Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Lívia Soman de Medeiros; José Vinícius da Silva; Lucas Magalhães Abreu; Ludwig Heinrich Pfenning; Carolina Lúcia Silva; Sérgio Secherrer Thomasi; Tiago Venâncio; Karl-Heinz van Pée; Kristian Fog Nielsen; Edson Rodrigues-Filho

doi:10.3390/molecules200917627

Molecules (Sep 2015)

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Lívia Soman de Medeiros,
José Vinícius da Silva,
Lucas Magalhães Abreu,
Ludwig Heinrich Pfenning,
Carolina Lúcia Silva,
Sérgio Secherrer Thomasi,
Tiago Venâncio,
Karl-Heinz van Pée,
Kristian Fog Nielsen,
Edson Rodrigues-Filho

Affiliations

Lívia Soman de Medeiros: Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark
José Vinícius da Silva: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil
Lucas Magalhães Abreu: Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark
Ludwig Heinrich Pfenning: Department of Phytopathology, Federal University of Lavras, P. O. Box 3037, Lavras 37200-000, Brazil
Carolina Lúcia Silva: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil
Sérgio Secherrer Thomasi: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil
Tiago Venâncio: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil
Karl-Heinz van Pée: Allgemeine Biochemie, Technical University of Dresden, Bergstraβe 66, Dresden 01062, Germany
Kristian Fog Nielsen: Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark
Edson Rodrigues-Filho: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil

DOI: https://doi.org/10.3390/molecules200917627
Journal volume & issue: Vol. 20, no. 9
pp. 17627 – 17644

Abstract

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

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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