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Bioorg Chem. 2019 Jul 22;91:103140. doi: 10.1016/j.bioorg.2019.103140. [Epub ahead of print]

Tyrosol from marine Fungi, a novel Quorum sensing inhibitor against Chromobacterium violaceum and Pseudomonas aeruginosa.

Author information

1
Fujian Provincial University Engineering Research Center of Industrial Biocatalysis, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, College of Chemistry and Materials Science, Fujian Normal University, 32 Shangsan Road, Fuzhou 350007, People's Republic of China.
2
Department of Natural Medicine and Pharmacognosy, School of Pharmacy, Qingdao University, 308 Ningxia Road, Qingdao 266071, People's Republic of China.
3
Centre for Bioengineering and Biotechnology, China University of Petroleum (East China), 66 Changjiang West Road, Qingdao 266580, People's Republic of China.
4
Fujian Provincial University Engineering Research Center of Industrial Biocatalysis, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, College of Chemistry and Materials Science, Fujian Normal University, 32 Shangsan Road, Fuzhou 350007, People's Republic of China. Electronic address: zhuhu@fjnu.edu.cn.

Abstract

An ethyl acetate extracts isolated from a marine fungal strain, Penicillium chrysogenum DXY-1, obtained from marine sediments surrounding the East Sea, was found to exhibit anti-quorum sensing (anti-QS) activity. Interestingly, a novel active compound was identified as tyrosol by the purification and structural characterization. At a concentration of 0.5 mg/mL, tyrosol decreased QS-regulated violacein production in Chromobacterium violaceum CV026 by 53.5% and decreased QS-regulated pyocyanin production, elastase activity and proteolytic activity in Pseudomonas aeruginosa PA01 by 63.3%, 57.8% and 9.9%, respectively. SEM images showed that tyrosol inhibited biofilm formation in P. aeruginosa PA01 without having any effect on bacterial growth. Molecular docking results revealed that the natural signal molecule C6HSL and tyrosol bound to different receptor pockets of CviR, and tyrosol inhibited the QS activity of CviR in C. violaceum by binding to the DNA-binding domain and blocking pathogenic gene expression. All the data suggest that tyrosol may act as a potential inhibitor of the QS systems to solve the looming crisis of bacterial resistance. We believe that there are other active compounds with relatively high anti-QS activity or synergistic inhibitory effects on QS in the crude extract, which warrants further research.

KEYWORDS:

Inhibitor; Penicillium chrysogenum DXY-1; Quorum sensing; Tyrosol

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