A phytochemical investigation of two South African plants with the screening of extractives for biological activity.

Abstract

Two South African medicinal plants, Strophanthus speciosus and Eucomis montana, were investigated phytochemically. From Strophanthus speciosus a cardenolide, neritaloside, was isolated, whilst Eucomis montana yielded three homoisoflavanones, 3,9- dihydroeucomin, 4'-demethyl-3,9-dihydroeucomin, and 4'-demethyl-5-0-methyl-3,9- dihydroeucomin. The structures were elucidated on the basis of spectroscopic data. The homoisoflavanones were screened for anti-inflammatory activity using a chemiluminescent luminol assay, modified for microplate usage. All of the homoisoflavanones exhibited good inhibition of chemiluminescence, with IC50 values for 3,9-dihydroeucomin, 4'-demethyl-3,9-dihydroeucomin, and 4'-demethyl-5-0-methyl-3,9- dihydroeucomin being 14mg/mL, 7mg/mL, and 13mg/mL respectively. The IC50 value of 4'-demethyl-3,9-dihydroeucomin compared favourably with the NSAID control (meloxicam), which had an IC50 of 6mg/mL. Neritaloside was not screened for biological activity as the yield of 14.4mg was insufficient for the muscle-relaxant screen for which it was intended. An assay for antioxidant/free radical scavenging activity was also performed. All the compounds had excellent antioxidant/free radical scavenging activity, with percentage inhibition of the reaction being 92%, 96%, and 94% for 3,9-dihydroeucomin, 4'-demethyl- 3,9-dihydroeucomin, and 4'-demethyl-5-0-methyl-3,9-dihydroeucomin respectively at a concentration of 10mg/mL. However, the control compounds, diclofenac and meloxicam, also exhibited strong activity, with the result that the precise mode of anti-inflammatory activity could not be unequivocally determined. The results from the biological screenings thus provided a rational scientific basis for the indigenous ethnomedicinal use of Eucomis species in the treatment of rheumatism, inflammation and pain.