Antileishmanial macrolides from ant-associated Streptomyces sp. ISID311.
DOMINGUEZ, Humberto Enrique Ortega; LOURENZON, Vitor Bruno; CHEVRETTE, Marc G.; FERREIRA, Leonardo Luiz Gomes; ALVARENGA, René F. Ramos; MELO, Weilan Gomes da Paixão; VENÂNCIO, Tiago; CURRIE, Cameron R.; ANDRICOPULO, Adriano Defini; BUGNI, Tim S.; PUPO, Mônica Tallarico.
DOMINGUEZ, Humberto Enrique Ortega; LOURENZON, Vitor Bruno; CHEVRETTE, Marc G.; FERREIRA, Leonardo Luiz Gomes; ALVARENGA, René F. Ramos; MELO, Weilan Gomes da Paixão; VENÂNCIO, Tiago; CURRIE, Cameron R.; ANDRICOPULO, Adriano Defini; BUGNI, Tim S.; PUPO, Mônica Tallarico.
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 IC50 values of 2.32, 0.091 and 0.073 µM, respectively, with high selectivity indexes.
@article={003018371,author = {DOMINGUEZ, Humberto Enrique Ortega; LOURENZON, Vitor Bruno; CHEVRETTE, Marc G.; FERREIRA, Leonardo Luiz Gomes; ALVARENGA, René F. Ramos; MELO, Weilan Gomes da Paixão; VENÂNCIO, Tiago; CURRIE, Cameron R.; ANDRICOPULO, Adriano Defini; BUGNI, Tim S.; PUPO, Mônica Tallarico.},title={Antileishmanial macrolides from ant-associated Streptomyces sp. ISID311},journal={Bioorganic and Medicinal Chemistry},note={v. 32, n. 2, p. 116016-1-116016-9 + supplementary data},year={2021}}