Differential effects of cholesterol and lanosterol on artificial membranes.
The effects of cholesterol, 4,4-dimethylcholesterol, and lanosterol (4,4',14alpha-trimethyl-delta8,24-cholestadiene-3beta-ol) on some properties of lecithin vesicles have been compared. Unlike cholesterol, lanosterol retards the exit of trapped glucose from phospholipid vesicles only slightly. The 13C nuclear magnetic resonance spectrum of cholesterol/lecithin vesicles shows no resonances attributable to the sterol. By contrast, several resonances attributable to quaternary carbon atoms or methyl groups are seen in the 13C nuclear magnetic resonance spectrum of lanosterol/lecithin vesicles, indicating that lanosterol is much less immobilized than cholesterol. Because the membrane behavior of 4,4-dimethylcholesterol is closely similar to that of cholesterol, it is concluded that the axial 14-alpha-methyl group is responsible for the lessened membrane immobilization of lanosterol. The results emphasize the importance of a planar sterol alpha-face for interaction with phospholipid acyl chains.
D002784:Cholesterol / Q000378:metabolism*; D005947:Glucose / Q000378:metabolism; D007810:Lanosterol / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008567:Membranes, Artificial; D010539:Permeability; D010713:Phosphatidylcholines / Q000378:metabolism
D008567:Membranes, Artificial; D010713:Phosphatidylcholines; D007810:Lanosterol; D002784:Cholesterol; D005947:Glucose
FEBS Lett. 1972 Jul 1;23(3):285-297
11946637
Proc Natl Acad Sci U S A. 1970 Oct;67(2):606-12
4943175
J Biol Chem. 1974 Aug 10;249(15):4872-8
4367809
Biochim Biophys Acta. 1972 Jun 20;266(3):561-83
4625141
Biochemistry. 1976 May 18;15(10):2121-4
1276127
Biochem Soc Trans. 1975;3(5):618-21
1193252
Proc Natl Acad Sci U S A. 1977 Mar;74(3):832-6
265577
Biochim Biophys Acta. 1970 Sep 8;210(3):486-9
5528599
J Am Oil Chem Soc. 1965 Jan;42:53-6
14228472
J Biol Chem. 1959 Oct;234:2578-82
13810427
Nat New Biol. 1972 May 10;237(71):42-4
4503742
Science. 1965 Oct 1;150(3692):19-28
5319508
Biochemistry. 1976 Mar 23;15(6):1271-6
130164
Biochim Biophys Acta. 1972 Jan 17;255(1):321-30
5011000
Lipids. 1974 Sep;9(9):645-50
4414692
Proc Natl Acad Sci U S A. 1975 Sep;72(9):3477-81
1059134
Nature. 1976 Dec 16;264(5587):646-8
1004606
Nature. 1975 Aug 14;256(5518):582-4
1165775
Nature. 1976 Jan 22;259(5540):242-4
1250357