Verrulactones A and B, new inhibitors of Staphylococcus aureus enoyl-ACP reductase produced by Penicillium verruculosum F375

Kim, Nyung; Sohn, Mi Jin; Kim, Chang‐Jin; Kwon, Ho Jeong; Kim, Won Gon

doi:10.1016/j.bmcl.2012.02.001

Cited by 20 publications

(9 citation statements)

References 15 publications

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“…The biosynthesis of 7 and 8 was proposed in 2012, while their biosynthetic enzyme SnPKS19 was identified from a wheat pathogen Parastagonospora nodorum ( Kim et al, 2012 ; Chooi et al, 2015 ). Therefore, the biosynthesis of dibenzo-α-pyrone 5 – 8 in Diaporthe sp.…”

Section: Resultsmentioning

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: Resultsmentioning

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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“…The known compounds were identified as 4‐hydroxyalternariol‐9‐methyl ether ( 1 ), 27 (−)‐talaroflavone ( 4a ), 26 altenuene ( 5 ), 28 altertoxin I ( 6 ), 29 and verrulactone A ( 8 ) (Figure 4). 30 …”

Section: Resultsmentioning

confidence: 99%

Novel metabolites from the Cercis chinensis derived endophytic fungus Alternaria alternataZHJG5 and their antibacterial activities

Zhao

Wang

Tian

et al. 2021

Pest Management Science

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BACKGROUND Phytopathogenic bacteria, such as Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs), seriously threaten crop production and are the cause of enormous yield losses. Endophytic fungi are abundant sources of bioactive metabolites that may be potential candidates in the development of new agrochemicals. This work emphasizes the discovery of bioactive polyketides from endophytic Alternaria alternata ZHJG5 and reports their structural elucidation and antibacterial activities in detail. RESULTS Five novel polyketide derivatives, isotalaroflavone (2), (+/−)‐5′‐dehydroxytalaroflavone (3a/3b), (+)‐talaroflavone (4b), and bialternacin G (7), along with five known compounds (1, 4a, 5, 6, and 8), were obtained from the Cercis chinensis‐derived fungus A. alternata ZHJG5. The compounds' structures were characterized using spectroscopic methods and X‐ray diffraction. Chiral high‐performance liquid chromatography was used to separate the racemates 3 and 4, whose absolute configurations were unambiguously confirmed by comparing their experimental and calculated electron circular dichroism data. All isolated compounds were tested for antibacterial activity against the phytopathogenic bacteria Xoo, Xanthomonas oryzae pv. oryzicola (Xoc) and Rs. Compounds 1, 2 and 8 showed pronounced antibacterial activity against all tested bacteria, with minimal inhibitory concentrations ranging from 0.5 to 64 μg/ml. In addition, compound 1 showed a potent protective effect against rice bacterial leaf blight caused by Xoo with a protective efficacy of 75.1% at a concentration of 200 μg/ml. CONCLUSION These findings highlight the practical potential of antibacterial compounds as candidates for the discovery of novel bactericides. © 2021 Society of Chemical Industry

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“…Studies in the past have established that InhA is the primary molecular target for INH which has been the frontline drug for over 40 years used in the treatment of TB. The INH‐NADH adduct functions as a potent inhibitor of InhA and the well‐known non‐selective InhA inhibitors diazoborines and triclosan, InhA direct inhibitors, pyrrole derivatives and piperazines have all been reported to exhibit in vivo as well as in vitro antitubercular activities.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 6‐[4‐(4‐Propoxyphenyl)piperazin‐1‐yl]‐9H‐purine Derivatives as Antimycobacterial and Antifungal Agents: In Vitro Evaluation and In Silico Study

Nadaf

Najare

Garbhagudi

et al. 2020

Chemistry & Biodiversity

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A series of novel alkyl substituted purines were synthesized. 6-[4-(4-Propoxyphenyl)piperazin-1-yl]-9H-purine was used as the key starting material, which was synthesized via a multistep protocol and finally subjected for Nalkylation with various alkyl halides with an aim to get prospective antimicrobial agents. The structures of the novel compounds were established by substantiating them through spectral techniques like 1 H-NMR, 13 C-NMR, FT-IR and EI-MS. They were explored for antitubercular activity against Mycobacterium tuberculosis H37RV. Furthermore, they were checked for their antimicrobial activity concerning bacterial and fungal strains. The title compounds exhibited considerable antimicrobial activity without any significant toxicity. In silico studies depicted their good binding profile against Mycobacterium tuberculosis enoyl reductase (InhA; PDB ID: 4TZK) and Candida albicans dihydrofolate reductase (PDB ID: 1AI9). The title compounds obeyed Lipinski's parameters and have exhibited good drug-like properties.

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Verrulactones A and B, new inhibitors of Staphylococcus aureus enoyl-ACP reductase produced by Penicillium verruculosum F375

Cited by 20 publications

References 15 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

Novel metabolites from the Cercis chinensis derived endophytic fungus Alternaria alternataZHJG5 and their antibacterial activities

Synthesis of 6‐[4‐(4‐Propoxyphenyl)piperazin‐1‐yl]‐9H‐purine Derivatives as Antimycobacterial and Antifungal Agents: In Vitro Evaluation and In Silico Study

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