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- MakaleAçık Erişim2019Scopus SJRQ4α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]
Kyeremeh, Kwaku; Kwain, Samuel; Tetevi, Gilbert Mawuli; Camas, Anil Sazak; Camas, Mustafa; Dofuor, Aboagye Kwarteng; Deng, Hai; Jaspars, Marcel
The Mycobacterium sp. BRS2A-AR2 is an endophyte of the mangrove plant Rhizophora racemosa G. Mey., which grows along the banks of the River Butre, in theWestern Region of Ghana. Chemical profiling using 1H-NMR and HRESI-LC-MS of fermentation extracts produced by the strain led to the isolation of the new compound, α-D-Glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β- D-fructofuranoside] or simply tortomycoglycoside (1). Compound 1 is an aminoglycoside consisting of a tryptophan moiety esterified to a disaccharide made up of β-D-fructofuranose and α-D-glucopyranose sugars. The full structure of 1 was determined using UV, IR, 1D, 2D-NMR and HRESI-LC-MS data. When tested against Trypanosoma brucei subsp. brucei, the parasite responsible for Human African Trypanosomiasis in sub-Saharan Africa, 1 (IC50 11.25 µM) was just as effective as Coptis japonica (Thunb.) Makino. (IC50 8.20 µM). The extract of Coptis japonica (Thunb.) Makino. is routinely used as laboratory standard due to its powerful antitrypanosomal activity. It is possible that, compound 1 interferes with the normal uptake and metabolism of tryptophan in the T. brucei subsp. brucei parasite.
AtıfScopus2WoS2OpenAlex2
İncele - MakaleAçık Erişim2019Scopus SJRQ4Digyaindoleacid A: 2-(1-(4-hydroxyphenyl)-3-oxobut-1-en-2-yloxy)-3-(1H-indol-3-yl)propanoic acid, a novel indole alkaloid
Kwain, Samuel; Tetevi, Gilbert Mawuli; Mensah, Thomas; Camas, Anil Sazak; Camas, Mustafa; Dofuor, Aboagye Kwarteng; Azerigyik, Faustus Akankperiwen; Deng, Hai; Jaspars, Marcel; Kyeremeh, Kwaku
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 927/4 GUTat10.1, 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 927/4 GUTat10.1. 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).
AtıfScopus4WoS3OpenAlex4İncele - MakaleAçık Erişim2019Scopus SJRQ4Paenidigyamycin g: 1-acetyl-2,4-dimethyl-3-phenethyl-1H-imidazol-3-ium
Tetevi, Gilbert Mawuli; Kwain, Samuel; Mensah, Thomas; Camas, Anil Sazak; Camas, Mustafa; Dofuor, Aboagye Kwarteng; Azerigyik, Faustus Akankperiwen; Oluwabusola, Emmanuel; Deng, Hai; Jaspars, Marcel
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.
AtıfScopus4WoS3OpenAlex4İncele - MakaleAçık Erişim2019Scopus SJRQ2Paenidigyamycin A, potent antiparasitic imidazole alkaloid from the ghanaian Paenibacillus sp. De2Sh
Osei, Enoch; Kwain, Samuel; Mawuli, Gilbert Tetevi; Anang, Abraham Kwabena; Owusu, Kofi Baffour-Awuah; Camas, Mustafa; Camas, Anil Sazak; Ohashi, Mitsuko; Alexandru-Crivac, Cristina-Nicoleta; Deng, Hai
A new alkaloid paenidigyamycin A (1) was obtained from the novel Ghanaian Paenibacillus sp. isolated from the mangrove rhizosphere soils of the Pterocarpus santalinoides tree growing in the wetlands of the Digya National Park, Ghana. Compound 1 was isolated on HPLC at tR = 37.0 min and its structure determined by MS, 1D, and 2D-NMR data. When tested against L. major, 1 (IC50 0.75 µM) was just as effective as amphotericin B (IC50 0.31 µM). Against L. donovani, 1 (IC50 7.02 µM) was twenty-two times less active than amphotericin B (IC50 0.32 µM), reinforcing the unique effectiveness of 1 against L. major. For T. brucei brucei, 1 (IC50 0.78 µM) was ten times more active than the laboratory standard Coptis japonica (IC50 8.20 µM). The IC50 of 9.08 µM for 1 against P. falciparum 3d7 compared to artesunate (IC50 36 nM) was not strong, but this result suggests the possibility of using the paenidigyamycin scaffold for the development of potent antimalarial drugs. Against cercariae, 1 showed high anticercaricidal activity compared to artesunate. The minimal lethal concentration (MLC) and minimal effective concentration (MEC) of the compound were 25 and 6.25 µM, respectively, while artesunate was needed in higher quantities to produce such results. However, 1 (IC50 > 100 µM) was not active against T. mobilensis.
AtıfScopus32OpenAlex32
İncele - MakaleAçık Erişim2014Scopus SJRQ2Butrepyrazinone, a New Pyrazinone with an Unusual Methylation Pattern from a Ghanaian Verrucosispora sp K51G
Kyeremeh, Kwaku; Acquah, Kojo Sekyi; Camas, Mustafa; Tabudravu, Jioji; Houssen, Wael; Deng, Hai; Jaspars, Marcel
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