Journal
MOLECULES
Volume 20, Issue 9, Pages 17627-17644Publisher
MDPI
DOI: 10.3390/molecules200917627
Keywords
halogenation; tryptophan; rugulovasine; dereplication; Talaromyces
Funding
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [2009/18584-3]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)
- Coordenacao de Aperfeicoamento de Ensino Superior (CAPES) [0229-12-1]
- Danish Research Agency for Technology and Production
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UHPLC-DAD-HRMS based dereplication guided the detection of new halogenated alkaloids co-produced by Talaromyces wortmannii. From the fungal growth in large scale, the epimers 2,8-dichlororugulovasines A and B were purified and further identified by means of a HPLC-SPE/NMR hyphenated system. Brominated rugulovasines were also detected when the microbial incubation medium was supplemented with bromine sources. Studies from 1D/2D NMR and HRMS spectroscopy data allowed the structural elucidation of the dichlorinated compounds, while tandem MS/HRMS data analysis supported the rationalization of brominated congeners. Preliminary genetic studies revealed evidence that FADH(2) dependent halogenase can be involved in the biosynthesis of the produced halocompounds.
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