Vialinin B, a novel potent inhibitor of TNF-α production, isolated from an edible mushroom, Thelephora vialis

Xie, Chun; Koshino, Hiroyuki; Esumi, Yasuaki; Onose, Jun‐ichi; Yoshikawa, Kunie; Abe, Naoki

doi:10.1016/j.bmcl.2006.07.068

Cited by 33 publications

(12 citation statements)

References 12 publications

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“…Cyclic heteroatom containing compounds are commonly found in pharmaceuticals, and a variety of methods have been established to obtain these important structures. Among these heterocyclic compounds, oxygenated heterocyclic dibenzofurans and xanthones are privileged scaffolds in many pharmaceutically active compounds, such as eriobofuran, vialinin B, griseoxanthone C, and α‐mangostin (Figure ) . Xanthene derivatives are another special class of oxygen‐incorporating tricyclic compounds, demonstrating impressive photophysical property arising from their π‐conjugation systems, used as common building blocks of dyes and fluorescent materials .…”

Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed One‐Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums

Zhu

et al. 2019

Eur J Org Chem

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Oxygenation of cyclic diphenyl iodoniums (CDPIs) with varied medium‐ring sizes has been fully investigated. This practical copper‐catalyzed tandem reaction of CDPIs with water as the oxygen source enables the construction of derivatised dibenzofurans and xanthenes at moderate to good yields. Moreover, structurally important xanthones are also successfully accessed under the oxygenation conditions with additional TEMPO.

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Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed One‐Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums

Zhu

et al. 2019

Eur J Org Chem

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“…It is a novel dibenzofuran compound isolated from dry fruiting bodies of an edible mushroom, Thelephora vialis, which potently inhibits TNF-alpha production in RBL-2H3 cells (IC (50) = 0.02 nM) and acts as a promising anti-allergic agent (X. C et al 2006 ). It displayed a binding affinity of −8.9 kcal/mol with CotH3.…”

Section: Discussionmentioning

confidence: 99%

In silico prediction and structure-based multitargeted molecular docking analysis of selected bioactive compounds against mucormycosis

2022

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Background During the second wave of the COVID-19 pandemic, an unusual increase in cases of mucormycosis was observed in India, owing to immunological dysregulation caused by the SARS-CoV-2 and the use of broad-spectrum antibiotics, particularly in patients with poorly controlled diabetes with ketoacidosis to have contributed to the rise, and it has been declared an epidemic in several states of India. Because of the black colouring of dead and dying tissue caused by the fungus, it was dubbed "black fungus" by several Indian media outlets. In this study, attempts were taken to unmask novel therapeutic options to treat mucormycosis disease. Rhizopus species is the primary fungi responsible for 70% of mucormycosis cases. Results We chose three important proteins from the Rhizopus delemar such as CotH3, Lanosterol 14 alpha-demethylase and Mucoricin which plays a crucial role in the virulence of Mucorales. Initially, we explored the physiochemical, structural and functional insights of proteins and later using AutoDock Vina, we applied computational protein–ligand binding modelling to perform a virtual screening around 300 selected compounds against these three proteins, including FDA-approved drugs, FDA-unapproved drugs, investigational-only drugs and natural bioactive compounds. ADME parameters, toxicity risk and biological activity of those compounds were approximated via in silico methods. Our computational studies identified six ligands as potential inhibitors against Rhizopus delemar, including 12,28-Oxamanzamine A, vialinin B and deoxytopsentin for CotH3; pramiconazole and saperconazole for Lanosterol 14 alpha-demethylase; and Hesperidin for Mucoricin. Interestingly, 12,28-Oxamanzamine A showed a maximum binding affinity with all three proteins (CotH3: − 10.2 kcal/mol Lanosterol 14 alpha-demethylase: − 10.9 kcal/mol Mucoricin: − 8.6 kcal/mol). Conclusions In summary, our investigation identified 12,28-Oxamanzamine A, vialinin B, deoxytopsentin, pramiconazole, saperconazole and hesperidin as potent bioactive compounds for treating mucormycosis that may be considered for further optimisation techniques and in vitro and in vivo studies.

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“…It is a novel dibenzofuran compound isolated from dry fruiting bodies of an edible mushroom, Thelephora vialis, which potently inhibits TNF-alpha production in RBL-2H3 cells (IC (50) = 0.02nM) and acts as a promising anti-allergic agent [57]. It displayed a binding a nity of -8.9 kcal/mol with CotH3.…”

Section: Vialinin Bmentioning

confidence: 99%

In Silico Prediction and Structure Based Multitargeted Molecular Docking Analysis of Selected Bioactive Compounds Against Mucormycosis

Madanagopal

Ramprabhu

Jagadeesan

2021

Preprint

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Background: During the second wave of the COVID-19 pandemic, an unusual increase in cases of mucormycosis was observed in India, owing to immunological dysregulation caused by the SARS-CoV-2 and the use of broad-spectrum antibiotics, particularly in patients with poorly controlled diabetes with ketoacidosisto have contributed to the rise and it has been declared an epidemic in several states of India.Because of the black colouring of dead and dying tissue caused by the fungus, it was dubbed "black fungus" by several Indian media outlets. In this study, attempts were taken to unmask novel therapeutic options to treat mucormycosis disease. Rhizopus species is the primary fungi responsible for 70% of mucormycosis cases.Results: We chose three important proteins from the Rhizopus delemar such as CotH3, Lanosterol 14 alpha-demethylase and Mucoricin which plays a crucial role in the virulence of Mucorales. Initially, we explored the physiochemical, structural and functional insights of proteins and later using AutoDock Vina, we applied computational protein-ligand binding modelling to perform a virtual screening around 300 selected compounds against these three proteins, including FDA-approved drugs, FDA-unapproved drugs, investigational-only drugs, and natural bioactive compounds. ADME parameters, Toxicity risk and biological activity of those compounds were approximated via in silico methods. Our computational studies identified six ligands as potential inhibitors against Rhizopus delemar, including 12,28-Oxamanzamine A, vialinin B and deoxytopsentin for CotH3; pramiconazole and saperconazole for Lanosterol 14 alpha-demethylase; and Hesperidin for Mucoricin. Interestingly, 12,28-Oxamanzamine A showed a maximum binding affinity with all three proteins(CotH3: -10.2 kcal/mol Lanosterol 14 alpha-demethylase: -10.9 kcal/mol Mucoricin:-8.6 kcal/mol).Conclusions: In summary, our investigation identified 12,28-Oxamanzamine A, vialinin B, deoxytopsentin, pramiconazole, saperconazole and hesperidin as potent bioactive compounds for treating mucormycosis that may be considered for further optimization techniques and in-vitro and in-vivo studies.

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Vialinin B, a novel potent inhibitor of TNF-α production, isolated from an edible mushroom, Thelephora vialis

Cited by 33 publications

References 12 publications

Copper‐Catalyzed One‐Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums

Copper‐Catalyzed One‐Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums

In silico prediction and structure-based multitargeted molecular docking analysis of selected bioactive compounds against mucormycosis

In Silico Prediction and Structure Based Multitargeted Molecular Docking Analysis of Selected Bioactive Compounds Against Mucormycosis

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