Natural polyketide 6-pentyl-2H-pyrone-2-one and its synthetic analogues efficiently prevent marine biofouling

Abstract

Biofouling is a widespread phenomenon in oceans worldwide. With increasing human development and activities in open and coastal waters, and due to the environmental impact of AF organotins and copper-based paint, the demand for nontoxic antifouling (AF) paints is increasing. Various bioassays for antimicrobial activity, anti-biofilm formation and anti-barnacle settlement were established to evaluate the possibility of using marine natural products as AF agents. A series of natural products, isolated from the marine-derived fungi Trichoderma atroviride and T. reesei, were evaluated for their AF activity. One pyrone-type compound (1) demonstrated significant inhibitory activities toward barnacle cyprid settlement. Furthermore, a series of pyrone analogues (S1–S6) were synthesized, and their bioactivities were evaluated in the established systems. The results showed that compounds S5 and S6 exhibited a broad spectrum of bioactivities, such as anti-barnacle settlement, anti-biofilm formation and antimicrobial activities.

GRAPHICAL ABSTRACT

Keywords:

• Marine-derived fungi
• secondary metabolites
• synthetic pyrones
• antifouling agents
• antimicrobial activity
• anti-biofilm formation

Acknowledgements

The authors appreciate Mr Guo-Kai Hong’s assistance on the barnacle cyprid screening assay. This manuscript was edited by Wallace Academic Editing.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This research work was supported in part by a Ministry of Science and Technology, Taiwan grant [MOST108-2320-B-110-006-MY3], a grant from the National Sun Yat-sen University-Kaohsiung Medical University Joint Research Project [NSYSU-KMU 109-I005] and by the Taiwan Protein Project [grant number AS-KPQ-109-TPP2] to CCL.