干旱区生态环境知识资源中心(Arid): Phytotoxic Activity and Structure-Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)

Arid

DOI	10.3390/molecules24152793
	Phytotoxic Activity and Structure-Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)
	Masi, Marco 1; Freda, Fabrizio 2; Clement, Suzette 3; Cimmino, Alessio 1; Cristofaro, Massimo 2,4; Meyer, Susan 3; Evidente, Antonio 1
通讯作者	Masi, Marco
来源期刊	MOLECULES
EISSN	1420-3049
出版年	2019
卷号	24 期号:15
英文摘要	Radicinin (1), is a fungal dihydropyranopyran-4,5-dione isolated together with some analogues, namely 3-epi-radicinin, radicinol, 3-epi-radicinol, and cochliotoxin (2-5), from the culture filtrates of the fungus Cochliobolus australiensis, a foliar pathogen of buffelgrass (Cenchrus ciliaris), an invasive weed in North America. Among the different metabolites 1 showed target-specific activity against the host plant and no toxicity on zebrafish embryos, promoting its potential use to develop a natural bioherbicide formulation to manage buffelgrass. These data and the peculiar structural feature of 1 suggested to carry out a structure-activity relationship study, preparing some key hemisynthetic derivatives and to test their phytotoxicity. In particular, p-bromobenzoyl, 5-azidopentanoyl, stearoyl, mesyl and acetyl esters of radicinin were semisynthesized as well as the monoacetyl ester of 3-epi-radicinin, the diacetyl esters of radicinol and its 3 epimer, and two hexa-hydro derivatives of radicinin. The spectroscopic characterization and the activity by leaf puncture bioassay against buffelgrass of all the derivatives is reported. Most of the compounds showed phytotoxicity but none of them had comparable or higher activity than radicinin. Thus, the presence of an alpha,beta unsaturated carbonyl group at C-4, as well as, the presence of a free secondary hydroxyl group at C-3 and the stereochemistry of the same carbon proved to be the essential feature for activity.
英文关键词	buffelgrass Cochliobolus australiensis radicinin derivatives SAR leaf puncture bioassay phytotoxicity
类型	Article
语种	英语
国家	Italy ; USA
开放获取类型	Green Published, Green Submitted, gold
收录类别	SCI-E
WOS记录号	WOS:000482441100116
WOS关键词	POTENTIAL HERBICIDAL ACTIVITY ; COCHLIOBOLUS-AUSTRALIENSIS ; DESERT
WOS类目	Biochemistry & Molecular Biology ; Chemistry, Multidisciplinary
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
资源类型	期刊论文
条目标识符	http://119.78.100.177/qdio/handle/2XILL650/217683
作者单位	1.Univ Napoli Federico II, Complesso Univ Monte S Angelo, Dipartimento Sci Chim, Via Cintia 4, I-80126 Naples, Italy; 2.BBCA Onlus, Via A Signorelli 105, I-00123 Rome, Italy; 3.US Forest Serv, Shrub Sci Lab, Rocky Mt Res Stn, 735 North 500 East, Provo, UT 84606 USA; 4.ENEA CR Casaccia, SSPT BIOAG PROBIO, Via Anguillarese 301, I-00123 Rome, Italy
推荐引用方式 GB/T 7714	Masi, Marco,Freda, Fabrizio,Clement, Suzette,et al. Phytotoxic Activity and Structure-Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)[J],2019,24(15).
APA	Masi, Marco.,Freda, Fabrizio.,Clement, Suzette.,Cimmino, Alessio.,Cristofaro, Massimo.,...&Evidente, Antonio.(2019).Phytotoxic Activity and Structure-Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris).MOLECULES,24(15).
MLA	Masi, Marco,et al."Phytotoxic Activity and Structure-Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)".MOLECULES 24.15(2019).