β-amyrin heptadecanoate, a new oleanane triterpenoid with α-glucosidase inhibitory and cytotoxic activities from the leaves of Averrhoa bilimbi L.

Le Thuy Thuy Trang Hoang, Phan Si Nguyen Dong, Van Kieu Nguyen, Vo Thi Minh Thao, Rico Ramadhan, Rumpa Jutakanoke, Jirapast Sichaem

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
JournalNatural Product Research
DOIs
Publication statusAccepted/In press - 2024

Keywords

  • Averrhoa bilimbi
  • cytotoxicity
  • Oxalidaceae
  • triterpenoids
  • α-glucosidase inhibition

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