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This work describes the isolation of pure bergenin from Peltophorum dubium roots with good yields and its further derivatization through Williamson synthesis. The alkyl derivatives of the bergenin were identified by nuclear magnetic resonance and mass spectrometry data analysis. Among them, three derivatives were reported for the first time herein, 8,10-dihexyl-bergenin, 8,10-didecyl-bergenin, and 8,10-ditetradecyl-bergenin, along with three previously reported ones (8,10-dimethylbergenin, 8-methylbergenin, 8,10-dioctyl-bergenin). Most derivatives of the bergenin displayed moderate cytotoxicity against Artemia salina, except the 8,10-dihexyl-bergenin (lethal concentration doses for 50% (LC50) = 70.55 μg mL). The antimicrobial assay showed that all derivatives selectively inhibited the Gram-positive bacteria Staphylococcus aureus, and two of them (8,10-dihexyl-bergenin and 8,10-didecyl-bergenin) had promising activities (minimum inhibitory concentration (MIC) = 5.1-6.2 μmol L). In addition, bergenin displayed interesting inhibition on acetylcholinesterase (half maximal inhibitory concentration (IC50) = 141.19 ± 0.41 μmol L), while its semi-synthetic derivatives displayed modest activity. Our results revealed that the antibacterial activity of bergenin could be greatly improved through its structural modification.

Bergenin of Peltophorum dubium (Fabaceae) Roots and Its Bioactive Semi‑Synthetic Derivatives