Phenylbutene dimers and saturated phenylbutene derivatives from Zingiber montanum with anti-inflammatory potential

A phytochemical investigation of the rhizomes of Zingiber montanum was undertaken, leading to the isolation and identification of eight previously undescribed compounds. These compounds were categorized as three phenylbutene dimers (1-3) and five saturated phenylbutene-type derivatives (4-8). Their structures were unequivocally determined through extensive spectroscopic analysis, including 1D/2D NMR, UV, IR and MS spectroscopy. The absolute configurations of these compounds were established by a combination of electronic circular dichroism calculations and DP4+ probability analysis. The anti-inflammatory activity of these compounds was evaluated on the LPS/IFN-γ-stimulated RAW 264.7 macrophages. The results revealed that compounds 1 and 4-8 exhibited significant inhibition on the production of nitric oxide at the concentration of 10 μM. These findings enhance the understanding of the chemical composition of Zingiber montanum, and provide a robust scientific foundation for its traditional application in the treatment of inflammatory disease, highlighting these novel compounds as promising leads for further anti-inflammatory agent development.