Novel Polyprenylphenols from Chroogomphus rutilus with Cytotoxic Activities against HCT116 Cells by Inducing Apoptosis.

In this work, 14 new polyprenylphenols, named bischroogomphin A-E (1-5) and chroogolactone A-I (6-14), along with 6 known polyprenylphenols (15-20), were isolated from the wild edible mushroom Chroogomphus rutilus. Compounds 1-5 possess rare asymmetric dimeric meroterpenoids featuring a unique benzofuran-benzopyran-fused dione or ring-opened core skeleton. Their structures were assigned based on HR-ESI-MS spectroscopy and 1D and 2D NMR data. Compounds 1-14 were evaluated for their cytotoxic activity against HCT116 cells, and all compounds exhibited moderate to potent cytotoxicity, with IC50 values spanning from 5.5 ± 1.3 to 25.2 ± 3.1 μM. Furthermore, the antiproliferative effect of bischroogomphin D (4) against HCT116 cells was found to be associated with cell cycle perturbation, characterized by significant G2/M phase arrest, and it triggered apoptosis through caspase activation in association with the MAPK signaling pathway.