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 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.
Departamento de Biologia, Universidade Federal de Lavras , Lavras, MG CEP 37.200-000, Brazil.
Suellen F
SF
Mota
Departamento de Química, Universidade Federal de Lavras , Lavras, MG CEP 37.200-000, Brazil.
Denilson F
http://orcid.org/0000-0001-9326-8716
DF
Oliveira
Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca , Franca, SP CEP 14.404-600, Brazil.
Vladimir C G
http://orcid.org/0000-0002-4505-6978
VC
Heleno
Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca , Franca, SP CEP 14.404-600, Brazil.
Ana Carolina F
AC
Soares
Department of Chemistry, University of Nairobi , Nairobi 00100, Kenya.
Jacob O
JO
Midiwo
Departamento de Biologia, Universidade Federal de Lavras , Lavras, MG CEP 37.200-000, Brazil.
Elaine A
EA
Souza
D020231:Colletotrichum / Q000187:drug effects* / Q000502:physiology; D004224:Diterpenes / Q000737:chemistry* / Q000494:pharmacology*; D004952:Esters / Q000494:pharmacology; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D027805:Phaseolus / Q000382:microbiology*; D010935:Plant Diseases / Q000382:microbiology*
D004224:Diterpenes; D004952:Esters; D005659:Fungicides, Industrial; C051436:kaurenoic acid
Colletotrichum lindemuthianum; ent-kauran-18-oic acid methyl ester; ent-kauran-18-oic acid p-bromobenzyl ester; fungicide; ketosteroid isomerase