植物天然农药除虫菊酯的生物合成和应用研究进展

doi:10.12211/2096-8280.2021-068

合成生物学 ›› 2021, Vol. 2 ›› Issue (5): 751-763.DOI: 10.12211/2096-8280.2021-068

植物天然农药除虫菊酯的生物合成和应用研究进展

王凤姣¹^,², 徐海洋³, 闫建斌¹, 李伟¹

^1.中国农业科学院深圳农业基因组研究所，深圳市农业合成生物学重点实验室，广东深圳 518120
^2.华中农业大学植物科学技术学院，湖北武汉 430071
^3.重庆大学生命科学学院，重庆 400044

收稿日期:2021-06-21 修回日期:2021-08-17 出版日期:2021-11-19 发布日期:2021-11-19
通讯作者: 闫建斌,李伟
作者简介:王凤姣（1995—），女，博士研究生。研究方向为药用植物代谢。E-mail：fjwang@webmail.hzau.edu.cn
闫建斌（1979—），男，研究员，博士生导师。研究方向为植物分子生物学与合成生物学。E-mail：jianbinlab@caas.cn
李伟（1985—），男，研究员，博士生导师。研究方向为植物天然产物代谢。E-mail：liwei11@caas.cn
基金资助:
国家重点研发计划“合成生物学”重点专项(2020YFA0907900);中国农业科学院科技创新工程;中国农业科学院青年英才计划

Biosynthesis and application of pyrethrins: a natural pesticide from plants

Fengjiao WANG¹^,², Haiyang XU³, Jianbin YAN¹, Wei LI¹

^1.Shenzhen Key Laboratory of Agricultural Synthetic Biology，Agricultural Genomics Institute at Shenzhen，Chinese Academy of Agricultural Sciences，Shenzhen 518120，Guangdong，China
^2.College of Plant Science & Technology，Huazhong Agricultural University，Wuhan 430071，Hubei，China
^3.School of Life Sciences，Chongqing University，Chongqing 400044，China

Received:2021-06-21 Revised:2021-08-17 Online:2021-11-19 Published:2021-11-19
Contact: Jianbin YAN, Wei LI

摘要/Abstract

摘要：

利用生物底盘进行生物农药的绿色低耗能生产是合成生物学未来发展的重要方向。除虫菊酯是一种源自菊科植物除虫菊的天然高效杀虫剂，具有广谱和强力的杀虫和驱虫作用，相较于化学合成的类似物（拟除虫菊酯），对哺乳动物毒性小，无环境危害，是生物农药的最优选择之一，具有广阔的应用前景。天然除虫菊酯含有六种主要成分，由两种异型萜类酸配体和茉莉酸合成途径来源的三种醇配体缩合而成。本文总结了除虫菊酯的研究历程，重点介绍了其生物合成途径解析与生物制造等方面的进展，综述了近期解析的细胞色素P450等相关生物合成酶，并讨论除虫菊酯生产中涉及的调控、转运和底盘适配等尚待解决的问题。随着合成生物学技术的发展，利用已解析的代谢合成途径在微生物等底盘表达体系规模化生产除虫菊酯，能够为合成生物学生产绿色生物农药的科学理论与应用实践提供重要范例。

关键词: 合成生物学, 生物农药, 除虫菊酯, 合成途径, 异源表达

Abstract:

How to produce safe pesticides in chassis through energy-saving and environmentally friendly methods is one of challenges for synthetic biology. As a natural botanical insecticide, Pyrethrins derived from Pyrethrum (Tanacetum cinerariifolium) have good insecticidal and deworming activities with broad spectrum. Compared with chemical synthetic counterparts (pyrethroids), pyrethrins are less toxic and harmful to environment and human. These characteristics make pyrethrins not only one of the most ideal biological pesticides so far with broad applications and great potentials, but also candidates for their production via synthetic biology in the future. In this article, we review the discovery and chemical and biological characteristics of pyrethrins as well as the elucidation of their biosynthetic pathway by summarizing the catalytic enzymes identified recently including cytochrome P450s, dehydrogenases, methyltransferase and phosphatase etc. The synthesis process is mainly involved three parts: the synthesis of acid moieties, the synthesis of alcohol moieties and the condensation of acids and alcohols to esters. At present, the synthesis of acid moieties has been largely deciphered, and genes encoding key enzymes for acid-alcohol condensation have also been determined, but the synthesis of alcohol moieties needs to be explored further. With the identification of a large number of gene elements and the function of related genes in the plants, the rise of synthetic biology and the progress of synthetic technology, it is possible to express heterologous genes in chassis, integrate the pathway of heterologous synthesis to produce targeted products. This also makes it possible to express the metabolic pathway for the production of pyrethrins and their derivatives in suitable microbial chassis. Therefore, this review also focuses on challenges that need to be addressed in this regard, including regulation, transportation and chassis adaptation for more efficient production, and forecasts future development. We hope that more research progress could provide a solid scientific basis and application guidance for the biosynthesis of the green and effective pesticide, and finally realize the large-scale production of pyrethrins.

Key words: synthetic biology, biopesticide, pyrethrins, biosynthetic pathway, exogenous expression

中图分类号:

王凤姣, 徐海洋, 闫建斌, 李伟. 植物天然农药除虫菊酯的生物合成和应用研究进展[J]. 合成生物学, 2021, 2(5): 751-763.

