Variability of the antibacterial potential among analogue diterpenes against Gram-positive bacteria: considerations on the structure-activity relationship

Author(s)

Ferreira Soares, Ana Carolina ^[1] ; Matos, Priscilla Mendonca ^[1] ; Dias, Herbert Junior ^[2] ; Aguiar, Gabriela de Paula ^[1] ; dos Santos, Eliene Silverio ^[1] ; Gomes Martins, Carlos Henrique ^[1] ; Sola Veneziani, Rodrigo Cassio ^[1] ; Ambrosio, Sergio Ricardo ^[1] ; Gomes Heleno, Vladimir Constantino ^[1]

Affiliation

^[1] Univ Franca, Nucleo Pesquisas Ciencias Exatas & Tecnol, Franca, SP - Brazil

^[2] Univ Sao Paulo, Dept Quim FFCLRP, Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: Canadian Journal of Chemistry; v. 97, n. 7, p. 568-575, JUL 2019.
• Web of Science Citations: 0

Abstract

The search for new antibacterial agents and a better comprehension of substances with antimicrobial behavior is mandatory nowadays due to the serious public health problem of infection diseases. In the present work, 30 diterpenes were studied, with 2 natural derivatives, named ent-16-kauren-19-oic acid and ent-pimara-8(14), 15-dien-19-oic acid, and 28 semisynthetic derivatives. The natural diterpenes were isolated from Mikania glomerata and Viguiera arenaria, respectively. All diterpenes were submitted to antimicrobial assays against six different Gram-positive microorganisms to better understand the structure-activity relationship of antimicrobial diterpenes. The semi-synthetic derivatives were all obtained from the two natural derivatives by structural modifications, mainly esterification reactions. Both natural derivatives, together with the derivative ent-8(14)-pimaren-19-oic acid, displayed the most relevant antibacterial activities, with minimal inhibitory concentration (MIC) values that were less than 10 mu g mL(-1) for most pathogens; thus, they were considered promising antimicrobial agents. Moreover, in light of the hypothesis of Urzua and colleagues, several considerations about the structure-activity relationship of antimicrobial diterpenes could be stated. (AU)

• FAPESP's process: 11/07885-2 - Antimicrobial potential of kaurane diterpene derivatives and their NMR structural studies.
• Grantee: Ana Carolina Ferreira Soares
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• FAPESP's process: 09/09491-1 - Structural modifications and detailed NMR studies of biologically active natural products
• Grantee: Vladimir Constantino Gomes Heleno
• Support Opportunities: Regular Research Grants