Absolute Stereochemistry and Cytotoxic Effects of Vismione E from Marine Sponge-Derived Fungus IAspergillus/I sp. 1901NT-1.2.2

The metabolic profile of the Aspergillus sp. 1901NT-1.2.2 sponge-associated fungal strain was investigated using the HPLC MS technique, and more than 23 peaks in the HPLC MS chromatogram were detected. Only two minor peaks were identified as endocrocin and terpene derivative MS data from the GNPS da...

Full description

Saved in:
Bibliographic Details
Published in:International journal of molecular sciences 2023-05, Vol.24 (9)
Main Authors: Girich, Elena V, Trinh, Phan Thi Hoai, Nesterenko, Liliana E, Popov, Roman S, Kim, Natalya Yu, Rasin, Anton B, Menchinskaya, Ekaterina S, Kuzmich, Aleksandra S, Chingizova, Ekaterina A, Minin, Artem S, Ngoc, Ngo Thi Duy, Van, Tran Thi Thanh, Yurchenko, Ekaterina A, Yurchenko, Anton N, Berdyshev, Dmitry V
Format: Article
Language:English
Subjects:
Analysis
Cancer
Care and treatment
Fungi
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The metabolic profile of the Aspergillus sp. 1901NT-1.2.2 sponge-associated fungal strain was investigated using the HPLC MS technique, and more than 23 peaks in the HPLC MS chromatogram were detected. Only two minor peaks were identified as endocrocin and terpene derivative MS data from the GNPS database. The main compound was isolated and identified as known anthraquinone derivative vismione E. The absolute stereochemistry of vismione E was established for the first time using ECD and quantum chemical methods. Vismione E showed high cytotoxic activity against human breast cancer MCF-7 cells, with an IC[sub.50] of 9.0 µM, in comparison with low toxicity for normal human breast MCF-10A cells, with an IC[sub.50] of 65.3 µM. It was found that vismione E inhibits MCF-7 cell proliferation and arrests the cell cycle in the G1 phase. Moreover, the negative influence of vismione E on MCF-7 cell migration was detected. Molecular docking of vismione E suggested the IMPDH2 enzyme as one of the molecular targets for this anthraquinone derivative.
ISSN:1422-0067
1422-0067
DOI:10.3390/ijms24098150