Abstract
Flash column chromatographic fractionation of tree of heaven (Ailanthus altissima) stem and trunk bark extracts, guided by thin-layer chromatography (TLC)-Bacillus subtilis assay and TLC-heated electrospray high-resolution tandem mass spectrometry (HESI-HRMS/MS), lead to the isolation of six known compounds: (9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (13-HODE, A1), (10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (9-HODE, A2), hexadecanedioic acid (thapsic acid, A3), 16-hydroxyhexadecanoic acid (juniperic acid, A4), 16-feruloyloxypalmitic acid (alpinagalanate, A5), and canthin-6-one (A6). Their structures were elucidated by HESI-HRMS/MS and one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy. This is the first study identifying A1-A5 in A. altissima tree. Except for A5, all isolated compounds exhibited antibacterial activity against B. subtilis in microdilution assays. A6 showed the strongest effect with a minimum inhibitory concentration (MIC) value of 8.3 µg/mL. The antibacterial activity of A3 and A4 is newly described.