Induction of secondary metabolites from the marine-derived fungus Aspergillus versicolor through co-cultivation with Bacillus subtilis

Nada M. Abdel-Wahab, Sebastian Scharf, Ferhat C. Özkaya, T. Kurtán, Attila Mándi, Mostafa A. Fouad, Mohamed S. Kamel, Werner E.G. Müller, Rainer Kalscheuer, Wenhan Lin, Georgios Daletos, Weaam Ebrahim, Zhen Liu, Peter Proksch

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3 Citations (Scopus)

Abstract

A new cyclic pentapeptide, cotteslosin C (1), a new aflaquinolone, 22-epi-aflaquinolone B (3), and two new anthraqui-nones (9 and 10), along with thirty known compounds (2, 4–8, 11–34) were isolated from a co-culture of the sponge-associated fungus Aspergillus versicolor with Bacillus subtilis. The new metabolites were only detected in the co-culture extract, but not when the fungus was grown under axenic conditions. Furthermore, the co-culture extract exhibited an enhanced accumulation of the known constituents versicolorin B (14), averufin (16), and sterigmatocyctin (19) by factors of 1.5, 2.0, and 4.7, respectively, compared to the axenic fungal culture. The structures of the isolated compounds were elucidated on the basis of 1D and 2D NMR spectra and mass spectrometry as well as by comparison with literature data. The absolute configuration of compounds 3, 9, and 10 was determined by ECD (electronic circular dichroism) analysis aided by TDDFT-ECD (time-dependent density functional theory electronic circular dichroism) calculations. Compounds 15, 18–21, and 26 exhibited strong to moderate cytotoxic activity against the mouse lymphoma cell line L5178Y, with IC50 values ranging from 2.0 to 21.2 μM, while compounds 14, 16, 31, 32, and 33 displayed moderate inhibitory activities against several gram-positive bacteria, with MIC values ranging from 12.5 to 50 μM.

Original languageEnglish
Pages (from-to)503-512
Number of pages10
JournalPlanta Medica
Volume85
Issue number6
DOIs
Publication statusPublished - Jan 1 2019

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Keywords

  • Antibacterial activity
  • Aspergillus versicolor
  • Co-culture
  • Cyclic pentapeptide
  • Cytotoxicity
  • ECD calculations
  • Sponge-derived fungus

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Abdel-Wahab, N. M., Scharf, S., Özkaya, F. C., Kurtán, T., Mándi, A., Fouad, M. A., Kamel, M. S., Müller, W. E. G., Kalscheuer, R., Lin, W., Daletos, G., Ebrahim, W., Liu, Z., & Proksch, P. (2019). Induction of secondary metabolites from the marine-derived fungus Aspergillus versicolor through co-cultivation with Bacillus subtilis. Planta Medica, 85(6), 503-512. https://doi.org/10.1055/a-0835-2332