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Issue 18, 2019
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Novel anthraquinone derivatives as inhibitors of protein tyrosine phosphatases and indoleamine 2,3-dioxygenase 1 from the deep-sea derived fungus Alternaria tenuissima DFFSCS013

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Abstract

A novel hydroanthraquinone possessing an unprecedented hexacyclic spiro-fused ring system, anthrininone A (1), and two new anthraquinones with a 4,5-disubstituted butylaminolate unit, anthrininones B and C (2 and 3), together with six known analogues including 6-O-methylalaternin (4) and so on, were obtained from the deep-sea derived fungus Alternaria tenuissima DFFSCS013. Their structures were determined by spectroscopic methods, and the absolute configurations were further determined by single crystal X-ray diffraction analysis for 1 and quantum chemical calculations for 2 and 3, respectively. Compounds 1–4 had significant inhibition activity against indoleamine 2,3-dioxygenase 1 (IDO1), and 2–4 also exhibited selective inhibition activity against different protein tyrosine phosphatases. In addition, 1 could obviously stimulate intracellular calcium levels at a concentration of 10 μM. Their structure–bioactivity relationship was also discussed.

Graphical abstract: Novel anthraquinone derivatives as inhibitors of protein tyrosine phosphatases and indoleamine 2,3-dioxygenase 1 from the deep-sea derived fungus Alternaria tenuissima DFFSCS013

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Publication details

The article was received on 17 Jun 2019, accepted on 02 Aug 2019 and first published on 08 Aug 2019


Article type: Research Article
DOI: 10.1039/C9QO00775J
Org. Chem. Front., 2019,6, 3252-3258

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    Novel anthraquinone derivatives as inhibitors of protein tyrosine phosphatases and indoleamine 2,3-dioxygenase 1 from the deep-sea derived fungus Alternaria tenuissima DFFSCS013

    D. Pan, X. Zhang, H. Zheng, Z. Zheng, X. Nong, X. Liang, X. Ma and S. Qi, Org. Chem. Front., 2019, 6, 3252
    DOI: 10.1039/C9QO00775J

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