Antitrypanosomal Activity of Sesquiterpene Lactones from Helianthus tuberosus L. Including a New Furanoheliangolide with an Unusual Structure

Molecules

Constantin G. Daniliuc¹  Anna Galkina²  Thomas J. Schmidt²  Nico Krause²  Mairin Lenz²  Marcel Kaiser³ 

[1]Institute of Organic Chemistry, University of Münster, Corrensstraße 40, D-48149 Münster, Germany

[2]Institute of Pharmaceutical Biology and Phytochemistry (IPBP), University of Münster, PharmaCampus–Corrensstrasse 48, D-48149 Münster, Germany

[3]Swiss Tropical and Public Health Institute (Swiss TPH), Socinstrasse 57, CH-4051 Basel, Switzerland

关键词: sesquiterpene lactone;    furanoheliangolide;    X-ray crystallography;    antiprotozoal activity;    Trypanosoma brucei rhodesiense;    Trypanosoma cruzi;    Leishmania donovani;    Plasmodium falciparum;    cytotoxicity;   

DOI  :  10.3390/molecules24061068

来源: DOAJ

【 摘 要 】

As part of our efforts to exploit the antitrypanosomal potential of sesquiterpene lactones (STL) from Helianthus tuberosus L. (Asteraceae), besides the known 4,15-iso-atriplicolide tiglate, -methacrylate and -isobutyrate, a hitherto unknown STL was isolated. Its structure was solved by extensive NMR measurements and confirmed by single crystal X-ray crystallography. This novel compound is a structural analog 4,15-iso-atriplicolide tiglate that possesses the same basic furanoheliangolide skeleton but differs in the position of the oxo function which is at C-2 instead of C-1, as well as in the fact that the oxygen atom of the furanoid ring is part of a hemiketal structure at C-3 and a double bond between C-5 and C-6. For this new STL we propose the name heliantuberolide-8-O-tiglate. Its activity against Trypanosoma brucei rhodesiense (causative agent of East African Human Typanosomiasis, Trypanosoma cruzi (Chagas Disease), Leishmania donovani (Visceral Leishmaniasis) and Plasmodium falciparum (Tropical Malaria) as well as cytotoxicity against rat skeletal myoblasts (L6 cell line) was determined along with those of the hitherto untested 4,15-iso-atriplicolide methacrylate and isobutyrate. In comparison with the iso-atriplicolide esters, the new compound showed a much lower level of bioactivity.

【 授权许可】

Unknown