Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Molecules

Lívia Soman de Medeiros⁴  José Vinໜius da Silva¹  Lucas Magalh฾s Abreu⁴  Ludwig Heinrich Pfenning³  Carolina Lྫྷia Silva¹  Sérgio Secherrer Thomasi¹  Tiago Venâncio¹  Karl-Heinz van Pພ²  Kristian Fog Nielsen⁴  Edson Rodrigues-Filho¹ 

[1] Department of Chemistry, Federal University of São Carlos, Rod. Washington Luís, Km 265, São Carlos 13565-905, Brazil; E-Mails:;Allgemeine Biochemie, Technical University of Dresden, Bergstraβe 66, Dresden 01062, Germany; E-Mail:;Department of Phytopathology, Federal University of Lavras, P. O. Box 3037, Lavras 37200-000, Brazil; E-Mail:;Department of Systems Biology, Technical University of Denmark, Søltofts Plads, Building 221, Kgs. Lyngby DK-2800, Denmark; E-Mails:

关键词: halogenation;    tryptophan;    rugulovasine;    dereplication;    Talaromyces;   

DOI  :  10.3390/molecules200917627

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.