623938-87-4Relevant academic research and scientific papers
Total synthesis and elucidation of the absolute configuration of the diterpene tonantzitlolone
Jasper, Christian,Wittenberg, Ruediger,Quitschalle, Monika,Jakupovic, Jasmin,Kirschning, Andreas
, p. 479 - 482 (2005)
(Chemical Equation Presented) The first enantioselective total synthesis of tonantzitlolone, a novel 15-membered macrocyclic diterpene, utilized a Julia olefination, a highly selective, potassium enolate-based anti-Felkin aldol reaction, and an E-selectiv
The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function
Pfeffer, Tobias J.,Sasse, Florenz,Schmidt, Christoph F.,Lak?mper, Stefan,Kirschning, Andreas,Scholz, Tim
supporting information, p. 164 - 170 (2016/02/26)
Tonantzitlolone A, a diterpene isolated from the Mexican plant Stillingia sanguinolenta, shows cytostatic activity. Both the natural product tonantzitlolone A and its synthetic enantiomer induce monoastral spindle formation in cell experiments which indicates inhibitory activity on kinesin-5 mitotic motor molecules. These inhibitory effects on kinesin-5 could be verified in in vitro single-molecule motility assays, where both tonantzitlolones interfered with kinesin-5 binding to its cellular interaction partner microtubules in a concentration-dependent manner, yet with a larger effect of the synthetic enantiomer. In contrast to kinesin-5 inhibition, both tonantzitlolone A enantiomers did not affect conventional kinesin-1 function; hence tonantzitlolones are not unspecific kinesin inhibitors. The observed stronger inhibitory effect of the synthetic enantiomer demonstrates the possibility to enhance the overall moderate anti-proliferative effect of the lead compound tonantzitlolon A by chemical modification.
