Okaramine类生物碱——一类具有新颖杀虫机制的天然吲哚化合物

doi:10.14088/j.cnki.issn0439-8114.2019.23.020

湖北农业科学 ›› 2019, Vol. 58 ›› Issue (23): 86-90.doi: 10.14088/j.cnki.issn0439-8114.2019.23.020

Okaramine类生物碱——一类具有新颖杀虫机制的天然吲哚化合物

张遵霞, 王月莹, 张亚妮, 张志刚, 王开梅

湖北省生物农药工程研究中心,武汉 430064

收稿日期:2019-09-10 出版日期:2019-12-10 发布日期:2019-12-18
通讯作者: 王开梅,研究员,主要从事微生物农药资源研究与开发,（电话）027-59101996（电子信箱） kaimei.wang@nberc.com。
作者简介:张遵霞（1970-）,女,贵州湄潭人,助理研究员,主要从事微生物农药资源筛选评价研究,（电话）13971430512（电子信箱）1612336040@qq.com
基金资助:
国家重点研发计划项目（2017YFD0201205）; 湖北省农业科技创新中心创新团队项目（2019-620-000-001-27）

Okaramines：A group of natural insecticidal indole alkaloids with new mode of action

ZHANG Zun-xia, WANG Yue-yin, ZHANG Ya-ni, ZHANG Zhi-gang, WANG Kai-mei

Hubei Biopesticide Engineering Research Centre,Wuhan 430064,China

Received:2019-09-10 Online:2019-12-10 Published:2019-12-18

摘要/Abstract

摘要： Okaramine类生物碱是一类具有新颖杀虫机制的天然吲哚化合物,其产生菌主要包括青霉属（Penicillium spp.）、曲霉属（Aspergillus spp.）的某些真菌。目前已经发现20多个Okaramine类生物碱的衍生物,大部分Okaramine类生物碱衍生物具有杀虫活性,但其中以Okaramine B的杀虫活性最强。构效关系研究表明,Okaramine类生物碱的杀虫活性与氮杂环丁烷结构、氮杂环辛烷结构及C环上的甲氧基与杀虫活性高度相关。Okaramine类生物碱作用于昆虫神经元的谷氨酸门控氯离子通道。通过基因组挖掘、基因缺失突变、基因失活及异源表达,发现Okaramine类生物碱在真菌中的合成以色氨酸为起始单元,并在一系列成簇排列的生物合成基因的产物,包括非核糖体肽类合成酶、核黄素依赖单加氧酶、异戊烯转移酶、P450单加氧酶、α-酮戊二酸依赖双加氧酶及甲基转移酶等的作用下,合成了结构丰富多样的类似物。

关键词: Okaramine, 产生菌, 杀虫活性, 构效关系, 作用机制, 生物合成

Abstract: Okaramines, produced by some species of Penicillium spp. and Aspergillus spp., are a group of natural indole alkaloids with new mode of action of insecticidal activity. Up to now, more than 20 Okaramine analogues have been discovered, and most of them showed insecticidal activity with Bombyx mori as target insect. Of the Okaramine analogues, Okaramine B showed the highest insecticidal activity. The studies on structure-activity relationship showed that the azetidine and azocine rings and the methoxy group were highly related to the insecticidal activity. Okaramines can activate the glutamate gated chloride channel in insect neurons. The okaramines were biosynthesized in fungi with tryptoan as the starting unit. Okaramines were diversely biosynthesized through the catalysis by nonribosomal peptide synthase, flavin-dependent monooxygenase, prenyltransferase, P450 monooxygenase, α-ketoglutarate-dependent dioxygenase, and methyltransferase, etc. encoded by clustered biosynthetic genes as clarified through genome mining, gene deletion and inactivation, and heterogenous expression.

Key words: Okaramine, producing microorganism, insecticidal activity, structure-activity relationship, mode of action, biosynthesis

中图分类号:

Q599

张遵霞, 王月莹, 张亚妮, 张志刚, 王开梅. Okaramine类生物碱——一类具有新颖杀虫机制的天然吲哚化合物[J]. 湖北农业科学, 2019, 58(23): 86-90.

ZHANG Zun-xia, WANG Yue-yin, ZHANG Ya-ni, ZHANG Zhi-gang, WANG Kai-mei. Okaramines：A group of natural insecticidal indole alkaloids with new mode of action[J]. HUBEI AGRICULTURAL SCIENCES, 2019, 58(23): 86-90.

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Okaramine类生物碱——一类具有新颖杀虫机制的天然吲哚化合物

Okaramines：A group of natural insecticidal indole alkaloids with new mode of action

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