Pyrenocine A induces monopolar spindle formation and suppresses proliferation of cancer cells

Myobatake, Yusuke; Kamisuki, Shinji; Tsukuda, Senko; Higashi, Taishi; Chinen, Takumi; Takemoto, Kenji; Hachisuka, Masami; Suzuki, Yuka; Takei, Maya; Tsurukawa, Yukine; Maekawa, Hiroaki; Takeuchi, Toshifumi; Matsunaga, Tomoko; Sahara, Hiroeki; Usui, Takeo; Matsunaga, Satoru; Sugawara, Fumio

doi:10.1016/j.bmc.2019.115149

Cited by 9 publications

(4 citation statements)

References 21 publications

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“…Compound 7 showed cytotoxicity against several cancer cells, with IC 50 values ranging from 2.6 to 12.9 µM. Terrein ( 14) displayed strong cytotoxicities against human breast cancer MCF-7 cells [38] and human lung cancer A 549 cells [39]. Hence, our findings were consistent with those reported in previous experiments, though different cancer cell lines were evaluated.…”

Section: Resultssupporting

confidence: 90%

Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects

Zou

Zhang²,

Zhou

et al. 2022

Marine Drugs

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Six new citreoviridins (citreoviridins J–O, 1–6) and twenty-two known compounds (7–28) were isolated from the deep-sea-derived Penicillium citreonigrum MCCC 3A00169. The structures of the new compounds were determined by spectroscopic methods, including the HRESIMS, NMR, ECD calculations, and dimolybdenum tetraacetate-induced CD (ICD) experiments. Citreoviridins J−O (1–6) are diastereomers of 6,7-epoxycitreoviridin with different chiral centers at C-2–C-7. Pyrenocine A (7), terrein (14), and citreoviridin (20) significantly induced apoptosis for HeLa cells with IC50 values of 5.4 μM, 11.3 μM, and 0.7 μM, respectively. To be specific, pyrenocine A could induce S phase arrest, while terrein and citreoviridin could obviously induce G0-G1 phase arrest. Citreoviridin could inhibit mTOR activity in HeLa cells.

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Section: Resultssupporting

confidence: 90%

Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects

Zou

Zhang²,

Zhou

et al. 2022

Marine Drugs

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“…WST-8 Assay WST-8 assay was performed as described previously. 33) Anti-HCV Assay The anti-HCV assay was performed as described previously. 23,24) Anti-SARS-CoV-2 Assay SARS-CoV-2 was handled at biosafety level 3 (BSL3).…”

Section: Methodsmentioning

confidence: 99%

Cyclic Phthalate Esters as Liver X Receptor Antagonists with Anti-hepatitis C Virus and Anti-severe Acute Respiratory Syndrome Coronavirus 2 Properties

Saito

Ohashi

Nakamura

et al. 2022

CHEMICAL & PHARMACEUTICAL BULLETIN

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The liver X receptor is a nuclear hormone receptor that regulates lipid metabolism. Previously, we had demonstrated the antiviral properties of a liver X receptor antagonist associated with the hepatitis C virus and severe acute respiratory syndrome coronavirus 2. In this study, we screened a chemical library and identified two potential liver X receptor antagonists. Spectroscopic analysis revealed that the structures of both antagonists (compounds 1 and 2) were cyclic dimer and trimer of esters, respectively, that consisted of phthalate and 1,6-hexane diol. This study is the first to report the structure of the cyclic trimer of phthalate ester. Further experiments revealed that the compounds were impurities of solvents used for purification, although their source could not be traced. Both phthalate esters exhibited anti-hepatitis C virus activity, whereas the cyclic dimer showed anti-severe acute respiratory syndrome coronavirus 2 activity. Cyclic phthalate derivatives may constitute a novel class of liver X receptor antagonists and broad-spectrum antivirals.

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“…13,14) In our previous studies, we have focused on fungal metabolites as a source of novel bioactive compounds and found physiologically active compounds such as antiviral, anticancer, and neuroprotective molecules. [15][16][17] In this study, we screened a natural product library containing secondary metabolites that were partially purified from extracts of fungal culture broths using a reporter gene assay and identified methylsulochrin as an AhR partial agonist. Methylsulochrin decreased HCV production and suppressed the production of inflammatory cytokine interleukin-6 (IL-6) in cells.…”

Section: Chemical and Pharmaceutical Bulletin Advance Publicationmentioning

confidence: 99%

Identification of Methylsulochrin as a Partial Agonist for Aryl Hydrocarbon Receptors and Its Antiviral and Anti-inflammatory Activities

Nakamura,

Yamasaki,

Ohashi

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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Although aryl hydrocarbon receptors (AhRs) are related to the metabolic pathway of xenobiotics, recent studies have revealed that this receptor is also associated with the life cycle of viruses and inflammatory reactions. For example, flutamide, used to treat prostate cancer, inhibits hepatitis C virus proliferation by acting as an AhR antagonist, and methylated-pelargonidin, an AhR agonist, suppresses pro-inflammatory cytokine production. To discover a novel class of AhR ligands, we screened 1000 compounds derived from fungal metabolites using a reporter assay and identified methylsulochrin as a partial agonist of the aryl hydrocarbon receptor. Methylsulochrin was found to inhibit the production of hepatitis C virus (HCV) in Huh-7.5.1 cells. Methylsulochrin also suppressed the production of interleukin-6 in RAW264.7 cells. Furthermore, a preliminary structure-activity relationship study using sulochrin derivatives was performed. Our findings suggest the use of methylsulochrin derivatives as anti-HCV compounds with anti-inflammatory activity.

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Pyrenocine A induces monopolar spindle formation and suppresses proliferation of cancer cells

Cited by 9 publications

References 21 publications

Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects

Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects

Cyclic Phthalate Esters as Liver X Receptor Antagonists with Anti-hepatitis C Virus and Anti-severe Acute Respiratory Syndrome Coronavirus 2 Properties

Identification of Methylsulochrin as a Partial Agonist for Aryl Hydrocarbon Receptors and Its Antiviral and Anti-inflammatory Activities

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