A Fungal N-Dimethylallyltryptophan Metabolite from Fusarium fujikuroi

Birgit Arndt; Slavica Janevska; Robin Schmid; Florian Hübner; Bettina Tudzynski; Hans-Ulrich Humpf

doi:10.1002/cbic.201600691

A Fungal N-Dimethylallyltryptophan Metabolite from Fusarium fujikuroi

Chembiochem. 2017 May 18;18(10):899-904. doi: 10.1002/cbic.201600691. Epub 2017 Apr 13.

Authors

Birgit Arndt¹, Slavica Janevska², Robin Schmid¹, Florian Hübner¹, Bettina Tudzynski², Hans-Ulrich Humpf¹

Affiliations

¹ Institute of Food Chemistry, University of Münster, Corrensstrasse 45, 48149, Münster, Germany.
² Institute of Plant Biology and Biotechnology, University of Münster, Schlossplatz 8, 48143, Münster, Germany.

PMID: 28295904
DOI: 10.1002/cbic.201600691

Abstract

The range of secondary metabolites (SMs) produced by the rice pathogen Fusarium fujikuroi is quite broad. Several polyketides, nonribosomal peptides and terpenes have been identified. However, no products of dimethylallyltryptophan synthases (DMATSs) have been elucidated, although two putative DMATS genes are present in the F. fujikuroi genome. In this study, the in vivo product derived from one of the DMATSs (DMATS1, FFUJ_09179) was identified with the help of the software MZmine 2. Detailed structure elucidation showed that this metabolite is a reversely N-prenylated tryptophan with a rare form of prenylation. Further identified products probably resulted from side reactions of DMATS1. The genes adjacent to DMATS1 were analyzed; this showed no influence on the biosynthesis of the product.

Keywords: NMR spectroscopy; alkaloids; biosynthesis; mass spectrometry; natural products.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkyl and Aryl Transferases / metabolism*
Fungal Proteins / metabolism*
Fusarium / metabolism*
Oryza / microbiology
Prenylation
Tryptophan / metabolism*

Substances

Fungal Proteins
Tryptophan
Alkyl and Aryl Transferases
tryptophan dimethylallyltransferase