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Mycol Prog
2022 Jan 01;213:38. doi: 10.1007/s11557-022-01790-4.
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Fungal perylenequinones.
Khiralla A
,
Mohammed AO
,
Yagi S
.
Abstract
Perylenequinones (PQs) are aromatic polyketides with an oxidized pentacyclic core that make up a family of natural compounds. Naturally occurring PQs mostly are produced by phytopathogenic fungi, with few aphides, crinoids, and plants. PQs, also known as photosensitizers, absorb light energy which empowers them to produce reactive oxygen species that damage host cells. Therefore, PQs gained a considerable interest in pharmaceutical application notably in photodynamic therapy. This review presents a comprehensive overview of fungal PQs. Their occurrence, categorization, biosynthesis, structures, and bioactivities are all discussed in detail. After that, an analysis outlines their distribution across the kingdom of fungi. A total of 66 fungal PQs have been described from 22 ascomycete genera (Alternaria, Aspergillus, Bulgaria, Cenococcum, Cercospora, Cladosporium, Curvularia, Daldinia, Elsinoë, Hypocrella, Hypomyces, Parastagonospora, Phaeosphaeria, Phylacia, Pyrenochaeta, Rhopalostroma, Rubroshiraia, Setophoma, Shiraia, Stemphylium, Stagonospora, and Thamnomyces). Dothideomycetes account for the majority of documented fungal PQs (82%), followed by Sordariomycetes (14%), Leotiomycetes (3%), and Eurotiomycetes (1%). Herein, five families Pleosporaceae, Phaeosphaeriaceae, Cladosporiaceae, Shiraiaceae, and Hypoxylaceae are highlighted as potential sources of novel PQs due to their diversity. The review intends to pique bioprospectors' interest in fungal PQs. Indeed, the pharmaceutical and agrochemical industries might gain greatly by exploiting fungal perylenequinones. Graphical abstract.
Fig. 2. Axial chirality P and M of perylenequinones
Fig. 3. The biosynthetic gene clusters of cercosporin CTB, elsinochrome A (45) elc, and hypocrellin A (50) HYP. Modified from Chooi et al. (2017) and Hu et al. (2019)
Fig. 4. Proposed biosynthetic pathway for three perylenequinones of class B: cercosporin (30), elsinochrome A (45), and hypocrellin (50). Modified from Hu et al. (2019)
Fig. 5. Perylenequinones described from the genera Alternaria and Setophoma
Fig. 6. Reported perylenequinones from the genera Alternaria, Aspergillus, Bulgaria, Cenococcum, Curvularia, Daldinia, Phylacia, Rhopalostroma, Setophoma, Stemphylium, and Thamnomyces
Fig. 7. Reported perylenequinones from the genera Cercospora and Cladosporium
Fig. 8. Produced perylenequinones by the genera Elsinoë, Hypocrella, Hypomyces, Parastagonospora, Pyrenochaeta, and Stagonospora
Fig. 9. Described perylenequinones from the genera Phaeosphaeria and Shiraia
Ackroyd,
The history of photodetection and photodynamic therapy.
2001, Pubmed
Ackroyd,
The history of photodetection and photodynamic therapy.
2001,
Pubmed
Al Subeh,
Enhanced Production and Anticancer Properties of Photoactivated Perylenequinones.
2020,
Pubmed
Ayers,
Scutiaquinones A and B, perylenequinones from the roots of Scutia myrtina with anthelmintic activity.
2007,
Pubmed
Becker,
Recent progress in biodiversity research on the Xylariales and their secondary metabolism.
2021,
Pubmed
Bensch,
Cladosporium species in indoor environments.
2018,
Pubmed
Boss,
Elsinochrome A production by the bindweed biocontrol fungus Stagonospora convolvuli LA39 does not pose a risk to the environment or the consumer of treated crops.
2007,
Pubmed
Chaverri,
A monograph of the entomopathogenic genera Hypocrella, Moelleriella, and Samuelsia gen. nov. (Ascomycota, Hypocreales, Clavicipitaceae), and their aschersonia-like anamorphs in the Neotropics.
2008,
Pubmed
Chen,
Functional characterization of three genes encoding putative oxidoreductases required for cercosporin toxin biosynthesis in the fungus Cercospora nicotianae.
2007,
Pubmed
Cheng,
Phylogenetic study on Shiraia bambusicola by rDNA sequence analyses.
2004,
Pubmed
Chooi,
Functional genomics-guided discovery of a light-activated phytotoxin in the wheat pathogen Parastagonospora nodorum via pathway activation.
2017,
Pubmed
Choquer,
Deletion of a MFS transporter-like gene in Cercospora nicotianae reduces cercosporin toxin accumulation and fungal virulence.
