Expanding the Chemical Repertoire of the Endophyte Streptomyces albospinus RLe7 Reveals Amphotericin B as an Inducer of a Fungal Phenotype

Autor(es)

Chagas, Fernanda Oliveira ; Caraballo-Rodriguez, Andres Mauricio ; Dorrestein, Pieter C. ; Pupo, Monica Tallarico

• Tipo de documento: Artigo Científico
• Fonte: Journal of Natural Products; v. 80, n. 5, p. 1302-1309, MAY 2017.
• Citações Web of Science: 9

Resumo

During an investigation of the chemistry of the endophytic actinobacterium Streptomyces albospinus RLe7, which was isolated from the roots of the Brazilian medicinal plant Lychnophora ericoides, three new natural products, (2R{*},4S{*})-2-((1'S{*})-hydroxy-4'-methylpenty1)-4-(hydroxymethyl)buta nolide (1), (3R{*},4S{*},5R{*},6S{*})-tetrahydro-4-hydroxy-3,5,6-trimethy1-2-pyranon e (2), and 1-O-(phenylacetyl)glycerol (3), together with known secondary metabolites (S)-4-benzyl-3-oxo-3,4-dihydro-1H-pyrrolo {[}2,1-c] {[}1,4]oxazine-6-carbaldehyde (4), (S)-4-isobuty1-3-oxo-3,4-dihydro-1H-pyrrolo{[}2,1-c]-{[}1,4]oxazine-6-ca rbaldehyde (5), and the diketopiperazines cyclo(L-Tyr-L-Pro) (6) and cyclo(L-Val-L-Pro) (7), were isolated. The role of isolated natural products in the interaction between S. albospinus RLe7 and the fungus Coniochaeta sp. FLe4, an endophyte from the same plant, was investigated. None of these isolated actinobacterial compounds were able to inhibit the fungus or induce the fungal red pigmentation observed when both endophytes interact. Further investigation using mass spectrometry approaches enabled identifying the well-known antifungal compound amphotericin B (9) as a microbial metabolite of S. albospinus RLe7. Finally, compound 9 was demonstrated as at least one of the agents responsible for both the antifungal activity and induction of red pigmented fungal phenotype. (AU)

• Processo FAPESP: 08/09540-0 - Novas estratégias na pesquisa em antibióticos naturais: microrganismos simbiontes como fontes de substâncias e ensaio in vivo baseado no modelo de infecção em Caenorhabditis elegans
• Beneficiário: Mônica Tallarico Pupo
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 14/01651-8 - Eliciação da biossíntese de produtos naturais a partir da interação de micro-organismos endofíticos
• Beneficiário: Andrés Mauricio Caraballo Rodríguez
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado
• Processo FAPESP: 09/17695-6 - Novas estratégias para acessar produtos naturais microbianos: culturas mistas de endofíticos, modulação química e epigenética de vias biossintéticas
• Beneficiário: Fernanda Oliveira das Chagas
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 12/21803-1 - Eliciação da biossíntese de produtos naturais a partir da interação de micro-organismos endofíticos
• Beneficiário: Andrés Mauricio Caraballo Rodríguez
• Modalidade de apoio: Bolsas no Brasil - Doutorado