Biological activities and mass fragmentation pathways of meroterpenoid cochlioquinones from plant pathogenic fungus Bipolaris sorokiniana

Cochlioquinones are a member of meroterpenoids that partially possessed phenolic hydroxyls with potential antioxidant activities. This study investigated the mass fragmentation pathways, antioxidant, cytotoxic, and phytotoxic activities of cochlioquinone analogs. The mass fragmentation pathways of cochlioquinones (1–7) were firstly analyzed using UPLC-Q-TOF-MS/MS, in which Retro Diels-Alder reaction, neutral loss, and McLafferty rearrangement were the main cleavage patterns. Compound 8 and 9 (a unique new analog) were then isolated in target. Cochlioquinones (4–6, 9) displayed strong antioxidant activities for DPPH radical scavenging assay as the first antioxidant effects report. In addition, 1–9 exhibited cytotoxic activities against B16 cells (IC50 from 1.91 to 12.33 μM) and Hep G2 cells (IC50 from 3.21 to 77.15 μM), and 5, 7, and 8 showed phytotoxic activities against foxtail leaves. These biological activities imply that cochlioquinones can be as antioxidant agents for food additives or bioactive molecules for cancer drugs and pesticides.