Structural modification of trilobolide for upgrading its immunobiological properties and reducing its cytotoxic action

0505590 - ÚOCHB 2020 RIV IT eng J - Journal Article
Harmatha, Juraj - Buděšínský, Miloš - Jurášek, M. - Zimmermann, T. - Drašar, P. - Zídek, Zdeněk - Kmoníčková, Eva - Vejvodová, L.
Structural modification of trilobolide for upgrading its immunobiological properties and reducing its cytotoxic action.
Fitoterapia. Roč. 134, Apr (2019), s. 88-95. ISSN 0367-326X. E-ISSN 1873-6971
Institutional support: RVO:61388963 ; RVO:68378041
Keywords : sesquiterpene lactones * trilobolide derivatives * cytotoxicity * nitric oxide production * immunomodulatory activity
OECD category: Organic chemistry; Pharmacology and pharmacy (UEM-P)
Impact factor: 2.527, year: 2019
Method of publishing: Limited access
https://www.sciencedirect.com/science/article/abs/pii/S0367326X18320987?via%3Dihub

Five new and three known sesquiterpene lactones were prepared by chemical transformation of trilobolide originally isolated from seeds of Laser trilobum (L.) Borkh. Chemical identity of the known compounds, and structural analysis of the new ones, were determined by HR MS and by 1H and 13C NMR spectroscopy. The new trilobolide derivatives were obtained by modification of the acyl substituent in the position C-8, the others by acetylating of the specific lactone diol moiety. The purposefully selected representative set of these trilobolide derivatives was tested for specific immunobiological properties. The obtained results demonstrated that trilobolide and some of its C-8 acyl analogs are strong activators of NO production, i.e. potent immunostimulatory agents. On contrary the C-8 deacyl derivative or the per-acetylated derivative are only very mild activators, or even inhibitors of the nitric oxide production.
Permanent Link: http://hdl.handle.net/11104/0297060