Toward the synthesis and pharmacological screening of a natural cycloheptapeptide of plant origin

Abstract

The solution-phase synthesis of a proline and glycine-rich plant-derived cyclic heptapeptide, gypsophin E (8), is reported via coupling of a tetrapeptide unit Glycyl-L-leucyl-L-valyl-L-proline-OMe with a tripeptide unit Boc-L-isoleucyl-glycyl-L-proline-OH, followed by cyclization of the linear fragment having seven amino acid units. The structure of the newly synthesized cycloheptapeptide was confirmed by means of chemical and spectroscopic methods. The newly synthesized cyclopolypeptide displayed potent antifungal and anthelmintic activities against the pathogenic yeast Candida albicans, the dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at the 6 μg/mL level, and the earthworms Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at a concentration of 2 mg/mL.