Abstract
Cerulenin, an antifungal antibiotic produced by Cephalosporium caerulens, is a potent inhibitor of fatty acid synthase in various organisms, including Saccharomyces cerevisiae. The antibiotic inhibits the enzyme by binding covalently to the active center cysteine of the condensing enzyme domain. We isolated 12 cerulenin-resistant mutants of S. cerevisiae following treatment with ethyl methanesulfonate. The mechanism of cerulenin resistance in one of the mutants, KNCR-1, was studied. Growth of the mutant was over 20 times more resistant to cerulenin than that of the wild-type strain. Tetrad analysis suggested that all mutants mapped at the same locus, FAS2, the gene encoding the alpha subunit of the fatty acid synthase. The isolated fatty acid synthase, purified from the mutant KNCR-1, was highly resistant to cerulenin. The cerulenin concentration causing 50% inhibition (IC50) of the enzyme activity was measured to be 400 microM, whereas the IC50 value was 15 microM for the enzyme isolated from the wild-type strain, indicating a 30-fold increase in resistance to cerulenin. The FAS2 gene was cloned from the mutant. Sequence replacement experiments suggested that an 0.8 kb EcoRV-HindIII fragment closely correlated with cerulenin resistance. Sequence analysis of this region revealed that the GGT codon encoding Gly-1257 of the FAS2 gene was altered to AGT in the mutant, resulting in the codon for Ser. Furthermore, a recombinant FAS2 gene, in which the 0.8 Kb EcoRV-HindIII fragment of the wild-type FAS2 gene was replaced with the same region from the mutant, when introduced into FAS2-defective S. cerevisiae complemented the FAS2 phenotype and showed cerulenin resistance.(ABSTRACT TRUNCATED AT 250 WORDS)
MeSH Terms
Amino Acid Sequence
Base Sequence
Cerulenin/pharmacology
DNA, Fungal
Drug Resistance, Microbial/genetics
Fatty Acid Synthases/genetics
Genes, Fungal
Molecular Sequence Data
Mutation
Plasmids
Saccharomyces cerevisiae/drug effects,enzymology,genetics
Chemicals
DNA, Fungal
Cerulenin
Fatty Acid Synthases
Authors & Affiliations
6 authors, click to expand affiliations / ORCID
Inokoshi J
Research Center for Biological Function, Kitasato Institute, Tokyo, Japan.
Tomoda H
Hashimoto H
Watanabe A
Takeshima H
Omura S
References (28)
28 references, click to expand
-
Inhibition of the biosynthesis of leucomycin, a macrolide antibiotic, by cerulenin.
J Biochem. 1974 Jan;75(1):193-5
PMID: 4826539
-
Primary structure of a cerulenin-binding beta-ketoacyl-[acyl carrier protein] synthase from barley chloroplasts.
Proc Natl Acad Sci U S A. 1991 May 15;88(10):4114-8
PMID: 2034657
-
Studies on transformation of Escherichia coli with plasmids.
J Mol Biol. 1983 Jun 5;166(4):557-80
PMID: 6345791
-
Mechanism of action of cerulenin on fatty acid synthetase. Effect of cerulenin on iodoacetamide-induced malonyl-CoA decarboxylase activity.
J Biochem. 1982 Jul;92(1):7-12
PMID: 6749834
-
A ten-minute DNA preparation from yeast efficiently releases autonomous plasmids for transformation of Escherichia coli.
Gene. 1987;57(2-3):267-72
PMID: 3319781
-
On the structure of fatty acid synthetase of yeast.
Eur J Biochem. 1980 Dec;112(3):431-42
PMID: 7007046
-
The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis.
Bacteriol Rev. 1976 Sep;40(3):681-97
PMID: 791237
-
Studies on cerulenin, 3. Isolation and physico-chemical properties of cerulenin.
J Antibiot (Tokyo). 1967 Nov;20(6):344-8
PMID: 5631576
-
Binding site of cerulenin in fatty acid synthetase.
