Mudassir Shah

Abbottabad University of Science and Technology

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Guojian Zhang

Qingdao National Laboratory for Marine Science and Technology

Tianjiao Zhu

Ocean University of China

Qian Che

Ocean University of China

Dehai Li

Ocean University of China

Chunxiao Sun

Nanjing Medical University

Qianqun Gu

Ocean University of China

Luning Zhou

Fudan University

Wenxue Wang

Ocean University of China

Yuqi Jiang

Qingdao University

Changlong Li

Zhaoqing University

Cooperative Institutions

Ocean University of China

Qingdao National Laboratory for Marine Science and Technology

Qingdao Center of Resource Chemistry and New Materials

Chinese Academy of Sciences

Ministry of Education of the People's Republic of China

Ministry of Education

Beijing Institute of Technology

Abbottabad University of Science and Technology

Sun Yat-sen University

Sichuan University

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Discovery, Total Synthesis, and Anti‐inflammatory Evaluation of Naturally Occurring Naphthopyrone‐Macrolide Hybrids as Potent NLRP3 Inflammasome Inhibitors

Angewandte Chemie International Edition (2024)

Chunxiao Sun Yuqi Jiang Changlong Li Simin Sun Jiaqi Lin

Numerous clinical disorders have been linked to the etiology of dysregulated NLRP3 (NACHT, LRR, and PYD domain-containing protein 3) inflammasome activation. Despite its potential as a pharmacological target, modulation of NLRP3 activity remains challenging. Only a sparse number of compounds have been reported that can modulate NLRP3 and none of them have been developed into a commercially available drug. In this research, we identified three potent NLRP3 inflammasome inhibitors, gymnoasins A-C (1-3), with unprecedented pentacyclic scaffolds, from an Antarctic fungus Pseudogymnoascus sp. HDN17-895, which represent the first naturally occurring naphthopyrone-macrolide hybrids. Additionally, biomimetic synthesis of gymnoasin A (1) was also achieved validating the chemical structure and affording ample amounts of material for exhaustive bioactivity assessments. Biological assays indicated that 1 could significantly inhibited in vitro NLRP3 inflammasome activation and in vivo pro-inflammatory cytokine IL-1β release, representing a valuable new lead compound for the development of novel therapeutics with the potential to inhibit the NLRP3 inflammasome.

10.1002/anie.202405860

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Citations (2)

Talaverrucin A, Heterodimeric Oxaphenalenone from Antarctica Sponge-Derived Fungus Talaromyces sp. HDN151403, Inhibits Wnt/β-Catenin Signaling Pathway

Organic Letters (2022)

Chunxiao Sun Qianwen Liu Mudassir Shah Qian Che Guojian Zhang

The Wnt/β-catenin signaling pathway is an evolutionarily conserved signaling cascade involved in a broad range of biological roles. Dysregulation of the Wnt/β-catenin pathway is implicated in congenital malformations and various kinds of cancers. We discovered a novel Wnt/β-catenin inhibitor, talaverrucin A (1), featuring an unprecedented 6/6/6/5/5/5/6 fused ring system, from an Antarctica sponge-derived fungus Talaromyces sp. HDN151403. Talaverrucin A exhibits inhibitory activity on the Wnt/β-catenin pathway in both zebrafish embryos in vivo and cultured mammalian cells in vitro, providing a naturally inspired small molecule therapeutic lead to target the Wnt/β-catenin pathway.

