Journal
TETRAHEDRON LETTERS
Volume 65, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.152756
Keywords
Diarylpropane; Horsfiequinone A; Biomimetic synthesis; Aerobic oxidation; Anti-inflammation
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Funding
- National Natural Science Foundation of China [81960631, 31860097, 81803396]
- Yunnan Fundamental Research Project [202001AS070038]
- Top Young Talent of Ten Thousand Talents Program of Yunnan Province
- Startup fund of Yunnan University of Chinese Medicine [2019YZG03]
- Discipline Funding of School of Chinese Materia Medica, Yunnan University of Chinese Medicine [2020TD15]
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Inspired by the oxy-tyrosinase type II copper enzyme, a biomimetic synthesis of the natural product hors-fiequinone A was achieved, showing inhibitory activity on nitric oxide production and potential anti-inflammatory effects.
Inspired by the oxy-tyrosinase type II copper enzyme, a biomimetic synthesis of the natural product hors-fiequinone A (1) has been achieved using CuOTf/DBED/O-2 catalyzed oxidation as a key step. The synthetic route furnished 1 in 33% overall yield (64% brsm) from commercially available para-hydroxybenzalde-hyde. Moreover, revisiting the biological activity of 1 resulted in the discovery of its in vitro inhibitory activity towards nitric oxide (NO) production in LPS-induced RAW264.7 cells with an IC50 value of 4.42 +/- 0.81 mu M. The anti-inflammatory effect of 1 was further supported by an iNOS expression inhibition assay and molecular docking simulation. (C) 2021 Elsevier Ltd. All rights reserved.
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