Bioactive sesquiterpenoids from the flower buds of Tussilago farfara.
Bioorg Chem
; 107: 104632, 2021 02.
Article
in En
| MEDLINE
| ID: mdl-33450544
ABSTRACT
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 13C 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.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Sesquiterpenes
/
Tussilago
Limits:
Humans
Language:
En
Journal:
Bioorg Chem
Year:
2021
Type:
Article
Affiliation country:
China