Azaphilone Derivatives from the Fungus Coniella fragariae Inhibit NF-κB Activation and Reduce Tumor Cell Migration

Haiqian Yu, Julia Sperlich, Attila Mándi, T. Kurtán, Haofu Dai, Nicole Teusch, Zhi Yong Guo, Kun Zou, Zhen Liu, Peter Proksch

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Seven new azaphilones, coniellins A-G (1-7), were obtained from the fungus Coniella fragariae that had been isolated from goose dung. Their structures were elucidated by analysis of 1D and 2D NMR as well as HRESIMS data. TDDFT-ECD calculation was used to determine the absolute configuration of 1, while Mosher's method was applied to determine the absolute configuration of 5. While displaying only moderate cytotoxicity, compound 1 exhibited significant inhibition of NF-κB activation in the triple negative breast cancer cell line MDA-MB-231 with an IC50 value of 4.4 μM. Moreover, compounds 1, 4, and 5 clearly reduced tumor cell migration. Compound 1 was the most active derivative tested in this assay and displayed 60% inhibition of tumor cell migration at a dose of 5 μM and 98% inhibition at 10 μM after 24 h.

Original languageEnglish
JournalJournal of Natural Products
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

Fragaria
Fungi
Cell Movement
Tumors
Chemical activation
Cells
Cell Migration Inhibition
Triple Negative Breast Neoplasms
Derivatives
Geese
Inhibitory Concentration 50
Neoplasms
Cytotoxicity
Cell Line
Assays
Nuclear magnetic resonance
azaphilone
1-(2-(3-methoxyphenyl)ethyl)phenoxy-3-(dimethylamino)-2-propanol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Azaphilone Derivatives from the Fungus Coniella fragariae Inhibit NF-κB Activation and Reduce Tumor Cell Migration. / Yu, Haiqian; Sperlich, Julia; Mándi, Attila; Kurtán, T.; Dai, Haofu; Teusch, Nicole; Guo, Zhi Yong; Zou, Kun; Liu, Zhen; Proksch, Peter.

In: Journal of Natural Products, 01.01.2018.

Research output: Contribution to journalArticle

Yu, Haiqian ; Sperlich, Julia ; Mándi, Attila ; Kurtán, T. ; Dai, Haofu ; Teusch, Nicole ; Guo, Zhi Yong ; Zou, Kun ; Liu, Zhen ; Proksch, Peter. / Azaphilone Derivatives from the Fungus Coniella fragariae Inhibit NF-κB Activation and Reduce Tumor Cell Migration. In: Journal of Natural Products. 2018.
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abstract = "Seven new azaphilones, coniellins A-G (1-7), were obtained from the fungus Coniella fragariae that had been isolated from goose dung. Their structures were elucidated by analysis of 1D and 2D NMR as well as HRESIMS data. TDDFT-ECD calculation was used to determine the absolute configuration of 1, while Mosher's method was applied to determine the absolute configuration of 5. While displaying only moderate cytotoxicity, compound 1 exhibited significant inhibition of NF-κB activation in the triple negative breast cancer cell line MDA-MB-231 with an IC50 value of 4.4 μM. Moreover, compounds 1, 4, and 5 clearly reduced tumor cell migration. Compound 1 was the most active derivative tested in this assay and displayed 60{\%} inhibition of tumor cell migration at a dose of 5 μM and 98{\%} inhibition at 10 μM after 24 h.",
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AU - Dai, Haofu

AU - Teusch, Nicole

AU - Guo, Zhi Yong

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