Anthraquinones and Their Analogues from Marine-Derived Fungi: Chemistry and Biological Activities

Abstract

Anthraquinones are an interesting chemical class of polyketides since they not only exhibit a myriad of biological activities but also contribute to managing ecological roles. In this review article, we provide a current knowledge on the anthraquinoids reported from marine-derived fungi, isolated from various resources in both shallow waters such as mangrove plants and sediments of the mangrove habitat, coral reef, algae, sponges, and deep sea. This review also tentatively categorizes anthraquinone metabolites from the simplest to the most complicated scaffolds such as conjugated xanthone–anthraquinone derivatives and bianthraquinones, which have been isolated from marine-derived fungi, especially from the genera Apergillus, Penicillium, Eurotium, Altenaria, Fusarium, Stemphylium, Trichoderma, Acremonium, and other fungal strains. The present review, covering a range from 2000 to 2021, was elaborated through a comprehensive literature search using the following databases: ACS publications, Elsevier, Taylor and Francis, Wiley Online Library, MDPI, Springer, and Thieme. Thereupon, we have summarized and categorized 296 anthraquinones and their derivatives, some of which showed a variety of biological properties such as enzyme inhibition, antibacterial, antifungal, antiviral, antitubercular (against Mycobacterium tuberculosis), cytotoxic, anti-inflammatory, antifouling, and antioxidant activities. In addition, proposed biogenetic pathways of some anthraquinone derivatives are also discussed.

Biosynthetic Pathways of Dimeric Natural Products Containing Bisanthraquinone and Related Xanthones

“…Anthraquinone [16–21] and the related xanthone [22–31] are important skeletons widely occurring in bioactive compounds with the anticancer, anti‐inflammatory, antifungal, antibacterial, antiviral, and neuroprotection effects. In addition to anthraquinone and the related xanthone monomers, dimeric natural products containing bisanthraquinone [32] and related xanthones [33] show not only great bioactivities against bacteria and cancer cells, also excellent photodynamic activity for potential applications in photodynamic therapy (Figure 1).…”

“…[10][11][12][13] Moreover, the study on the gene cluster and biosynthetic pathways of natural products attracts attention of chemists, biologists, and pharmacists, because they might help scientists improve the production through metabolic engineering and modify the structure by enzyme engineering to produce a series of derivatives. [14,15] Anthraquinone [16][17][18][19][20][21] and the related xanthone [22][23][24][25][26][27][28][29][30][31] are important skeletons widely occurring in bioactive compounds with the anticancer, anti-inflammatory, antifungal, antibacterial, antiviral, and neuroprotection effects. In addition to anthraquinone and the related xanthone monomers, dimeric natural products containing bisanthraquinone [32] and related xanthones [33] show not only great bioactivities against bacteria and cancer cells, also excellent photodynamic activity for potential applications in photodynamic therapy (Figure 1).…”

Integrating Enzymes with Supramolecular Polymers for Recyclable Photobiocatalytic Catalysis

“…[39] Moreover, AQ is known as electron acceptors/donors in key biological processes, suggesting its biocompatibility and harmlessness to enzymes. [40] Furthermore, the blocks of Ada and AQ were incorporated into the polymers for their host-guest interactions with β-CD, [41] along with ammonium groups interacting with negative charges on SupEnzyme. Following the same procedure as described for SupEnzyme/PAD, the addition of PAD-AQ to SupEnzyme successfully enabled the supramolecular aggregates, denoted as SupEnzyme/PAD-AQ (Figure 3a), which could be easily identified as shown in Figure 2b.…”

Quinones as Promising Compounds against Respiratory Viruses: A Review

“…Likewise, anthraquinones can have various substituents such as -CH 3 , -OCH 3 , -OH, -CHO, -COOH, -CH 2 OH, and/or more complex groups. Anthraquinone derivatives include hydroanthraquinones (compounds obtained by the reduction of double bonds in the benzene ring), anthrols (analogs with one -OH group in the central ring), anthrones (derivatives with one carbonyl group in the central ring), dimeric anthraquinones, and naphthodianthrones [ 93 , 94 , 95 ]. The chemical structures of the different types of quinones are represented in Figure 2 .…”