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Digyaindoleacid A: 2-(1-(4-Hydroxyphenyl)-3-oxobut-1-en-2-yloxy)-3-(1H-indol-3-yl)propanoic Acid, a Novel Indole Alkaloid

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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, 62000 Tunceli, Turkey
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Department of Biochemistry, Cell and Molecular Biology, University of Ghana, P.O. Box LG 54 Legon-Accra, Ghana
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Noguchi Memorial Institute for Medical Research (NMIMR), College of Health Sciences, University of Ghana, P.O. Box LG 581 Legon, 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(3), M1080; https://doi.org/10.3390/M1080
Received: 22 August 2019 / Revised: 9 September 2019 / Accepted: 12 September 2019 / Published: 14 September 2019
(This article belongs to the Section Natural Products)
Digyaindoleacid A (1) is one of the novel alkaloids produced by the Ghanaian Paenibacillus sp. DE2SH (GenBank Accession Number: MH091697) isolated from the mangrove rhizosphere soils of the Pterocarpus santalinoides tree growing in the wetlands of the Digya National Park, Brong Ahafo Region, Ghana. This compound was isolated on HPLC at tR ≈ 60 min and its structure determined by MS, 1D, and 2D-NMR data. When tested against Trypanosoma brucei subsp. brucei strain GUTat 3.1, 1 produced a half-maximal inhibitory concentration (IC50) 5.21 μM compared to the standard diminazene aceturate (IC50 = 1.86 μM). In the presence of normal mouse macrophages RAW 264.7, 1 displayed a higher selectivity towards T. brucei subsp. brucei (selectivity indices (SI) = 30.2) with low toxicity. This result is interesting given that the drug diminazene aceturate is considerably toxic and 1 is a natural product isolate. The structure of 1 incorporates the backbone of the amino acid tryptophan which is crucial in the metabolism of Trypanosoma brucei subsp. brucei strain GUTat 3.1. It is possible that 1, could interfere with the normal uptake and metabolism of tryptophan in the parasite. However, 1 (IC50 = 135.41 μM) produced weak antileishmanial activity when tested against Leishmania donovani (Laveran and Mesnil) Ross (D10). View Full-Text
Keywords: tryptophan; trypanosomiasis; antitrypanosomals; leishmaniasis; antileishmanials; cell cycle; cell viability; spectroscopy; spectrometry tryptophan; trypanosomiasis; antitrypanosomals; leishmaniasis; antileishmanials; cell cycle; cell viability; spectroscopy; spectrometry
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Kwain, S.; Tetevi, G.M.; Mensah, T.; Camas, A.S.; Camas, M.; Dofuor, A.K.; Azerigyik, F.A.; Deng, H.; Jaspars, M.; Kyeremeh, K. Digyaindoleacid A: 2-(1-(4-Hydroxyphenyl)-3-oxobut-1-en-2-yloxy)-3-(1H-indol-3-yl)propanoic Acid, a Novel Indole Alkaloid. Molbank 2019, 2019, M1080.

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