Hostname: page-component-8448b6f56d-cfpbc Total loading time: 0 Render date: 2024-04-15T14:08:10.245Z Has data issue: false hasContentIssue false
  • English
  • Français

Oxyphytosterols are present in plasma of healthy human subjects

Published online by Cambridge University Press:  09 March 2007

André Grandgirard ,
Lucy Martine ,
Luc Demaison ,
Catherine Cordelet ,
Corinne Joffre ,
Olivier Berdeaux  and
Etienne Semon
André Grandgirard*
Affiliation:
Unité de Nutrition Lipidique, INRA, 17 rue Sully, BP 86510, 21065, DIJON cedex, France
Lucy Martine
Affiliation:
Unité de Nutrition Lipidique, INRA, 17 rue Sully, BP 86510, 21065, DIJON cedex, France
Luc Demaison
Affiliation:
Unité de Nutrition Lipidique, INRA, 17 rue Sully, BP 86510, 21065, DIJON cedex, France
Catherine Cordelet
Affiliation:
Unité de Nutrition Lipidique, INRA, 17 rue Sully, BP 86510, 21065, DIJON cedex, France
Corinne Joffre
Affiliation:
Unité de Nutrition Lipidique, INRA, 17 rue Sully, BP 86510, 21065, DIJON cedex, France
Olivier Berdeaux
Affiliation:
Unité de Nutrition Lipidique, INRA, 17 rue Sully, BP 86510, 21065, DIJON cedex, France
Etienne Semon
Affiliation:
Laboratoire de Recherches sur les Arômes, INRA, Dijon, France
*
*Corresponding author: Dr André Grandgirard, fax +33 3 80 69 32 23, email grandgi@dijon.inra.fr
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

The oxidised derivatives of phytosterols (oxyphytosterols) were identified in plasma samples from thirteen healthy human volunteers, using MS. All the samples contained noticeable quantities of (24R)-5β,6β-epoxy-24-ethylcholestan-3β-ol (β-epoxysitostanol) and (24R)-ethylcholestan-3β,5α,6β-triol (sitostanetriol) and also trace levels of (24R)-5α,6α-epoxy-24-ethylcholestan-3β-ol (α-epoxysitostanol), (24R)-methylcholestan-3β,5α,6β-triol (campestanetriol) and (24R)-ethylch olest-5-en-3β-ol-7-one(7-ketositosterol). The amounts of these oxyphytosterols in plasma varied from 4·8 to 57·2 ng/ml. There are two possibilities concerning the origin of these compounds. First, they could come from the small amounts of oxyphytosterols in food. Second, they could originate from the in vivo oxidation of phytosterols in plasma. Very few data actually exist concerning these compounds. Their identification in human samples suggests that further research is necessary in this field.

Keywords

OxyphytosterolsPhytosterolsHuman plasmaMass spectrometry
Type
Research Article
Information
British Journal of Nutrition , Volume 91 , Issue 1 , January 2004 , pp. 101 - 106
Copyright
Copyright © The Nutrition Society 2004