Sponge

Beta-catenin

WNT3A

10.1021/acs.orglett.2c01394

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Citations (17)

Secondary Metabolites from Deep-Sea Derived Microorganisms

Current Medicinal Chemistry (2019)

Chunxiao Sun Mudassir Shah Zhenzhen Zhang Yanyan Feng Yimin Chang

Microorganisms obtained from the deep sea are a rich source of marine natural products with distinctive chemical structures and bioactivities. In this review, we will provide a retrospective of outstanding research within the scope of deep-sea (≥1000 m) microbial natural products, which has produced up to 442 compounds by the end of 2017. Approximetely, 60% of these structures have demonstrated various biological activities with more than 30% showing cytotoxic function. In this review, we particularly summarize those successful research on secondary metabolites produced by deep-sea derived microorganisms with inclusion of structural characteristics, biological activities, together with biogenetic origins and taxonomic features of the source microorganisms, from which, we expect to provide more comprehensive understanding of small molecules obtained from deep-sea environment and benefit the ongoing scholarly endeavors in the search for novel pharmaceutical agents from the deep-sea derived microorganisms.

Scope (computer science)

10.2174/0929867326666190618153950

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Citations (26)

Phenylhydrazone Alkaloids from the Deep-Sea Cold Seep Derived Fungus Talaromyces amestolkiae HDN21-0307

Journal of Natural Products (2024)

Jiajin Wu Wenxue Wang Yuhuan Yang Mudassir Shah Jixing Peng

Alkaloids with a phenylhydrazone architecture are rarely found in nature. Four unusual phenylhydrazone alkaloids named talarohydrazones A–D (1–4) were isolated from the deep-sea cold seep derived fungus Talaromyces amestolkiae HDN21-0307 using the one strain–many compounds (OSMAC) approach and MS/MS-based molecular networking (MN) combined with network annotation propagation (NAP) and the unsupervised substructure annotation method MS2LDA. Their structures were elucidated by spectroscopic data analysis, single-crystal X-ray diffraction, and quantum chemical calculations. Talarohydrazone A (1) possessed an unusual skeleton combining 2,4-pyridinedione and phenylhydrazone. Talarohydrazone B (2) represents the first natural phenylhydrazone-bearing azadophilone. Bioactivity evaluation revealed that compound 1 exhibited cytotoxic activity against NCI-H446 cells with an IC50 value of 4.1 μM. In addition, compound 1 displayed weak antibacterial activity toward Staphylococcus aureus with an MIC value of 32 μg/mL.

Strain (injury)

10.1021/acs.jnatprod.4c00132

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Citations (7)

Discovery, Total Synthesis, and Anti‐inflammatory Evaluation of Naturally Occurring Naphthopyrone‐Macrolide Hybrids as Potent NLRP3 Inflammasome Inhibitors

Angewandte Chemie (2024)

Chunxiao Sun Yuqi Jiang Changlong Li Simin Sun Jiaqi Lin

Abstract Numerous clinical disorders have been linked to the etiology of dysregulated NLRP3 (NACHT, LRR, and PYD domain‐containing protein 3) inflammasome activation. Despite its potential as a pharmacological target, modulation of NLRP3 activity remains challenging. Only a sparse number of compounds have been reported that can modulate NLRP3 and none of them have been developed into a commercially available drug. In this research, we identified three potent NLRP3 inflammasome inhibitors, gymnoasins A‐C ( 1 – 3 ), with unprecedented pentacyclic scaffolds, from an Antarctic fungus Pseudogymnoascus sp. HDN17‐895, which represent the first naturally occurring naphthopyrone‐macrolide hybrids. Additionally, biomimetic synthesis of gymnoasin A ( 1 ) was also achieved validating the chemical structure and affording ample amounts of material for exhaustive bioactivity assessments. Biological assays indicated that 1 could significantly inhibited in vitro NLRP3 inflammasome activation and in vivo pro‐inflammatory cytokine IL‐1β release, representing a valuable new lead compound for the development of novel therapeutics with the potential to inhibit the NLRP3 inflammasome.

