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Keywords = isodaucane

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25 pages, 6623 KB  
Article
Isolation, Structure Determination of Sesquiterpenes from Neurolaena lobata and Their Antiproliferative, Cell Cycle Arrest-Inducing and Anti-Invasive Properties against Human Cervical Tumor Cells
by Andrea Vasas, Ildikó Lajter, Norbert Kúsz, Sándor Balázs Király, Tibor Kovács, Tibor Kurtán, Noémi Bózsity, Nikolett Nagy, Zsuzsanna Schelz, István Zupkó, Georg Krupitza, Richard Frisch, Attila Mándi and Judit Hohmann
Pharmaceutics 2021, 13(12), 2088; https://doi.org/10.3390/pharmaceutics13122088 - 5 Dec 2021
Cited by 7 | Viewed by 4183
Abstract
Seven new germacranolides (13, 58), among them a heterodimer (7), and known germacranolide (4), eudesmane (9) and isodaucane (10) sesquiterpenes were isolated from the aerial parts of Neurolaena [...] Read more.
Seven new germacranolides (13, 58), among them a heterodimer (7), and known germacranolide (4), eudesmane (9) and isodaucane (10) sesquiterpenes were isolated from the aerial parts of Neurolaena lobata. 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, 13C and 1H NMR chemical shift and ECD and OR calculations were performed on several stereoisomers of two derivatives. The isolated compounds (110) 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 (6) exhibited substantial antiproliferative properties, antimigratory effect, and it induced cell cycle disturbance in SiHa cells. Full article
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