2007,
Pubmed
Corrochano,
Fungal photoreceptors: sensory molecules for fungal development and behaviour.
2007,
Pubmed
Dai,
Rubroshiraia gen. nov., a second hypocrellin-producing genus in Shiraiaceae (Pleosporales).
2019,
Pubmed
Daub,
Reactive oxygen species in plant pathogenesis: the role of perylenequinone photosensitizers.
2013,
Pubmed
Davis,
Mutagenicity of stemphyltoxin III, a metabolite of Alternaria alternata.
1991,
Pubmed
Deng,
Characterisation of a monooxygenase in Shiraia bambusicola.
2018,
Pubmed
Diwu,
Novel therapeutic and diagnostic applications of hypocrellins and hypericins.
1995,
Pubmed
Diwu,
Photosensitization with anticancer agents. 15. Perylenequinonoid pigments as potential photodynamic therapeutic agents: formation of semiquinone radicals and reactive oxygen species on illumination.
1993,
Pubmed
Dubauskas,
Activated calphostin C cytotoxicity is independent of p53 status and in vivo metastatic potential.
1998,
Pubmed
Ehrenshaft,
Isolation of Light-Enhanced cDNAs of Cercospora kikuchii.
1991,
Pubmed
Fan,
Phylogeny and taxonomy of the scab and spot anthracnose fungus Elsinoë (Myriangiales, Dothideomycetes).
2017,
Pubmed
Fang,
Hypocrellin D, a cytotoxic fungal pigment from fruiting bodies of the ascomycete Shiraia bambusicola.
2006,
Pubmed
Gao,
Perylene derivatives produced by Alternaria alternata, an endophytic fungus isolated from Laurencia species.
2009,
Pubmed
Hanke,
Significance of Perylene for Source Allocation of Terrigenous Organic Matter in Aquatic Sediments.
2019,
Pubmed
Helaly,
Diversity of biologically active secondary metabolites from endophytic and saprotrophic fungi of the ascomycete order Xylariales.
2018,
Pubmed
Hu,
Heterologous biosynthesis of elsinochrome A sheds light on the formation of the photosensitive perylenequinone system.
2019,
Pubmed
Hudson,
Antiviral activities of photoactive perylenequinones.
1997,
Pubmed
Hudson,
Hypocrellin, from Hypocrella bambuase, is phototoxic to human immunodeficiency virus.
1994,
Pubmed
Iida,
Calphostins, novel and specific inhibitors of protein kinase C. II. Chemical structures.
1989,
Pubmed
Jiao,
Elsinochrome phytotoxin production and pathogenicity of Elsinoë arachidis isolates in China.
2019,
Pubmed
Kishi,
New perylenequinones from Shiraia bambusicola.
1991,
Pubmed
Kobayashi,
Calphostin C (UCN-1028C), a novel microbial compound, is a highly potent and specific inhibitor of protein kinase C.
1989,
Pubmed
Krishnamoorthy,
Synthesis of hydroxy and methoxy perylene quinones, their spectroscopic and computational characterization, and their antiviral activity.
2005,
Pubmed
Kuhnert,
Secondary metabolite biosynthetic diversity in the fungal family Hypoxylaceae and Xylaria hypoxylon.
2021,
Pubmed
Lee,
Diaporthin and Orthosporin from the Fruiting Body of Daldinia concentrica.
2006,
Pubmed
Lei,
Transcriptomic responses involved in enhanced production of hypocrellin A by addition of Triton X-100 in submerged cultures of Shiraia bambusicola.
2017,
Pubmed
Li,
Phaeosphaerins A-F, cytotoxic perylenequinones from an endolichenic fungus, Phaeosphaeria sp.
2012,
Pubmed
Li,
Axial Chiral Binaphthoquinone and Perylenequinones from the Stromata of Hypocrella bambusae Are SARS-CoV-2 Entry Inhibitors.
2021,
Pubmed
Liao,
Genetic dissection defines the roles of elsinochrome Phytotoxin for fungal pathogenesis and conidiation of the citrus pathogen Elsinoë fawcettii.
2008,
Pubmed
Liu,
[Structural elucidation of a new perylenequinone].
2001,
Pubmed
MAINS,
Species of Hypocrella.
1959,
Pubmed
Ma,
Antimicrobial and antileishmanial activities of hypocrellins A and B.
2004,
Pubmed
Ma,
Enhanced Production of Hypocrellin A in Submerged Cultures of Shiraia bambusicola by Red Light.
2019,
Pubmed
Ma,
Inducing perylenequinone production from a bambusicolous fungus Shiraia sp. S9 through co-culture with a fruiting body-associated bacterium Pseudomonas fulva SB1.
2019,
Pubmed
Mastrangelopoulou,
Cytotoxic and Photocytotoxic Effects of Cercosporin on Human Tumor Cell Lines.
