Pharmaceutics. 2021 Dec 5. pii: pharmaceutics13122088. doi: 10.3390/pharmaceutics13122088 |
Isolation, Structure Determination of Sesquiterpenes from and Their Antiproliferative, Cell Cycle Arrest-Inducing and Anti-Invasive Properties against Human Cervical Tumor Cells. |
Vasas A1, Lajter I2, Kúsz N3, Király SB4, Kovács T5, Kurtán T6, Bózsity N7, Nagy N8, Schelz Z9, Zupkó I10, Krupitza G11, Frisch R12, Mándi A13, Hohmann J14 |
Abstract Seven new germacranolides (-, -), among them a heterodimer (), and known germacranolide (), eudesmane () and isodaucane () sesquiterpenes were isolated from the aerial parts of . Their structures were determined by using a combination of different spectroscopic methods, including HR-ESIMS and 1D and 2D NMR techniques supported by DFT-NMR calculations. The enantiomeric purity of the new compounds was investigated by chiral HPLC analysis, while their absolute configurations were determined by TDDFT-ECD and OR calculations. Due to the conformationally flexible macrocycles and difficulties in assigning the relative configuration, C and H NMR chemical shift and ECD and OR calculations were performed on several stereoisomers of two derivatives. The isolated compounds (-) were shown to have noteworthy antiproliferative activities against three human cervical tumor cell line with different HPV status (HeLa, SiHa and C33A). Additionally, lobatolide C () exhibited substantial antiproliferative properties, antimigratory effect, and it induced cell cycle disturbance in SiHa cells. |
KEYWORDS: Asteraceae, Neurolaena lobata, SiHa cells, antimigratory effect, antiproliferative, eudesmanes, germacranolides, isodaucane, sesquiterpenes |
Publikations ID: 34959370 Quelle: öffnen |