Quick guide to secondary metabolites from Apiospora and Arthrinium

Fungal Biology Reviews - Tập 43 - Trang 100288 - 2023
Marie L. Overgaard1, Trine Aalborg1, Emil J. Zeuner1, Klaus R. Westphal1, Frederik A. Lau1, Vibeke S. Nielsen1, Kasper B. Carstensen1, Emil A. Hundebøll1, Tia A. Westermann1, Gustav G. Rathsach1, Jens L. Sørensen2, Jens C. Frisvad3, Reinhard Wimmer1, Teis E. Sondergaard1
1Department of Chemistry and Bioscience, Aalborg University, Fredrik Bajers Vej 7H, DK-9220 Aalborg, Denmark
2Department of Chemistry and Bioscience, Aalborg University, Niels Bohrs Vej 8, DK-6700, Esbjerg, Denmark
3Department of Biotechnology and Biomedicine, Technical University of Denmark, 2800, Kongens Lyngby, Denmark

Tài liệu tham khảo

Alfatafta, 1994, Apiosporamide, a New Antifungal Agent from the Coprophilous Fungus Apiospora montagnei, J. Nat. Prod., 57, 1696, 10.1021/np50114a012 Arthan, 2017, A new xanthone from the fungus Apiospora montagnei, Nat. Prod. Res., 31, 1766, 10.1080/14786419.2017.1290622 Bao, 2018, Bioactive Pyridone Alkaloids from a Deep-Sea-Derived Fungus Arthrinium sp. UJNMF0008, Mar. Drugs, 16, 174, 10.3390/md16050174 Bao, 2018, New Chromones from a Marine-Derived Fungus, Arthrinium sp., and Their Biological Activity, Molecules, 23, 10.3390/molecules23081982 Birkelund, 2021, Fatal 3-Nitropropionic Acid Poisoning after Consuming Coconut Water, Emerg. Infect. Dis., 27, 278, 10.3201/eid2701.202222 Bloor, 2008, Arthrinic Acid, a Novel Antifungal Polyhydroxyacid from Arthrinium phaeospermum, J. Antibiot., 61, 515, 10.1038/ja.2008.69 Brugger, 2006, Mutagenicity of the mycotoxin alternariol in cultured mammalian cells, Toxicol. Lett., 164, 221, 10.1016/j.toxlet.2006.01.001 Burdock, 2001, Safety assessment of β-nitropropionic acid: A monograph in support of an acceptable daily intake in humans, Food Chem., 75, 1, 10.1016/S0308-8146(01)00194-7 Cabello, 2001, Arundifungin, a novel antifungal compound produced by fungi: biological activity and taxonomy of the producing organisms, Int. Microbiol., 4, 93, 10.1007/s101230100020 Chen, 2012, Studies on the Synthesis of Derivatives of Marine-Derived Bostrycin and Their Structure-Activity Relationship against Tumor Cells, Mar. Drugs, 10, 932, 10.3390/md10040932 Christiansen, 2021, Fungal quinones: diversity, producers, and applications of quinones from Aspergillus, Penicillium, Talaromyces, Fusarium, and Arthrinium, Appl. Microbiol. Biotechnol, 10.1007/s00253-021-11597-0 Cooke, 1954, The Genus Arthrinium, Mycologia, 46, 815, 10.1080/00275514.1954.12024418 Crous, 2013, A phylogenetic re-evaluation of Arthrinium, IMA Fungus, 4, 133, 10.5598/imafungus.2013.04.01.13 Crous, 2021, New and interesting Fungi. 4, Fungal Systematics and Evolution, 7, 255, 10.3114/fuse.2021.07.13 Ebada, 2011, Arthrinins A-D: Novel diterpenoids and further constituents from the sponge derived fungus Arthrinium sp, Bioorg. Med. Chem., 19, 4644, 10.1016/j.bmc.2011.06.013 Elissawy, 2017, Spiroarthrinols a and B, two novel meroterpenoids isolated from the sponge- derived fungus Arthrinium sp, Phytochemistry Letters, 20, 246, 10.1016/j.phytol.2017.05.008 Ellis, 1951, British marsh and fen fungi. II, Trans. Br. Mycol. Soc., 34, 497, 10.1016/S0007-1536(51)80034-2 Ellis, 1965, Dematiaceous hyphomycetes. VI, Mycological Papers, 103, 1 Fang, 2005, Mycoediketopiperazine, a novel fungal metabolite from a Papularia sp, Tetrahedron Lett., 46, 2147, 10.1016/j.tetlet.2005.01.140 Fang, 2021, Comparative Transcriptomics and Gene Knockout Reveal Virulence Factors of Arthrinium