References

Addis, PB (1986) Occurrence of lipid oxidation products in foods. Food Chem Toxicol 24, 1021–1030.CrossRefGoogle ScholarPubMed
Aringer, L & Eneroth, P (1974) Formation and metabolism in vitro of 5,6-epoxides of cholesterol and beta-sitosterol. J Lipid Res 15, 389–398.CrossRefGoogle ScholarPubMed
Breuer, O & Bjorkhem, I (1995) Use of an 18-O(2) inhalation technique and mass isotopomer distribution analysis to study oxygenation of cholesterol in rat - evidence for in vivo formation of 7-oxo-, 7 beta-hydroxy-, 24-hydroxy-, and 25-hydroxycholesterol. J Biol Chem 270, 20278–20284.CrossRefGoogle Scholar
Brooks, CJW, McKenna, RM, Cole, WJ, MacLachlan, J & Lawrie, TDV (1983) "Profile" analysis of oxygenated sterols in plasma and serum. Biochem Soc Trans 11, 700–701.CrossRefGoogle Scholar
Daly, GG, Finocchiaro, ET & Richardson, T (1983) Characterization of some oxidation products of beta-sitosterol. J Agric Food Chem 31, 46–50.CrossRefGoogle Scholar
Diczfalusy, U (2002) Origin and content of cholesterol oxidation products in biological samples. In Cholesterol and Phytosterol Oxidation Products. Analysis, Occurrence, and Biological Effects, pp. 217–240 [Guardiola, PC, Dutta, PC, R, R, Savage, GP, editors]. Champaign, IL: AOCS Press.Google Scholar
Dutta, PC (1997) Studies on phytosterol oxides. 2 Content in some vegetable oils and in French fries prepared in these oils. J Am Oil Chem Soc 74, 659–666.CrossRefGoogle Scholar
Dutta, PC & Appelqvist, LA (1997) Studies on phytosterol oxides 1 Effect of storage on the content in potato chips prepared in different vegetable oils. J Am Oil Chem Soc 74, 647–657.CrossRefGoogle Scholar
Dutta, PC & Savage, GP (2002) Formation and content of phytosterol oxidation products in foods. In Cholesterol and Phytosterol Oxidation Products. Analysis, Occurrence, and Biological Effects, pp. 319–334 [Guardiola, PC, Dutta, PC, Codony, R, Savage, GP, editors]. Champaign, IL: AOCS Press.Google Scholar
Dzeletovic, S, Breuer, O, Lund, E & Diczfalusy, U (1995) Determination of cholesterol oxidation products in human plasma by isotope dilution mass spectrometry. Anal Biochem 225, 73–80.CrossRefGoogle ScholarPubMed
Emanuel, HA, Hassel, CA, Addis, PB, Bergmann, SD & Zavoral, JH (1991) Plasma cholesterol oxidation products (oxysterols) in human subjects fed a meal rich in oxysterols. J Food Sci 56, 843–847.CrossRefGoogle Scholar
Garcia-Cruset, S, Carpenter, KLH, Codony, R & Guardiola, F (2002) Cholesterol oxidation products and atherosclerosis. In Cholesterol and Phytosterol Oxidation Products. Analysis, Occurrence, and Biological Effects, pp. 241–277 [Guardiola, PC, Dutta, PC, Codony, R, Savage, GP, editors]. Champaign, IL: AOCS Press.Google Scholar
Giacometti, J (2001) Determination of aliphatic alcohols, squalene, alpha-tocopherol and sterols in olive oils: direct method involving gas chromatography of the unsaponifiable fraction following silylation. Analyst 126, 472–475.CrossRefGoogle ScholarPubMed
Grandgirard, A, Sergiel, JP, Nour, M, Demaison-Meloche, J & Ginies, C (1999) Lymphatic absorption of phytosterol oxides in rats. Lipids 34, 563–570.CrossRefGoogle ScholarPubMed
Guardiola, F, Codony, R, Addis, PB, Rafecas, M & Boatella, J (1996) Biological effects of oxysterols: current status. Food Chem Toxicol 34, 193–211.CrossRefGoogle ScholarPubMed
Jacobson, MS, Price, MG, Shamoo, AE & Heald, FP (1985) Atherogenesis in White Carneau pigeons: effects of low-level cholestane-triol feeding. Atherosclerosis 57, 209–217.CrossRefGoogle ScholarPubMed
Janowski, BA, Willy, PJ, Devi, TR, Falck, JR & Mangelsdorf, DJ (1996) An oxysterol signalling pathway mediated by the nuclear receptor LXR alpha. Nature 383, 728–731.CrossRefGoogle ScholarPubMed
Kempen, HJM, De Knijff, P, Boomsma, DI, Van, D, Voort, HAGevers Leuven, JA & Havekes, L (1991) Plasma levels of lathosterol and phytosterols in relation to age, sex, anthropometric parameters, plasma lipids, and apolipoprotein-E phenotype, in 160 Dutch families. Metab Clin Exp 40, 604–611.CrossRefGoogle ScholarPubMed
Lai, SM, Gray, JI & Zabik, ME (1995) Evaluation of solid phase extraction and gas chromatography for determination of cholesterol oxidation products in spray-dried whole egg. J Agric Food Chem 43, 1122–1126.CrossRefGoogle Scholar
Lee, K, Herian, AM & Higley, NA (1985) Sterol oxidation products in french fries and in stored potato chips. J Food Protect 48, 158–161.CrossRefGoogle ScholarPubMed
Lyons, MA, Samman, S, Gatto, L & Brown, AJ (1999) Rapid hepatic metabolism of 7-ketocholesterol in vivo: implications for dietary oxysterols. J Lipid Res 40, 1846–1857.CrossRefGoogle ScholarPubMed
Matthias, D, Becker, CH, Godicke, W, Schmidt, R & Ponsold, K (1987) Action of cholestane-3beta,5alpha,6beta-triol on rats with particular reference to aorta. Atherosclerosis 63, 115–124.CrossRefGoogle Scholar
Moilanen, T & Nikkari, T (1981) The effect of storage on the fatty acid composition of human serum. Clin Chim Acta 114, 111–116.CrossRefGoogle ScholarPubMed
Nourooz-Zadeh, J & Appelqvist, LA (1992) Isolation and quantitative determination of sterol oxides in plant-based foods: soybean oil and wheat flour. J Am Oil Chem Soc 69, 288–293.CrossRefGoogle Scholar
Osada, K, Sasaki, E & Sugano, M (1994) Lymphatic absorption of oxidized cholesterol in rats. Lipids 29, 555–559.CrossRefGoogle ScholarPubMed
Park, PSW & Addis, PB (1989) Derivatization of 5a-cholestane-3b,5,6b-triol into trimethylsilyl ether sterol for GC analysis. J Am Oil Chem Soc 66, 1632–1634.CrossRefGoogle Scholar
Peng, SK, Hu, B & Morin, RJ (1991) Angiotoxicity and atherogenicity of cholesterol oxides. J Clin Lab Anal 5, 144–152.CrossRefGoogle ScholarPubMed
Peng, SK, Tham, P, Taylor, CB & Mikkelson, B (1979) Cytotoxicity of oxidation derivatives of cholesterol on cultured aortic smooth muscle cells and their effect on cholesterol biosynthesis. Am J Clin Nutr 32, 1033–1042.CrossRefGoogle ScholarPubMed
Piironen, V, Lindsay, DG, Miettinen, TA, Toivo, J & Lampi, AM (2000) Plant sterols: biosynthesis, biological function and their importance to human nutrition. J Sci Food Agric 80, 939–966.3.0.CO;2-C>CrossRefGoogle Scholar
Plat, J, Brzezinka, H, Lutjohann, D, Mensink, RP & von Bergmann, K (2001) Oxidized plant sterols in human serum and lipid infusions as measured by combined gas-liquid chromatography-mass spectrometry. J Lipid Res 42, 2030–2038.CrossRefGoogle ScholarPubMed
Wasilchuk, BALe Quesne, PW & Vouros, P (1992) Monitoring cholesterol autoxidation processes using multideuteriated cholesterol. Anal Chem 64, 1077–1087.CrossRefGoogle ScholarPubMed