J Biochem. 1989 May;105(5):751-5
PMID: 2666407
-
Isolation and sequence analysis of the fatty acid synthetase FAS2 gene from Penicillium patulum.
Eur J Biochem. 1988 Oct 15;177(1):69-79
PMID: 3053172
-
Factors affecting the isolation of CCC DNA from Streptomyces lividans and Escherichia coli.
Plasmid. 1984 Jul;12(1):19-36
PMID: 6387733
-
Sequence of a yeast DNA fragment containing a chromosomal replicator and the TRP1 gene.
Gene. 1980 Jul;10(2):157-66
PMID: 6248420
-
Primary structure of the multifunctional alpha subunit protein of yeast fatty acid synthase derived from FAS2 gene sequence.
J Biol Chem. 1988 Sep 5;263(25):12315-25
PMID: 2900835
-
Centromeric DNA from Saccharomyces cerevisiae.
J Mol Biol. 1982 Jun 25;158(2):157-90
PMID: 6750136
-
Effect of side-chain structure on inhibition of yeast fatty-acid synthase by cerulenin analogues.
Eur J Biochem. 1993 Jan 15;211(1-2):111-5
PMID: 8425521
-
DNA sequencing with chain-terminating inhibitors.
Proc Natl Acad Sci U S A. 1977 Dec;74(12):5463-7
PMID: 271968
-
beta-Ketoacyl-ACP synthase I of Escherichia coli: nucleotide sequence of the fabB gene and identification of the cerulenin binding residue.
Carlsberg Res Commun. 1988;53(6):357-70
PMID: 3076376
-
Complementation of mutations and nucleotide sequence of FAS1 gene encoding beta subunit of yeast fatty acid synthase.
J Biol Chem. 1987 Mar 25;262(9):4231-40
PMID: 3031066
-
Inhibition of fatty acid synthesis by the antibiotic cerulenin. Specific inactivation of beta-ketoacyl-acyl carrier protein synthetase.
Biochim Biophys Acta. 1973 Nov 29;326(2):155-6
PMID: 4587717
-
Cerulenin resistance in a cerulenin-producing fungus. III. Studies on active-site peptides of fatty acid synthetase from Cephalosporium caerulens.
J Biochem. 1984 Jun;95(6):1712-23
PMID: 6540772
-
The pentafunctional FAS1 gene of yeast: its nucleotide sequence and order of the catalytic domains.
Mol Gen Genet. 1986 Jun;203(3):479-86
PMID: 3528750
-
Cerulenin resistance in a cerulenin-producing fungus. Isolation of cerulenin insensitive fatty acid synthetase.
Arch Biochem Biophys. 1979 Oct 1;197(1):30-5
PMID: 575612
-
Improved M13 phage cloning vectors and host strains: nucleotide sequences of the M13mp18 and pUC19 vectors.
Gene. 1985;33(1):103-19
PMID: 2985470
-
Cerulenin resistance in a cerulenin-producing fungus. II. Characterization of fatty acid synthetase from Cephalosporium caerulens.
J Biochem. 1984 Jun;95(6):1705-12
PMID: 6381475
-
Conformational parameters for amino acids in helical, beta-sheet, and random coil regions calculated from proteins.
Biochemistry. 1974 Jan 15;13(2):211-22
PMID: 4358939
-
Studies on the yeast fatty acid synthetase. Subunit composition and structural organization of a large multifunctional enzyme complex.
J Biol Chem. 1978 Jun 25;253(12):4464-75
PMID: 350874
-
Sterile host yeasts (SHY): a eukaryotic system of biological containment for recombinant DNA experiments.
Gene. 1979 Dec;8(1):17-24
PMID: 395030
-
Transformation of intact yeast cells treated with alkali cations.
J Bacteriol. 1983 Jan;153(1):163-8
PMID: 6336730