phaeospermum in Bambusa pervariabilis × Dendrocalamopsis grandis, Journal of Fungi (Basel, Switzerland), 7, 1001 Feng, 2021, Additions to the Genus Arthrinium (Apiosporaceae) From Bamboos in China, Front. Microbiol., 12, 10.3389/fmicb.2021.661281 Gautschi, 2007, Chemical Investigations of a Deep Water Marine-Derived Fungus: Simple Amino Acid Derivatives from an Arthrinium sp, Nat. Prod. Commun., 2, 541 Hansen, 2015, An update to polyketide synthase and non-ribosomal synthetase genes and nomenclature in Fusarium, Fungal Genetic Biology, Feb, 75, 20, 10.1016/j.fgb.2014.12.004 Harris, 2001, APPLICATION OF pH-ZONE-REFINING CCC TO THE ISOLATION OF ANTIFUNGAL FERMENTATION PRODUCTS, J. Liq. Chromatogr. Relat. Technol., 24, 1775, 10.1081/JLC-100104378 Heo, 2018, Diversity and Ecology of Marine Algicolous Arthrinium Species as a Source of Bioactive Natural Products, Mar. Drugs, 16, 1 Heo, 2021, Comparative Genomics and Transcriptomics Depict Marine Algicolous Arthrinium Species as Endosymbionts That Help Regulate Oxidative Stress in Brown Algae, Front. Mar. Sci., 8, 1500, 10.3389/fmars.2021.753222 Hong, 2015, Investigation of Marine-Derived Fungal Diversity and Their Exploitable Biological Activities, Mar. Drugs, 13, 4137, 10.3390/md13074137 Hyde, 1998, Fungi from palms. XXXVI. Reflections on unitunicate ascomycetes with apiospores, Sydowia, 50, 21 Iimura, 1993, Terpestacin, a novel syncytium formation inhibitor, isolated from Arthrinium species, Tetrahedron Lett., 34, 493, 10.1016/0040-4039(93)85110-I IndexFungorum, 2022 Jiang, 2020, A novel bambusicolous fungus from China, Arthrinium chinense (Xylariales), Sydowia, 72 Jung, 2010, Terpestacin Inhibits Tumor Angiogenesis by Targeting UQCRB of Mitochondrial Complex III and Suppressing Hypoxia-induced Reactive Oxygen Species Production and Cellular Oxygen Sensing, J. Biol. Chem., 285, 11584, 10.1074/jbc.M109.087809 Khan, 2009, A new strain of Arthrinium phaeospermum isolated from Carex kobomugi Ohwi is capable of gibberellin production, Biotechnol. Lett., 31, 283, 10.1007/s10529-008-9862-7 Klemke, 2004, New secondary metabolites from the marine endophytic fungus Apiospora montagnei, J. Nat. Prod., 67, 1058, 10.1021/np034061x Kohno, 2000, Structures of TMC-95A-D: novel proteasome inhibitors from Apiospora montagnei sacc. TC 1093, J. Org. Chem., 65, 990, 10.1021/jo991375+ Kunze, 1817, Arthrinium, 9 Kwon, 2021, The genus Arthrinium (Ascomycota, Sordariomycetes, Apiosporaceae) from marine habitats from Korea, with eight new species, IMA Fungus, 12, 13, 10.1186/s43008-021-00065-z Kwon, 2021, A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells, J. Antibiot, 10.1038/s41429-021-00473-8 Larrondo, 1992, New Contributions to the Study of the Genus Arthrinium, Mycologia, 84, 475, 10.1080/00275514.1992.12026164 Larrondo, 1996, Influence of the culture medium on the inhibitory activity of Arthrinium strains, Microbios, 87, 39 Li, 2017, One Strain-Many Compounds Method for Production of Polyketide Metabolites Using the Sponge-Derived Fungus Arthrinium arundinis ZSDS1-F3, Chem. Nat. Compd., 53, 373, 10.1007/s10600-017-1994-3 Li, 2020, Whole-genome sequence of Arthrinium phaeospermum, a globally distributed pathogenic fungus, Genomics, 112, 919, 10.1016/j.ygeno.2019.06.007 Li, 2020, Study on the secondary metabolites of grasshopper-derived fungi Arthrinium sp. NF2410, Chin. J. Nat. Med., 18, 957 Liao, 2018, A New Xanthone from an Endophytic Fungus of Anoectochilus roxburghii, Chem. Nat. Compd., 54, 267, 10.1007/s10600-018-2320-4 Liao, 2021 Link, 1824 