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1
Inactivation of the polyketide synthase, 6-methylsalicylic acid synthase, by the specific modification of Cys-204 of the beta-ketoacyl synthase by the fungal mycotoxin cerulenin.真菌霉菌毒素浅蓝菌素通过对β-酮酰基合成酶的半胱氨酸-204进行特异性修饰，使聚酮合酶（6-甲基水杨酸合成酶）失活。
Biochem J. 1998 Mar 1;330 ( Pt 2)(Pt 2):933-7. doi: 10.1042/bj3300933.
2
Structural similarities between 6-methylsalicylic acid synthase from Penicillium patulum and vertebrate type I fatty acid synthase: evidence from thiol modification studies.展青霉素6-甲基水杨酸合酶与脊椎动物I型脂肪酸合酶的结构相似性：来自硫醇修饰研究的证据
Biochemistry. 1996 Sep 24;35(38):12267-74. doi: 10.1021/bi960422e.
3
Inhibition of 6-methylsalicyclic acid synthesis by the antibiotic cerulenin.抗生素浅蓝菌素对6-甲基水杨酸合成的抑制作用。
J Biochem. 1975 Dec;78(6):1149-52. doi: 10.1093/oxfordjournals.jbchem.a131010.
4
Investigation of the mechanism and steric course of the reaction catalyzed by 6-methylsalicylic acid synthase from Penicillium patulum using (R)-[1-13C;2-2H]- and (S)-[1-13C;2-2H]malonates.利用（R）-[1-¹³C；2-²H]-和（S）-[1-¹³C；2-²H]丙二酸对展青霉6-甲基水杨酸合酶催化反应的机制和立体过程进行研究。
Biochemistry. 1992 Sep 22;31(37):9107-16. doi: 10.1021/bi00152a055.
5
Purification and properties of 6-methylsalicylic acid synthase from Penicillium patulum.展青霉素6-甲基水杨酸合酶的纯化及性质
Biochem J. 1992 Dec 15;288 ( Pt 3)(Pt 3):839-46. doi: 10.1042/bj2880839.
6
Inhibition of unsaturated fatty acid synthesis in escherichia coli by the antibiotic cerulenin.抗生素浅蓝菌素对大肠杆菌中不饱和脂肪酸合成的抑制作用。
Biochemistry. 1978 Nov 28;17(24):5282-6. doi: 10.1021/bi00617a031.
7
Mechanism of action of cerulenin on fatty acid synthetase. Effect of cerulenin on iodoacetamide-induced malonyl-CoA decarboxylase activity.浅蓝菌素对脂肪酸合成酶的作用机制。浅蓝菌素对碘乙酰胺诱导的丙二酰辅酶A脱羧酶活性的影响。
J Biochem. 1982 Jul;92(1):7-12. doi: 10.1093/oxfordjournals.jbchem.a133933.
8
Role of reducing co-factor in cerulenin-insensitivity of 6-hydroxymellein synthase in carrot cell extract.
Biochem Mol Biol Int. 1998 Dec;46(6):1219-25. doi: 10.1080/15216549800204782.
9
Tolerance and specificity of recombinant 6-methylsalicyclic acid synthase.重组6-甲基水杨酸合酶的耐受性和特异性
Metab Eng. 1999 Apr;1(2):180-7. doi: 10.1006/mben.1999.0113.
10
Conversion of a beta-ketoacyl synthase to a malonyl decarboxylase by replacement of the active-site cysteine with glutamine.通过用谷氨酰胺取代活性位点的半胱氨酸，将β-酮酰基合成酶转化为丙二酸单酰脱羧酶。
Biochemistry. 1999 Sep 7;38(36):11643-50. doi: 10.1021/bi990993h.

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Interactions among filamentous fungi Aspergillus niger, Fusarium verticillioides and Clonostachys rosea: fungal biomass, diversity of secreted metabolites and fumonisin production.丝状真菌黑曲霉、轮枝镰孢菌和粉红粘帚霉之间的相互作用：真菌生物量、分泌代谢产物的多样性及伏马毒素的产生
BMC Microbiol. 2016 May 10;16:83. doi: 10.1186/s12866-016-0698-3.

