Structurally various sorbicillinoids from the deep-sea sediment derived fungus Penicillium sp. SCSIO06871

[Display omitted] •Eight new sorbicilinoids were isolated from the deep-sea sediment derived fungus Penicillium sp. SCSIO06871.•Their absolute configurations were elucidated based on X-ray crystallography analysis and ECD calculation.•The hypothetical biosynthetic pathway of the isolated sorbicillinoids with three different structural types was discussed.•Compound 6 displayed more potent inhibitory activity against α-glycosidase than acarbose. Two new hybrid sorbicillinoids (1 and 5), three new bisorbicillinoids (2–4), and three monomeric sorbicillinoids (6–8), along with eighteen known sorbicillinoids (9–26) were isolated from cultures of the deep-sea sediment derived fungus Penicillium sp. SCSIO06871. Their structures and absolute configurations were elucidated based upon the extensive spectroscopic analysis, X-ray crystallography analysis and the comparison of the experimental and calculated ECD data. Bisorbicillpyrone A (4) is the first example of bisorbicillinoid containing an α-pyrone derivative unit. All of the isolated compounds were evaluated for their antibacterial, antifungal and enzyme inhibitory activities against α-glycosidase and acetylcholinesterase (AChE) in vitro. Compound 6 displayed more potent inhibitory activity against α-glycosidase than acarbose with IC50 value of 36.0 μM and compounds 4, 12, 18, 22, 23 exhibited moderate inhibitory activity with IC50 values ranging from 115.8 to 208.5 μM. Compounds 10 and 22 showed weak enzyme inhibitory activities against AChE with 55.1% and 51.1% inhibitions at concentration of 50 μg/mL, respectively. Besides, compounds 11 and 12 exhibited significant antibacterial activities against Staphylococcus aureus with MIC values of 10.0 and 5.0 μg/mL, respectively. The hypothetical biosynthetic pathway of the isolated sorbicillinoids with three different structural types was discussed.