TY - JOUR
T1 - The Structural Requirements of Sterols for Membrane Function in Saccharomyces cerevisiae
AU - Nes, W. David
AU - Janssen, Giselle G.
AU - Crumley, Farrist G.
AU - Kalinowska, Malgorzata
AU - Akihisa, Toshihiro
PY - 1993
Y1 - 1993
N2 - Cultures of Saccharomyces cerevisiae strain GL7 auxotrophic for sterol were incubated with a series of sterols and sterol-like molecules (tetracyclic and pentacyclic triterpenoids) in order to determine the structural requirements of sterols for bulk membrane function. For growth support, the 3β-OH group could not be replaced by H, OMe, OBu, NH2, NHOH, OAc, keto, or 3α-OH. A methyl group at C-14 was neither deleterious nor essential for activity. Removal of the C-4 geminal methyl group was obligatory for activity. Thus, no sterol-like triterpenoid supported growth (e.g., tetrahymanol, lanosterol, and cycloartenol). Growth support required a sterol with the longest methylene segment extending from C-20 not to exceed six contiguous C-atoms and the stereochemistry must be C-20 R. No significance could be attributed to branching at C-20 (i.e., to C-21), C-24 (when alkylated), or C-25 (regarding the isopropyl group). Double bonds in the nucleus were not essential for activity since cholestanol supported growth. In several incubations, the addition of trace levels of dietary ergosterol (0.5 μg/ml) to the medium was necessary to promote growth and transformation of the bulk sterol to a membrane competent sterol(s).
AB - Cultures of Saccharomyces cerevisiae strain GL7 auxotrophic for sterol were incubated with a series of sterols and sterol-like molecules (tetracyclic and pentacyclic triterpenoids) in order to determine the structural requirements of sterols for bulk membrane function. For growth support, the 3β-OH group could not be replaced by H, OMe, OBu, NH2, NHOH, OAc, keto, or 3α-OH. A methyl group at C-14 was neither deleterious nor essential for activity. Removal of the C-4 geminal methyl group was obligatory for activity. Thus, no sterol-like triterpenoid supported growth (e.g., tetrahymanol, lanosterol, and cycloartenol). Growth support required a sterol with the longest methylene segment extending from C-20 not to exceed six contiguous C-atoms and the stereochemistry must be C-20 R. No significance could be attributed to branching at C-20 (i.e., to C-21), C-24 (when alkylated), or C-25 (regarding the isopropyl group). Double bonds in the nucleus were not essential for activity since cholestanol supported growth. In several incubations, the addition of trace levels of dietary ergosterol (0.5 μg/ml) to the medium was necessary to promote growth and transformation of the bulk sterol to a membrane competent sterol(s).
UR - http://www.scopus.com/inward/record.url?scp=0027205567&partnerID=8YFLogxK
U2 - 10.1006/abbi.1993.1100
DO - 10.1006/abbi.1993.1100
M3 - Article
C2 - 8434952
AN - SCOPUS:0027205567
SN - 0003-9861
VL - 300
SP - 724
EP - 733
JO - Archives of Biochemistry and Biophysics
JF - Archives of Biochemistry and Biophysics
IS - 2
ER -