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

Abstract

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.