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

  • Bioorg Chem. 2021 Feb:107:104600. doi: 10.1016/j.bioorg.2020.104600.
Xiaoyan Pang  1 ,  Xuefeng Zhou  2 ,  Xiuping Lin  2 ,  Bin Yang  2 ,  Xinpeng Tian  2 ,  Junfeng Wang  3 ,  Shihai Xu  4 ,  Yonghong Liu  5
Affiliations
  • 1. College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China; CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; College of Pharmacy, Jinan University, Guangzhou 510632, China.
  • 2. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China.
  • 3. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China. Electronic address: [email protected].
  • 4. College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China. Electronic address: [email protected].
  • 5. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China. Electronic address: [email protected].
PMID: 33453645 DOI: 10.1016/j.bioorg.2020.104600
Abstract

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.

Keywords
Deep-sea-derived fungus; Enzyme inhibitory activities; Penicillium sp.; Secondary metabolites; Sorbicillinoids.
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