Chemical Investigation of Saponins from Twelve Annual Medicago Species and their Bioassay with the Brine Shrimp Artemia salina

Abstract

The saponin and sapogenin composition of the aerial growth of 12 annual Medicago species sampled at full senescence were investigated. Saponins were extracted from the plant material and obtained in a highly pure grade by reverse-phase chromatography, with a yield ranging from 0.38 ± 0.04% to 1.35 ± 0.08% dry matter, depending on the species. Sapogenins were then obtained after acid hydrolysis of saponins, and evaluated by GC/FID and GC/MS methods. Different compositions of the aglycone moieties were observed in the 12 Medicago species. Medicagenic acid was the dominant aglycone in M. × blancheana, M. doliata, M. littoralis, M. rotata, M. rugosa, M. scutellata, M. tornata and M. truncatula, bayogenin and hederagenin in M. arabica and M. rigidula, echinocystic acid in M. polymorpha, and soyasapogenol B in M. aculeata. The purified saponin mixtures, characterized by different chemical compositions, were then used in a toxicity test using the brine shrimp Artemia salina. The most active compounds were the saponins from M. arabica and M. rigidula with LD50 values of 10.1 and 4.6 μg/mL, respectively. A structure-activity relationship for the tested saponin mixtures was observed.