Abstract
Seventeen lactones including eight territrem derivatives (1–8) and nine butyrolactone derivatives (9–17) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 1–3 and 9–10 were new, and their structures were elucidated by spectroscopic analysis. The acetylcholinesterase inhibitory activity and antiviral activity of compounds 1–17 were evaluated. Among them, compounds 1 and 2 showed strong inhibitory activity against acetylcholinesterase with IC50 values of 4.2 ± 0.6, 4.5 ± 0.6 nM, respectively. This is the first time it has been reported that 3, 6, 10, 12 had evident antiviral activity towards HSV-1 with IC50 values of 16.4 ± 0.6, 6.34 ± 0.4, 21.8 ± 0.8 and 28.9 ± 0.8 μg·mL−1, respectively. Antifouling bioassay tests showed that compounds 1, 11, 12, 15 had potent antifouling activity with EC50 values of 12.9 ± 0.5, 22.1 ± 0.8, 7.4 ± 0.6, 16.1 ± 0.6 μg·mL−1 toward barnacle Balanus amphitrite larvae, respectively.
Highlights
Alzheimer’s disease (AD) is a neurodegenerative disorder that is the most common cause of dementia among the elderly
The 13C NMR spectrum showed the presence of 28 carbons, including six methyls, three methylenes, five olefinicmethines, and 14 quaternary carbons.These data showed close similarity to those of 6 [15], which suggested that 1 had a territrem skeleton
Comparison of the NMR data of 1 and 6 showed that the only obvious difference between them was the additional appearance of one low-field quaternary carbon and the absence of one aromatic methine in 1
Summary
Alzheimer’s disease (AD) is a neurodegenerative disorder that is the most common cause of dementia among the elderly. The arisugacins, territrems and terreulactones, mostly containing α-pyrone and triketide-terpenoid moieties, were isolated from fungi [4,5,6], and most of them showed potent inhibitory activities against. Butyrolactones and aspernolides, with a basal skeleton characterized by a five-membered lactone bearing two aromatic rings [9,10], exhibited a wide range of activities, such as inhibitory activities against AChE [11], β-glucuronidase [12], protein kinase [13], and antimicrobial [11], cytotoxic activities [14]. We found that the crude extract of the culture medium of a marine-derived fungal strain Aspergillus terreus SCSGAF0162 had significant AChE inhibitory activity. The bioassay-guided investigation of the extract led to the obtainment of 17 lactones (1–17) (Figure 1), including eight territrem derivatives and nine butyrolactone derivatives. We report the structural elucidation of new compounds, and the isolation and bioactivity of all the compounds
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