Phomentrioloxin, a fungal phytotoxin with potential herbicidal activity, and its derivatives: A structure-activity relationship study

Cimmino, Alessio and Andolfi, Anna and Zonno, Maria Chiara and Boari, Angela and Troise, Ciro and Motta, Andrea and Vurro, Maurizio and Ash, Gavin and Evidente, Antonio (2013) Phomentrioloxin, a fungal phytotoxin with potential herbicidal activity, and its derivatives: A structure-activity relationship study. Journal of Agricultural and Food Chemistry, 61 (40). pp. 9645-9649. ISSN 1520-5118

Abstract

Phomentrioloxin is a phytotoxic geranylcyclohexenetriol produced in liquid culture by Phomopsis sp. (teleomorph: Diaporthe gulyae), a potential mycoherbicide proposed for the control of the annual weed Carthamus lanatus. In this study, seven derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on nonhost weedy and agrarian plants, fungi, Gram+ and Gram- bacteria, and on brine shrimp larvae. The results provide insights into an investigation of the structural requirements for activity. The hydroxy groups at C-2 and C-4 appeared to be important features for the phytotoxicity, as well as an unchanged cyclohexentriol ring. A role seemed also to be played by the unsaturations of the geranyl side chain. These findings could be useful for understanding the mechanisms of action of new natural products, for identifying the active sites, and possibly in devising new herbicides of natural origin.


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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Files associated with this item cannot be displayed due to copyright restrictions.
Faculty / Department / School: No Faculty
Date Deposited: 31 May 2017 05:41
Last Modified: 31 May 2017 05:41
Uncontrolled Keywords: Carthamus lanatus; Diaporthe gulyae; phomentrioloxin; Phomopsis sp.; phytotoxins; SAR; weeds; Carthamus lanatus; Diaporthe gulyae; phomentrioloxin; Phytotoxins; SAR; weeds; Chemical Reactions; Chemical Agents and Basic Industrial Chemicals;
Fields of Research : 07 Agricultural and Veterinary Sciences > 0703 Crop and Pasture Production > 070308 Crop and Pasture Protection (Pests, Diseases and Weeds)
Socio-Economic Objective: E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences
E Expanding Knowledge > 97 Expanding Knowledge > 970107 Expanding Knowledge in the Agricultural and Veterinary Sciences
Identification Number or DOI: 10.1021/jf4030618
URI: http://eprints.usq.edu.au/id/eprint/32062

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