Publication details

Cytotoxic Stilbenoids, Hetero- and Homodimers of Homoisoflavonoids from Prospero autumnale

Authors

KIRMIZIBEKMEZ Hasan ARU Basak KŘOUSTKOVÁ Jana ERDOGAN Murat TORRENCE Ian ANDO Kaori TANTILLO Dean J MALANÍK Milan KOSTURKO Stefan KUNES Jiri CAHLÍKOVÁ Lucie

Year of publication 2025
Type Article in Periodical
Magazine / Source Journal of Natural Products
MU Faculty or unit

Faculty of Pharmacy

Citation
web https://pubs.acs.org/doi/epdf/10.1021/acs.jnatprod.4c01263?ref=article_openPDF
Doi http://dx.doi.org/10.1021/acs.jnatprod.4c01263
Keywords DENSITY-FUNCTIONAL METHODSMOLECULAR-ORBITAL METHODSPROTON CHEMICAL-SHIFTSBASIS-SETSBULBSIII.H-1
Description An activity-guided isolation study on the EtOH extract prepared from the bulbs of Prospero autumnale yielded four new phenolic compounds, including a new stilbenoid (1), a new homoisoflavonoid derivative (8), a new homoisoflavonoid dimer (9), and an unprecedented homoisoflavone-stilbene heterodimer (10), together with six known (2-7) analogs. Their chemical structures were elucidated by spectroscopic analysis and theoretical NMR and ECD calculations. Compounds 9 and 10 are unique in their scaffolds. The in vitro cytotoxic activity of purified compounds was evaluated against eight tumor cell lines (HCT116, LoVo, DU145, PC3, HEP3B, HEPG2, MCF7, and MDA-MB-231) and one nontumor cell line (L929) by the MTS assay. Compounds 1, 2, 4, and 10 exhibited inhibition with IC50 values ranging from 8.2 to 37.6 mu M. Cytotoxic cell death mechanisms were further investigated, indicating variability in apoptosis, necrosis, or cell cycle arrest.

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