Bifusicoumarins A-D: Cytotoxic 3S-dihydroisocoumarins from the entomopathogenic fungus Cordyceps bifusispora (NBRC 108997)

Abdelsamed I Elshamy; Tarik A Mohamed; Tatsuro Yoneyama; Masaaki Noji; Sayaka Ban; Hiroshi Imagawa; Thomas Efferth; Mohamed-Elamir F Hegazy; Akemi Umeyama

doi:10.1016/j.phytochem.2023.113743

Bifusicoumarins A-D: Cytotoxic 3S-dihydroisocoumarins from the entomopathogenic fungus Cordyceps bifusispora (NBRC 108997)

Phytochemistry. 2023 Aug:212:113743. doi: 10.1016/j.phytochem.2023.113743. Epub 2023 Jun 1.

Authors

Abdelsamed I Elshamy¹, Tarik A Mohamed², Tatsuro Yoneyama³, Masaaki Noji³, Sayaka Ban⁴, Hiroshi Imagawa³, Thomas Efferth⁵, Mohamed-Elamir F Hegazy⁶, Akemi Umeyama⁷

Affiliations

¹ Chemistry of Natural Compounds Department, National Research Centre, 33 El Bohouth St., Dokki, Giza, 12622, Egypt. Electronic address: elshamynrc@yahoo.com.
² Chemistry of Medicinal Plants Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza, 12622, Egypt.
³ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan.
⁴ Medical Mycology Research Center, Chiba University, Japan.
⁵ Department of Pharmaceutical Biology, Institute of Pharmaceutical and Biomedical Sciences, Johannes Gutenberg University, Staudinger Weg 5, Mainz 55128, Germany.
⁶ Chemistry of Medicinal Plants Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza, 12622, Egypt; Department of Pharmaceutical Biology, Institute of Pharmaceutical and Biomedical Sciences, Johannes Gutenberg University, Staudinger Weg 5, Mainz 55128, Germany. Electronic address: mohegazy@uni-mainz.de.
⁷ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan. Electronic address: umeyama@ph.bunri-u.ac.jp.

PMID: 37269936
DOI: 10.1016/j.phytochem.2023.113743

Abstract

Cordyceps is a genus of ascomycete fungi with some of them being edible and/or having a long tradition in Chinese medicine. The chemical characterization of a solvent extract of the entomopathogenic fungus Cordyceps bifusispora afforded four undescribed coumarins, bifusicoumarin A-D (1-4), along with previously reported metabolites (5-8). Structural elucidation was performed via NMR, UV and HRMS analyses, X-ray single crystal diffraction and experimental ECD. A high throughput resazurin reduction assay, that measures cell viability, indicated that 5 has a IC₅₀ between 1 and 15 μM for several assayed tumor lines. Moreover, a protein-interaction network indicated that C. bifusispora is a promising source of additional antitumor metabolites based on SwissTargetPrediction software predictions.

Keywords: 3S-dihydroisocoumarins; Anticancer; Bifusicoumarin; Cordyceps bifusispora; Multidrug resistance; X-ray.

MeSH terms

Antineoplastic Agents* / pharmacology
Cell Survival
Cordyceps* / chemistry
Cordyceps* / metabolism
Solvents

Substances

Antineoplastic Agents
Solvents

Supplementary concepts

Cordyceps bifusispora