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Paenidigyamycin G: 1-Acetyl-2,4-dimethyl-3-phenethyl-1H-imidazol-3-ium

1
Marine and Plant Research Laboratory of Ghana, Department of Chemistry, School of Physical and Mathematical Sciences, University of Ghana, P.O. Box LG 56, Legon-Accra, Ghana
2
Department of Bioengineering, Munzur University, Tunceli 62000, Turkey
3
Department of Biochemistry, Cell and Molecular Biology, University of Ghana, P.O. Box LG 54, Legon-Accra, Ghana
4
Noguchi Memorial Institute for Medical Research (NMIMR), College of Health Sciences, University of Ghana, P.O. Box LG 581, Legon-Accra, Ghana
5
Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK
*
Author to whom correspondence should be addressed.
Molbank 2019, 2019(4), M1094; https://doi.org/10.3390/M1094
Received: 20 October 2019 / Revised: 9 November 2019 / Accepted: 11 November 2019 / Published: 21 November 2019
(This article belongs to the Section Natural Products)
The Ghanaian Paenibacillus sp. DE2SH (GenBank Accession Number: MH091697) is a prolific producer of potent antiparasitic alkaloids. Further detailed study of the culture broth of this strain produced the compound Paenidigyamycin G (1), which is a derivative of the known antiparasitic compound Paenidigyamycin A (2). Compound (1) was isolated on HPLC at tR ≈ 37.5 min and its structure determined by IR, UV, MS, 1D, and 2D-NMR data. Compound 1 produced weak to moderate antileishmanial and antitrypanosomal activity when tested against Leishmania donovani (Laveran and Mesnil) Ross (D10) and Trypanosoma brucei subsp. brucei strain GUTat 3.1 with IC50 = 115.41 and 28.75 μM, respectively. This result is interesting since the parent compound 2 is known to possess consistent and potent antiparasitic activity. However, 1 displayed a promising selectivity profile towards T. brucei subsp. brucei due to its relatively low toxicity against normal mouse macrophages RAW 264.7 cells (SI = 8.70). Given that compound 1 is also the main metabolite found in the hexane fraction of all extracts produced by Paenibacillus sp. DE2SH when it is co-cultured with other bacteria strains, it must possess some unique biological functions which should make it an excellent candidate for further biological activity screening in other bioassays. View Full-Text
Keywords: Paenibacillus; alkaloid; imidazole; antileishmanials; leishmaniasis; antitrypanosomals; trypanosomiasis Paenibacillus; alkaloid; imidazole; antileishmanials; leishmaniasis; antitrypanosomals; trypanosomiasis
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Tetevi, G.M.; Kwain, S.; Mensah, T.; Camas, A.S.; Camas, M.; Dofuor, A.K.; Azerigyik, F.A.; Oluwabusola, E.; Deng, H.; Jaspars, M.; Kyeremeh, K. Paenidigyamycin G: 1-Acetyl-2,4-dimethyl-3-phenethyl-1H-imidazol-3-ium. Molbank 2019, 2019, M1094.

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