Laburnicolamine: A Rare Penillic Acid Congener from the Nematode Cyst‐Associated Fungus Laburnicola nematophila

Author:

Wennrich Jan‐Peer12ORCID,Holzenkamp Caren12ORCID,Ashrafi Samad34,Maier Wolfgang3ORCID,Wang Hao5ORCID,Ibrahim Mahmoud A. A.67ORCID,Ebada Sherif S.18ORCID,Stadler Marc12ORCID

Affiliation:

1. Department of Microbial Drugs Helmholtz Centre for Infection Research (HZI) and German Centre for Infection Research Inhoffenstrasse 7 38124 Braunschweig Germany

2. Institute of Microbiology Technische Universität Braunschweig Spielmannstraße 7 38106 Braunschweig Germany

3. Institute for Epidemiology and Pathogen Diagonstics Julius Kühn Institute (JKI) – Federal Research Center for Cultivated Plants Messeweg 11–12 38104 Braunschweig Germany

4. Institute for Crop and Soil Science Julius Kühn Institute (JKI) – Federal Research Centre for Cultivated Plants Bundesallee 58 38116 Braunschweig Germany

5. Key Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province Institute of Tropical Bioscience and Biotechnology Chinese Academy of Tropical Agricultural Sciences Haikou Hainan 571101 China

6. Computational Chemistry Laboratory Chemistry Department Faculty of Science Minia University Minia 61519 Egypt

7. School of Health Sciences University of KwaZulu-Natal Westville Durban 4000 South Africa

8. Department of Pharmacognosy Faculty of Pharmacy Ain Shams University Cairo 11566 Egypt

Abstract

AbstractA chemical investigation of a methanol extract derived from a solid‐state rice culture of the nematode‐cyst associated fungus Laburnicola nematophila K01 led to the isolation and characterization of a previously undescribed penillic acid analogue named laburnicolamine (1). The chemical structure was elucidated through comprehensive 1D and 2D NMR spectroscopic analyses in methanol‐d4 and DMSO‐d6, alongside with HR‐ESI‐MS spectrometry. The absolute configuration of 1 was concluded through the electronic circular dichroism (ECD) and time‐dependent density functional theory‐ECD (TDDFT‐ECD) computations compared to its acquired spectrum. Biological assays revealed that compound 1 exhibited no significant cytotoxic, antimicrobial, or nematicidal activity.

Publisher

Wiley

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