Anti-inflammatory

10.1002/ange.202405860

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Citations (0)

New metabolites from a Mariana Trench-derived actinomycete Nocardiopsis sp. HDN 17-237

Journal of Asian Natural Products Research (2019)

Junxiao Wang Chunxiao Sun Mudassir Shah Guojian Zhang Qianqun Gu

One new β,γ-butenoate derivative phenylbutenote (1), and one new α-pyrone nocapyrone T (2) were isolated from the deep-sea derived actinomycete Nocardiopsis sp. HDN 17-237. Their structures were elucidated by extensive HRMS, IR and NMR analyses. Among them, compound 1 is the first microbial natural products bearing a rare β,γ-butenoate moiety, and compound 2 is the first α-pyrone isolated from strain of Mariana Trench. Compounds 1 and 2 were tested for antioxidant and antibacterial activities, while none of them showed significant activity.

Moiety

Pyrone

Derivative (finance)

Strain (injury)

10.1080/10286020.2019.1681411

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Citations (12)

Cytotoxic Nitrobenzoyl Sesquiterpenoids from an Antarctica Sponge-Derived Aspergillus insulicola

Journal of Natural Products (2022)

Chunxiao Sun Xiaoyu Liu Ning Sun Xiaomin Zhang Mudassir Shah

Pancreatic ductal adenocarcinoma (PDAC) is one of the most aggressive neoplastic diseases of the pancreas with fatal proliferation and metastasis and no medicine available for treatment. From an Antarctica sponge-derived fungus, Aspergillus insulicola HDN151418, four new nitrobenzoyl sesquiterpenoids, namely, insulicolides D–G (1–4), were isolated. Compounds 3 and 4 exhibited selective inhibition against human PDAC cell lines. Further studies indicated that compound 4 could significantly suppress cell proliferation to induce apoptosis and blocked migration and invasion of PDAC cells. Compound 4 could also avoid resistance and improved the therapeutic effect of the chemotherapy drug gemcitabine. A preliminary mechanism study showed that compound 4 can significantly inhibit the expression of EGFR and XIAP in PDAC cells. Altogether, 4 is a potential lead compound for anti-PDAC drug research.

Sponge

XIAP

10.1021/acs.jnatprod.1c01118

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Citations (14)

CCDC 2162710: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Chunxiao Sun Qianwen Liu Mudassir Shah Qian Che Guojian Zhang

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2blgv8

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Citations (0)

Dimeric Tetracenomycin Derivatives from a Taklamakan Desert-Derived Streptomyces sp. HDN154193

Journal of Natural Products (2021)

Li Xing Yimin Chang Xiaoqian Zhang Xuewen Hou Yaxin Han

Bitetracenomycin A (1) and its diastereomers [(±)-bitetracenomycin B, (±)-2] were discovered from the cultures of Streptomyces sp. HDN154193. Compounds 1 and (±)-2 were the first tetracenomycin dimers obtained from a natural source with sp3 methine protons at the bridge positions (C-12/12′), which also exhibited broad-spectrum antibacterial activity. The racemate (±)-2 was semisynthesized and separated into enantiomers (+)-2 and (−)-2, and the absolute configurations were determined by specific rotation and ECD data. These metabolites exhibited potent antibacterial activity especially against drug-resistant strains (MRSA and MRCNS) with MIC values ranging from 1.0 to 1.9 μg/mL.

Diastereomer

Absolute Configuration

Streptomycetaceae

10.1021/acs.jnatprod.1c00735

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Citations (2)

Frontispiz: Discovery, Total Synthesis, and Anti‐Inflammatory Evaluation of Naturally Occurring Naphthopyrone‐Macrolide Hybrids as Potent NLRP3 Inflammasome Inhibitors

Angewandte Chemie (2024)

Chunxiao Sun Yuqi Jiang Changlong Li Simin Sun Jiaqi Lin

Natural Products. The NLRP3 inflammasome plays a crucial role in regulating the innate immune system and inflammatory signaling. In their Research Article (e202405860), Dehai Li and co-workers report that a naphthopyrone-macrolide hybrid derived from Antarctic fungus serves as a potent NLRP3 inflammasome inhibitor.

10.1002/ange.202484361

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