Journal
BIOORGANIC CHEMISTRY
Volume 107, Issue -, Pages -Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2020.104600
Keywords
Deep-sea-derived fungus; Penicillium sp.; Secondary metabolites; Enzyme inhibitory activities; Sorbicillinoids
Funding
- National Key Research and Development Program of China [2018YFC0310900, 2019YFC0312503]
- National Natural Science Foundation of China [21502204, 21672084, 21772210, 41476135, 41776169, 41876145]
- China Postdoctoral Science Foundation [2019M663368]
- Special Funds for Promoting Economic Development (Marine Economic Development) of Guangdong Province [GDOE [2019]A28, [2020]037]
- Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) [GML2019ZD0406]
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Several new sorbicillinoid compounds were isolated from a deep-sea sediment-derived fungus, exhibiting inhibitory activities against enzymes and bacteria. Some of these compounds displayed stronger inhibitory effects compared to standard drugs.
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 alpha-pyrone derivative unit. All of the isolated compounds were evaluated for their antibacterial, antifungal and enzyme inhibitory activities against alpha-glycosidase and acetylcholinesterase (AChE) in vitro. Compound 6 displayed more potent inhibitory activity against alpha-glycosidase than acarbose with IC50 value of 36.0 mu M and compounds 4, 12, 18, 22, 23 exhibited moderate inhibitory activity with IC50 values ranging from 115.8 to 208.5 mu M. Compounds 10 and 22 showed weak enzyme inhibitory activities against AChE with 55.1% and 51.1% inhibitions at concentration of 50 mu g/mL, respectively. Besides, compounds 11 and 12 exhibited significant antibacterial activities against Staphylococcus aureus with MIC values of 10.0 and 5.0 mu g/mL, respectively. The hypothetical biosynthetic pathway of the isolated sorbicillinoids with three different structural types was discussed.
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