Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Author(s)

de Medeiros, Livia Soman ^{[1, 2]} ; da Silva, Jose Vinicius ^[1] ; Abreu, Lucas Magalhaes ^{[2, 3]} ; Pfenning, Ludwig Heinrich ^[3] ; Silva, Carolina Lucia ^[1] ; Thomasi, Sergio Secherrer ^[1] ; Venancio, Tiago ^[1] ; van Pee, Karl-Heinz ^[4] ; Nielsen, Kristian Fog ^[2] ; Rodrigues-Filho, Edson ^[1]

Affiliation

^[1] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Tech Univ Denmark, Dept Syst Biol, DK-2800 Lyngby - Denmark

^[3] Univ Fed Lavras, Dept Phytopathol, BR-37200000 Lavras - Brazil

^[4] Tech Univ Dresden, Allgemeine Biochem, D-01062 Dresden - Germany

• Document type: Journal article
• Source: Molecules; v. 20, n. 9, p. 17627-17644, SEP 2015.
• Web of Science Citations: 3

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 FADH(2) dependent halogenase can be involved in the biosynthesis of the produced halocompounds. (AU)

• FAPESP's process: 09/18584-3 - Chemical prospecting of the secondary metabolism of endophytic fungi isolated from apple (Malus domestica) and guava fruit (Psidium guajava)
• Grantee: Lívia Soman de Medeiros
• Support Opportunities: Scholarships in Brazil - Doctorate