Frontiers in Microbiology (Sep 2024)
Aplospojaveedins A–C, unusual sulfur-containing alkaloids produced by the endophytic fungus Aplosporella javeedii using OSMAC strategy
- Ying Gao,
- Ying Gao,
- Marian Frank,
- Nicole Teusch,
- Dennis Woschko,
- Christoph Janiak,
- Attila Mándi,
- Tibor Kurtán,
- Rudolf Hartmann,
- Katja Schiedlauske,
- Lasse van Geelen,
- Rainer Kalscheuer,
- Jesko Kaiser,
- Christoph G. W. Gertzen,
- Holger Gohlke,
- Holger Gohlke,
- Bin-Gui Wang,
- Peter Proksch,
- Zhen Liu
Affiliations
- Ying Gao
- Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha, China
- Ying Gao
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Marian Frank
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Nicole Teusch
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Dennis Woschko
- Institute of Inorganic and Structural Chemistry, Heinrich Heine University, Düsseldorf, Germany
- Christoph Janiak
- Institute of Inorganic and Structural Chemistry, Heinrich Heine University, Düsseldorf, Germany
- Attila Mándi
- Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary
- Tibor Kurtán
- Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary
- Rudolf Hartmann
- Institute of Biological Information Processing: Structural Biochemistry (IBI-7), Forschungszentrum Jülich GmbH, Jülich, Germany
- Katja Schiedlauske
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Lasse van Geelen
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Rainer Kalscheuer
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Jesko Kaiser
- Institute for Pharmaceutical and Medicinal Chemistry, Heinrich Heine University, Düsseldorf, Germany
- Christoph G. W. Gertzen
- Institute for Pharmaceutical and Medicinal Chemistry, Heinrich Heine University, Düsseldorf, Germany
- Holger Gohlke
- Institute for Pharmaceutical and Medicinal Chemistry, Heinrich Heine University, Düsseldorf, Germany
- Holger Gohlke
- Institute of Bio- and Geosciences (IBG-4: Bioinformatics), Forschungszentrum Jülich GmbH, Jülich, Germany
- Bin-Gui Wang
- CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, China
- Peter Proksch
- Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Düsseldorf, Germany
- Zhen Liu
- Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha, China
- DOI
- https://doi.org/10.3389/fmicb.2024.1458622
- Journal volume & issue
-
Vol. 15
Abstract
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
