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Secondary metabolites produced by the fungus Monascus pilosus and their anti-inflammatory activity

Cheng, Ming-Jen, Wu, Ming-Der, Yuan, Gwo-Fang, Su, Yung-Shun, Yanai, Hiromasa
Phytochemistry letters 2012 v.5 no.3 pp. 567-571
Monascus pilosus, anti-inflammatory activity, electrospray ionization mass spectrometry, ethanol, fungi, inhibitory concentration 50, lipopolysaccharides, nuclear magnetic resonance spectroscopy, red yeast rice, secondary metabolites, spectral analysis, tumor necrosis factor-alpha
A detailed phytochemical study of the n-BuOH-soluble fraction of the 95% EtOH extract of red yeast rice fermented with the fungus Monascus pilosus BCRC 38072 (Eurotiaceae) revealed a new azaphilone derivative, namely monascusazaphilol (1) (rel-(3S,3aR,9aR)-3-(1-hydroxydecyl)-9a-methyl-6-((E)-propenyl)-3a,4,8,9a-tetrahydro-3H-furo[3,2-g]isochromene-2,9-dione), along with ten known compounds (2–11). Their structures were established by direct interpretation of their spectral data, mainly high resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D and 2D NMR (COSY, ROESY, HSQC and HMBC), and comparison of the spectroscopic data with those reported for structurally related compounds. We also evaluated the inhibitory effects of some isolates on the production of tumor necrosis factor (TNF-α) induced by lipopolysaccharide (LPS). Among the isolates, compounds 1–3 inhibited TNF-α production in U937 cells in vitro, and the IC₅₀ values were 1.24, 2.35 and 3.75μg/ml, respectively.