本文引用的文献

1
A Cerulenin Insensitive Short Chain 3-Ketoacyl-Acyl Carrier Protein Synthase in Spinacia oleracea Leaves.菠菜叶片中一种对 Cerulenin 不敏感的短链 3-酮酰基-酰基辅酶 A 合成酶。
Plant Physiol. 1989 May;90(1):41-4. doi: 10.1104/pp.90.1.41.
2
Structural similarities between 6-methylsalicylic acid synthase from Penicillium patulum and vertebrate type I fatty acid synthase: evidence from thiol modification studies.展青霉素6-甲基水杨酸合酶与脊椎动物I型脂肪酸合酶的结构相似性：来自硫醇修饰研究的证据
Biochemistry. 1996 Sep 24;35(38):12267-74. doi: 10.1021/bi960422e.
3
Effect of side-chain structure on inhibition of yeast fatty-acid synthase by cerulenin analogues.侧链结构对浅蓝菌素类似物抑制酵母脂肪酸合酶的影响。
Eur J Biochem. 1993 Jan 15;211(1-2):111-5. doi: 10.1111/j.1432-1033.1993.tb19876.x.
4
Cerulenin-resistant mutants of Saccharomyces cerevisiae with an altered fatty acid synthase gene.脂肪酸合酶基因发生改变的酿酒酵母的浅蓝菌素抗性突变体。
Mol Gen Genet. 1994 Jul 8;244(1):90-6. doi: 10.1007/BF00280191.
5
The fabJ-encoded beta-ketoacyl-[acyl carrier protein] synthase IV from Escherichia coli is sensitive to cerulenin and specific for short-chain substrates.来自大肠杆菌的由fabJ编码的β-酮脂酰-[酰基载体蛋白] 合酶IV对浅蓝菌素敏感，且对短链底物具有特异性。
Proc Natl Acad Sci U S A. 1994 Nov 8;91(23):11027-31. doi: 10.1073/pnas.91.23.11027.
6
Cerulenin.浅蓝菌素
Methods Enzymol. 1981;72:520-32.
7
Cerulenin resistance in a cerulenin-producing fungus. III. Studies on active-site peptides of fatty acid synthetase from Cephalosporium caerulens.产浅蓝菌素真菌对浅蓝菌素的抗性。III. 产蓝头孢霉脂肪酸合成酶活性位点肽段的研究。
J Biochem. 1984 Jun;95(6):1712-23.
8
Animal fatty acid synthetase. A novel arrangement of the beta-ketoacyl synthetase sites comprising domains of the two subunits.动物脂肪酸合成酶。一种由两个亚基的结构域组成的β-酮酰基合成酶位点的新排列。
J Biol Chem. 1981 May 25;256(10):5128-33.
9
Conversion of 6-methylsalicylic acid into patulin by Penicillium urticae.荨麻青霉将6-甲基水杨酸转化为展青霉素。
Biochemistry. 1972 Mar 14;11(6):1102-7. doi: 10.1021/bi00756a025.
10
Inhibition of the biosynthesis of leucomycin, a macrolide antibiotic, by cerulenin.浅蓝菌素对大环内酯类抗生素柱晶白霉素生物合成的抑制作用。
J Biochem. 1974 Jan;75(1):193-5. doi: 10.1093/oxfordjournals.jbchem.a130375.

真菌霉菌毒素浅蓝菌素通过对β-酮酰基合成酶的半胱氨酸-204进行特异性修饰，使聚酮合酶（6-甲基水杨酸合成酶）失活。

Inactivation of the polyketide synthase, 6-methylsalicylic acid synthase, by the specific modification of Cys-204 of the beta-ketoacyl synthase by the fungal mycotoxin cerulenin.

作者信息

Child C J, Shoolingin-Jordan P M

机构信息

Department of Biochemistry and Molecular Biology, University of Southampton, Biomedical Sciences Building, Bassett Crescent East, Southampton SO16 7PX, U.K.

出版信息

Biochem J. 1998 Mar 1;330 ( Pt 2)(Pt 2):933-7. doi: 10.1042/bj3300933.

DOI:10.1042/bj3300933
PMID:9480912
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1219227/
Abstract

Cerulenin, [(2S,3R)-2,3-epoxy-4-oxo-7,10-dodecadienoylamide], a mycotoxin produced by Cephalosporium caerulens, irreversibly inactivated 6-methylsalicylic acid synthase from Penicillium patulum. A combination of radiolabelling studies with [3H]cerulenin, proteolytic and chemical digestion and N-terminal sequencing of labelled peptides indicated that the site of cerulenin modification is the highly reactive substrate-binding Cys-204 of the beta-ketoacyl synthase enzyme component. The thiol-specific inhibitor, iodoacetamide, was also shown to alkylate this residue. These findings are analogous with those observed for the reaction of cerulenin and iodoacetamide with type-I fatty acid synthases, demonstrating the close similarity between 6-methylsalicylic acid synthase and type-I fatty acid synthases.

摘要

浅蓝菌素，[(2S,3R)-2,3-环氧-4-氧代-7,10-十二碳二烯酰胺]，一种由蓝头孢霉产生的霉菌毒素，可使来自展青霉的6-甲基水杨酸合酶不可逆地失活。结合[3H]浅蓝菌素进行的放射性标记研究、蛋白水解和化学消化以及对标记肽段的N端测序表明，浅蓝菌素的修饰位点是β-酮酰基合酶酶组分中高反应性的底物结合半胱氨酸-204。巯基特异性抑制剂碘乙酰胺也被证明可使该残基烷基化。这些发现与浅蓝菌素和碘乙酰胺与I型脂肪酸合酶反应所观察到的结果相似，表明6-甲基水杨酸合酶与I型脂肪酸合酶之间存在密切的相似性。