Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

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. Brominat...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2015-09, Vol.20 (9), p.17627-17644
Main Authors: de Medeiros, Lívia Soman, da Silva, José Vinícius, Abreu, Lucas Magalhães, Pfenning, Ludwig Heinrich, Silva, Carolina Lúcia, Thomasi, Sérgio Secherrer, Venâncio, Tiago, van Pée, Karl-Heinz, Nielsen, Kristian Fog, Rodrigues-Filho, Edson
Format: Article
Language:English
Subjects:
Biological Products - chemistry
Biological Products - isolation & purification
Chromatography, High Pressure Liquid
Data analysis
dereplication
Electronic mail systems
Ergot Alkaloids - biosynthesis
Flavin-Adenine Dinucleotide - analogs & derivatives
Flavin-Adenine Dinucleotide - metabolism
Fungal Proteins - metabolism
Halogenation
Indoles - chemistry
Indoles - isolation & purification
Mass spectrometry
Metabolites
Molecular Structure
rugulovasine
Scientific imaging
Talaromyces
Talaromyces - chemistry
Talaromyces - enzymology
Talaromyces - growth & development
tryptophan
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules200917627