Structures and absolute configuration of three α-pyrones from an endophytic fungus Aspergillus niger

Talontsi, Ferdinand Mouafo; Tatong, Michel D. Kongue; Dittrich, Birger; Douanla‐Meli, Clovis; Laatsch, Hartmut

doi:10.1016/j.tet.2013.05.098

Cited by 22 publications

(8 citation statements)

References 20 publications

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“…& Schwein.) DitmarG340LeafVerrucarin A,Verrucarin J,Verrucarin L acetate, andMyrochromanolNMR, UV, and MS(Tamm et al 1972; Namikoshi et al 2000; Liu et al 2006) Chaetomidium arxii BennyG341LeafDihydro-5-(hydroxyphenylmethyl)-2(3H)-furanoneNMR, UV, and MS(Hargreaves et al 2002a) Daldinia loculata (Lév) Sacc.G343 1,8-dimethoxynaphthaleneNMR, UV, and MS(Yang et al 2008) Fusarium sp.G344G345LeafLeafBeauvericinNMR, UV, and MS (Zhan et al 2007) Microascus nidicola (Microascales)G377LeafMonascuskaoliaone,Nigragillin,Asperazine,Fonsecin,Fonsecin B, Epi -pestalamide A (6)Campyrone A,Campyrone C,Carbonarone A, andMonascuskaoliaone B (4)NMR, UV, and MS(Caesar et al 1969; Isogai et al 1975; Varoglu et al 1997; Zhang et al 2007; Ding et al 2008; Cheng et al 2010; Shaaban et al 2012; Mouafo Talontsi et al 2013) Alternaria sp.G378LeafAlternariol,9-O-methylalternariol, andAltenueneNMR, UV, and MS(Koch et al 2005; Altemöller et al 2006; de Souza et al 2013) Biscogniauxia mediterranea (De Not.) KuntzeG410Leaf(3R)-5-methylmellein,(3R,4R)- cis -4-hydroxy-5-methylmellein,Acuminatopyrone,Chlamydospordiol,Chlamydosporol (major:minor mixture of diastereomers), andCyclo-[L-Phe-L-Leu-L-Leu-L-Leu-L-Ile],Biscognin A (1)Biscognin B (3)NMR, UV, optical rotation, and MS(Okuno et al 1986; Solfrizzo et al 1994; Visconti et al 1994; Li et al 2004) Biscogniauxia atropunctata (Schwein.)…”

Section: Resultsmentioning

confidence: 99%

Phylogenetic and chemical diversity of fungal endophytes isolated fromSilybum marianum(L) Gaertn. (milk thistle)

et al. 2015

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Use of the herb milk thistle (Silybum marianum) is widespread, and its chemistry has been studied for over 50 years. However, milk thistle endophytes have not been studied previously for their fungal and chemical diversity. We examined the fungal endophytes inhabiting this medicinal herb to determine: (1) species composition and phylogenetic diversity of fungal endophytes; (2) chemical diversity of secondary metabolites produced by these organisms; and (3) cytotoxicity of the pure compounds against the human prostate carcinoma (PC-3) cell line. Forty-one fungal isolates were identified from milk thistle comprising 25 operational taxonomic units based on BLAST search via GenBank using published authentic sequences from nuclear ribosomal internal transcribed spacer sequence data. Maximum likelihood analyses of partial 28S rRNA gene showed that these endophytes had phylogenetic affinities to four major classes of Ascomycota, the Dothideomycetes, Sordariomycetes, Eurotiomycetes, and Leotiomycetes. Chemical studies of solid–substrate fermentation cultures led to the isolation of four new natural products. In addition, 58 known secondary metabolites, representing diverse biosynthetic classes, were isolated and characterized using a suite of nuclear magnetic resonance and mass spectrometry techniques. Selected pure compounds were tested against the PC-3 cell line, where six compounds displayed cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

Phylogenetic and chemical diversity of fungal endophytes isolated fromSilybum marianum(L) Gaertn. (milk thistle)

et al. 2015

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“…The newly identified compounds exhibited weak toxicity to brine shrimp larvae Artemia salina in the bioassay tests. [17] …”