Liu, 1989, Arthrinium spp. and the etiology of deteriorated sugarcane poisoning, Bioact. Mol., 10, 109 Liu, 1992, Studies on the epidemiology and etiology of moldy sugarcane poisoning in China, Biomed. Environ. Sci. : BES (Biomed. Environ. Sci.), 5, 161 Ming, 1995, Moldy sugarcane poisoning- A case report with a brief review, Clin. Toxicol., 33, 363 Monggoot, 2017, Fungal Endophytes: an Alternative Source for Production of Volatile Compounds from Agarwood Oil of Aquilaria subintegra, Microb. Ecol., 74, 54, 10.1007/s00248-016-0908-4 Morishita, 2019, Use of plant hormones to activate silent polyketide biosynthetic pathways in Arthrinium sacchari , a fungus isolated from a spider, Org. Biomol. Chem., 17, 780, 10.1039/C8OB02837K Morishita, 2019, The Discovery of Fungal Polyene Macrolides via a Postgenomic Approach Reveals a Polyketide Macrocyclization by trans-Acting Thioesterase in Fungi, Org. Lett., 21, 4788, 10.1021/acs.orglett.9b01674 Mukherjee, 2016, Tricking Arthrinium malaysianum into Producing Industrially Important Enzymes Under 2-Deoxy D-Glucose Treatment, Front. Microbiol., 7, 596 Oka, 1993, Terpestacin, a new syncytium formation inhibitor from Arthrinium sp, J. Antibiot., 46, 367, 10.7164/antibiotics.46.367 Ondeyka, 1995, A carotane sesquiterpene as a potent modulator of the Maxi-K channel from Arthrinium phaesospermum, Bioorg. Med. Chem. Lett, 5, 733, 10.1016/0960-894X(95)00104-2 Pansanit, 2018, Antibacterial secondary metabolites from an endophytic fungus, Arthrinium sp. MFLUCC16-1053 isolated from Zingiber cassumunar, Mycology, 9, 264, 10.1080/21501203.2018.1481154 Petersen, 2022, High molecular weight DNA extraction methods lead to high quality filamentous ascomycete fungal genome assemblies using Oxford Nanopore sequencing, Microb. Genom., 8 Pham, 2019, A Review of the Microbial Production of Bioactive Natural Products and Biologics, Front. Microbiol., 10, 1 Pintos, 2019, Six new species of Arthrinium from Europe and notes about A. Caricicola and other species found in Carex spp. Hosts, MycoKeys, 49, 15, 10.3897/mycokeys.49.32115 Pintos, 2021, Phylogenetic delimitation of Apiospora and Arthrinium, Fungal Systematics and Evolution, 7, 197, 10.3114/fuse.2021.07.10 Qian-Cutrone, 1994, Arthrinone, a Novel Fungal Metabolite from Arthrinium sp. FA 1744, J. Nat. Prod., 57, 1656, 10.1021/np50114a006 Quin, 2014, Traversing the fungal terpenome, Nat. Prod. Rep., 31, 1449, 10.1039/C4NP00075G Rai, 1989, Mycosis in Man Due to Arthrinium phaeospermum var. indicum. First Case Report: Mykose durch Arthrinium phaeospermum var. indicum beim Menschen. Erstbericht, Mycoses, 32, 472, 10.1111/j.1439-0507.1989.tb02285.x Ramos, 2010, Antimicrobial activity from endophytic fungi Arthrinium state of Apiospora montagnei Sacc. and Papulaspora immersa, Braz. Arch. Biol. Technol., 53, 629, 10.1590/S1516-89132010000300017 Ramos, 2013, Evaluation of dihydroisocoumarins produced by the endophytic fungus Arthrinium state of Apiospora montagnei against Schistosoma mansoni, Nat. Prod. Res., 27, 2240, 10.1080/14786419.2013.811659 Samuels, 1981, Ascomycetes of New Zealand 3. Two new species of Apiospora and their Arthrinium anamorphs on bamboo, N. Z. J. Bot., 19, 137, 10.1080/0028825X.1981.10425113 Schmidt-Dannert, 2014, Biosynthesis of Terpenoid Natural Products in Fungi, vol. 148, 19 She, 2022, New Carboxamides and a New Polyketide from the Sponge-Derived Fungus Arthrinium sp. SCSIO 41421, Mar. Drugs, 20, 475, 10.3390/md20080475 Shrestha, 2015, Fungi isolated from Miscanthus and sugarcane : biomass