Antimicrobial secondary metabolites from the aerial parts of Perilla frutescens

Phytochemical research of Perilla frutescens aerial parts led to isolation of 12 secondary metabolites, including one new 3-benzoxepin glucoside, perillafrutoside A (1), one new megastigmane glycoside, perillafrutoside B (2), and 10 known compounds. Their chemical structures were identified based on 1D/2D NMR, HRESIMS, and ECD spectroscopic analyses. The structure of 2 was elucidated based on revision of the previously reported stereoisomer, (6R,9R)-blumenyl α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside. Evaluation of their antimicrobial effect revealed that compounds 1 and 5-11 inhibit Enterococcus faecalis growth, compounds 6, 7 and 9 suppress Staphylococcus aureus growth, whereas compounds 6 and 11 attenuate Candida albicans growth. This is the first report of the isolation of 3-5, 8-10 and 12 from the genus Perilla and the antimicrobial effect of compounds 3, 8 and 10.