真菌除草活性次级代谢产物研究进展

doi:10.19586/j.2095-2341.2022.0141

生物技术进展 ›› 2023, Vol. 13 ›› Issue (2): 181-194.DOI: 10.19586/j.2095-2341.2022.0141

• 进展评述 • 上一篇

真菌除草活性次级代谢产物研究进展

宋开南(), 谢李楠, 徐玉泉()

中国农业科学院生物技术研究所，北京 100081

收稿日期:2022-08-09 接受日期:2022-09-09 出版日期:2023-03-25 发布日期:2023-04-07
通讯作者: 徐玉泉
作者简介:宋开南 E-mail: S15850653283@126.com;
基金资助:
国家自然科学基金项目(22277137)

Progress of Fungal Secondary Metabolites with Potential Herbicidal Activity

Kainan SONG(), Linan XIE, Yuquan XU()

Biotechnology Research Institute，Chinese Academy of Agricultural Sciences，Beijing 100081，China

Received:2022-08-09 Accepted:2022-09-09 Online:2023-03-25 Published:2023-04-07
Contact: Yuquan XU

摘要/Abstract

摘要：

在农业生产中，化学除草剂的广泛使用虽然能确保作物产量，但也引发了许多环境问题，同时杂草对除草剂的抗性也会随之进化。因此，亟需开发安全性更强、作用机制更新颖的除草剂。真菌可以合成多种结构复杂的次级代谢产物，其中一些具有良好的除草活性。按照结构类型，综述了近十年国内外从真菌中分离的具有除草活性的次级代谢产物，并对真菌除草活性化合物的发展方向及应用前景进行了展望，以期为新型除草剂的研究与开发提供参考。

关键词: 真菌, 次级代谢产物, 除草活性, 结构多样性

Abstract:

In agricultural production， the widespread use of chemical herbicides， while securing the crop production， has caused many environmental problems and the evolution of herbicide resistance. Therefore， herbicides with more safety and novel modes of action are an urgent need. Fungi can produce a variety of bioactive secondary metabolites， some of which have strong herbicidal activity. In this review， some secondary metabolites isolated from fungi and their herbicidal activities in the past ten years were reviewed according to their structures. The prospect of development and application of fungal herbicidal compounds was discussed，which was expected to provide reference for the research and development of new herbicide.

Key words: fungi, secondary metabolites, herbicidal activity, structural diversity

中图分类号:

Q939.5

宋开南, 谢李楠, 徐玉泉. 真菌除草活性次级代谢产物研究进展[J]. 生物技术进展, 2023, 13(2): 181-194.

Kainan SONG, Linan XIE, Yuquan XU. Progress of Fungal Secondary Metabolites with Potential Herbicidal Activity[J]. Current Biotechnology, 2023, 13(2): 181-194.

图/表 9

图1 α-吡喃酮类化合物结构式注：1—gulypyrones A；2—alterpyrones A；3—alterpyrones B；4—6-hydroxymellein；5—5-methylmellein；6—radicinin；7—3-epi-radicinin；

Fig. 1 Structural formula of α-pyrone compounds8—radicinol；9—3-epi-radicinol；10—cochliotoxin；11—alternariol；12—altenuisol；13—alternariol-9-methyl ether；14—colletopyrone。

图2 γ-吡喃酮类化合物结构式注：15—chloromonilinic acid C；16—chloromonilinic acid D；17—chloromonilinic acid B；18—sterigmatocystin；19—dihydrosterigmatocystin。

Fig. 2 Structural formula οf γ-pyrone compounds

图3 螺二萘类化合物结构式注：20—palmarumycin EG1；21—palmarumycin CP19；22—palmarumycin CP17；23—palmarumycin CP2；24—preussomerin EG1；25—preussomerin EG2；26—preussomerin EG3；27—preussomerin EG4。

Fig. 3 Structural formula οf spirodinaphthalene compounds

图4 大环内酯类化合物结构式注：28—(15S)-de-O-methyllasiodiplodin；29—(14S,15S)-14-hydroxy-de-O-methyllasiodiplodin；30—zeaenol；31—O-demethylated-zeaenol；

Fig. 4 Structural formula οf macrolide compounds32—ascotoxin；33—stagonolide J；34—stagonolide K；35—stagonolide A；36—herbarumin I。

图5 呋喃并吡喃类与环己酮类化合物结构式注：37—chenopodolan A；38—chenopodolan B；39—chenopodolan C；40—chenopodolan D；41—coriloxine；42—2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione；43—fumiquinone B；44—blumenol A。

