Elucidation of the Biosynthesis and Degradation of Allantofuranone by Isotopic Labelling and Fermentation of Modified Precursors

Schüffler, Anja; Liermann, Johannes C.; Opatz, Till; Anke, Timm

doi:10.1002/cbic.201000448

Cited by 18 publications

(29 citation statements)

References 27 publications

(46 reference statements)

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“…These were first isolated in 2011 from an Allantophomopsis sp. ( Schuffler et al, 2011) and later in the same year from a Leptosphaeria sp. ( Tayone et al, 2011b).…”

Section: Resultsmentioning

confidence: 91%

Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat

et al. 2014

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Six isochromenones (1-6), clearanols F (5) and G (6), one isobenzofuranone (7), and two tetrahydronaphthalene derivatives (8 and radinaphthalenone (9)), were isolated and identified from a culture of the fungus Paraphoma radicina, which was isolated from submerged wood in a freshwater lake. Compounds 5, 6 and 9 were previously unknown. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 5 and 6 were determined by comparison of their experimental ECD measurements with values predicted by TDDFT calculations. Compounds 1-9 were evaluated for antimicrobial activity against an array of bacteria and fungi. The inhibitory activity of compound 4 against Staphylococcus aureus biofilm formation was evaluated.

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“…These were first isolated in 2011 from an Allantophomopsis sp. ( Schuffler et al, 2011) and later in the same year from a Leptosphaeria sp. ( Tayone et al, 2011b).…”

Section: Resultsmentioning

confidence: 91%

Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat

et al. 2014

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“…Some NRPS-like enzymes containing a reduction rather than a thioesterase domain have been shown to perform substrate reduction without condensation (Wang et al, 2014). However, thioesterase-containing NRPS-like enzymes mediate the condensation of two identical aromatic a-keto acids, and two major classes of compounds are produced: terphenylquinones and furanones (Figure 7A) (Schneider et al, 2007;Balibar et al, 2007;Pauly et al, 2014;Braesel et al, 2015;Schuffler et al, 2011;Brachmann et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

“…The core motif of terphenylquinones is formed by two symmetric nucleophilic attacks of the C3 of one a-keto acid at the C1 of the other and vice versa, resulting in two new C-C-s bonds. For formation of the butenolide core structure of furanones, two divergent biosynthesis routes are possible: first, generation of a terphenylquinone intermediate, which is oxidatively cleaved and lactonized and may become decarboxylated (Schuffler et al, 2011;Figure 7B); second (Pauly et al, 2014), a direct aldol condensation of two building blocks in which a single new C-C-s bond is formed. This is followed by decarboxylation and lactonization (Figure 7C).…”

Section: Discussionmentioning

confidence: 99%

A Non-canonical Melanin Biosynthesis Pathway Protects Aspergillus terreus Conidia from Environmental Stress

Geib

Gressler

Viediernikova

et al. 2016

Cell Chemical Biology

100

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Melanins are ubiquitous pigments found in all kingdoms of life. Most organisms use them for protection from environmental stress, although some fungi employ melanins as virulence determinants. The human pathogenic fungus Aspergillus fumigatus and related Ascomycetes produce dihydroxynaphthalene- (DHN) melanin in their spores, the conidia, and use it to inhibit phagolysosome acidification. However, biosynthetic origin of melanin in a related fungus, Aspergillus terreus, has remained a mystery because A. terreus lacks genes for synthesis of DHN-melanin. Here we identify genes coding for an unusual NRPS-like enzyme (MelA) and a tyrosinase (TyrP) that A. terreus expressed under conidiation conditions. We demonstrate that MelA produces aspulvinone E, which is activated for polymerization by TyrP. Functional studies reveal that this new pigment, Asp-melanin, confers resistance against UV light and hampers phagocytosis by soil amoeba. Unexpectedly, Asp-melanin does not inhibit acidification of phagolysosomes, thus likely contributing specifically to survival of A. terreus conidia in acidic environments.

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“…In this study, fermentation of Coniothyrium sp. on solid rice medium yielded two new furoic acid derivatives ( 1 and 2 ) and two additional known compounds 2,3‐dihydroxy‐2,4‐diphenylcyclopent‐4‐en‐1‐one ( 3 ) and 2‐anhydromevalonic acid ( 4 ) . The structure elucidation of the new compounds and the results of cytotoxicity assay are described in this paper (Figure ).…”

Section: Introductionmentioning

confidence: 93%

Furoic acid derivatives from the endophytic fungus Coniothyrium sp.

et al. 2020

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The endophytic fungus Coniothyrium sp. was isolated from leaves of Quercus robur. Fermentation of this fungus on solid rice medium yielded two new furoic acid derivatives (1 and 2) and two additional known compounds. The structures of the new compounds were determined by extensive analysis of 1D and 2D nuclear magnetic resonance spectra as well as high-resolution mass spectrometry data. Compound 1, containing three aromatic chromophores attached by rotatable sigma bonds and a chirality center in benzylic position, was found to be a scalemic mixture with an excess of the (S) enantiomer, the absolute configuration of which was elucidated as by the solution timedependent density functional theory-electronic circular dichroism approach. The ωB97X/TZVP PCM/MeCN and SOGGA11-X/TZVP SMD/MeCN methods were used for geometry reoptimization to reproduce the solution conformational ensemble. All isolated compounds were tested for their cytotoxicity but proved to be inactive. K E Y W O R D SConiothyrium sp, electronic circular dichroism, furoic acid derivatives, TDDFT-ECD calculation

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Elucidation of the Biosynthesis and Degradation of Allantofuranone by Isotopic Labelling and Fermentation of Modified Precursors

Cited by 18 publications

References 27 publications

Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat

Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat

A Non-canonical Melanin Biosynthesis Pathway Protects Aspergillus terreus Conidia from Environmental Stress

Furoic acid derivatives from the endophytic fungus Coniothyrium sp.

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