2019,
Pubmed
Meille,
Structure of elsinochrome A: a perylenequinone metabolite.
1989,
Pubmed
Miskovsky,
Hypericin--a new antiviral and antitumor photosensitizer: mechanism of action and interaction with biological macromolecules.
2002,
Pubmed
Mulrooey,
Perylenequinones: Isolation, Synthesis, and Biological Activity.
2012,
Pubmed
Mulrooney,
Perylenequinone natural products: enantioselective synthesis of the oxidized pentacyclic core.
2010,
Pubmed
Newman,
Molecular Characterization of the Cercosporin Biosynthetic Pathway in the Fungal Plant Pathogen Cercospora nicotianae.
2016,
Pubmed
Olivo,
Apoptosis signalling mechanisms in human cancer cells induced by Calphostin-PDT.
2007,
Pubmed
Pang,
Perylenequione Derivatives with Anticancer Activities Isolated from the Marine Sponge-Derived Fungus, Alternaria sp. SCSIO41014.
2018,
Pubmed
Peter,
Ectomycorrhizal ecology is imprinted in the genome of the dominant symbiotic fungus Cenococcum geophilum.
2016,
Pubmed
Pettit,
Small-molecule elicitation of microbial secondary metabolites.
2011,
Pubmed
Podlech,
Determination of the absolute configuration of perylene quinone-derived mycotoxins by measurement and calculation of electronic circular dichroism spectra and specific rotations.
2014,
Pubmed
Robeson,
Alteichin: an unusual phytotoxin from Alternaria eichorniae, a fungal pathogen of water hyacinth.
1984,
Pubmed
Samson,
Phylogeny, identification and nomenclature of the genus Aspergillus.
2014,
Pubmed
Seto,
Production of phleichrome by Cladosporium phlei as stimulated by diketopiperadines of Epichloe typhina.
2005,
Pubmed
Shen,
Diversity and antimicrobial activity of culturable endophytic fungi isolated from moso bamboo seeds.
2014,
Pubmed
Shen,
[Studies on the chemical constituents of a fungus producing perylenequinones].
2003,
Pubmed
So,
Antimicrobial and Antitumor Photodynamic Effects of Phleichrome from the Phytopathogenic Fungus Cladosporium Phlei.
2018,
Pubmed
Stack,
Mutagenicity of the Alternaria metabolites altertoxins I, II, and III.
1986,
Pubmed
Stadler,
The phylogenetic position of Rhopalostroma as inferred from a polythetic approach.
2010,
Pubmed
Stadler,
Chemotaxonomy of Entonaema, Rhopalostroma and other Xylariaceae.
2004,
Pubmed
Sun,
Improved hypocrellin A production in Shiraia bambusicola by light-dark shift.
2018,
Pubmed
Sun,
Enhanced production of hypocrellin A by ultrasound stimulation in submerged cultures of Shiraia bambusicola.
2017,
Pubmed
Tantry,
Perylenequinones from an endophytic Alternaria sp. of Pinus ponderosa.
2018,
Pubmed
Tisch,
Light regulation of metabolic pathways in fungi.
2010,
Pubmed
Wang,
[Clinical analysis and observation of hypocrellin photochemotherapy in the treatment of lichen amyloidosis: report of 37 cases].
1985,
Pubmed
Weiss,
Red pigments of Dactynotus rudbeckiae and D. ambrosiae (Homoptera, Aphididae).
1965,
Pubmed
Weiss,
Naturally occurring perylenequinones.
1987,
Pubmed
Wiehe,
Trends and targets in antiviral phototherapy.
2019,
Pubmed
Williams,
Epigenetic remodeling of the fungal secondary metabolome.
2008,
Pubmed
Xian Li,
A new perylenequinone from the fruit bodies of Bulgaria inquinans.
2006,
Pubmed
Yadav,
Pyrenochaeta romeroi causing subcutaneous phaeohyphomycotic cyst in a diabetic female.
2015,
Pubmed
Yang,
Whole-Genome Shotgun Assembly and Analysis of the Genome of Shiraia sp. Strain Slf14, a Novel Endophytic Fungus Producing Huperzine A and Hypocrellin A.
2014,
Pubmed
Yu,
Hypomyces pseudolactifluorum sp. nov. (Hypocreales: Hypocreaceae) on Russula sp. from Yunnan, PR China.
2020,
Pubmed
Zeiner,
Comparative Analysis of Secretome Profiles of Manganese(II)-Oxidizing Ascomycete Fungi.
2016,
Pubmed
Zhang,
A new perylenequinone from a halotolerant fungus, Alternaria sp. M6.
2012,
Pubmed
Zhenjun,
Hypocrellins and their use in photosensitization.
1990,
Pubmed