Fig. 5 Structural formula of furopyran and cyclohexanone compounds

图6 酚类化合物结构式注：45—lathyroxin A；46—lathyroxin B；47—pyriculin A；48—pyriculin B；49—(10S,11S)‐(-)‐epi-pyriculol；50—colletochlorin A；51—colletochlorin E；52—colletochlorin F；53—4-chloroorcinol；54—curvulin；55—agropyrenol；56—agropyrenal；57—4-hydroxybenzaldehyde；58—ethyl 2,4-dihydroxy-6-(8-hydroxyheptyl)benzoate。

Fig. 6 Structural formula of phenol compounds

图7 萜类化合物结构式注：59—phomentrioloxin；60—phomentrioloxins B；61—phomentrioloxins C；62—ophiobolin A；63—drophiobiolin A；64—drophiobiolin B；

Fig. 7 Structural formula of terpenoid compounds65—chenopodolin；66—chenopodolin B；67—harzianelactone A；68—harzianelactone B；69—harzianone A；70—harzianone B；71—harzianone C；72—harziane。

图8 含氮类化合物结构式注：73—holadysenterine；74—destruxin A；75—destruxin B；76—destruxin C；77—decalintetracid A；78—decalintetracid B；79—cichorine；

Fig. 8 Structural formula of nitrogen-containing compounds80—8-methoxycichorine；81—8-epi-methoxycichorine；82—N-(4-carboxybutyl)cichorine；83—brevianamide F；84—3-nitropropionic； 85—phaeosphaeride A；86—acuminatopyrone。

表1 具有除草活性的真菌次级代谢产物(2012—2022)

Table 1 Herbicidal secondary metabolites from fungi (2012—2022)

菌株种属	化合物在文中的编号	靶向杂草	参考文献
间座壳属D. gulyae	1, 60~61, 84	向日葵H.annuus 虞美人P. rhoeas 异株荨麻U. dioica	[8]
甘蓝链格孢A. brassicicola	2~3	稗草E. crusgalli 狗尾草S. viridis	[9]
藜茎点霉P. chenopodiicola	4, 37~39	苦苣菜S. oleraceus L. 法国山靛M. annua	[10]
甜樱间座壳D. eres	5	西伯利亚剪股颖A. stolonifera 浮萍L. pausicostata	[11]
澳大利亚平脐蠕孢C. australiensis	5~10	绿毛蒺藜草C. ciliaris 加利福尼亚马唐D. californica	[12]
链格孢属Alternaria sp.	11~12	狼尾草P. alopecuroides 紫花苜蓿M. sativa	[13]
希金斯刺盘孢C. higginsianum	14, 50~53	浮萍L. minor 小苞列当属P. ramose	[15]
澳大利亚平脐蠕孢C. australiensis	15~17	绿毛蒺藜草C. ciliaris	[16]
杂色曲霉菌A. versicolor	18~19	反枝苋A. retroflexus L. 刺苋A. spinosus 绿穗苋A. hybrid	[17]
E. gomezpompae	20~27	千穗谷A. hypochondriacus 稗草E. crusgalli	[19]
龙眼焦腐病菌L. theobromae GC~22	28~29, 58	升马唐D. ciliaris	[21]
C. crepinii	30~31	稗草E. crusgalli	[22]
Paraconiothyrium sp.	32	稗草E. crusgalli	[23]
壳多胞属S. cirsii	33~36	苣荬菜S. arvensis	[24]
藜茎点霉P. chenopodiicola	40, 66	繁缕S. media 大荨麻U. dioica 苣荬菜S.arvensis 墙草P. officinalis	[25]
炭角菌属X. feejeensis	41~43	红车轴草T. pratense 紫花苜蓿M. sativa 黍P. miliaceum 千穗谷A. hypochondriacus	[26]
镰刀菌属Fusarium sp.	44, 57, 86	旱雀麦B. tectorum	[27]
壳二孢属A. lentis var. lathyri	45~46	列当属P. ramosa	[30]
梨孢属P.grisea	47~49	绿毛蒺藜草C. ciliaris	[31-32]
胶胞炭疽菌C. gloeosporioides	50	豚草A. artemisiifolia 浮萍L. minor	[34]
异茎点霉属Paraphoma sp. VIZR 1.46	54, 85	田蓟C. arvense 偃麦草E. repens	[35]
壳二孢叶斑病菌A. agropyrina var. nana	55~56	偃麦草E. repens 法国山靛M. annua 狗尾草S. viridis 黍P. miliaceum	[36]
拟茎点霉属Phomopsis sp.	59	毛红花C. lanatus	[37]
内脐蠕孢属D. gigantea	62~64	马唐D. sanguinalis 藜C. album	[40]
藜茎点霉P. chenopodiicola	65	山靛M. annua 田蓟C. arvense 狗尾草S. viridis	[41]
哈茨木霉T. harzianum XS~20090075	67~72	反枝苋A. retroflexus	[42]
澳大利亚德氏霉D. australiensis	73	齿果酸模R. dentatus	[43]
白僵菌B. felina	74~76	反枝苋A. retroflexus	[44]
木贼镰刀菌F. equiseti D39	77~78	反枝苋A. retroflexus A. hybrid	[45]
构巢曲霉A. nidulans	79~82	南苜蓿M. polymorpha	[46]
烟曲霉A. fumigatus	83	反枝苋A. mangostanus	[47]