conversion , fungal enzymes , and hydrolysis of plant cell wall polymers, Biotechnol. Biofuels, 8, 1 Shu, 2022, Bioactive cytochalasans from the fungus Arthrinium arundinis DJ-13, Phytochemistry, 194, 10.1016/j.phytochem.2021.113009 Sofian, 2021, The 2,3-epoxy naphthoquinol produced by endophyte Arthrinium marii M-211, Nat. Prod. Res., 1–7 Su, 2020, Arthrinins E–G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66, Natural Products and Bioprospecting, 10, 201, 10.1007/s13659-020-00248-y Sørensen, 2022, A Highly Contiguous Genome Assembly of Arthrinium puccinoides, Genome Biol. Evol., 14, 1, 10.1093/gbe/evac010 Traxler, 1977, Papulacandins, a new family of antibiotics with antifungal activity. Structures of papulacandins A, B, C and D, J. Antibiot., 33, 967, 10.7164/antibiotics.33.967 Tsukada, 2011, Chemical Constituents of a Marine Fungus, Arthrinium sacchari, J. Nat. Prod., 74, 1645, 10.1021/np200108h Tsukamoto, 2006, Hexylitaconic acid: A new inhibitor of p53–HDM2 interaction isolated from a marine-derived fungus, Arthrinium sp, Bioorg. Med. Chem. Lett, 16, 69, 10.1016/j.bmcl.2005.09.052 van Eijk, 1975, Bostrycin, a tetrahydroanthraquinone pigment and some other metabolites from the fungus Arthrinium phaeospermum, Experientia, 31, 783, 10.1007/BF01938463 Vijayakumar, 1996, Arthrichitin. A New Cell Wall Active Metabolite from Arthrinium phaeospermum, J. Org. Chem., 61, 6591, 10.1021/jo960769n Wang, 2013, Anti-Mycobacterial Activity of Marine Fungus-Derived 4-Deoxybostrycin and Nigrosporin, Molecules, 18, 1728, 10.3390/molecules18021728 Wang, 2014, A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3, Nat. Prod. Res., 28, 1070, 10.1080/14786419.2014.905935 Wang, 2015, Arthpyrones A–C, Pyridone Alkaloids from a Sponge-Derived Fungus Arthrinium arundinis ZSDS1-F3, Org. Lett., 17, 656, 10.1021/ol503646c Wang, 2015, Cytotoxic Cytochalasins from Marine-Derived Fungus Arthrinium arundinis, Planta Med., 81, 160, 10.1055/s-0034-1383403 Wang, 2017, Secondary metabolites of the lichen-associated fungus Apiospora montagnei, Tetrahedron Lett., 58, 1702, 10.1016/j.tetlet.2017.03.052 Wang, 2018, Eight new Arthrinium species from China, MycoKeys, 34, 1, 10.3897/mycokeys.34.24221 Wei, 1994, Production of 3-nitropropionic acid by Arthrinium species, Curr. Microbiol., 28, 1, 10.1007/BF01575978 Wei, 2016, A New Griseofulvin Derivative from the Marine-Derived Arthrinium sp. Fungus and Its Biological Activity, Chem. Nat. Compd., 52, 1011, 10.1007/s10600-016-1849-3 Xia, 2016, Secondary Metabolites Produced by Endophytic Fungus, Arthrinium phaeospermum, Korean J. Pharmacogn., 47, 217 Ye, 2019, Two New Sesterterpenes from Marine-Derived Fungus Arthrinium sp, Chem. Nat. Compd., 55, 281, 10.1007/s10600-019-02667-x Yuan, 2020, Proteomic characterization of Mycobacterium tuberculosis reveals potential targets of bostrycin, J. Proteonomics, 212 Zhang, 2018, Antifungal Prenylated Diphenyl Ethers from Arthrinium arundinis, an Endophytic Fungus Isolated from the Leaves of Tobacco (Nicotiana tabacum L.), Molecules, 23, 3179, 10.3390/molecules23123179 Zhang, 2021, Arthpyrone L, a New Pyridone Alkaloid from a Deep-Sea Arthrinium sp., Inhibits Proliferation of MG63 Osteosarcoma Cells by Inducing G0/G1 Arrest and Apoptosis, Chem. Biodivers., 18, 10.1002/cbdv.202000639 Zhao, 2019, Five polyketides isolated from the marine-derived fungus Arthrinium Sp, Nat. Prod. Res., 1 Zhou, 2014, [Study on secondary metabolites of endophytic fungus Arthrinium sp. A092 from Uvaria microcarpa], J. Chin. Med. Mater., 37, 2008