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

doi:10.3390/molecules200917627

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 FADH₂dependent halogenase can be involved in the biosynthesis of the produced halocompounds.

Original language	English
Journal	Molecules
Volume	20
Issue number	9
Pages (from-to)	17627-17644
Number of pages	18
ISSN	1420-3049
DOIs	https://doi.org/10.3390/molecules200917627
Publication status	Published - 2015

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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.

Keywords

Halogenation
Tryptophan
Rugulovasine
Dereplication
Talaromyces

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title = "Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii",

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.",

keywords = "Halogenation, Tryptophan, Rugulovasine, Dereplication, Talaromyces",

author = "{Soman De Medeiros}, L{\'i}via and {da Silva}, {Jos{\'e} Vin{\'i}cius} and Abreu, {Lucas Magalh{\~a}es} and Ludwig Pfenning and Carolina Silva and {Secherrer Thomasi}, S{\'e}rgio and Tiago Ven{\^a}ncio and {van P{\'e}e}, Karl-Heinz and Nielsen, {Kristian Fog} and Edson Rodrigues-Filho",

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.",

year = "2015",

doi = "10.3390/molecules200917627",

language = "English",

volume = "20",

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T1 - Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

AU - Soman De Medeiros, Lívia

AU - da Silva, José Vinícius

AU - Abreu, Lucas Magalhães

AU - Pfenning, Ludwig

AU - Silva, Carolina

AU - Secherrer Thomasi , Sérgio

AU - Venâncio, Tiago

AU - van Pée, Karl-Heinz

AU - Nielsen, Kristian Fog

AU - Rodrigues-Filho, Edson

N1 - 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.

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

KW - Halogenation

KW - Tryptophan

KW - Rugulovasine

KW - Dereplication

KW - Talaromyces

U2 - 10.3390/molecules200917627

DO - 10.3390/molecules200917627

M3 - Journal article

C2 - 26404231

SN - 1420-3049

VL - 20

SP - 17627

EP - 17644

JO - Molecules

JF - Molecules

IS - 9

ER -

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Abstract

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Keywords

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