Eight new cyclopentenone and cyclohexenone derivatives from the marine-derived fungus Aspergillus sp. SCSIO 41501 by OSMAC strategy

Abstract

One strain many compounds (OSMAC) strategy was an effective method to activate the silent biosynthetic genes of microorganisms. Comparison with our previous investigations on the secondary metabolites of the marine-derived fungus Aspergillus sp. SCSIO 41501, in this study, three new cyclopentenone derivatives, aspergispones A-C (1–3), and five new cyclohexenone derivatives, aspergispones D-H (4–8), together with two known analogues, were further isolated from the fungal strain by altering culture medium compositions. The structures of new compounds were elucidated by extensive spectroscopic analysis. And the absolute configurations of 4 and 7 were further confirmed by single-crystal X-ray diffraction experiments.

Graphical Abstract

Keywords:

• Marine-derived fungus
• Aspergillus sp.
• cyclopentenone
• cyclohexanone
• single-crystal X-ray
• OSMAC strategy

Acknowledgments

The authors are grateful for the financial support provided by the Guangdong Provincial-level Special Funds for Promoting High-quality Economic Development (NO25), National Natural Science Foundation of China (81673326), Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (GML2019ZD0406), and Regional Innovation Demonstration Project of Guangdong Province Marine Economic Development (GD2012-D01-002).

The authors also wished to appreciate the analytical facility center (Z. Xiao, A. Sun, X. Ma) of the South China Sea Institute of Oceanology, Chinese Academy of Sciences for acquiring NMR, HRESIMS, experimental CD data, testing X-ray data, and the use of the HPCC for all numeric simulations.

Disclosure statement

The authors declare no conflict of interest.