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麦角生物碱的生物合成途径。

Biosynthetic pathways of ergot alkaloids.

作者信息

Gerhards Nina, Neubauer Lisa, Tudzynski Paul, Li Shu-Ming

机构信息

Philipps-Universität Marburg, Institut für Pharmazeutische Biologie und Biotechnologie, Deutschhausstrasse 17A, D-35037 Marburg, Germany.

Institut für Biologie und Biotechnologie der Pflanzen, Westfälische Wilhelms Universität Münster, Schlossplatz 8, D-48143 Münster, Germany.

出版信息

Toxins (Basel). 2014 Dec 10;6(12):3281-95. doi: 10.3390/toxins6123281.

DOI:10.3390/toxins6123281
PMID:25513893
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4280535/
Abstract

Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes.

摘要

麦角生物碱是属于吲哚生物碱的含氮天然产物。最著名的生产者是子囊菌门的真菌,例如麦角菌属、香柱菌属、青霉属和曲霉属的物种。根据其结构,麦角生物碱可分为三类:棒麦角碱类、麦角酸酰胺类和肽类(麦角肽碱类)。它们都共享最初的生物合成步骤,这些步骤导致四环麦角灵环系统的形成(最简单的三环化合物:棒麦角黄素除外)。特定酶对麦角灵环的不同修饰产生了大量具有生物活性的天然产物,这些产物被用作药物或其前体。从20世纪50年代到近年来,大多数生物合成途径已被阐明。通过基因组挖掘已鉴定出几种麦角生物碱生产者的基因簇,并且其中许多基因的功能已通过敲除实验或对过量产生的酶进行生化研究得到证实。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/23f33716c8d4/toxins-06-03281-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/d0ebdc9c917b/toxins-06-03281-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/87dde840ea58/toxins-06-03281-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/08565cfdaed0/toxins-06-03281-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/4800f41a92e6/toxins-06-03281-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/4fa87d0e91f3/toxins-06-03281-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/e1bab75b7ac1/toxins-06-03281-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/23f33716c8d4/toxins-06-03281-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/d0ebdc9c917b/toxins-06-03281-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/87dde840ea58/toxins-06-03281-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/08565cfdaed0/toxins-06-03281-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/4800f41a92e6/toxins-06-03281-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/4fa87d0e91f3/toxins-06-03281-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/e1bab75b7ac1/toxins-06-03281-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61cb/4280535/23f33716c8d4/toxins-06-03281-g007.jpg

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本文引用的文献

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2
The important ergot alkaloid intermediate chanoclavine-I produced in the yeast Saccharomyces cerevisiae by the combined action of EasC and EasE from Aspergillus japonicus.重要的麦角生物碱中间体棒麦角缬氨酸-I由来自日本曲霉的EasC和EasE共同作用在酿酒酵母中产生。
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3
Heterologous expression of lysergic acid and novel ergot alkaloids in Aspergillus fumigatus.
两个卫星基因簇增强了 Aspergillus 中麦角生物碱生物合成能力。
Appl Environ Microbiol. 2023 Aug 30;89(8):e0079323. doi: 10.1128/aem.00793-23. Epub 2023 Jul 11.
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Fungal P450 Deconstructs the 2,5-Diazabicyclo[2.2.2]octane Ring to the Complete Biosynthesis of 21-Citrinadin A.真菌 P450 拆环 2,5-二氮杂双环[2.2.2]辛烷 生成 21-西替利定 A 的全生物合成途径。
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Derivation of the multiply-branched ergot alkaloid pathway of fungi.真菌中多分枝麦角生物碱途径的推导。
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