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Molecules 2015, 20(9), 17627-17644; doi:10.3390/molecules200917627

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

1
Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark
2
Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil
3
Department of Phytopathology, Federal University of Lavras, P. O. Box 3037, Lavras 37200-000, Brazil
4
Allgemeine Biochemie, Technical University of Dresden, Bergstraβe 66, Dresden 01062, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 1 August 2015 / Revised: 17 September 2015 / Accepted: 21 September 2015 / Published: 23 September 2015
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [1241 KB, uploaded 24 September 2015]   |  

Abstract

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. View Full-Text
Keywords: halogenation; tryptophan; rugulovasine; dereplication; Talaromyces halogenation; tryptophan; rugulovasine; dereplication; Talaromyces
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

de Medeiros, L.S.; da Silva, J.V.; Abreu, L.M.; Pfenning, L.H.; Silva, C.L.; Thomasi, S.S.; Venâncio, T.; van Pée, K.-H.; Nielsen, K.F.; Rodrigues-Filho, E. Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii. Molecules 2015, 20, 17627-17644.

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