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. 2016 Aug 18;21(8):1084.
doi: 10.3390/molecules21081084.

Antibacterial Activity and Membrane-Disruptive Mechanism of 3-p-trans-Coumaroyl-2-hydroxyquinic Acid, a Novel Phenolic Compound from Pine Needles of Cedrus deodara, against Staphylococcus aureus

Yanping Wu  1 , Jinrong Bai  2 , Kai Zhong  3 , Yina Huang  4 , Huayi Qi  5 , Yan Jiang  6 , Hong Gao  7
Affiliations

Antibacterial Activity and Membrane-Disruptive Mechanism of 3-p-trans-Coumaroyl-2-hydroxyquinic Acid, a Novel Phenolic Compound from Pine Needles of Cedrus deodara, against Staphylococcus aureus

Yanping Wu et al. Molecules. .

Abstract

Recently, we reported that a novel phenolic compound isolated from Cedrus deodara, 3-p-trans-coumaroyl-2-hydroxyquinic acid (CHQA), exhibits a potent antioxidant activity. The present study aimed to evaluate the antibacterial activity of CHQA against eleven food-borne pathogens and to elucidate its mechanism of action against Staphylococcus aureus. The results from minimum inhibitory concentration (MIC) determinations showed that CHQA exhibited moderate inhibitory effects on all of the tested pathogens with MIC values ranging from 2.5-10 mg/mL. Membrane potential measurements and flow cytometric analysis demonstrated that CHQA damaged the cytoplasmic membrane of S. aureus, causing a significant membrane hyperpolarization with a loss of membrane integrity. Moreover, CHQA induced an increase in membrane fluidity and conformational changes in membrane protein of S. aureus, suggesting that CHQA probably acts on the cell membrane by interactions with membrane lipid and protein. Transmission electron microscopic observations further confirmed that CHQA disrupted the cell membrane of S. aureus and caused severe morphological changes, which even led to leakage of intracellular constituents. These findings indicated that CHQA could have the potential to serve as a natural antibacterial agent to control and prevent the growth of pathogens in food and in food-processing environments.

Keywords: Staphylococcus aureus; antibacterial activity; antibacterial mechanism; membrane damage; phenolic compound.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of 3-p-trans-coumaroyl-2-hydroxyquinic acid (CHQA, 1) and chlorogenic acid (2).
Figure 2
Figure 2
Effect of CHQA on the membrane potential of S. aureus ATCC 6538. Bars represent the standard deviation (n = 3). ** p < 0.01.
Figure 3
Figure 3
Flow cytometric analysis of SYTO 9-PI (propidium iodide)-stained S. aureus ATCC 6538. (A) untreated; (B) treated with CHQA at 2 × MIC for 3 h; (C) treated with 70% isopropyl alcohol for 3 h. Regions R1 and R2 represent the membrane damaged or dead cells and live cells, respectively.
Figure 4
Figure 4
Effect of CHQA on the membrane fluidity of S. aureus ATCC 6538. Bars represent the standard deviation (n = 3). ** p < 0.01.
Figure 5
Figure 5
Effect of CHQA on fluorescence intensity of the S. aureus ATCC 6538 membrane protein at λex 258 nm.
Figure 6
Figure 6
Transmission electron microscopy images of S. aureus ATCC 6538. (A) untreated bacteria; (B) and (C) bacteria treated with CHQA at 2 × MIC for 6 h.
See this image and copyright information in PMC

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