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Synthesis and characterization of synthetic analogs of cinnacidin, a novel phytotoxin from Nectria sp.
Author(s) -
Irvine Nicholas M,
Yerkes Carla N,
Graupner Paul R,
Roberts Roben E,
Hahn Don R,
Pearce Cedric,
Gerwick B Clifford
Publication year - 2008
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.1579
Subject(s) - phytotoxin , coronatine , jasmonic acid , bioassay , isoleucine , biological activity , biology , stereochemistry , valine , chemistry , botany , amino acid , in vitro , leucine , toxin , biochemistry , arabidopsis , salicylic acid , genetics , gene , mutant
BACKGROUND: The novel natural product cinnacidin was isolated from a fungal fermentation extract of Nectria sp. DA060097. The compound was found to contain a cyclopentalenone ring system with an isoleucine subunit linked through an amide bond. Initial biological characterization of cinnacidin suggested promising herbicidal activity. RESULTS: Two synthetic analogs, (2 S ,3 S )‐2‐[(3 RS ,3a SR ,6a RS )‐3‐methoxy‐4‐oxo‐3,3a,4,5,6,6a‐hexahydropentalen‐1‐ylcarbamoyl]‐3‐methylvaleric acid and benzyl (2 S ,3 S )‐2‐[(3 RS ,3a SR ,6a RS )‐3‐methoxy‐4‐oxo‐3,3a,4, 5,6,6a‐hexahydropentalen‐1‐ylcarbamoyl]‐3‐methylvalerate, were prepared for further characterization, and their herbicidal activities were compared with that of cinnacidin. CONCLUSIONS: The synthetic compounds were highly phytotoxic on a range of weeds. Based on the symptoms in treated plants, the mode of action of these compounds is suggested to be similar to that of coronatine and jasmonic acid. Coronatine was more active against warm‐season grasses, while the cinnacidin benzyl ester analog was more effective on cool‐season grasses. In a seedling growth bioassay conducted on bentgrass, the cinnacidin analog was equivalent in activity to coronatine. Copyright © 2008 Society of Chemical Industry