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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Ortega, Humberto E. [1] ; Batista, Jr., Joao M. [2, 3] ; Melo, Weilan G. P. [1] ; de Paula, Gabriela T. [1] ; Pupo, Monica T. [1]
Total Authors: 5
Affiliation:
[1] Univ Sao Paulo, FCFRP, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Fed Sao Paulo UNIFESP, Inst Ciencia & Tecnol, BR-12231280 Sao Jose Dos Campos, SP - Brazil
[3] Univ Fed Sao Carlos UFSCar, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Journal of the Brazilian Chemical Society; v. 30, n. 12, SI, p. 2672-2680, DEC 2019.
Web of Science Citations: 0
Abstract

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. (AU)

FAPESP's process: 15/07089-2 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support Opportunities: Scholarships in Brazil - Young Researchers
FAPESP's process: 13/50954-0 - Novel therapeutic agents from the bacterial symbionts of Brazilian invertebrates
Grantee:Mônica Tallarico Pupo
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support Opportunities: Research Grants - Young Investigators Grants
FAPESP's process: 14/14095-6 - Bacterial symbionts isolated from fungus-growing ants collected in remaining hotspots of biodiversity in São Paulo State as sources of antiparasitic compounds
Grantee:Humberto Enrique Ortega Dominguez
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
FAPESP's process: 17/05920-1 - Chemical and ecological study of actinobacterium MG28-1.10 isolated from winged males of Mycocepurus goeldii
Grantee:Gabriela Toninato de Paula
Support Opportunities: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 15/01001-6 - Discovering bacterial symbionts diversity associated with ants in different Brazilian biomes
Grantee:Weilan Gomes da Paixão Melo
Support Opportunities: Scholarships in Brazil - Post-Doctoral