Interaction of cholesterol with saturated phospholipids: role of the C(17) side chain.

Cholesterol and 5-androsten-3 beta-ol differ structurally only in the presence of an eight carbon side chain at the C(17) position in the former sterol. Both molecules decrease the main transition enthalpy change (delta H) in a series of phosphatidylcholines and phosphatidylethanolamines, of acyl chain length n, with the reduction being a linear function of sterol concentration (c). The sterol concentrations at which delta H = 0 bear a straight line relationship to n and are equivalent for both cholesterol and 5-androsten-3 beta-ol. In addition, both sterols give identical delta H versus c slopes. These results underscore the importance of acyl chain length in the cholesterol/phospholipid interaction and also indicate that the cholesterol C(17) side group is not an essential requirement for the capacity of the sterol to decrease the enthalpy change of the main transition.