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    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
    Author information
    1Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary.
    2Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary.
    3Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary.
    4Department of Organic Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
    5Department of Organic Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
    6Department of Organic Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
    7Department of Pharmacodynamics and Biopharmacy, Faculty of Pharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
    8Department of Pharmacodynamics and Biopharmacy, Faculty of Pharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
    9Department of Pharmacodynamics and Biopharmacy, Faculty of Pharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
    10Department of Pharmacodynamics and Biopharmacy, Faculty of Pharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
    11Clinical Institute of Pathology, Medical University of Vienna, Waehringer Guertel 18-20, A-1090 Vienna, Austria.
    12Institute for Ethnobiology, Playa Diana, San José GT-170, Petén, Guatemala.
    13Department of Organic Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
    14Department of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary.
    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
     
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