Synthesis and Antiproliferative Effects of Grossheimin-Derived Aminoanalogues
Ashimbayeva M. Szakonyi Z. Adekenov S.M. Szemerédi N. Spengler G. Le T.M.
April 2025Multidisciplinary Digital Publishing Institute (MDPI)
Biomolecules
2025#15Issue 4
Grossheimin, a guaiane-type sesquiterpene lactone, displayed a diverse range of biological activities, including anticancer, anti-inflammatory and antimicrobial effects. Various amino analogues of grossheimin were prepared through a Michael addition at its highly active α-methylene-γ-lactone motif. On the other hand, grossheimin was reduced to diol, which was then subjected to nucleophilic addition or acetylation to introduce heteroatoms associated with oxygen, sulfur or nitrogen functionalities. All of the synthesised Michael and acetylated adducts were evaluated for their in vitro cytotoxic action on human colon adenocarcinoma lines, including Colo205 and Colo320. The bioassay results indicated that the acetylated adducts displayed a potent cytotoxic effect compared to grossheimin, the parent molecule. A docking study was also performed to exploit the observed results.
amino lactone , aminoanalogues , colon adenocarcinoma , cytotoxic , grossheimin , Michael addition
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Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary
JSC Research and Production Center “Phytochemistry”, Karaganda, 100009, Kazakhstan
Department of Medical Microbiology, Albert Szent-Györgyi Health Center, Albert Szent-Györgyi Medical School, University of Szeged, Semmelweis utca 6, Szeged, H-6725, Hungary
HUN-REN–SZTE Stereochemistry Research Group, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary
Institute of Pharmaceutical Chemistry
JSC Research and Production Center “Phytochemistry”
Department of Medical Microbiology
HUN-REN–SZTE Stereochemistry Research Group
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