The main biological cause of oxysterols is the oxidation of cholesterol. They differ from cholesterol by the presence of additional polar groups that are typically hydroxyl, keto, hydroperoxy, epoxy, or carboxyl moieties. Under typical conditions, oxysterol concentration is maintained at a very low and precisely regulated level, with an excess of cholesterol. Like cholesterol, many oxysterols are hydrophobic and hence confined to cell membranes. However, small chemical differences between the sterols can significantly affect how they interact with other membrane components, and this in turn can have a substantial effect on membrane properties. In this spirit, this review describes the biological importance and the roles of oxysterols in the human body. We focus primarily on the effect of oxysterols on lipid membranes, but we also consider other issues such as enzymatic and nonenzymatic synthesis processes of oxysterols as well as pathological conditions induced by oxysterols.

Department of Physics Tampere University of Technology P O Box 692 FI 33101 Tampere Finland

Department of Physics University of Helsinki P O Box 64 FI 00014 Helsinki Finland

Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic Flemingovo nám 2 16610 Prague 6 Czech Republic

J Heyrovský Institute of Physical Chemistry Academy of Sciences of the Czech Republic v v i Dolejskova 3 18223 Prague 8 Czech Republic

MEMPHYS Center for Biomembrane Physics University of Southern Denmark Odense Denmark

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$a Kulig, Waldemar $u Department of Physics, Tampere University of Technology, P. O. Box 692, FI-33101 Tampere, Finland; Department of Physics, University of Helsinki, P.O. Box 64, FI-00014 Helsinki, Finland. Electronic address: waldemar.kulig@tut.fi.

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$a Cholesterol oxidation products and their biological importance / $c W. Kulig, L. Cwiklik, P. Jurkiewicz, T. Rog, I. Vattulainen,

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$a The main biological cause of oxysterols is the oxidation of cholesterol. They differ from cholesterol by the presence of additional polar groups that are typically hydroxyl, keto, hydroperoxy, epoxy, or carboxyl moieties. Under typical conditions, oxysterol concentration is maintained at a very low and precisely regulated level, with an excess of cholesterol. Like cholesterol, many oxysterols are hydrophobic and hence confined to cell membranes. However, small chemical differences between the sterols can significantly affect how they interact with other membrane components, and this in turn can have a substantial effect on membrane properties. In this spirit, this review describes the biological importance and the roles of oxysterols in the human body. We focus primarily on the effect of oxysterols on lipid membranes, but we also consider other issues such as enzymatic and nonenzymatic synthesis processes of oxysterols as well as pathological conditions induced by oxysterols.

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$a Cwiklik, Lukasz $u J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v. v. i., Dolejskova 3, 18223 Prague 8, Czech Republic; Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic.

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$a Jurkiewicz, Piotr $u J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v. v. i., Dolejskova 3, 18223 Prague 8, Czech Republic.

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$a Rog, Tomasz $u Department of Physics, Tampere University of Technology, P. O. Box 692, FI-33101 Tampere, Finland; Department of Physics, University of Helsinki, P.O. Box 64, FI-00014 Helsinki, Finland.

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$a Vattulainen, Ilpo $u Department of Physics, Tampere University of Technology, P. O. Box 692, FI-33101 Tampere, Finland; Department of Physics, University of Helsinki, P.O. Box 64, FI-00014 Helsinki, Finland; MEMPHYS-Center for Biomembrane Physics, University of Southern Denmark, Odense, Denmark.

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