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ORIGINAL RESEARCH article

Front. Microbiol.
Sec. Microbiotechnology
Volume 15 - 2024 | doi: 10.3389/fmicb.2024.1458622

Aplospojaveedins A-C, unusual sulfur-containing alkaloids produced by the endophytic fungus Aplosporella javeedii using OSMAC strategy

Provisionally accepted
Ying Gao Ying Gao 1,2Marian Frank Marian Frank 2Nicole E. Teusch Nicole E. Teusch 2Dennis Woschko Dennis Woschko 3Christoph Janiak Christoph Janiak 3Attila Mándi Attila Mándi 4Tibor Kurtán Tibor Kurtán 4Rudolf Hartmann Rudolf Hartmann 5Katja Schiedlauske Katja Schiedlauske 2Lasse van Geelen Lasse van Geelen 2Rainer Kalscheuer Rainer Kalscheuer 2Jesko Kaiser Jesko Kaiser 6Christoph G. Gertzen Christoph G. Gertzen 6Holger Gohlke Holger Gohlke 6,7Bin-Gui Wang Bin-Gui Wang 8Peter Proksch Peter Proksch 2Zhen Liu Zhen Liu 1*
  • 1 Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha, China
  • 2 Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University of Düsseldorf, Düsseldorf, Germany
  • 3 Institute of Inorganic and Structural Chemistry, Heinrich Heine University, Düsseldorf, Germany
  • 4 University of Debrecen, Debrecen, Hajdu-Bihar, Hungary
  • 5 Structural Biochemistry (IBI-7), Institute of Biological Information processing, Julich Research Center, Helmholtz Association of German Research Centres (HZ), Jülich, North Rhine-Westphalia, Germany
  • 6 Institute for Pharmaceutical and Medicinal Chemistry, Heinrich Heine University of Düsseldorf, Düsseldorf, North Rhine-Westphalia, Germany
  • 7 Bioinformatics (IBG-4), Institute of Bio- and Geosciences, Julich Research Center, Helmholtz Association of German Research Centres (HZ), Jülich, North Rhine-Westphalia, Germany
  • 8 Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences (CAS), Qingdao, Shandong Province, China

The final, formatted version of the article will be published soon.

    Three sulfur-containing alkaloids aplospojaveedins A-C (1-3) with a hitherto undescribed carbon skeleton comprising octahy-dronaphthalene, α, β-unsaturated lactam and glycine-cysteine moieties were isolated from Aplosporella javeedii. Their structures were elucidated by 1D and 2D NMR spectroscopy, HR-MS, X-ray diffraction analysis, DFT-NMR and TDDFT-ECD calculations. A plausible biosynthetic pathway and putative targets are described. The blind docking suggested that 1 -3 may have functional effects on several putative targets such as the GPCR cannabinoid receptor 2 or the integrin α5β1 complex.

    Keywords: Aplosporella javeedii, Alkaloids, OSMAC approach, X-Ray Diffraction, DFT-NMR calculations, TDDFT-ECD calculations, target prediction

    Received: 02 Jul 2024; Accepted: 18 Sep 2024.

    Copyright: © 2024 Gao, Frank, Teusch, Woschko, Janiak, Mándi, Kurtán, Hartmann, Schiedlauske, van Geelen, Kalscheuer, Kaiser, Gertzen, Gohlke, Wang, Proksch and Liu. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

    * Correspondence: Zhen Liu, Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha, China

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