Geigeria poisoning, referred to as 'vermeersiekte' is an important plant poisoning in southern Africa. Three sesquiterpene lactones, isogeigerin acetate (1) ivalin(2) and geigerin (3) were isolated and purified from Geigeria aspera Harv.(Asteraceae). Structures were deduced using 1 and 2D, 1 H-and 13 C-NMR spectroscopy and mass spectrometry, while the absolute configurations of compounds 1 and 3 were determined for the first time by X-ray crystal diffraction analyses. Cytotoxicity of isogeigerin acetate, ivalin and geigerin were compared by exposing a murine skeletal myoblast (C2C12) cell line to varying concentrations of the three sesquiterpene lactones isolated. Cell viability was assessed using the methyl-thiazolyl-tetrazolium (MTT) assay. The EC 50 s were 3.746 mM, 0.0029 mM and 3.792 mM for isogeigerin acetate (1), ivalin (2) and geigerin (3), respectively. The results indicate that ivalin is much more toxic, approximately 1000 times, in vitro compared to isogeigerin acetate and geigerin.
Vermeersiekte or “vomiting disease” is an economically important disease of ruminants following ingestion of Geigeria (G.) species in South Africa. Sheep are more susceptible, and poisoning is characterized by stiffness, regurgitation, bloat, paresis, and paralysis. Various sesquiterpene lactones have been implicated as the cause of poisoning. The in vitro cytotoxicity of two sesquiterpene lactones, namely, ivalin (purified from Geigeria aspera) and parthenolide (a commercially available sesquiterpene lactone), were compared using mouse skeletal myoblast (C2C12) and rat embryonic cardiac myocyte (H9c2) cell lines, representing the oesophageal, skeletal and cardiac muscles, which are affected in sheep. For 24, 48, and 72 h, both cell lines were exposed. A colorimetric viability assay, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), was used to assess cytotoxicity. A concentration-dependent cytotoxic response was observed in both cell lines, however, the C2C12 cells were more sensitive, with the half-maximal effective concentrations (EC50s) ranging between 2.7 and 3.3 µM. In addition, the effect that ivalin and parthenolide has on desmin, an important cytoskeletal intermediate filament in myocytes, was evaluated using the C2C12 myoblasts. Disorganization and aggregation of desmin were caused by both sesquiterpene lactones, which could clarify some of the ultrastructural lesions described in vermeersiekte.
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