title: A Fungal N-Dimethylallyltryptophan Metabolite from Fusarium fujikuroi.
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.
authors.affiliation: Institute of Food Chemistry, University of Münster, Corrensstrasse 45, 48149, Münster, Germany.
authors.forename: Birgit
authors.initials: B
authors.lastname: Arndt
authors.affiliation: Institute of Plant Biology and Biotechnology, University of Münster, Schlossplatz 8, 48143, Münster, Germany.
authors.forename: Slavica
authors.initials: S
authors.lastname: Janevska
authors.affiliation: Institute of Food Chemistry, University of Münster, Corrensstrasse 45, 48149, Münster, Germany.
authors.forename: Robin
authors.initials: R
authors.lastname: Schmid
authors.affiliation: Institute of Food Chemistry, University of Münster, Corrensstrasse 45, 48149, Münster, Germany.
authors.forename: Florian
authors.initials: F
authors.lastname: Hübner
authors.affiliation: Institute of Plant Biology and Biotechnology, University of Münster, Schlossplatz 8, 48143, Münster, Germany.
authors.forename: Bettina
authors.initials: B
authors.lastname: Tudzynski
authors.affiliation: Institute of Food Chemistry, University of Münster, Corrensstrasse 45, 48149, Münster, Germany.
authors.forename: Hans-Ulrich
authors.identifier: 0000-0003-3296-3058
authors.initials: HU
authors.lastname: Humpf
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000378:metabolism*; D005656:Fungal Proteins / Q000378:metabolism*; D005670:Fusarium / Q000378:metabolism*; D012275:Oryza / Q000382:microbiology; D054876:Prenylation; D014364:Tryptophan / Q000378:metabolism*
chemical_list: D005656:Fungal Proteins; D014364:Tryptophan; D019883:Alkyl and Aryl Transferases; C032409:tryptophan dimethylallyltransferase
keywords: NMR spectroscopy; alkaloids; biosynthesis; mass spectrometry; natural products