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. 2019 Dec 23;25(1):61.
doi: 10.3390/molecules25010061.

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

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

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

Olga F Smetanina et al. Molecules. .

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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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The structures of isolated compounds 1–7.
Figure 2
Figure 2
CD curves of 1a (magenta, ■) and 1b (blue, ●).
Figure 3
Figure 3
Effects of compounds 1–7 on the viability of Neuro-2a cells treated with rotenone (a), PQ (b), and 6-OHDA (c). Cells were pretreated with 10 µM of the tested compound (1–7) for 1 h, and then the neurotoxin was added. * Statistically significant difference (p ≤ 0.05, Student’s t-test).
See this image and copyright information in PMC

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