Bioactive sesquiterpenoids from the flower buds of Tussilago farfara.

Autor: Song XQ; School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China; School of Biological Science and Technology, University of Jinan, Jinan 250022, China., Yu JH; School of Biological Science and Technology, University of Jinan, Jinan 250022, China., Sun J; School of Biological Science and Technology, University of Jinan, Jinan 250022, China., Liu KL; School of Biological Science and Technology, University of Jinan, Jinan 250022, China., Zhang JS; School of Biological Science and Technology, University of Jinan, Jinan 250022, China., Zhang H; School of Biological Science and Technology, University of Jinan, Jinan 250022, China. Electronic address: bio_zhangh@ujn.edu.cn.
Jazyk: angličtina
Zdroj: Bioorganic chemistry [Bioorg Chem] 2021 Feb; Vol. 107, pp. 104632. Date of Electronic Publication: 2021 Jan 07.
DOI: 10.1016/j.bioorg.2021.104632
Abstrakt: Eleven new compounds including five bisabolane (1-5) and three oplopane (6-8) sesquiterpenoids, a pair of benzopyran enantiomers (9 & 10) and a benzofuran derivative (11), along with six known sesquiterpenoid co-metabolites (12-17), have been obtained from the flower buds of Tussilago farfara. Their structures were elucidated by comprehensive spectroscopic analyses and comparison with structurally related known analogues. The absolute configurations of all the compounds except 11 were unequivocally assigned by various techniques, including Mosher's method and time-dependent density functional theory (TD-DFT) based calculations of 13 C NMR and electronic circular dichroism (ECD) data. The C-8 absolute configuration on the sidechain of this group of bisabolane sesquiterpenoids was assigned for the first time. Our bioassays have established that compounds 3, 4, 13 and 14 showed significant α-glucosidase inhibitory activities, while 6, 8 and 14 displayed moderate antiproliferative effects against two human tumor cell lines A549 and MDA-MB-231. Further flow cytometric analysis revealed that 14 effectively induced cell apoptosis and arrested cell cycle at the S/G2 phases in A549 cells, in a dose-dependent manner.
(Copyright © 2021. Published by Elsevier Inc.)
Databáze: MEDLINE
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