A new benzophenanthridine alkaloid from stem bark of Zanthoxylum rhetsa and its biological activities

Nat Prod Res. 2023 Dec 25:1-13. doi: 10.1080/14786419.2023.2297261. Online ahead of print.

Abstract

A new benzophenanthridine alkaloid 6-butanoyldihydrochelerythrine (1) and five known alkaloids 6-acetonyldihydronitidine (2), 6-acetonyldihydrochelerythrine (3), isocorydine (4), (O)-methyltembamide (5), N-(4-methoxyphenethyl)benzamide (6) were isolated from the stem barks of Zanthoxylum rhetsa. These structures were elucidated by 1D, 2D NMR spectroscopy and by mass spectrometry. This is the first time that compounds 2-6 were identified from Zanthoxylum rhetsa and the first time that compounds 4 and 6 were identified from the genus Zanthoxylum. Bioactivity results of isolated compounds showed that 1, 2, 5 and 6 exhibited inhibitory activity against MCF7 and A549 cell lines, while 3 showed the inhibitory activity against A549 cell line; all isolated compounds 1-6 inhibited at least two strain microorganisms; compound 4 showed angiotensin II converting enzyme inhibitory activity in vitro with IC50 value of 65.58 µM and in silico with a docking score of -11.52 kcal/mol.

Keywords: 6-butanoyldihydrochelerythrine; ACE2-inhibiting activity; Zanthoxylum rhetsa; antimicrobial; cytotoxic; in silico; in vitro.