A new ionone from n-butanol fraction of Curcuma phaeocaulis

The n-butanol fraction of Curcuma phaeocaulis was separated and purified using a combination of chromatographic techniques, including reversed-phase medium-pressure liquid chromatography, gel column chromatography, silica gel column chromatography, preparative thin-layer chromatography and reversed-phase semi-preparative high-performance liquid chromatography. The structures of the isolated compounds were elucidated through comprehensive spectroscopic analyses, including high-resolution mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectroscopy. Finally, three ionone glycosides were isolated from C. phaeocaulis and identified as (6Z, 9S)-4, 6-megastigmadien-3-one-9-O-β-D-glucopyranoside (1), (3R, 9S)-megastigman-5-en-3, 9-diol 3-O-β-D-glucopyranoside (2), and blumenol C glucoside (3). Notably, compound 1 was a new ionone, while compounds 2 and 3 were isolated from C. phaeocaulis for the first time. Subsequent evaluation of cytotoxic and anti-inflammatory activities revealed that all three compounds exhibited cytotoxic and anti-inflammatory effects.