In this study, a compound of 532.24 Da named BF-4 was separated from the ribose-tryptophan Maillard reaction products by solvent extraction and purified through reverse phase high performance liquid chromatography. The purified compound BF-4 was identified as 3-((1 H-indol-3-yl)methyl)-8-(5-((1 H-indol-3-yl)methyl)-6-oxomorpholin-2-yl)-9-hydroxy-1,7,4-dioxazecan-2-one in accordance with 1D- and 2D-NMR spectra and LC-ESI-MS/MS analysis. BF-4 significantly reduced the production of nitric oxide (NO), interleukin-6 (IL-6), and tumor necrosis factor α (TNF-α) in lipopolysaccharide-stimulated RAW 264.7 cells. It inhibited nuclear factor κB (NF-κB) activation and mitogen-activated protein kinase (MAPK) phosphorylation through suppressing phosphorylation of IκBα, P65, P38 and c-Jun N-terminal kinase (JNK). The anti-inflammatory activity of BF-4 was comparable to dexamethasone, and more importantly, BF-4 showed less cytotoxicity than dexamethasone on the normal human liver cell LO2. The results indicate that BF-4 is a promising anti-inflammatory agent with pharmaceutical potential.
Keywords: Maillard reaction; anti-inflammatory activity; ribose; structure; tryptophan.