Heteroatom-Containing Natural Sesquiterpene Lactones and Methods for their Obtaining

Abstract

This review shows the data about isolated heteroatom-containing sesquiterpene lactones from various genera of <em>Asteraceae</em> family, natural occurence, isolation methods and their biological activity. Chlorinecontaining sesquiterpene lactones were isolated from genera of<em> Artemisia</em> L., <em>Achillea</em> L., <em>Acroptilon Cass</em>, <em>Centaurea</em> L., <em>Chartolepis Cass</em>, <em>Eupatorium</em> L., <em>Jurinea Cass</em>, <em>Rhaponticum Adams</em>, <em>Saussurea</em> DC. The greatest quantity of chlorine-containing sesquiterpene lactones were isolated from Centaurea genus. 25 new sesquiterpene lactones with chlorine atom in molecule were isolated and characterized. The sesquiterpene lactones, which in their structure contained a sulphur atom as a component of various alkoxyl-, thiohydroxygroups and acid residues, were isolated from genera of <em>Eupatorium</em> L., <em>Petasites </em>Mill, <em>Helenium</em> L.,<em> Acritopappus</em> R.M. King and H. Rob., <em>Arctium</em> L., <em>Saussurea</em> DC. Nitrogen atom in the structure of natural sesquiterpene lactones is present in the form of amino groups as a part of ester groups as well as amino acids as Michael adducts. Nitrogen-containing sesquiterpene lactones were isolated from <em>Acanthospermum</em> Schrank, <em>Saussurea</em> DC. Isolated heteroatom-containing sesquiterpene lactones possess bactericidal, antifungal, cytotoxic, antiviral, virucidal, antiulcer and others activities. Another method for obtaining heteroatom-containing sesquiterpene lactones is a directed synthesis of chlorine-, fluorine-, bromine-, sulphur- and nitrogen-containing sesquiterpene lactones. On the basis of sesquiterpene lactone artemisinin known as an effective antimalarial preparation, we synthesized over 200 derivatives, among which fluorine-, chlorine-, bromine-, nitrogen-, sulphur- and azide-containing derivatives of artemisinin were obtained.