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 NMR-2D (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 IC 50 values were 1.24, 2.35 and 3.75 μg/ml, respectively
metabolites, anti-inflammatory activity, azaphilone, Monascus pilosus, red yeast rice
Publication DOI: 10.1016/j.phytol.2012.05.015Journal NLM ID: 101513432Publisher: Amsterdam: Elsevier
Correspondence: chengmingjen2001@yahoo.com.tw
Institutions: Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan, Graduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung, Taiwan, Kino Dental Clinical, Hokkaido, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS, UV, extraction, CC, cytokine production, cytotoxicity assay, DEPT
Found