A glyoxylate-containing benzene derivative and butenolides from a marine algicolous fungus Aspergillus sp. SCSIO 41304

A new glyoxylate-containing benzene derivative, methyl 2-(4-hydroxy-3-(3′-methyl-2′-butenyl)phenyl)-2-oxoacetate (1), together with ten known compounds (2-11), were isolated from the marine algicolous fungus, Aspergillus sp. SCSIO 41304. Their planar structures and absolute configurations were eluci...

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Bibliographic Details
Published in:Natural product research 2023-02, Vol.37 (3), p.441-448
Main Authors: Qi, Xin, Chen, Wei-Hao, Lin, Xiu-Ping, Liao, Sheng-Rong, Yang, Bin, Zhou, Xue-Feng, Liu, Yong-Hong, Wang, Jun-Feng, Li, Yong
Format: Article
Language:English
Subjects:
Acetylcholinesterase
Acetylcholinesterase - metabolism
Algicolous fungus
Aspergillus
Aspergillus - chemistry
Aspergillus sp
Benzene
enzyme inhibitory activities
Fungi
glyoxylate
Glyoxylates - metabolism
Metabolites
Molecular docking
Molecular Docking Simulation
Molecular Structure
NMR
Nuclear magnetic resonance
Planar structures
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Summary:A new glyoxylate-containing benzene derivative, methyl 2-(4-hydroxy-3-(3′-methyl-2′-butenyl)phenyl)-2-oxoacetate (1), together with ten known compounds (2-11), were isolated from the marine algicolous fungus, Aspergillus sp. SCSIO 41304. Their planar structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analysis and comparing with literature data. Compound 1 was isolated as a new fungal secondary metabolite, possessing a methyl glyoxylate moiety R-CO-CO-OCH 3 , which is rare in natural sources. All the isolated compounds (1-11) were tested for their antibacterial and enzyme inhibitory activities against acetylcholinesterase (AChE) and pancreatic lipase (PL). Among these compounds, aspulvinone H (4) showed moderate inhibition against AChE and PL with IC 50 values of 25.95 and 47.06 μM, respectively. Further molecular docking simulation exhibited that compound 4 could well bind to the catalytic pockets of the AChE and PL.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2021.1978994