Methyl and p‑Bromobenzyl Esters of Hydrogenated Kaurenoic Acid for Controlling Anthracnose in Common Bean Plants

Kaurenoic acid derivatives were prepared and submitted to in vitro assays with the fungus Colletotrichum lindemuthianum, which causes anthracnose disease in the common bean. The most active substances were found to be methyl and p-bromobenzylesters, 7 and 9, respectively, of the hydrogenated kaureno...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2017-03, Vol.65 (8), p.1489-1495
Main Authors: Mota, Suellen F, Oliveira, Denilson F, Heleno, Vladimir C. G, Soares, Ana Carolina F, Midiwo, Jacob O, Souza, Elaine A
Format: Article
Language:English
Subjects:
Colletotrichum - drug effects
Colletotrichum - physiology
Diterpenes - chemistry
Diterpenes - pharmacology
Esters - pharmacology
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Molecular Structure
Phaseolus - microbiology
Plant Diseases - microbiology
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Summary:Kaurenoic acid derivatives were prepared and submitted to in vitro assays with the fungus Colletotrichum lindemuthianum, which causes anthracnose disease in the common bean. The most active substances were found to be methyl and p-bromobenzylesters, 7 and 9, respectively, of the hydrogenated kaurenoic acid, which presented a minimum inhibitory concentration (MIC) of 0.097 and 0.131 mM, respectively, while the commercial fungicide methyl thiophanate (MT) presented a MIC of 0.143 mM. Substances 7 (1.401 mM) and 9 (1.886 mM) reduced the severity of anthracnose in common bean to values statistically comparable to MT (2.044 mM). According to an in silico study, both compounds 7 and 9 are inhibitors of the ketosteroid isomerase (KSI) enzyme produced by other organisms, the amino acid sequence of which could be detected in fungal genomes. These substances appeared to act against C. lindemuthianum by inhibiting its KSI. Therefore, substances 7 and 9 are promising for the development of new fungicides.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.6b05159