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Review
. 2023 Jul 10;14(8):1446-1471.
doi: 10.1039/d3md00116d. eCollection 2023 Aug 16.

Antibacterial activities of anthraquinones: structure-activity relationships and action mechanisms

Tang Qun  1 , Tiantian Zhou  2 , Jiongkai Hao  1 , Chunmei Wang  1   3 , Keyu Zhang  1   3 , Jing Xu  4 , Xiaoyang Wang  1   3 , Wen Zhou  1   3
Affiliations
Review

Antibacterial activities of anthraquinones: structure-activity relationships and action mechanisms

Tang Qun et al. RSC Med Chem. .

Abstract

With the increasing prevalence of untreatable infections caused by antibiotic-resistant bacteria, the discovery of new drugs from natural products has become a hot research topic. The antibacterial activity of anthraquinones widely distributed in traditional Chinese medicine has attracted much attention. Herein, the structure and activity relationships (SARs) of anthraquinones as bacteriostatic agents are reviewed and elucidated. The substituents of anthraquinone and its derivatives are closely related to their antibacterial activities. The stronger the polarity of anthraquinone substituents is, the more potent the antibacterial effects appear. The presence of hydroxyl groups is not necessary for the antibacterial activity of hydroxyanthraquinone derivatives. Substitution of di-isopentenyl groups can improve the antibacterial activity of anthraquinone derivatives. The rigid plane structure of anthraquinone lowers its water solubility and results in the reduced activity. Meanwhile, the antibacterial mechanisms of anthraquinone and its analogs are explored, mainly including biofilm formation inhibition, destruction of the cell wall, endotoxin inhibition, inhibition of nucleic acid and protein synthesis, and blockage of energy metabolism and other substances.

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Conflict of interest statement

The authors confirm that this review article has no conflicts of interest.

Figures

Fig. 1
Fig. 1. Interconversion of the anthraquinone parent nucleus with different redox degrees.
Fig. 2
Fig. 2. The structure–activity relationships of anthraquinones.
Fig. 3
Fig. 3. Cleavage mechanism of 9,10 monoalkoxy anthracene under the action of singlet oxygen.
Fig. 4
Fig. 4. Antibacterial structure–activity relationship of hydrogenated anthraquinone derivatives.
Fig. 5
Fig. 5. Antibacterial structure–activity relationship of mangostin derivatives.
Fig. 6
Fig. 6. Structure–activity relationship of oxaanthone, thiaanthone, azaanthone.
Fig. 7
Fig. 7. 7A1 The original five-step model of biofilm development. 1) In the reversible attachment stage, bacteria attach to the substrate surface non-specifically; 2) in the irreversible attachment stage, bacteria interact with the substrate surface through adhesion protein or adhesion factor; 3) at the micro colony formation stage, bacteria produce extracellular polymers; 4) in the mature stage of the biofilm, bacteria synthesize and release signal molecules; 5) in the bacterial abscission/diffusion stage, bacteria leave the biofilm and return to an independent planktonic lifestyle; 7A2. Expanded conceptual model of biofilm formation; 7B1. The general structure of lipopolysaccharide (LPS), based on that present in E. coli; 7B2. The biosynthetic pathway of lipopolysaccharide in E. coli. The name of the enzyme is highlighted in red, and the name of the substrate is highlighted in blue; 7C1. The peptidoglycan biosynthetic pathway and sites of action of natural product inhibitors. MurA, known as enol acetone transferase, MurB flavin dependent reductase, MurC, MurD, MurE, and MurF, are four kinds of amino acid ligases, bacterial transposase (MraY), and MurG are transferases responsible for the synthesis of lipid II. 7C2. Antibacterial targets acting on the cell wall. 7D. Purpurin's antibacterial mechanisms.
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