α-Pyrones, secondary metabolites from fungus Cephalotrichum microsporum and their bioactivities

Zhu, He; Li, Dawei; Yan, Quansheng; An, Yue; Huo, Xiaokui; Zhang, Tianyuan; Zhang, Mengyue; Wang, Chao; Xia, Mingyu; Ma, Xiaochi; Zhang, Yixuan

doi:10.1016/j.bioorg.2018.10.022

Cited by 19 publications

(13 citation statements)

References 20 publications

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“…In addition, natural products with α-pyrone sub-structure have antibacterial ( Zhang et al, 2013 ), anti-influenza A virus ( Hou et al, 2018 ), and anti-HIV ( Appendino et al, 2007 ) activities. Some of them are signal molecules ( Brachmann et al, 2013 ), while some are also cytotoxic agents against tumor cells ( Rivera-Chávez et al, 2019 ; Zhu et al, 2019 ). In particular, dibenzo-α-pyrone ( 3 ) belongs to a significant group of heptaketide coumarin metabolites that have a fused tricyclic core ( Figure 1A ), commonly identified from fungi, bacteria, and plants ( Lai et al, 2016 ).…”

Section: Introductionmentioning

confidence: 99%

Bioactive α-Pyrone Derivatives from the Endophytic Fungus Diaporthe sp. CB10100 as Inducible Nitric Oxide Synthase Inhibitors

Liu

Wang

et al. 2021

Front. Chem.

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Inducible nitric oxide synthase (iNOS) produces NO from l-arginine and plays critical roles in inflammation and immune activation. Selective and potent iNOS inhibitors may be potentially used in many indications, such as rheumatoid arthritis, pain, and neurodegeration. In the current study, five new compounds, including a dibenzo-α- pyrone derivative ellagic acid B (5) and four α-pyrones diaporpyrone A–D (9–12), together with three known compounds (6–8), were isolated from the endophytic fungus Diaporthe sp. CB10100. The structures of these new natural products were unambiguously elucidated using NMR, HRESIMS or electronic circular dichroism calculations. Ellagic acid B (5) features a tetracyclic 6/6/6/6 ring system with a fused 2H-chromene, which is different from ellagic acid (4) with a fused 2H-chromen-2-one. Both 2-hydroxy-alternariol (6) and alternariol (7) reduced the expression of iNOS at protein levels in a dose-dependent manner, using a lipopolysaccharide (LPS)-induced RAW264.7 cell models. Also, they decreased the protein expression levels of pro-inflammatory cytokines, such as tumor necrosis factor-α, interleukin-6 and monocyte chemotactic protein 1. Importantly, 6 and 7 significantly reduced the production of NO as low as 10 μM in LPS-induced RAW264.7 cells. Molecular docking of 6 and 7 to iNOS further suggests that both of them may interact with iNOS. Our study suggests that 6 and 7, as well as the alternariol scaffold may be further developed as potential iNOS inhibitors.

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Section: Introductionmentioning

confidence: 99%

Bioactive α-Pyrone Derivatives from the Endophytic Fungus Diaporthe sp. CB10100 as Inducible Nitric Oxide Synthase Inhibitors

Liu

Wang

et al. 2021

Front. Chem.

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“…Bacterial strains used in our anti-bacterial studies are from National Center for Medical Culture Collections (CMCC), and the CMCC numbers are listed as below: B. subtilis (CMCC63501), S. aureus (CMCC26003), P. aeruginosa (CMCC10104), K. pneumonia (CMCC46117), and E. coli (CMCC44102) 49,50 . The antimicrobial assay was performed according to the procedure of Zhu et al .…”

Section: Methodsmentioning

confidence: 99%

“…The antimicrobial assay was performed according to the procedure of Zhu et al . 50 . Briefly, DMSO was used to dissolved the positive control and compounds 1 – 9 at an initial concentration of 10 mg/ml, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…Minimal inhibitory concentration (MIC) of compounds 1 , 2 and 5 were assessed against bacteria S. aureus (CMCC26003). The MIC values of the isolated compounds against human pathogenic bacteria were determined by the modified CLSI M38-A method 49,50 . Briefly, compounds 1 , 2 and 5 were dissolved using DMSO with the final concentrations of 100, 50, 25, 12.5, and 6.25 ug/mL, respectivly for the MIC determination.…”

