Marginaols G-M, anti-inflammatory isopimarane diterpenoids, from the rhizomes of Kaempferia marginata

Abstract

Marginaols G-M, a series of undescribed isopimarane diterpenoids, together with four known analogs were isolated from the rhizomes of Kaempferia marginata. The structures of these isolated compounds were characterized using high-resolution mass spectrometry and extensive 1D- and 2D-nuclear magnetic resonance (NMR) analyses. In addition, the absolute configurations of marginaol G and H were determined by X-ray crystallographic analysis and comparison with the literature values. When compared to the standard drug dexamethasone (IC₅₀ 4.7 μM), marginaol G, H, and 6β-acetoxysandaracopimaradien-1α,9α-diol had an intriguing anti-inflammatory effect on NO inhibition in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with IC₅₀ values ranging from 4.5 to 7.3 μM and being less cytotoxic to the cells. The anti-inflammatory action of these isopimarane diterpenoids from K. marginata supports the use of Thai traditional medicine for inflammation treatment.

Keywords: Anti-inflammatory activity; Isopimarane diterpenes; Kaempferia marginata; Marginaols; Zingiberaceae.