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.
authors.affiliation: Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark. livis@bio.dtu.dk.|Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil. livis@bio.dtu.dk.
authors.forename: Lívia Soman
authors.initials: LS
authors.lastname: de Medeiros
authors.affiliation: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil. zeh.vinicius@gmail.com.
authors.forename: José Vinícius
authors.initials: JV
authors.lastname: da Silva
authors.affiliation: Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark. ludwig@ufla.br.|Department of Phytopathology, Federal University of Lavras, P. O. Box 3037, Lavras 37200-000, Brazil. ludwig@ufla.br.
authors.forename: Lucas Magalhães
authors.initials: LM
authors.lastname: Abreu
authors.affiliation: Department of Phytopathology, Federal University of Lavras, P. O. Box 3037, Lavras 37200-000, Brazil. ludwig@ufla.br.
authors.forename: Ludwig Heinrich
authors.initials: LH
authors.lastname: Pfenning
authors.affiliation: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil. carolina.l@hotmail.com.br.
authors.forename: Carolina Lúcia
authors.initials: CL
authors.lastname: Silva
authors.affiliation: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil. secherrer@yahoo.com.br.
authors.forename: Sérgio Secherrer
authors.initials: SS
authors.lastname: Thomasi
authors.affiliation: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil. venancio@ufscar.br.
authors.forename: Tiago
authors.initials: T
authors.lastname: Venâncio
authors.affiliation: Allgemeine Biochemie, Technical University of Dresden, Bergstraβe 66, Dresden 01062, Germany. Karl-Heinz.vanPee@chemie.tu-dresden.de.
authors.forename: Karl-Heinz
authors.initials: KH
authors.lastname: van Pée
authors.affiliation: Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark. kfn@bio.dtu.dk.
authors.forename: Kristian Fog
authors.initials: KF
authors.lastname: Nielsen
authors.affiliation: Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil. edinho@pq.cnpq.br.
authors.forename: Edson
authors.initials: E
authors.lastname: Rodrigues-Filho
mesh_terms: D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D004876:Ergot Alkaloids / Q000096:biosynthesis; D005182:Flavin-Adenine Dinucleotide / Q000031:analogs & derivatives / Q000378:metabolism; D005656:Fungal Proteins / Q000378:metabolism; D054879:Halogenation; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D032901:Talaromyces / Q000737:chemistry* / Q000201:enzymology / Q000254:growth & development*
chemical_list: D001688:Biological Products; D004876:Ergot Alkaloids; D005656:Fungal Proteins; D007211:Indoles; C027115:rugulovasine B; D005182:Flavin-Adenine Dinucleotide; C058805:1,5-dihydro-FAD; C027114:rugulovasine A
keywords: Talaromyces; dereplication; halogenation; rugulovasine; tryptophan