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

Samuel Kwain; Gilbert Mawuli Tetevi; Thomas Mensah; Anil Sazak Camas; Mustafa Camas; Aboagye Kwarteng Dofuor; Faustus Akankperiwen Azerigyik; Hai Deng; Marcel Jaspars; Kwaku Kyeremeh

doi:10.3390/M1080

Molbank (Sep 2019)

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

Samuel Kwain,
Gilbert Mawuli Tetevi,
Thomas Mensah,
Anil Sazak Camas,
Mustafa Camas,
Aboagye Kwarteng Dofuor,
Faustus Akankperiwen Azerigyik,
Hai Deng,
Marcel Jaspars,
Kwaku Kyeremeh

Affiliations

Samuel Kwain: 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
Gilbert Mawuli Tetevi: 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
Thomas Mensah: 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
Anil Sazak Camas: Department of Bioengineering, Munzur University, 62000 Tunceli, Turkey
Mustafa Camas: Department of Bioengineering, Munzur University, 62000 Tunceli, Turkey
Aboagye Kwarteng Dofuor: Department of Biochemistry, Cell and Molecular Biology, University of Ghana, P.O. Box LG 54 Legon-Accra, Ghana
Faustus Akankperiwen Azerigyik: Noguchi Memorial Institute for Medical Research (NMIMR), College of Health Sciences, University of Ghana, P.O. Box LG 581 Legon, Ghana
Hai Deng: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK
Marcel Jaspars: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK
Kwaku Kyeremeh: 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

DOI: https://doi.org/10.3390/M1080
Journal volume & issue: Vol. 2019, no. 3
p. M1080

Abstract

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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).

Published in Molbank

ISSN: 1422-8599 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Inorganic chemistry
Website: https://www.mdpi.com/journal/molbank

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