Section: Natural Sourcesmentioning

confidence: 99%

“…Currently, α-pyrones constitute a promising class of natural products that are abundantly recovered from animals, plants, microorganisms, and insects, where they share several types of biological defense processes. [15] Specifically, α-pyrone-type natural products extensively exist in the fungal genera Aspergillus, [16][17] Phomopsis, [18] Alternaria, [12,19] Pestalotiopsis, [20] Dictyostelium, [21] and Xylaria. [22][23] According to the chemical structure (Figure 1), γ-pyrone is the vinylogous form of α-pyrone, which possesses a lactone ring.…”

Section: Historical Investigationmentioning

confidence: 99%

Unravelling the Secrets of α‐Pyrones from Aspergillus Fungi: A Comprehensive Review of Their Natural Sources, Biosynthesis, and Biological Activities

Asmaey

2023

Chemistry & Biodiversity

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Aspergillus, one of the most product‐rich and genetically robust genera, contains a diverse range of species with potential economic and ecological implications. Chemically, Aspergillus is one of the essential sources of polyketides, alkaloids, diphenyl ethers, diketopiperazines, and other miscellaneous compounds, displaying a variety of pharmacological activities. The α‐pyrones are unsaturated six‐membered lactones. Although α‐pyrone has a small structure, it is responsible for the structural diversity of several natural and synthetic compounds and multiple biological activities. In this review, we have summarized approximately 178 α‐pyrone containing metabolites derivatives identified/reported from terrestrial, marine, endophytic, and filamentous Aspergillus species, including their sources, biological properties, and biosynthetic pathways until mid‐2023, for the first time. This review is the first to compile and analyze the available data on α‐pyrone metabolites from Aspergillus, which could facilitate further research and innovation in this field. Additionally, it offers a valuable source of scaffolds for future bioactive drug development, as some of these metabolites have shown potent antimicrobial, anti‐inflammatory, and anticancer effects. Therefore, this review has significant implications for the advancement of natural product chemistry, pharmacology, biotechnology, and medicine.

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“…Chemical analysis of an endophytic A. niger strain colonizing in liverwort Heteroscyphus tener (Steph.) Schiffn resulted in isolation of three new amide campyrones A-C (38-40) together with compounds 33 and 34 (Talontsi et al, 2013;Li et al, 2015). One possible biosynthetic pathway proposed by Reber and Burdge (2018) suggested that compounds 38-40 were, respectively, formed by one malonyl-CoA and three N-acetyl aliphatic amino acids including L-valine, L-leucine, and L-isoleucine (Figure 4), along with two congeners asnipyrones A (42) and B (46) and nigerapyrones A-H (35-37, 43-45, 48-49) were first discovered from a mangrove plant-derived strain MA-132 (Liu et al, 2011).…”

Section: α-Pyranonesmentioning

confidence: 99%

Aspergillus niger as a Secondary Metabolite Factory

Liu

Wang

et al. 2021

Front. Chem.

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Aspergillus niger, one of the most common and important fungal species, is ubiquitous in various environments. A. niger isolates possess a large number of cryptic biosynthetic gene clusters (BGCs) and produce various biomolecules as secondary metabolites with a broad spectrum of application fields covering agriculture, food, and pharmaceutical industry. By extensive literature search, this review with a comprehensive summary on biological and chemical aspects of A. niger strains including their sources, BGCs, and secondary metabolites as well as biological properties and biosynthetic pathways is presented. Future perspectives on the discovery of more A. niger-derived functional biomolecules are also provided in this review.

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Structures and absolute configuration of three α-pyrones from an endophytic fungus Aspergillus niger

Cited by 22 publications

References 20 publications

Phylogenetic and chemical diversity of fungal endophytes isolated fromSilybum marianum(L) Gaertn. (milk thistle)

Phylogenetic and chemical diversity of fungal endophytes isolated fromSilybum marianum(L) Gaertn. (milk thistle)

Unravelling the Secrets of α‐Pyrones from Aspergillus Fungi: A Comprehensive Review of Their Natural Sources, Biosynthesis, and Biological Activities

Aspergillus niger as a Secondary Metabolite Factory

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