New cytotoxic azaphilones from Monascus purpureus-fermented rice (red yeast rice)

Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2010-03, Vol.15 (3), p.1958-1966
Main Authors: Li, Jin-Jie, Shang, Xiao-Ya, Li, Ling-Ling, Liu, Ming-Tao, Zheng, Jian-Quan, Jin, Zong-Lian
Format: Article
Language:English
Subjects:
absolute configurations
azaphilones
Benzopyrans - isolation & purification
Benzopyrans - pharmacology
Biological Products - chemistry
Cell Line, Tumor
Circular Dichroism
Cytotoxicity
Drug Screening Assays, Antitumor
Humans
Magnetic Resonance Spectroscopy
Medical research
Monascus purpureus
Pigments, Biological - isolation & purification
Pigments, Biological - pharmacology
Spectrophotometry, Ultraviolet
Spectroscopy, Fourier Transform Infrared
Toxicity
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Summary:Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and chemical data. The relative configurations were assigned on the basis of analysis of NOE data, and the absolute configurations were determined by direct comparison of their CD spectra with those of known azaphilones and chemical correlations. In the in vitro assays, monapurones A-C (1-3) showed selective cytotoxicity against human cancer cell line A549 with IC50 values of 3.8, 2.8 and 2.4 microM respectively, while exhibiting no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules15031958