A new cytotoxic phenalenone derivative from <i>Penicillium oxalicum</i>

Qi, Xiaoying; Liu, Bing; Jiang, Zhongxiu

doi:10.1080/14786419.2021.2008388

Cited by 4 publications

(3 citation statements)

References 17 publications

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“…Three isolates exhibited significant inhibitory effects on LPS-stimulated nitric oxide (NO) production in murine brain microglial BV-2 cells in a dose-response manner [57]. Peniciphenalenin G (142) (Figure 3) was isolated from the marine-derived P. oxalicum [58]. Penicinone C (143) (Figure 3) was identified from the mangrove-derived Penicillium sp.…”

Section: Hydroxybenzenesmentioning

confidence: 99%

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

Lv,

Zeng

2024

Marine Drugs

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Marine-derived Penicillium fungi are productive sources of structurally unique and diverse bioactive secondary metabolites, representing a hot topic in natural product research. This review describes structural diversity, bioactivities and statistical research of 452 new natural products from marine-derived Penicillium fungi covering 2021 to 2023. Sediments are the main sources of marine-derived Penicillium fungi for producing nearly 56% new natural products. Polyketides, alkaloids, and terpenoids displayed diverse biological activities and are the major contributors to antibacterial activity, cytotoxicity, anti-inflammatory and enzyme inhibitory capacities. Polyketides had higher proportions of new bioactive compounds in new compounds than other chemical classes. The characteristics of studies in recent years are presented.

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Section: Hydroxybenzenesmentioning

confidence: 99%

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

Lv,

Zeng

2024

Marine Drugs

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“…The filamentous fungus Penicillium oxalicum is a patented biocontrol and industrial producing strain that is used to prepare biological pesticides and degrading enzymes ( Tian et al, 2018 ). Compared with those of other species in the Penicillium genus ( Zhang et al, 2020 ), the secondary metabolites of P. oxalicum have not been extensively studied, and only a limited family of metabolites, such as phenalenone derivatives ( Qi et al, 2023 ), dihydrothiophene-condensed chromones ( Sun et al, 2012 ), decaturin alkaloids ( Wang et al, 2013 ), and phenolic enamides and meroterpenoids ( Li et al, 2015 ), has been reported. The fungus P. oxalicum 2021CDF-3 used in this study was previously isolated from the inner tissue of the marine red alga Rhodomela confervoides .…”

Section: Introductionmentioning

confidence: 99%

New cytotoxic indole derivatives with anti-FADU potential produced by the endophytic fungus Penicillium oxalicum 2021CDF-3 through the OSMAC strategy

Song,

Ji,

Zhang

et al. 2024

Front. Microbiol.

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Fungi possess well-developed secondary metabolism pathways that are worthy of in-depth exploration. The One Strain Many Compounds (OSMAC) strategy is a useful method for exploring chemically diverse secondary metabolites. In this study, continued chemical investigations of the marine red algae-derived endophytic fungus Penicillium oxalicum 2021CDF-3 cultured in PDB media yielded six structurally diverse indole derivatives, including two new prenylated indole alkaloids asperinamide B (1) and peniochroloid B (5), as well as four related derivatives (compounds 2–4 and 6). The chemical structures of these compounds, including the absolute configurations of 1 and 5, were determined by extensive analyses of HRESIMS, 1D and 2D NMR spectroscopic data, and TDDFT-ECD calculations. Compound 1 was found to possess an unusual 3-pyrrolidone dimethylbenzopyran fused to the bicyclo[2.2.2]diazaoctane moiety, which was rare in previously reported prenylated indole alkaloids. In vitro cytotoxic experiments against four human tumor cell lines (HeLa, HepG2, FADU, and A549) indicated that 1 strongly inhibited the FADU cell line, with an IC50 value of 0.43 ± 0.03 μM. This study suggested that the new prenylated indole alkaloid 1 is a potential lead compound for anti-FADU drugs.

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“…Numerous structures of natural products and bioactive synthetic compounds were embedded with dihydronaphthofuran motif 2 as demonstrated in Figure which acts as Antimicrobial, NF-κB and liver tumor growth inhibitors …”

Section: Introductionmentioning

confidence: 99%

Synergistic Lewis–Brønsted Acid Catalysis in Cascade Cyclization ofortho-Alkynylaryl Cyclopropylketones for the Synthesis of 2,3-Dihydronaphtho[1,2-b]furans

et al. 2022

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In this work, a synthetic method for the synthesis of 2,3-dihydronaphtho[1,2-b]furans employing synergistic Lewis–Brønsted Acid catalyzed cyclization of ortho-alkynylarylcyclopropylketones has been developed. Benefits of our method included low catalyst loading, low cost of catalyst, short reaction time, and mild conditions which could be applied to a broad range of substrates, including a terminal alkyne (R = H), to provide generally high yields of the desired products. In addition, we found that 2,3-dihydronaphtho[1,2-b]furan derivatives could be isomerized to give 5,6-dihydrotetraphen-7-ol anaologs under acidic conditions via Friedel–Crafts-type alkylation in good to excellent yields. However, these products were not stable and gradually converted to the corresponding quinones. The competent transformation was successfully obtained by treating with m-CPBA in the presence of NaHCO3 to provide the desired quinone products in good to excellent yields.

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A new cytotoxic phenalenone derivative from Penicillium oxalicum

Cited by 4 publications

References 17 publications

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

New cytotoxic indole derivatives with anti-FADU potential produced by the endophytic fungus Penicillium oxalicum 2021CDF-3 through the OSMAC strategy

Synergistic Lewis–Brønsted Acid Catalysis in Cascade Cyclization ofortho-Alkynylaryl Cyclopropylketones for the Synthesis of 2,3-Dihydronaphtho[1,2-b]furans

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