Stewartiacids A–N, C-23 carboxylated triterpenoids from Chinese Stewartia and their inhibitory effects against ATP-citrate lyase and NF-κB
| Autor: | Juan Xiong, De-Lei Chen, Na Li, Jia Li, Yi Zang, Dao-An Xiao, Jin-Feng Hu, Junmin Li, Ze-Xin Jin, Jiang Wan |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
0303 health sciences Circular dichroism biology ATP citrate lyase 010405 organic chemistry Chemistry Stereochemistry General Chemical Engineering General Chemistry biology.organism_classification Lyase 01 natural sciences 0104 chemical sciences Stewartia sinensis Adduct 03 medical and health sciences Triterpene Stewartia IC50 030304 developmental biology |
| Zdroj: | RSC Advances. 10:3343-3356 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c9ra09542j |
| Popis: | Fourteen previously undescribed naturally occurring C-23 carboxylated triterpenoids, stewartiacids A–N (1–14), were isolated and characterized from the twigs and leaves of the ornamental and medicinal plant Stewartia sinensis (Chinese Stewartia), a ‘vulnerable’ species endemic to China. The new structures were elucidated on the basis of spectroscopic data, single crystal X-ray diffraction, and electronic circular dichroism (ECD) analyses. Stewartiacids A (1) and B (2) are isoursenol derivatives. Stewartiacid C (3) is a 12-oxo-γ-amyrin analogue. Both isoursenol and γ-amyrin derivatives are quite rare in nature. Stewartiacids D (4) and E (5) are 13,27-cycloursane-type compounds. Stewartiacids K (11) and L (12) are ursane-type triterpene and phenylpropanol adducts built through a 1,4-dioxane ring, which are also seldom reported in the literature. The rest are common C-23 carboxylated ursane-type (6–10) and oleanane-type (13, 14) pentacyclic triterpenoids. Stewartiacids G (7), K (11), and L (12) showed moderate inhibitory effects against ATP-citrate lyase (ACL), with IC50 values of 12.5, 2.8, and 10.6 μM, respectively. Stewartiacid K (11) also exhibited moderate inhibition (IC50: 16.8 μM) of NF-κB. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|