Fengjiao WANG, Haiyang XU, Jianbin YAN, Wei LI. Biosynthesis and application of pyrethrins: a natural pesticide from plants[J]. Synthetic Biology Journal, 2021, 2(5): 751-763.

图/表 4

图1 除虫菊酯发展与应用年鉴

Fig. 1 Chronicles for the development and application of pyrethrins and their derivatives

图2 除虫菊酯不同组分的化学结构

Fig. 2 Chemical structures of pyrethrins

图3 除虫菊酯生物合成途径（除虫菊酯的配体合成起始于在除虫菊花器官的子房外壁腺体腺毛中，TcCDS催化2分子的DMAPP生成菊醇二磷酸，并在磷酸水解酶TcNudix1、脱氢酶TcADH2和TcALDH1的作用下生成菊酸，以及另外的氧化酶TcCHH和甲基转移酶TcCCMT的参与下形成第二菊酸；醇配体的前体茉莉酮通过茉莉酸的合成途径生成，而下游醇配体的合成由细胞色素P450酶TcJMH和TcPYS催化形成茉莉酮醇和除虫酮醇，瓜菊酮醇的合成途径尚不清楚；两种醇配体和三种酸配体在TcGLIP酶的催化下形成六种化合物。酸配体合成前期在质体中进行，后进入细胞质中进行进一步的氧化；茉莉酸的合成前体在质体中，后进入过氧化物酶体进行进一步反应，参与醇配体合成的细胞色素P450定位于内质网。分别定位于质体膜和过氧化物酶体膜的转运蛋白Jassy和CTS参与茉莉酸的合成，菊醇从质体中运出到细胞质和各配体从腺体腺毛运送到胞间是否需要转运蛋白还需要进一步验证）

Fig. 3 Pyrethrin biosynthesis pathway(Synthesis of pyrethrin moieties are originated in the ovary trichome, TcCDS catalyzes 2 DMAPP to generate chrysanthemyl diphosphate, which is further catalyzed by phosphatase TcNudix1, dehydrogenases TcADH2 and TcALDH1 to generate chrysanthemic acid, and two additional enzymes oxidase TcCHH and methyltransferase TcCCMT participate the reaction to form pyrethric acid. Alcohol moieties are generated from the jasmonic acid biosynthesis pathway, and the downstream biosynthesis are catalyzed by cytochrome P450 TcJMH and TcPYS for the biosynthesis of jasmolone and pyrethrolone, but the reactions for cinerolone biosynthesis are still unknown. One of two acid moieties and one of three alcohol moieties are condensed by the catalysis of TcGLIP to produce six different pyrethrins. Upstream steps of the acid moiety pathway are located within plastid, and then the intermediates are transferred to cytosol for further oxidation. The biosynthesis of jasmonic acid is in the plastid and peroxisome under the catalysis of the cytochrome P450s localized at endoplasmic reticulum. Two transporter proteins Jassy and CTS involved in the biosynthesis of jasmonic acid are localized at the membrane of plastid and peroxisome, respectively, and more transporters may exist for transferring chrysanthemol from plastid to cytosol and also for transferring moieties from trichome to apoplast, which need further validation)

表1 参与除虫菊酯生物合成途径的基因

Tab. 1 Genes involved in the pyrethrin biosynthesis pathway

基因	英文名称	中文名称	功能	文献
TcAOS	allene oxide synthase	丙二烯氧化物合酶	13-HPOT 12、13位C的氧化	[62-63]
TcAOC	allene oxide cyclase	丙二烯氧化物环化酶	13-EOT生成OPDA（12-氧-植物二烯酸）	[62]
TcOPR	3-oxo-2-(2-pentenyl)-cyclopentane-1- octanoic acid reductase 3	12-氧-植物二烯酸还原酶	OPDA 10、11位C还原	[59, 64]
TcJMH	jasmone hydroxylase	茉莉酮羟化酶	茉莉酮4位C羟基化反应	[12-13]
TcPYS	pyrethrolone synthase	除虫酮醇合成酶	茉莉酮醇戊烯基侧链去饱和	[12]
TcCDS	chrysanthemyl diphosphate synthase	菊醇二磷酸合酶	酸配体骨架合成	[22，56]
TcNudix1	nudix-family phosphatase	Nudix磷酸水解酶	CPP去磷酸化	[57]
TcADH2	alcohol dehydrogenase 2	醇脱氢酶	酸配体侧链氧化	[11, 16]
TcALDH1	aldehyde dehydrogenase 1	醛脱氢酶	酸配体侧链氧化	[11, 16]
TcCHH	chrysanthemol 10-hydroxylase	菊醇羟化酶	酸配体侧链羟化	[15]
TcCCMT	10-carboxychrysanthemic acid 10- methyltransferase	10-羧菊酸-10-甲基转移酶	10-羧基的甲基化	[15]
TcGLIP	GDSL lipase-like protein	GDSL脂肪酶	酸配体和醇配体缩合反应	[51]
TcLOX1	lipoxygenase1	脂氧合酶	亚麻酸13位C的氧化	[65]

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植物天然农药除虫菊酯的生物合成和应用研究进展

Biosynthesis and application of pyrethrins: a natural pesticide from plants

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