Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

  • Molecules. 2019 Dec 23;25(1):61. doi: 10.3390/molecules25010061.
Olga F Smetanina  1 ,  Anton N Yurchenko  1 ,  Elena V Girich Ivanets  1 ,  Phan Thi Hoai Trinh  2 ,  Alexander S Antonov  1 ,  Sergey A Dyshlovoy  1  3  4  5 ,  Gunhild von Amsberg  4  5 ,  Natalya Y Kim  1 ,  Ekaterina A Chingizova  1 ,  Evgeny A Pislyagin  1 ,  Ekaterina S Menchinskaya  1 ,  Ekaterina A Yurchenko  1 ,  Tran Thi Thanh Van  2 ,  Shamil S Afiyatullov  1
Affiliations
  • 1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russia.
  • 2. Department of Marine Biotechnology, Nhatrang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, 650000 Nha Trang, Vietnam.
  • 3. School of Natural Science, Far Eastern Federal University, Sukhanova St., 8, Vladivostok 690000, Russia.
  • 4. Laboratory of Experimental Oncology, Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, Germany.
  • 5. Martini-Klinik Prostate Cancer Center, University Hospital Hamburg-Eppendorf, 20246 Hamburg, Germany.
PMID: 31878044 DOI: 10.3390/molecules25010061
Abstract

Seven known echinulin-related indolediketopiperazine Alkaloids (1-7) were isolated from the Vietnamese sediment-derived fungus Aspergillus niveoglaucus. Using chiral HPLC, the enantiomers of cryptoechinuline B (1) were isolated as individual compounds for the first time. (+)-Cryptoechinuline B (1a) exhibited neuroprotective activity in 6-OHDA-, paraquat-, and rotenone-induced in vitro models of Parkinson's disease. (-)-Cryptoechinuline B (1b) and neoechinulin C (5) protected the neuronal cells against paraquat-induced damage in a Parkinson's disease model. Neoechinulin B (4) exhibited cytoprotective activity in a rotenone-induced model, and neoechinulin (7) showed activity in the 6-OHDA-induced model.

Keywords
6-OHDA; Aspergillus niveoglaucus; NMR data; cryptoechinuline; cytotoxic activity; echinulin; neoechinulin; neuroprotective activity; paraquat; rotenone; urease inhibition.
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