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Journal article

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

In Molecules — 2015, Volume 20, Issue 9, pp. 17627-17644

By Soman De Medeiros, Lívia1; da Silva, José Vinícius2; Abreu, Lucas Magalhães1; Pfenning, Ludwig3; Silva, Carolina3; Secherrer Thomasi, Sérgio2; Venâncio, Tiago2; van Pée, Karl-Heinz4; Nielsen, Kristian Fog1,5; Rodrigues-Filho, Edson2

Edited by Schmidt, Thomas J.

From

Department of Systems Biology, Technical University of Denmark1

Federal University of São Carlos2

Federal University of Lavras3

Dresden University of Technology4

Metabolomics Platform, Department of Systems Biology, Technical University of Denmark5

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 FADH2 dependent halogenase can be involved in the biosynthesis of the produced halocompounds.

Language: English
Publisher: MDPI
Year: 2015
Pages: 17627-17644
ISSN: 14203049 and 14315157
Types: Journal article
DOI: 10.3390/molecules200917627
ORCIDs: Nielsen, Kristian Fog
Keywords

Dereplication Halogenation Rugulovasine Talaromyces Tryptophan

Other keywords

1,5-dihydro-FAD Biological Products Chromatography, High Pressure Liquid Ergot Alkaloids Flavin-Adenine Dinucleotide Fungal Proteins Indoles Molecular Structure Organic chemistry QD241-441 dereplication halogenation rugulovasine rugulovasine A rugulovasine B tryptophan

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