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Review
. 2022 Jul 25;20(8):474.
doi: 10.3390/md20080474.

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

Salar Hafez Ghoran  1   2 , Fatemeh Taktaz  3   4 , Seyed Abdulmajid Ayatollahi  1 , Anake Kijjoa  5
Affiliations
Review

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

Salar Hafez Ghoran et al. Mar Drugs. .

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.

Keywords: Aspergillus sp.; Penicillium sp.; anthraquinones; antibacterial activity; bianthraquinones; cytotoxicity; hydroanthraquinones; marine-derived fungi.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Plausible biosynthetic pathways of fungal anthraquinones.
Figure 2
Figure 2
Anthraquinone scaffolds reported from marine-derived fungi.
Figure 3
Figure 3
Structures of 1–19.
Figure 4
Figure 4
Structures of 20–43.
Figure 5
Figure 5
Structures of 44–59.
Figure 6
Figure 6
Structures of 60–78.
Figure 7
Figure 7
Structures of 79–95.
Figure 8
Figure 8
Structures of 96 and 97.
Figure 9
Figure 9
Structures of 98–121.
Figure 10
Figure 10
Structures of 122–134 and a plausible biosynthesis of 133 and 134.
Figure 11
Figure 11
Structures of 135–152.
Figure 12
Figure 12
Structures of 153–155.
Figure 13
Figure 13
Structures of 156–159.
Figure 14
Figure 14
Structures of 160–167.
Figure 15
Figure 15
Structures of 168–180.
Figure 16
Figure 16
Structures of 181–189.
Figure 17
Figure 17
Structures of 190–193 and plausible biosynthetic pathways of 190 and 192.
Figure 18
Figure 18
Structures of 194–196 and plausible biosynthetic pathways of 194–196.
Figure 19
Figure 19
Structures of 197–227.
Figure 20
Figure 20
Structures of 228–232.
Figure 21
Figure 21
Plausible biosynthetic pathway for 233.
Figure 22
Figure 22
Structures of 234–236.
Figure 23
Figure 23
Structures of 237 and 238.
Figure 24
Figure 24
Structures of 239–252.
Figure 25
Figure 25
Structures of 253–269.
Figure 26
Figure 26
Structures of 270–278 and a plausible biosynthetic pathway of 278.
Figure 27
Figure 27
Structures of 279–296.
Figure 28
Figure 28
The number of isolated anthraquinone metabolites and their derivatives from the marine-derived fungal resources.
See this image and copyright information in PMC

References

    1. Gladfelter A.S., James T.Y., Amend A.S. Marine fungi. Curr. Biol. 2019;29:R191–R195. doi: 10.1016/j.cub.2019.02.009. - DOI - PubMed
    1. Amend A., Burgaud G., Cunliffe M., Edgcomb V.P., Ettinger C.L., Gutiérrez M., Heitman J., Hom E.F., Ianiri G., Jones A.C. Fungi in the marine environment: Open questions and unsolved problems. MBio. 2019;10:e01189-18. doi: 10.1128/mBio.01189-18. - DOI - PMC - PubMed
    1. Kis-papo T. Marine fungal communities. In: Dighton J., White J.F., Oudemans P., editors. The Fungal Community: Its Organization and Role in the Ecosystem. 3rd ed. Volume 23. CRC Press; Boca Raton, FL, USA: Taylor & Francis Group; Oxfordshire, UK: 2005. pp. 61–92.
    1. Kohlmeyer J., Kohlmeyer E. Marine Mycology, the Higher Fungi. Academic Press; New York, NY, USA: 1979. pp. 1–3.
    1. Pang K.-L., Overy D.P., Jones E.G., da Luz Calado M., Burgaud G., Walker A.K., Johnson J.A., Kerr R.G., Cha H.-J., Bills G.F. ‘Marine fungi’and ‘marine-derived fungi’in natural product chemistry research: Toward a new consensual definition. Fungal Biol. Rev. 2016;30:163–175. doi: 10.1016/j.fbr.2016.08.001. - DOI

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