Laboratory bioassay, greenhouse experiment and 3D-QSAR studies on berberine analogues: a search for new herbicides based on natural products

doi:10.1002/ps.6233

	Laboratory bioassay, greenhouse experiment and 3D-QSAR studies on berberine analogues: a search for new herbicides based on natural products
	Zhang, Xiaohong 1; Zhu, Tingfei 2; Bi, Xiaoyang 1; Yang, Sifan 1; Huang, Jiguang 1; Zhou, Lijuan 1
刊名	PEST MANAGEMENT SCIENCE
	2021-01-21
页码	14
关键词	berberine analogues worenine chloride coptisine chloride natural herbicide 3D-QSAR
ISSN号	1526-498X
DOI	10.1002/ps.6233
通讯作者	Huang, Jiguang(hnnyzx@scau.edu.cn) ; Zhou, Lijuan(zhoulj@scau.edu.cn)
英文摘要	BACKGROUND: Berberine is a herbicidal chemical that we isolated from Coptis chinensis. In continuation of our program aimed at discovering and developing natural botanical herbicides, we evaluated the herbicidal activities of 39 berberine analogues and developed a three-dimensional quantitative structure-activity relationship (3D-QSAR) model. RESULTS: Among these 39 analogs, the most active compounds were determined to be worenine chloride and coptisine chloride, with median inhibitory concentration (IC50) values on all eight tested weed species of < 10 mg L-1. As a reference, the IC50 values of berberine on six weed species were < 10 mg L-1. Furthermore, the results of a greenhouse experiment showed that at 10 mg L-1, and 7 days after treatment, the effects of worenine chloride and coptisine chloride on Lemna minor and Ageratum conyzoides were significantly higher than those of glyphosate and sulcotrione. In the 3D-QSAR analysis, the electrostatic field contour map indicated that introducing an electropositive group in the N-7, C-9 and C-10 positions would potentially improve the inhibition rate. A positively charged nitrogen atom at the N-7 position was important for activity. Replacement of -OCH3 by -OH at the C-9 and C-10 positions could decrease the inhibitory activity, while the hydrophobic field contour map revealed that the hydrophobicity of the C-10 position was associated with high activity. Moreover, the hydrogen bond acceptor field contour map suggested that the existence of a hydrogen bond acceptor at the C-3 and C-9 positions might affect the inhibition rate. CONCLUSIONS: 3D-QSAR provided meaningful clues to the structural features of berberine analogues that will assist the design of more potent herbicidal compounds in the future. (c) 2020 Society of Chemical Industry
资助项目	Science and Technology Planning Programs of Guangdong Province, China[2016A050502047] ; Science and Technology Planning Programs of Guangdong Province, China[2015A020209151] ; Science and Technology Program of Guangzhou, China[201607010125]
WOS研究方向	Agriculture ; Entomology
语种	英语
出版者	JOHN WILEY & SONS LTD
WOS记录号	WOS:000609355700001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/296171]
专题	中国科学院上海药物研究所
通讯作者	Huang, Jiguang; Zhou, Lijuan
作者单位	1.South China Agr Univ, Key Lab Nat Pesticide & Chem Biol, Minist Educ, Guangzhou 510642, Guangdong, Peoples R China 2.Chinese Acad Sci, Drug Discovery & Design Ctr, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai, Peoples R China
推荐引用方式 GB/T 7714	Zhang, Xiaohong,Zhu, Tingfei,Bi, Xiaoyang,et al. Laboratory bioassay, greenhouse experiment and 3D-QSAR studies on berberine analogues: a search for new herbicides based on natural products[J]. PEST MANAGEMENT SCIENCE,2021:14.
APA	Zhang, Xiaohong,Zhu, Tingfei,Bi, Xiaoyang,Yang, Sifan,Huang, Jiguang,&Zhou, Lijuan.(2021).Laboratory bioassay, greenhouse experiment and 3D-QSAR studies on berberine analogues: a search for new herbicides based on natural products.PEST MANAGEMENT SCIENCE,14.
MLA	Zhang, Xiaohong,et al."Laboratory bioassay, greenhouse experiment and 3D-QSAR studies on berberine analogues: a search for new herbicides based on natural products".PEST MANAGEMENT SCIENCE (2021):14.