表1 具有除草活性的真菌次级代谢产物(2012—2022)

Table 1 Herbicidal secondary metabolites from fungi (2012—2022)

菌株种属	化合物在文中的编号	靶向杂草	参考文献
间座壳属D. gulyae	1, 60~61, 84	向日葵H.annuus 虞美人P. rhoeas 异株荨麻U. dioica	[8]
甘蓝链格孢A. brassicicola	2~3	稗草E. crusgalli 狗尾草S. viridis	[9]
藜茎点霉P. chenopodiicola	4, 37~39	苦苣菜S. oleraceus L. 法国山靛M. annua	[10]
甜樱间座壳D. eres	5	西伯利亚剪股颖A. stolonifera 浮萍L. pausicostata	[11]
澳大利亚平脐蠕孢C. australiensis	5~10	绿毛蒺藜草C. ciliaris 加利福尼亚马唐D. californica	[12]
链格孢属Alternaria sp.	11~12	狼尾草P. alopecuroides 紫花苜蓿M. sativa	[13]
希金斯刺盘孢C. higginsianum	14, 50~53	浮萍L. minor 小苞列当属P. ramose	[15]
澳大利亚平脐蠕孢C. australiensis	15~17	绿毛蒺藜草C. ciliaris	[16]
杂色曲霉菌A. versicolor	18~19	反枝苋A. retroflexus L. 刺苋A. spinosus 绿穗苋A. hybrid	[17]
E. gomezpompae	20~27	千穗谷A. hypochondriacus 稗草E. crusgalli	[19]
龙眼焦腐病菌L. theobromae GC~22	28~29, 58	升马唐D. ciliaris	[21]
C. crepinii	30~31	稗草E. crusgalli	[22]
Paraconiothyrium sp.	32	稗草E. crusgalli	[23]
壳多胞属S. cirsii	33~36	苣荬菜S. arvensis	[24]
藜茎点霉P. chenopodiicola	40, 66	繁缕S. media 大荨麻U. dioica 苣荬菜S.arvensis 墙草P. officinalis	[25]
炭角菌属X. feejeensis	41~43	红车轴草T. pratense 紫花苜蓿M. sativa 黍P. miliaceum 千穗谷A. hypochondriacus	[26]
镰刀菌属Fusarium sp.	44, 57, 86	旱雀麦B. tectorum	[27]
壳二孢属A. lentis var. lathyri	45~46	列当属P. ramosa	[30]
梨孢属P.grisea	47~49	绿毛蒺藜草C. ciliaris	[31-32]
胶胞炭疽菌C. gloeosporioides	50	豚草A. artemisiifolia 浮萍L. minor	[34]
异茎点霉属Paraphoma sp. VIZR 1.46	54, 85	田蓟C. arvense 偃麦草E. repens	[35]
壳二孢叶斑病菌A. agropyrina var. nana	55~56	偃麦草E. repens 法国山靛M. annua 狗尾草S. viridis 黍P. miliaceum	[36]
拟茎点霉属Phomopsis sp.	59	毛红花C. lanatus	[37]
内脐蠕孢属D. gigantea	62~64	马唐D. sanguinalis 藜C. album	[40]
藜茎点霉P. chenopodiicola	65	山靛M. annua 田蓟C. arvense 狗尾草S. viridis	[41]
哈茨木霉T. harzianum XS~20090075	67~72	反枝苋A. retroflexus	[42]
澳大利亚德氏霉D. australiensis	73	齿果酸模R. dentatus	[43]
白僵菌B. felina	74~76	反枝苋A. retroflexus	[44]
木贼镰刀菌F. equiseti D39	77~78	反枝苋A. retroflexus A. hybrid	[45]
构巢曲霉A. nidulans	79~82	南苜蓿M. polymorpha	[46]
烟曲霉A. fumigatus	83	反枝苋A. mangostanus	[47]

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真菌除草活性次级代谢产物研究进展

Progress of Fungal Secondary Metabolites with Potential Herbicidal Activity

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