Section: Methodsmentioning

confidence: 99%

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New antimicrobial compounds produced by Seltsamia galinsogisoli sp. nov., isolated from Galinsoga parviflora as potential inhibitors of FtsZ

Zhang

et al. 2019

Sci Rep

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A total amount of 116 fungal strains, belonging to 30 genera, were acquired from the rhizosphere soil and plant of Galinsoga parviflora . A strain SYPF 7336, isolated from the rhizospheric soil, was identified as Seltsamia galinsogisoli sp. nov., by morphological and molecular analyses, which displayed high antibacterial activity. In order to study the secondary metabolites of Seltsamia galinsogisoli sp. nov., nine compounds were successfully seperated from the strain fermentation broth, including two new compounds and seven known compounds. Their structures were elucidated based on spectral analysis including 1D and 2D NMR. All the seperated compounds were evaluated for their antimicrobial activities. Compounds 2, 5 and 1 displayed antimicrobial activities against Staphylococcus aureus with MIC values of 25, 32 and 75 μg/mL, respectively. Moreover, morphological observation showed the coccoid cells of S. aureus to be swollen to a volume of 1.4 to 1.7-fold after treatment with compounds 1 , 2 and 5 , respectively. Molecular docking was carried out to investigate interactions of filamentous temperature-sensitive protein Z (FtsZ) with compounds 1 , 2 and 5 .

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“…Several α-pyrones and alkylresorcinols produced by marine and terrestrial fungi have shown cytotoxic activities against several cancer cell lines [58][59][60][61]. Therefore, molecules produced by PKSIII Mo29 could have cytotoxic effects on human tumoral cell lines.…”

Section: Cytotoxicity Activity Against Tumoral Cell Linesmentioning

confidence: 99%

Identification and Characterization of a New Type III Polyketide Synthase from a Marine Yeast, Naganishia uzbekistanensis

et al. 2020

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A putative Type III Polyketide synthase (PKSIII) encoding gene was identified from a marine yeast, Naganishia uzbekistanensis strain Mo29 (UBOCC-A-208024) (formerly named as Cryptococcus sp.) isolated from deep-sea hydrothermal vents. This gene is part of a distinct phylogenetic branch compared to all known terrestrial fungal sequences. This new gene encodes a C-terminus extension of 74 amino acids compared to other known PKSIII proteins like Neurospora crassa. Full-length and reduced versions of this PKSIII were successfully cloned and overexpressed in a bacterial host, Escherichia coli BL21 (DE3). Both proteins showed the same activity, suggesting that additional amino acid residues at the C-terminus are probably not required for biochemical functions. We demonstrated by LC-ESI-MS/MS that these two recombinant PKSIII proteins could only produce tri- and tetraketide pyrones and alkylresorcinols using only long fatty acid chain from C8 to C16 acyl-CoAs as starter units, in presence of malonyl-CoA. In addition, we showed that some of these molecules exhibit cytotoxic activities against several cancer cell lines.

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α-Pyrones, secondary metabolites from fungus Cephalotrichum microsporum and their bioactivities

Cited by 19 publications

References 20 publications

Bioactive α-Pyrone Derivatives from the Endophytic Fungus Diaporthe sp. CB10100 as Inducible Nitric Oxide Synthase Inhibitors

Bioactive α-Pyrone Derivatives from the Endophytic Fungus Diaporthe sp. CB10100 as Inducible Nitric Oxide Synthase Inhibitors

New antimicrobial compounds produced by Seltsamia galinsogisoli sp. nov., isolated from Galinsoga parviflora as potential inhibitors of FtsZ

Identification and Characterization of a New Type III Polyketide Synthase from a Marine Yeast, Naganishia uzbekistanensis

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