Argolide from Artemisia glabella Kar. et Kir. and syntheses of new biologically active compounds

The article is dedicated to the chemical transformations of the natural sesquiterpene γ-lactone molecule 3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide (argolide). For the first time, 18 new derivatives based on 3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide have been synthesized, representing polyfunctional molecules with oxygen functionalities, halogen atoms, phosphorus, and nitrogen. The reaction of forming a hybrid compound based on sesquiterpene γ-lactone and alkaloids is discussed. Stereoselectivity and regioselectivity of the reaction of the molecule 3-oxo-4,7α,6β(H)-germacr-1(10)(E),11(13)-dien-6,12-olide with reagents are noted. The new germacranolide compounds were studied for cytotoxicity, antitumor, antiparasitic, and antimicrobial activities. In in vitro experiments, antiparasitic activity of argolide samples and their derivatives against the promastigote of Leishmania amazonensis and the trypomastigote of Trypanosoma brucei brucei was observed. In in vivo conditions, 100 % effectiveness of argolide against helminths Toxocara canis, Ancylostoma caninum, and Uncinaria stenocephala was determined in dogs.