Structure and Absolute Configuration of Secondary Metabolites from Two Strains of Streptomyces chartreusis Associated with Attine Ants

Autor:	Mônica Tallarico Pupo, Humberto E. Ortega, João M. Batista, Weilan G. P. Melo, Gabriela Toninato de Paula
Rok vydání:	2019
Předmět:	food.ingredient Natural product Strain (chemistry) Stereochemistry Absolute configuration General Chemistry Pathogenic fungus chemistry.chemical_compound food chemistry Vibrational circular dichroism STREPTOMYCES Escovopsis Streptazolin Mycocepurus goeldii
Zdroj:	Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP
ISSN:	0103-5053
DOI:	10.21577/0103-5053.20190194
Popis:	The antibiotic streptazolin (1), its E-isomer (2), along with the stereoisomers strepchazolin A (3) and strepchazolin B (4) and the inorganic compound cyclooctasulfur (5) were produced in solid culture by Streptomyces chartreusis ICBG377, which was isolated from the fungal garden of the leaf-cutter ant Acromyrmex subterraneus brunneus. This is the first time compound 2 is reported as a natural product. Compound 5, which showed antagonist activity against the specialized pathogenic fungus Escovopsis sp., was also produced by Streptomyces chartreusis ICBG323, isolated from the exoskeleton of winged male of Mycocepurus goeldii. The absolute configurations of 3 and 4 were confirmed by the combination of vibrational circular dichroism (VCD) spectroscopy and density functional theory (DFT) calculations. These results clearly demostrate the power of VCD to tell apart epimeric natural products. Compounds 1, 3 and 4 were produced by geographically distant but phylogenetically close strains, S. chartreusis ICBG 377 isolated in Brazil, and S. chartreusis NA02069, a marine sediment strain isolated in China.
Databáze:	OpenAIRE
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