Agropyrenol, a phytotoxic fungal metabolite, and its derivatives: a structure-activity relationship study.
Agropyrenol is a phytotoxic substituted salicylic aldehyde produced in liquid culture by Ascochyta agropyrina var. nana , a potential mycoherbicide proposed for the control of the perennial weed Elytrigia repens. In this study, six 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 non-host weedy and agrarian plants, fungi, Gram-positive and Gram-negative bacteria, and brine shrimp larvae. The results provide insights into the structure-activity relationships of agropyrenol. Both the double bond and the diol system of the 3,4-dihydroxypentenyl side chain as well as the aldehyde group at C-1 of the phenolic ring of agropyrenol proved to be important for the phytotoxicity. The lesser polar 3',4'-O,O'-isopropylidene of agropyrenol also showed significant zootoxic and slight antimicrobial activities. This finding could be useful in devising new natural herbicides for practical application in agriculture.
Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
Alessio
A
Cimmino
Maria Chiara
MC
Zonno
Anna
A
Andolfi
Ciro
C
Troise
Andrea
A
Motta
Maurizio
M
Vurro
Antonio
A
Evidente
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry* / Q000378:metabolism; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006540:Herbicides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D057685:Plant Weeds / Q000187:drug effects; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D006540:Herbicides; D009183:Mycotoxins; D009281:Naphthalenes; C575645:agropyrenol