Sesquiterpene lactones from Sonchus palustris L. (Asteraceae, Cichorieae)

0523125 - ÚEB 2020 RIV GB eng J - Článek v odborném periodiku
Shulha, O. - Çiçek, S. S. - Piccolella, S. - Rárová, Lucie - Strnad, Miroslav - Sönnichsen, F. - Pacifico, S. - Zidorn, C.
Sesquiterpene lactones from Sonchus palustris L. (Asteraceae, Cichorieae).
Phytochemistry. Roč. 170, FEB (2020), č. článku 112196. ISSN 0031-9422. E-ISSN 1873-3700
Institucionální podpora: RVO:61389030
Klíčová slova: Biological activities * Chemophenetics * Quinic acid derivatives * Schleswig-Holstein * Sesquiterpene lactones * Sonchus palustris
Obor OECD: Biochemical research methods
Impakt faktor: 4.072, rok: 2020
Způsob publikování: Open access
https://www.sciencedirect.com/science/article/pii/S0031942219305850

Seven previously undescribed sesquiterpene lactones, three known sesquiterpene lactones (ixerin D, 15-p-hydroxyphenylacetyllactucin, and 15-p-hydroxyphenylacetyllactucin-8-sulfate), and two known quinic acid derivatives (3-O-feruloylquinic acid and 3,5-di-O-caffeoylquinic acid) were isolated from Sonchus palustris L. roots. Four formerly undescribed compounds were elucidated to be 3β,14-dihydroxycostunolide-3-O-β-D-glucopyranosyl-(2-O-p-hydroxyphenylacetyl)-14-O-p-hydroxyphenylacetate, 15-p-methoxyphenylacetyllactucin, 15-p-methoxyphenylacetyllactucin-8-sulfate, and 8-p-hydroxyphenylacetyllactucin-15-sulfate. Additionally, three undescribed conjugates of lactucin and a eudesmanolide type sesquiterpenic acid, sonchpalustrin, 4″-O-methylsonchpalustrin, and isosonchpalustrin, were characterized. The structures of the newly discovered natural products were elucidated using 1D and 2D NMR spectroscopy and UHPLC-HRMS. 15-p-Hydroxyphenylacetyllactucin and 15-p-methoxyphenylacetyllactucin showed significant in vitro cytotoxicity against CEM and BJ cells with IC50 values ranging from 3.9 to 9.8 μM. Compounds 3 and 4 showed also strong anti-inflammatory activity in vitro.
Trvalý link: http://hdl.handle.net/11104/0307528