Bioassay-Guided Isolation and Identification of Antibacterial Compounds from Invasive Tree of Heaven Stem and Trunk Bark

• Published in: Molecules (Basel, Switzerland) Switzerland), 2024-12, Vol.29 (24), p.5846
• Main Authors: Cselőtey, Anna, Baglyas, Márton, Király, Nóra, Ott, Péter G, Glavnik, Vesna, Vovk, Irena, Móricz, Ágnes M
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antibacterial agents; antibacterial effect; Antibiotics; Bacillus subtilis - drug effects; bioassay-guided isolation; Bioassays; Biological Assay - methods; canthin-6-one alkaloid; Chromatography; Chromatography, Thin Layer; fatty acid derivatives; Fractionation; Magnetic Resonance Spectroscopy; Mass spectrometry; Microbial Sensitivity Tests; Molecular Structure; Natural products; NMR; Nuclear magnetic resonance; Nuclear magnetic resonance spectroscopy; Plant Bark - chemistry; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Stems - chemistry; Scientific imaging; Tandem Mass Spectrometry; TLC–effect-directed analysis; tree of heaven (Ailanthus altissima); Trees; Trees - chemistry
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules29245846

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