Antimycobacterial activities of the zanthoxylum leprieurii metabolite adubangoamide and non-natural fagaramide analogues

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dc.contributor.authorOloya, Benson
dc.contributor.authorNamukobe, Jane
dc.contributor.authorKrüger, Mandy
dc.contributor.authorSsengooba, Willy
dc.contributor.authorSperlich, Eric
dc.contributor.authorKwesiga, George
dc.contributor.authorKomakech, Kevin
dc.contributor.authorHeydenreich, Matthias
dc.contributor.authorByamukama, Robert
dc.contributor.authorSchmidt, Bernd
dc.date.accessioned2025-02-28T13:36:46Z
dc.date.available2025-02-28T13:36:46Z
dc.date.issued2025-02-11
dc.description.abstracttrans-Fagaramide (1) and adubangoamide (2) are natural products with a cinnamic acid amide skeleton that have recently been isolated from Zanthoxylum leprieurii, a medicinal plant used locally in Uganda for the treatment of tuberculosis. Insufficient quantities of material from the natural source originally prevented the antimycobacterial evaluation of the new natural product 2. Herein, a synthesis of 2 is reported, and its antimycobacterial activity was determined using the synthetic material. Adubangoamide (2) is three times more active against the drug-susceptible M. tuberculosis strain H37Rv than trans-fagaramide (1), with an MIC value of 10.0 μM. In addition, we synthesized eight non-natural analogues of trans-fagaramide (1, MIC = 32.0 μM against H37Rv strain), in which benzylamide groups mimic the isobutylamide part of the trans-fagaramide structure. Five out of eight synthetic analogues are more active than the parent natural product: 11b (MIC = 6.0 μM), 11d (21.0 μM), 11e (6.1 μM), 11g (17.0 μM), and 11h (4.5 μM).
dc.identifier.citationOloya, B., Namukobe, J., Krüger, M., Ssengooba, W., Sperlich, E., Kwesiga, G., Komakech, K., Heydenreich, M., Byamukama, R., Schmidt, B. (2025). Antimycobacterial activities of the zanthoxylum leprieurii metabolite adubangoamide and non-natural fagaramide analogues. Journal of Natural Products, 88, 530−536. https://doi.org/10.1021/acs.jnatprod.4c01377
dc.identifier.urihttps://dir.muni.ac.ug/handle/20.500.12260/730
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.subjectAmides
dc.subjectAmines
dc.subjectMixtures
dc.subjectNuclear magnetic resonance spectroscopy
dc.subjectPharmaceuticals
dc.titleAntimycobacterial activities of the zanthoxylum leprieurii metabolite adubangoamide and non-natural fagaramide analogues
dc.typeArticle

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