Two new compounds and the anti-mycobacterial activity of the constituents from Zanthoxylum leprieurii root bark. (April 2023)

• Record Type: Journal Article
• Authors: Oloya, Benson; Namukobe, Jane; Heydenreich, Matthias; Ssengooba, Willy; Martin, Johannes; Möller, Heiko Michael; Schmidt, Bernd; Byamukama, Robert
• Is Part Of: Phytochemistry letters. Volume 54(2023)
• Page Start: 107
• Page End: 113
• Publication Date: 2023-04
• Subjects: Anti-mycobacterial activity -- Zanthoxylum leprieurii -- Tuberculosis -- Adubangoamide -- Dranzoanol; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2023.02.002
• Languages: English
• ISSNs: 1874-3900

Abstract

Abstract: The emergence of resistance to the existing TB drugs necessitated a search for new anti-mycobacterial compounds from Z. leprieurii root bark, which is used locally for the treatment of tuberculosis (TB) in Uganda. Two new compounds: ( E )- N -isobutyl-3-(4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylamide (1 ) and 4-(5, 5a, 6, 8, 8a, 9-hexahydrofuro[3′, 4′:6, 7]-naphtha[2, 3- d ][1, 3]dioxol-5-yl)-2-methoxyphenol (2 ), were isolated from the dichloromethane (DCM) extract. In addition, sixteen known compounds were isolated from the DCM and methanol extracts, with two of them, N -isobutylcinnamamide (9 ) and ( E )-3-(4-hydroxy-3-methoxyphenyl)- N -isobutylacrylamide (14 ), being reported from a natural source for the first time. The structures of the isolates were elucidated by a combination of spectroscopic techniques. The isolated compounds were subjected to anti-mycobacterial activity testing using the microplate Alamar blue assay (MABA). Five compounds, 10 (MIC, 0.98 μg/mL), 11 (MIC, 7.82 μg/mL), 12 (MIC, 1.95 μg/mL), 13 (MIC, 3.91 μg/mL), and 14 (MIC, 3.91 μg/mL) exhibited significant anti-mycobacterial activities against the susceptible (H37 Rv) strain and could provide vital templates for developing new and highly effective TB drugs. Also, compounds 4 (MIC, 62.50 μg/mL), 7 (MIC, 62.50 μg/mL) and 16 (MIC, 62.50 μg/mL) exhibited moderate activity against H37 Rv. Graphical Abstract: ga1 Highlights: Two new compounds: adubangoamide and dranzoanol are reported. The isolation of 9 and 14 from a natural source is reported for the first time. Compounds 10–14 showed significant anti-mycobacterial activity.