Acremochlorin S and other prenylated chlorophenol antimicrobial metabolites from the fungus Acremonium sp. Strain MNA-F-1

Mohamed S Elnaggar; Nada M Mostafa; Ahmed M Elissawy; Kunthida Phutthacharoen; Paul Eckhardt; Birthe Sandargo; Lasse van Geelen; Sherif S Ebada; Till Opatz; Abdel Nasser B Singab; Rainer Kalscheuer

doi:10.1016/j.fitote.2024.106254

Acremochlorin S and other prenylated chlorophenol antimicrobial metabolites from the fungus Acremonium sp. Strain MNA-F-1

Fitoterapia. 2024 Dec:179:106254. doi: 10.1016/j.fitote.2024.106254. Epub 2024 Oct 11.

Authors

Affiliations

¹ Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität, 40225 Düsseldorf, Germany; Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, 11566 Cairo, Egypt.
² Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, 11566 Cairo, Egypt.
³ Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, 11566 Cairo, Egypt; Center of Drug Discovery Research and Development, Ain Shams University, 11566 Cairo, Egypt.
⁴ Center of Excellence in Fungal Research, Mae Fah Luang University, Chiang Rai 57100, Thailand; School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand.
⁵ Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
⁶ Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), 38124 Braunschweig, Germany.
⁷ Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität, 40225 Düsseldorf, Germany.
⁸ Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, 11566 Cairo, Egypt. Electronic address: [email protected].
⁹ Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, 11566 Cairo, Egypt; Center of Drug Discovery Research and Development, Ain Shams University, 11566 Cairo, Egypt. Electronic address: [email protected].
¹⁰ Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität, 40225 Düsseldorf, Germany. Electronic address: [email protected].

PMID: 39396652
DOI: 10.1016/j.fitote.2024.106254

Abstract

Chemical prospection for the mycelial extract of the fungus Acremonium sp. Strain MNA-F-1, derived from the inner tissue of anise roots (Pimpnella anisum L., family Apiaceae), led to the isolation and characterization of one previously undescribed natural product, acremochlorin S (1), together with five related derivatives (2-6) and an alkaloidal metabolite, ilicicolin H (7). Structure elucidation of the isolated compounds was determined through comprehensive 1D/2D NMR spectroscopic analyses and HR-ESI-MS measurements. The absolute configuration of acremochlorin S (1) was concluded based on the comparison of its experimental and calculated electronic circular dichroism (ECD) spectra implementing Time-dependent density functional theory (TDDFT). All isolated compounds were assessed for their antibacterial activity against Staphylococcus aureus, Escherichia coli and Mycobacterium tuberculosis, where several compounds revealed potent activities against tested Gram-positive strains.

Keywords: Acremonium sp.; Antitubercular; Fungal endophyte; Prenylated chlorophenols.

MeSH terms

Acremonium* / chemistry
Anti-Bacterial Agents* / chemistry
Anti-Bacterial Agents* / isolation & purification
Anti-Bacterial Agents* / pharmacology
Chlorophenols* / pharmacology
Escherichia coli / drug effects
Microbial Sensitivity Tests
Molecular Structure
Mycobacterium tuberculosis / drug effects
Plant Roots / chemistry
Prenylation
Staphylococcus aureus / drug effects

Substances

Anti-Bacterial Agents
Chlorophenols