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

Author(s)

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

• Document type: Journal article
• Source: Journal of Natural Products; v. 80, n. 5, p. 1302-1309, MAY 2017.
• Web of Science Citations: 9

Abstract

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)

• FAPESP's process: 08/09540-0 - New strategies in the search of natural antibiotics: symbiotic microorganisms as sources of compounds and in vivo assay based on Caenorhabditis elegans infection model
• Grantee: Mônica Tallarico Pupo
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 14/01651-8 - Elicitation of natural products biosynthesis from endophytic microorganisms' interactions
• Grantee: Andrés Mauricio Caraballo Rodríguez
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 09/17695-6 - New strategies to access microbial natural products: mixed cultures of endophytes, chemical and epigenetic remodeling of biosynthetic pathways
• Grantee: Fernanda Oliveira das Chagas
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 12/21803-1 - Elicitation of natural products biosynthesis by endophytic microorganisms’ interaction
• Grantee: Andrés Mauricio Caraballo Rodríguez
• Support Opportunities: Scholarships in Brazil - Doctorate