Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus Aspergillus puniceus

Liu, Chengmei; Yao, Fei-Hua; Lu, Xinhua; Zhang, Xuexia; Luo, Lianxiang; Xiao, Liang; Qi, Shu‐Hua

doi:10.3390/md20010078

Cited by 20 publications

(6 citation statements)

References 20 publications

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“…Based on their even high-resolution masses and improved response in positive ionization mode, 11 alkaloids (peaks 22–32) were annotated. Peak 24, for example, was annotated as puniceusine F 35 , with the molecular formula (C 14 H 16 NO 4 ) + . Furthermore, peak 32, (C 25 H 42 NO 2 ) + was annotated as dihydroxybuxadine-M. T. boudieri contains 7 alkaloids, whereas T. claveryi contains only 5 alkaloids, with Vincapyridine C being the only alkaloid present in both.…”

Section: Resultsmentioning

confidence: 99%

Terfezia boudieri and Terfezia claveryi inhibit the LPS/IFN-γ-mediated inflammation in RAW 264.7 macrophages through an Nrf2-independent mechanism

Dawood

Sedeek

Farag

et al. 2023

Sci Rep

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Desert truffles have been used as traditional treatments for numerous inflammatory disorders. However, the molecular mechanisms underlying their anti-inflammatory effects in RAW 264.7 macrophages have yet to be fully elucidated. The present study investigated the anti-inflammatory activities of two main desert truffles, Terfezia boudieri and T. claveryi, and the underlying mechanisms associated with their anti-inflammatory activities in RAW 264.7 macrophages stimulated with lipopolysaccharide/interferon-gamma (LPS/IFN-γ). Our results demonstrated that treatment with T. boudieri and T. claveryi extracts effectively suppressed the inflammatory response in LPS/IFN-γ-stimulated RAW 264.7 macrophages. Specifically, T. boudieri extract was found to reduce the production of nitric oxide and inhibit the expression of various pro-inflammatory markers, including inducible nitric oxide synthase, cyclooxygenase-2 (COX-2), tumor necrosis factor-α, and interleukin-6 (IL-6) at both the mRNA and protein levels. Similarly, T. claveryi extract exhibited comparable inhibitory effects, except for the expression of IL-6 and COX-2 at the protein level, where no significant effect was observed. Moreover, both studied extracts significantly downregulated the microRNA expression levels of miR-21, miR-146a, and miR-155, suggesting that T. boudieri and T. claveryi suppress the inflammatory response in LPS/IFN-γ-stimulated RAW 264.7 cells through an epigenetic mechanism. Furthermore, our study reveals a new mechanism for the anti-inflammatory properties of desert truffle extracts. We show for the first time that Terfezia extracts do not rely on the nuclear factor erythroid 2-related factor 2 pathway, previously linked to anti-inflammatory responses. This expands our understanding of natural product anti-inflammatory mechanisms and could have important implications for developing new therapies. To account for differences in truffle effects, extracts prepared were subjected to secondary metabolites profiling using UPLC-MS. UPLC-MS led to the annotation of 87 secondary metabolites belonging to various classes, including amino acids, carbohydrates, alkaloids, amides, fatty acids, sterols, and phenolic compounds. Therefore, these results indicate that T. boudieri and T. claveryi exhibit anti-inflammatory activities through suppressing multiple inflammatory mediators and cytokines and may be potential anti-inflammatory agents.

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Section: Resultsmentioning

confidence: 99%

Terfezia boudieri and Terfezia claveryi inhibit the LPS/IFN-γ-mediated inflammation in RAW 264.7 macrophages through an Nrf2-independent mechanism

Dawood

Sedeek

Farag

et al. 2023

Sci Rep

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“…Cytotoxic activity was evaluated using the human lung adenocarcinoma cell line H1975 and HepG2 by the CCK-8 method as described previously . Details are listed in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Microascones, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Microascus sp. SCSIO 41821

Yao,

Liang,

Shen

et al. 2024

J. Nat. Prod.

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Eight new decahydrofluorene-class alkaloids, microascones A and B (1 and 2), 2,3-epoxyphomapyrrolidone C (3), 14,16-epiascomylactam B (4), 24-hydroxyphomapyrrolidone A (5), and microascones C−E (6−8), along with five known analogs (9−13) were isolated from the marine-derived fungus Microascus sp. SCSIO 41821. Compounds 1 and 2 have an unprecedented complex macrocyclic alkaloid skeleton with a 6/5/6/5/6/5/13 polycyclic system. Their structures and absolute configurations were determined by spectroscopic analysis, quantum chemical calculations of ECD spectra, and 13 C NMR chemical shifts. Compounds 10−13 showed selective enzyme inhibitory activity against PTPSig, PTP1B, and CDC25B, and 4, 9, and 10 exhibited strong antibacterial activity against seven tested pathogens. Their structure−bioactivity relationship was discussed, and a plausible biosynthetic pathway for 1−8 was also proposed.

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“…Cytotoxic activity was evaluated using the human lung adenocarcinoma cell line H1975 by the CCK-8 method as described in a previous study . Briefly, each of the test compounds was dissolved in DMSO and further diluted to give a final concentration of 80, 40, 20, 10, 5, 2.5, and 1.25 μg/mL, respectively.…”

Section: Methodsmentioning

confidence: 99%

Pyrrospirones K–Q, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Penicillium sp. SCSIO 41512

Yao

Xiao

Lu³

et al. 2022

J. Nat. Prod.

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Seven new decahydrofluorene-class alkaloids, pyrrospirones K–Q (1–7), together with six known analogues (8–13) were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41512. Their structures were determined by extensive spectroscopic analysis, and their absolute configurations were established by single-crystal X-ray diffraction analysis and quantum chemical calculations of electronic circular dichroism spectra. Compounds 1 and 3 possess a novel decahydrofluorene-class alkaloid skeleton with a 6/5/6/8/5/6/13 and a 6/5/6/5/6/13 polycyclic system, respectively. Biologically, 13 displayed significant inhibitory activity against protein tyrosine phosphatases CD45, TCPTP, SHP1, and PTP1B with IC50 values of 8.1–17.8 μM, and 1, 2, 5, 8–10, 12, and 13 showed antibacterial activity against six pathogens. Their structure–activity relationship is also discussed.

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Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus Aspergillus puniceus

Cited by 20 publications

References 20 publications

Terfezia boudieri and Terfezia claveryi inhibit the LPS/IFN-γ-mediated inflammation in RAW 264.7 macrophages through an Nrf2-independent mechanism

Terfezia boudieri and Terfezia claveryi inhibit the LPS/IFN-γ-mediated inflammation in RAW 264.7 macrophages through an Nrf2-independent mechanism

Microascones, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Microascus sp. SCSIO 41821

Pyrrospirones K–Q, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Penicillium sp. SCSIO 41512

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