Article

Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.

Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, School of Medicine, Nanjing University, Nanjing 210093, People's Republic of China.
Phytochemistry (impact factor: 3.35). 02/2008; 69(2):571-6. DOI:10.1016/j.phytochem.2007.07.014 pp.571-6
Source: PubMed

ABSTRACT Along with the known secondary metabolites lumichrome, physcion, and emodin-1,6-dimethyl ether, three alkaloids named penicidones A-C (1-3) were isolated from the culture of Penicillium sp. IFB-E022, an endophytic fungal strain residing in the stem of Quercus variabilis (Fagaceae). The structures of penicidones A-C were established by a correlative interpretation of spectroscopic data including IR, UV and HR-ESI-MS, as well as by analysis of a set of 1D and 2D NMR experiments. The stereochemistry of compounds 1 and 2 was obtained by comparison of the optical rotation with those of vermistatin and its analogues. Penicidones A-C were the first group of natural products possessing a penicidone framework. Compounds 1-3 exhibited moderate cytotoxicity against four cancer cell lines.

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Keywords

2D NMR experiments
 
cancer cell lines
 
compounds 1
 
Compounds 1-3 exhibited moderate cytotoxicity
 
correlative interpretation
 
emodin-1,6-dimethyl ether
 
endophytic fungal strain residing
 
known secondary metabolites lumichrome
 
natural products
 
optical rotation
 
penicidones A-C
 
spectroscopic data
 
UV
 
vermistatin
 

Hui Ming Ge