Orsellides A–E: An Example for 6‐Deoxyhexose Derivatives Produced by Fungi

Schlörke, Oliver; Zeeck, Axel

doi:10.1002/ejoc.200500793

Cited by 26 publications

(36 citation statements)

References 22 publications

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“…chaetomin, [16] chaetoglobosins, [17] chaetoquadrins, [18] oxaspirodion, [19] chaetospiron [20] and the orsellides. [21] Thus, Chaetomium sp. can be seen as a rich source for isolating new secondary metabolites.…”

Section: Discussionmentioning

confidence: 96%

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

et al. 2007

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Three new fungal polyketide metabolites, chaetocyclinone A to C, were produced by cultures of Chaetomium sp. (strain Gö 100/2), which was isolated from marine algae. The structures of the novel compounds were established by detailed spectroscopic analysis. Additionally, an X‐ray analysis of chaetocyclinone C (5) was performed. Chaetocyclinone A (1) exhibits inhibitory activity against selected phytopathogenic fungi. The biosynthesis of 1 and 5 was studied by feeding 13C‐labelled acetate. The results suggest the polyketide pathway for the isolated metabolites. In the case of chaetocyclinone C (5), we assume an unusual condensation of two highly reactive heptaketide intermediates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Discussionmentioning

confidence: 96%

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

et al. 2007

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“…The orsellinic acid moiety was diacetylated as expected and chemical shift data was consistent with the literature. 39 Acetylation of the hydroxyl group at C-8 induced a large downfield shift of H-8 from q 3.58 to δ5.00 (d, J = 9.9 Hz) and a downfield shift of H-8a from δ H 2.82 to δ 3.34 ppm. H-8 was 3 J -coupled to H-8a and showed HMBC correlations to C-8a, C-1, C-7 and to an acetate carbonyl.…”

mentioning

confidence: 98%

Caspase-1 Inhibitors from an Extremophilic Fungus That Target Specific Leukemia Cell Lines

Stierle

Girtsman

2012

J. Nat. Prod.

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Berkeley Pit Lake, Butte, Montana is a 540 m. deep abandoned open-pit copper mine filled with over 140 billion liters of acidic, metal-sulfate contaminated water. This harsh environment has yielded several microorganisms that produce interesting biologically active compounds. Several polyketide metabolites including the new berkazaphilones A (1) and B (2) and octadienoic acid derivatives berkedienoic acid (13) and berkedienolactone (15), as well as previously reported azaphilone 4, vermistatin (6), dihydrovermistatin (7), penisimplicissin (8), aldehyde 9 and methyl paraconic acid (11) were isolated from a culture broth of Penicillium rubrum taken from a depth of 270 m. The structures of these compounds were deduced by interpretation of spectroscopic data. The compounds were isolated either for their inhibition of the signal transduction enzyme caspase-1 or because of their structural similarity to these inhibitors. Selected compounds were further evaluated for their ability to inhibit interleukin-1β production by inflammasomes in induced THP-1 cells. Berkazaphilone B (2) and C (4) and vermistatin analogue penisimplicissin (8) exhibited selective activity against leukemia cancer cell lines in the National Cancer Institute 60 human cell line assay.

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“…Chaetomium Kuntze ex Fries ( Chaetomiaceae ) is a cosmopolitan fungus found in soil and cellulose-containing substrates [ 13 ]. Members of this genus are rich sources of bioactive secondary metabolites with different chemical structures [ 14 – 16 ], such as alkaloids [ 17 , 18 ], esters [ 19 ] and polyketides [ 20 ]. Among the secondary metabolites produced by this genus, aureonitol, a tetrahydrofuran (THF) derivative [ 21 ], is an abundant metabolite.…”

Section: Introductionmentioning

confidence: 99%

Aureonitol, a Fungi-Derived Tetrahydrofuran, Inhibits Influenza Replication by Targeting Its Surface Glycoprotein Hemagglutinin

et al. 2015

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The influenza virus causes acute respiratory infections, leading to high morbidity and mortality in groups of patients at higher risk. Antiviral drugs represent the first line of defense against influenza, both for seasonal infections and pandemic outbreaks. Two main classes of drugs against influenza are in clinical use: M2-channel blockers and neuraminidase inhibitors. Nevertheless, because influenza strains that are resistant to these antivirals have been described, the search for novel compounds with different mechanisms of action is necessary. Here, we investigated the anti-influenza activity of a fungi-derived natural product, aureonitol. This compound inhibited influenza A and B virus replication. This compound was more effective against influenza A(H3N2), with an EC50 of 100 nM. Aureonitol cytoxicity was also very low, with a CC50 value of 1426 μM. Aureonitol inhibited influenza hemagglutination and, consequently, significantly impaired virus adsorption. Molecular modeling studies revealed that aureonitol docked in the sialic acid binding site of hemagglutinin, forming hydrogen bonds with highly conserved residues. Altogether, our results indicate that the chemical structure of aureonitol is promising for future anti-influenza drug design.

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Orsellides A–E: An Example for 6‐Deoxyhexose Derivatives Produced by Fungi

Cited by 26 publications

References 22 publications

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

Caspase-1 Inhibitors from an Extremophilic Fungus That Target Specific Leukemia Cell Lines

Aureonitol, a Fungi-Derived Tetrahydrofuran, Inhibits Influenza Replication by Targeting Its Surface Glycoprotein Hemagglutinin

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