TY - JOUR
T1 - β-amyrin heptadecanoate, a new oleanane triterpenoid with α-glucosidase inhibitory and cytotoxic activities from the leaves of Averrhoa bilimbi L.
AU - Hoang, Le Thuy Thuy Trang
AU - Dong, Phan Si Nguyen
AU - Nguyen, Van Kieu
AU - Thao, Vo Thi Minh
AU - Ramadhan, Rico
AU - Jutakanoke, Rumpa
AU - Sichaem, Jirapast
N1 - Publisher Copyright:
© 2024 Informa UK Limited, trading as Taylor & Francis Group.
PY - 2024
Y1 - 2024
N2 - A previously unreported oleanane triterpenoid, β-amyrin heptadecanoate (1), was isolated from the leaves of Thai Averrhoa bilimbi (Oxalidaceae), along with five known compounds, β-amyrin (2), β-sitosterol (3), β-sitosterol-D-glucoside (4), β-sitosteryl oleate (5), and α-tocopherol (6). Their structures were elucidated through spectroscopic analysis, including extensive NMR and HRESIMS, and by comparison with the previous literature. All isolated compounds were evaluated for their α-glucosidase inhibitory and cytotoxic activities. Compound 6 exhibited the highest α-glucosidase inhibition (IC50 of 0.72 ± 1.02 µM), significantly outperforming the standard acarbose (IC50 of 82.00 ± 0.24 μM). Furthermore, compound 4 demonstrated the most potent cytotoxicity against HeLa cells (IC50 of 34.92 ± 0.45 μM), while compound 3 exhibited the strongest cytotoxicity towards A549 cells (IC50 of 9.17 ± 0.30 μM). Additionally, a molecular docking study was conducted on the active α-glucosidase inhibitors to estimate their binding affinities and to identify the ligand-binding sites within the enzyme.
AB - A previously unreported oleanane triterpenoid, β-amyrin heptadecanoate (1), was isolated from the leaves of Thai Averrhoa bilimbi (Oxalidaceae), along with five known compounds, β-amyrin (2), β-sitosterol (3), β-sitosterol-D-glucoside (4), β-sitosteryl oleate (5), and α-tocopherol (6). Their structures were elucidated through spectroscopic analysis, including extensive NMR and HRESIMS, and by comparison with the previous literature. All isolated compounds were evaluated for their α-glucosidase inhibitory and cytotoxic activities. Compound 6 exhibited the highest α-glucosidase inhibition (IC50 of 0.72 ± 1.02 µM), significantly outperforming the standard acarbose (IC50 of 82.00 ± 0.24 μM). Furthermore, compound 4 demonstrated the most potent cytotoxicity against HeLa cells (IC50 of 34.92 ± 0.45 μM), while compound 3 exhibited the strongest cytotoxicity towards A549 cells (IC50 of 9.17 ± 0.30 μM). Additionally, a molecular docking study was conducted on the active α-glucosidase inhibitors to estimate their binding affinities and to identify the ligand-binding sites within the enzyme.
KW - Averrhoa bilimbi
KW - cytotoxicity
KW - Oxalidaceae
KW - triterpenoids
KW - α-glucosidase inhibition
UR - http://www.scopus.com/inward/record.url?scp=85209550040&partnerID=8YFLogxK
U2 - 10.1080/14786419.2024.2425045
DO - 10.1080/14786419.2024.2425045
M3 - Article
C2 - 39506514
AN - SCOPUS:85209550040
SN - 1478-6419
JO - Natural Product Research
JF - Natural Product Research
ER -