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Article

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

1
Plant Protection Institute, HUN-REN Centre for Agricultural Research, Fehérvári út 132–144, 1116 Budapest, Hungary
2
Doctoral School, Semmelweis University, Üllői út 26, 1085 Budapest, Hungary
3
Laboratory for Food Chemistry, National Institute of Chemistry, Hajdrihova 19, 1000 Ljubljana, Slovenia
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(24), 5846; https://doi.org/10.3390/molecules29245846
Submission received: 25 November 2024 / Revised: 4 December 2024 / Accepted: 9 December 2024 / Published: 11 December 2024

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 A1A5 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.
Keywords: tree of heaven (Ailanthus altissima); fatty acid derivatives; canthin-6-one alkaloid; TLC–effect-directed analysis; bioassay-guided isolation; antibacterial effect tree of heaven (Ailanthus altissima); fatty acid derivatives; canthin-6-one alkaloid; TLC–effect-directed analysis; bioassay-guided isolation; antibacterial effect

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MDPI and ACS Style

Cselőtey, A.; Baglyas, M.; Király, N.; Ott, P.G.; Glavnik, V.; Vovk, I.; Móricz, Á.M. Bioassay-Guided Isolation and Identification of Antibacterial Compounds from Invasive Tree of Heaven Stem and Trunk Bark. Molecules 2024, 29, 5846. https://doi.org/10.3390/molecules29245846

AMA Style

Cselőtey A, Baglyas M, Király N, Ott PG, Glavnik V, Vovk I, Móricz ÁM. Bioassay-Guided Isolation and Identification of Antibacterial Compounds from Invasive Tree of Heaven Stem and Trunk Bark. Molecules. 2024; 29(24):5846. https://doi.org/10.3390/molecules29245846

Chicago/Turabian Style

Cselőtey, Anna, Márton Baglyas, Nóra Király, Péter G. Ott, Vesna Glavnik, Irena Vovk, and Ágnes M. Móricz. 2024. "Bioassay-Guided Isolation and Identification of Antibacterial Compounds from Invasive Tree of Heaven Stem and Trunk Bark" Molecules 29, no. 24: 5846. https://doi.org/10.3390/molecules29245846

APA Style

Cselőtey, A., Baglyas, M., Király, N., Ott, P. G., Glavnik, V., Vovk, I., & Móricz, Á. M. (2024). Bioassay-Guided Isolation and Identification of Antibacterial Compounds from Invasive Tree of Heaven Stem and Trunk Bark. Molecules, 29(24), 5846. https://doi.org/10.3390/molecules29245846

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