Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025

Xu, Xin‐Ya; Zhang, Xiaoyong; Nong, Xu‐Hua; Wang, Jie; Qi, Shu‐Hua

doi:10.3390/md15020043

Cited by 40 publications

(34 citation statements)

References 34 publications

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“…Hence, the development of novel drugs that can selectively and specifically target TNBC cells is urgently needed. In recent years, marine-derived natural products have been found to have better antitumor activities against many kinds of cancer, thus providing a constant source for new drug discovery against cancer [40][41][42]. Our previous study showed that Ilamycin C, a novel compound separated Fig.…”

Section: Discussionmentioning

confidence: 99%

Ilamycin C induces apoptosis and inhibits migration and invasion in triple-negative breast cancer by suppressing IL-6/STAT3 pathway

et al. 2019

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Background: Triple-negative breast cancer (TNBC) is the most aggressive subtype of breast cancer with poor prognosis, and its treatment remains a challenge due to few targeted medicines and high risk of relapse, metastasis, and drug resistance. Thus, more effective drugs and new regimens for the therapy of TNBC are urgently needed. Ilamycins are a kind of cyclic peptides and produced by Streptomyces atratus and Streptomyces islandicus with effective anti-tuberculosis activity. Ilamycin C is a novel compound isolated from the deep South China Seaderived Streptomyces atratus SCSIO ZH16 and exhibited a strong cytotoxic activity against several cancers including breast cancer cell line MCF7. However, the cytotoxic activity of Ilamycin C to TNBC cells and a detailed antitumor mechanism have not been reported. Methods: CCK-8 assays were used to examine cell viability and cytotoxic activity of Ilamycin C to TNBC, non-TNBC MCF7, and nonmalignant MCF10A cells. EdU assays and flow cytometry were performed to assess cell proliferation and cell apoptosis. Transwell migration and Matrigel invasion assays were utilized to assess the migratory and invading capacity of TNBC cells following the treatment of Ilamycin C. The expressions of proteins were detected by western blot. Results: In this study, we found that Ilamycin C has more preferential cytotoxicity in TNBC cells than non-TNBC MCF7 and nonmalignant MCF10A cells. Notably, our studies revealed the mechanism that Ilamycin C can induce Bax/Bcl-2-related caspase-dependent apoptosis and inhibit migration and invasion through MMP2/MMP9/vimentin/ fascin in TNBC by suppressing IL-6-induced STAT3 phosphorylation. Conclusions: This study provides the first evidence that Ilamycin C has significant implications for the potential as a novel IL-6/STAT3 inhibitor for TNBC treatment in the future.

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Section: Discussionmentioning

confidence: 99%

Ilamycin C induces apoptosis and inhibits migration and invasion in triple-negative breast cancer by suppressing IL-6/STAT3 pathway

et al. 2019

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“…In addition to the automatic comparison of the dataset against the publicly-available spectral databases on the Global Natural Product Social Molecular Network (GNPS) platform, we conducted manual dereplication. A total of 18 annotated compound classes included some known mycotoxins of Penicillium spp., such as the meroterpenoid mycophenolic acid [13] and the cyclic tetrapeptide fungisporin [14] ( Figure 3A). Others included the meroterpenoids andrastin A [15] and prestaunoid A1 [16], polyketides italicic acid [17], xanthoepocin [18], rubratoxin B [19] and canadensolide [20], indole alkaloids brevianamide A [21], communesin G [22] and fumiquinazoline A [23], diketopiperazine roquefortine C [24], phenylalanine derivative asperphenamate [25], tropolone viticolin C [26], pentacyclic alkaloid citrinadin A [27] Another MF shared by all three Penicillium strains was the fungisporin cluster ( Figure 3A).…”

Section: Metabolomicsmentioning

confidence: 99%

“…The cluster analysis ( Figure 3A) based on the differences in atomic mass units (amus) relative to the annotated mycophenolic acid node revealed the presence of a methylated analog (m/z 335.1340 in isolates 31.68F1B and 36.97F1C), which was annotated as mycophenolic acid methyl ester [13] (Table S2). Other nodes in this cluster included the demethylated (m/z 307.1001 specific to isolate 31.68F1B), dehydrogenated (m/z 319.1010 in isolates 31.68F1B and 36.97F1C) and dehydroxylated (m/z 303.1070 in all Penicillii) derivatives of mycophenolic acid, as well as a loss of 26 amu derivative (m/z 295.1010, corresponding to loss of an ethylene group specific to isolate 31.68F1B).…”

Section: Metabolomicsmentioning

confidence: 99%

Mining the Metabolome and the Agricultural and Pharmaceutical Potential of Sea Foam-Derived Fungi

et al. 2020

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Sea foam harbors a diverse range of fungal spores with biological and ecological relevance in marine environments. Fungi are known as the producers of secondary metabolites that are used in health and agricultural sectors, however the potentials of sea foam-derived fungi have remained unexplored. In this study, organic extracts of six foam-derived fungal isolates belonging to the genera Penicillium, Cladosporium, Emericellopsis and Plectosphaerella were investigated for their antimicrobial activity against plant and human pathogens and anticancer activity. In parallel, an untargeted metabolomics study using UPLC-QToF–MS/MS-based molecular networking (MN) was performed to unlock their chemical inventory. Penicillium strains were identified as the most prolific producers of compounds with an average of 165 parent ions per strain. In total, 49 known mycotoxins and functional metabolites were annotated to specific and ubiquitous parent ions, revealing considerable chemical diversity. This allowed the identification of putative new derivatives, such as a new analog of the antimicrobial tetrapeptide, fungisporin. Regarding bioactivity, the Penicillium sp. isolate 31.68F1B showed a strong and broad-spectrum activity against seven plant and human pathogens, with the phytopathogen Magnaporthe oryzae and the human pathogen Candida albicans being the most susceptible (IC50 values 2.2 and 6.3 µg/mL, respectively). This is the first study mining the metabolome of the sea foam-derived fungi by MS/MS-based molecular networking, and assessing their biological activities against phytopathogens.

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“…The fungal strain Penicillium brevicompactum DFFSCS025 (depth 3928 m, the South China Sea) produced two new brevianamides, brevianamids X–Y ( 104 – 105 ) and two new mycochromenic acid derivatives ( 106 – 107 ) ( Figure 17 ). Compound 106 showed strong antilarval activity against Bugula neritina with an EC 50 value of 13.7 μM [ 43 ].…”

Section: Piezophilic Fungimentioning

confidence: 99%

Novel Natural Products from Extremophilic Fungi

Zhang

et al. 2018

Marine Drugs

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Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025

Cited by 40 publications

References 34 publications

Ilamycin C induces apoptosis and inhibits migration and invasion in triple-negative breast cancer by suppressing IL-6/STAT3 pathway

Ilamycin C induces apoptosis and inhibits migration and invasion in triple-negative breast cancer by suppressing IL-6/STAT3 pathway

Mining the Metabolome and the Agricultural and Pharmaceutical Potential of Sea Foam-Derived Fungi

Novel Natural Products from Extremophilic Fungi

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