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ID: ALA4715906

Journal: Bioorg Med Chem

Title: Antileishmanial macrolides from ant-associated Streptomyces sp. ISID311.

Authors: Ortega HE,Lourenzon VB,Chevrette MG,Ferreira LLG,Alvarenga RFR,Melo WGP,Venâncio T,Currie CR,Andricopulo AD,Bugni TS,Pupo MT

Abstract: Three antifungal macrolides cyphomycin (1), caniferolide C (2) and GT-35 (3) were isolated from Streptomyces sp. ISID311, a bacterial symbiont associated with Cyphomyrmex fungus-growing ants. The planar structures of these compounds were established by 1 and 2D NMR data and MS analysis. The relative configurations of 1-3 were established using Kishi's universal NMR database method, NOE/ROE analysis and coupling constants analysis assisted by comparisons with NMR data of related compounds. Detailed bioinformatic analysis of cyphomycin biosynthetic gene cluster confirmed the stereochemical assignments. Compounds 1-3 displayed high antagonism against different strains of Escovopsis sp., pathogen fungi specialized to the fungus-growing ant system. Compounds 1-3 also exhibited potent antiprotozoal activity against intracellular amastigotes of the human parasite Leishmania donovani with IC values of 2.32, 0.091 and 0.073 µM, respectively, with high selectivity indexes.

CiteXplore: 33493972

DOI: 10.1016/j.bmc.2021.116016