Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

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

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    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.
    Original languageEnglish
    JournalMolecules
    Volume20
    Issue number9
    Pages (from-to)17627-17644
    Number of pages18
    ISSN1420-3049
    DOIs
    Publication statusPublished - 2015

    Bibliographical note

    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.

    Keywords

    • Halogenation
    • Tryptophan
    • Rugulovasine
    • Dereplication
    • Talaromyces

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