, G., Holmbom, B., Mannila, E., Oikari, A., and Santti, R., Wood-derived estrogens: studies in vitro with breast cancer cell lines and in vivo in trout.Toxicol. Appl. Pharmacol., 136, 381–388 (1996).

    Article  PubMed  CAS  Google Scholar 

  • Roy, P. K., Khan, A. W., and Basu, S. K., Transformation of sitosterol to androsta-1,4-diene-3,17-dione by immobilized Mycobacterium cells.Indian J. Biochem. Biophys., 28, 150–154 (1991).

    PubMed  CAS  Google Scholar 

  • Skrede, B., Bjorkhem, I., Bergesen, O., Kayden, H. J., and Skrede, S., The presence of 5 alpha-sitostanol in the serum of a patient with phytosterolemia, and its biosynthesis from plant steroids in rats with bile fistula.Biochim. Biophys. Acta., 836, 368–375 (1985).

    PubMed  CAS  Google Scholar 

  • Weststrate, J. A. and Meijer, G. W., Plant sterol-enriched margarines and reduction of plasma total- and LDL-cholesterol concentrations in normocholesterolaemic and mildly hypercholesterolaemic subjects.Eur. J. Clin. Nutr., 52, 334–343 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Weststrate, J. A., Ayesh, R., Bauer-Plank, C., and Drewitt, P. N., Safety evaluation of phytosterol esters. Part 4. Faecal concentrations of bile acids and neutral sterols in healthy normolipidaemic volunteers consuming a controlled diet either with or without a phytosterol ester- enriched margarine.Food. Chem. Toxicol., 37, 1063–1071 (1999).

    Article  PubMed  CAS  Google Scholar 

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Correspondence to Eun-Hee Park.

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Song, Y.S., Jin, C. & Park, EH. Identification of metabolites of phytosterols in rat feces using GC/MS. Arch Pharm Res 23, 599–604 (2000). https://doi.org/10.1007/BF02975248

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