Ustiloxin G, a New Cyclopeptide Mycotoxin from Rice False Smut Balls

Ustiloxins were cyclopeptide mycotoxins from rice false smut balls (FSBs) that formed in rice spikelets infected by the fungal pathogen Ustilaginoidea virens. To investigate the chemical diversity of these metabolites and their bioactivities, one new cyclopeptide, ustiloxin G (1), together with four known congeners—ustiloxins A (2), B (3), D (4), and F (5)—were isolated from water extract of rice FSBs. Their structures were elucidated by analyses of their physical and spectroscopic data, including ultraviolet spectrometry (UV), infrared spectroscopy (IR), 1D and 2D nuclear magnetic resonance (NMR), and high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS). All the compounds were evaluated for their cytotoxic as well as radicle and germ elongation inhibitory activities. Ustiloxin B (3) showed the best activity against the cell line BGC-823 with an IC(50) value of 1.03 µM, while ustiloxin G (1) showed moderate activity against the cell lines A549 and A375 with IC(50) values of 36.5 µM and 22.5 µM, respectively. Ustiloxins A (2), B (3), and G (1) showed strong inhibition of radicle and germ elongation of rice seeds. When their concentrations were at 200 µg/mL, the inhibitory ratios of radicle and germ elongation were more than 90% and 50%, respectively, the same effect as that of positive control (glyphosate). They also induced abnormal swelling of the roots and germs of rice seedlings.