Four new steroids from the endophytic fungus Chaetomium sp. M453 derived of Chinese herbal medicine Huperzia serrata

An endophytic fungus, Chaetomium sp. M453, was isolated from Huperzia serrata (Thunb. ex Murray) Trev. and subjected to phytochemical investigation. Three unusual C25 steroids, neocyclocitrinols E-G (1–3), and 3β-hydroxy-5,9-epoxy-(22E,24R)-ergosta-7,22-dien-6-one (4) together with three known stero...

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Bibliographic Details
Published in:Fitoterapia 2017-03, Vol.117, p.41-46
Main Authors: Yu, Fei-Xue, Li, Zhe, Chen, Yao, Yang, Yin-He, Li, Guo-Hong, Zhao, Pei-Ji
Format: Article
Language:English
Subjects:
Absolute configuration
Acetylcholinesterase
Bacteria
Biodiversity
C25 steroids
Chaetomium sp. M453
Crystallography
Endophytes
Endophytic fungus
Fermentation
Fungi
Herbal medicine
Huperzia serrata
In vitro methods and tests
NMR
Nuclear magnetic resonance
Spectroscopic analysis
Steroid hormones
Steroids
Structure identification
X-ray
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Summary:An endophytic fungus, Chaetomium sp. M453, was isolated from Huperzia serrata (Thunb. ex Murray) Trev. and subjected to phytochemical investigation. Three unusual C25 steroids, neocyclocitrinols E-G (1–3), and 3β-hydroxy-5,9-epoxy-(22E,24R)-ergosta-7,22-dien-6-one (4) together with three known steroids were isolated from solid fermentation products of the fungus, which were elucidated by extensive spectroscopic analyses, including 1D-, 2D-NMR, and HR-ESI-MS experiments. The absolute configuration of 1 was determined by X-ray crystallographic analysis and CD analyses. The acetylcholinesterase inhibitory activities of compounds 1–4 were tested in vitro. Compound 4 showed weak acetylcholinesterase inhibitory activity. [Display omitted] •The chemical constituents of the entophytic fungus Chaetomium sp. M453 were investigated.•Three unusual C25 steroids, neocyclocitrinols E-G and 3β-hydroxy-5,9-epoxy-(22E,24R)-ergosta-7,22-dien-6-one were isolated.•Their structures were elucidated by extensive 1D- and 2D-NMR, and HR-ESI-MS experiments.•The absolute configuration of 1 was determined by X-ray crystallographic analysis and CD analyses.•Compound 4 showed weak acetylcholinesterase inhibitory activity.
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2016.12.012