Curindolizine, an Anti-Inflammatory Agent Assembled via Michael Addition of Pyrrole Alkaloids Inside Fungal Cells

  • Org Lett. 2016 Apr 15;18(8):1816-9. doi: 10.1021/acs.orglett.6b00549.
Wen Bo Han  1 ,  Ai Hua Zhang  1  2 ,  Xin Zhao Deng  1 ,  Xinxiang Lei  3 ,  Ren Xiang Tan  1
Affiliations
  • 1. Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University , Nanjing 210093, China.
  • 2. State Key Laboratory of Elemento-organic Chemistry, Nankai University , Tianjin 300071, China.
  • 3. College of Chemistry & Materials Engineering, Wenzhou University , Wenzhou 325035, China.
PMID: 27046459 DOI: 10.1021/acs.orglett.6b00549
Abstract

Curvularia sp. IFB-Z10, a white croaker-associated fungus, generates a skeletally unprecedented indolizine alkaloid named curindolizine (1), which displays an anti-inflammatory action in lipopolyssacharide (LPS)-induced RAW 264.7 macrophages with an IC50 value of 5.31 ± 0.21 μM. The enzymatic transformation test demonstrated that the unique curindolizine architecture was most likely produced by the regiospecific in-cell Michael addition reaction between Pyrrole Alkaloids, curvulamine, and 3,5-dimethylindolizin-8(5H)-one.

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