Results
Natural secondary metabolites provide an ample source of bioactive compounds with numerous applications, e.g. in the agricultural sector for pest management. Derivatization of their chemical structures is a powerful means to obtain tailored compounds with enhanced bioactivity. The TaiLead project aimed at contributing to the development of sustainable crop protection solutions against the serious pest Heterodera schachtii, a plant parasitic nematode. We could build on previous work within the BioSC, including in particular the CombiCom FocusLab, where natural products, which are produced by soil-dwelling bacteria, were found to be active against the pathogen. We hence established an effective production of specific new prodiginine tripyrroles, and investigated their specific bioactivity alone and in combination with rhamnolipids. Like prodiginines, these biosurfactants are on their own effective against nematodes, but have never been assessed in combinatorial applications with them. In our studies, we focused on prodiginines, which are decorated with a hydroxyl group at the alkyl chain of the C-pyrrole ring. We therefore established a hybrid muta- and semisynthesis production strategy. We realized mutasynthesis by utilizing a new Pseudomonas putida KT2440-derived strain for the effective biosynthesis of a bipyrrole precursor, and for the conversion of supplemented, chemically synthesized monopyrrole precursors into tripyrroles with an ω-alkenyl chain. Semisynthesis facilitated introduction of the hydroxyl group. Therefore, a feasible production route to new prodiginines was established. The prodiginines reduced nematode fitness and infection of Arabidopsis and sugar beet plants. In combination with rhamnolipids, effectivity was found to be enhanced: For a reduction of nematode infection by ~50%, only ca. ¼ of each compound was needed compared to the required amounts when the compounds were applied alone. In summary, we therefore developed a production route towards hydroxyl prodiginines and demonstrate a potential applicability – especially in combination with rhamnolipids – as antinematodal agents.
Dr. Anita Loeschcke
Molecular Enzyme Technology (IMET)
Heinrich Heine University Düsseldorf
phone: +49 2461 613790
Email: a.loeschcke@fz-juelich.de
Prof. Jörg Pietruszka, Dr. Thomas Classen, IBOC – Bioorganic Chemistry, HHUD.
Prof. Dr. Florian Grundler, Dr. Sylvia Schleker, INRES – Molecular Phytomedicine, Rhenish Friedrich-Wilhelms University Bonn.
01.08.2020 - 31.10.2021
TaiLead is is part of the NRW-Strategieprojekt BioSC and thus funded by the Ministry of Culture and Science of the German State of North Rhine-Westphalia.
Kossmann, DF, Huang, M, Weihmann, R, Xiao, X, Gätgens, F, Weber, TM, Brass, HUC, Bitzenhofer, NL, Ibrahim, S, Bangert, K, Rehling, L, Mueller, C, Tiso, T, Blank, LM, Drepper, T, Jaeger, K-E, Grundler, FMW, Pietruszka, J, Schleker, ASS and Loeschcke, A (2023). Production of tailored hydroxylated prodiginine showing combinatorial activity with rhamnolipids against plant-parasitic nematodes. Frontiers in Microbiology 14.
Johann, S, Weichert, FG, Schröer, L, Stratemann, L, Kämpfer, C, Seiler, T-B, Heger, S, Töpel, A, Sassmann, T, Pich, A, Jakob, F, Schwaneberg, U, Stoffels, P, Philipp, M, Terfrüchte, M, Loeschcke, A, Schipper, K, Feldbrügge, M, Ihling, N, Büchs, J, Bator, I, Tiso, T, Blank, LM, Roß-Nickoll, M and Hollert, H (2022). A plea for the integration of Green Toxicology in sustainable bioeconomy strategies – Biosurfactants and microgel-based pesticide release systems as examples. Journal of Hazardous Materials 426: 127800.
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