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Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica

The powdered roots of the medicinal plant Acacia nilotica were extracted with hexane and ethyl acetate, and the extracts were subjected to column chromatography for the isolation of potentially bioactive compounds and their screening against kinetoplastid pathogens. NMR and HREI mass spectrometric a...

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Autores principales: Anyam, John V., Daikwo, Priscilla E., Ungogo, Marzuq A., Nweze, Nwakaego E., Igoli, Ngozichukwuka P., Gray, Alexander I., De Koning, Harry P., Igoli, John O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8097170/
https://www.ncbi.nlm.nih.gov/pubmed/33968894
http://dx.doi.org/10.3389/fchem.2021.624741
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author Anyam, John V.
Daikwo, Priscilla E.
Ungogo, Marzuq A.
Nweze, Nwakaego E.
Igoli, Ngozichukwuka P.
Gray, Alexander I.
De Koning, Harry P.
Igoli, John O.
author_facet Anyam, John V.
Daikwo, Priscilla E.
Ungogo, Marzuq A.
Nweze, Nwakaego E.
Igoli, Ngozichukwuka P.
Gray, Alexander I.
De Koning, Harry P.
Igoli, John O.
author_sort Anyam, John V.
collection PubMed
description The powdered roots of the medicinal plant Acacia nilotica were extracted with hexane and ethyl acetate, and the extracts were subjected to column chromatography for the isolation of potentially bioactive compounds and their screening against kinetoplastid pathogens. NMR and HREI mass spectrometric analyses identified two new diterpenes, characterized as 16, 19-dihydroxycassa-12-en-15-one (Sandynone, 1) and (5S, 7R, 8R, 9R, 10S, 13Z, 17S)-7,8:7,17:16,17-triepoxy-7,8-seco-cassa-13-ene (niloticane B, 2). The previously reported (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-diene-7,17-diol (3), (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-dien-7-ol-17-al (4), and (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-dien-7-ol (5) a, mixture of stigmasterol (6a) and sitosterol (6b), and lupeol (7) were also isolated. Several column fractions displayed significant activity against a panel of Trypanosoma and Leishmania spp., and from the most active fraction, compound 4 was isolated with high purity. The compound displayed high activity, particularly against T. brucei, T. evansi, and L. mexicana (0.88–11.7 µM) but only a modest effect against human embryonic kidney cells and no cross-resistance with the commonly used melaminophenyl arsenical and diamidine classes of trypanocides. The effect of compound 4 against L. mexicana promastigotes was irreversible after a 5-h exposure, leading to the sterilization of the culture between 24 and 48 h.
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spelling pubmed-80971702021-05-06 Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica Anyam, John V. Daikwo, Priscilla E. Ungogo, Marzuq A. Nweze, Nwakaego E. Igoli, Ngozichukwuka P. Gray, Alexander I. De Koning, Harry P. Igoli, John O. Front Chem Chemistry The powdered roots of the medicinal plant Acacia nilotica were extracted with hexane and ethyl acetate, and the extracts were subjected to column chromatography for the isolation of potentially bioactive compounds and their screening against kinetoplastid pathogens. NMR and HREI mass spectrometric analyses identified two new diterpenes, characterized as 16, 19-dihydroxycassa-12-en-15-one (Sandynone, 1) and (5S, 7R, 8R, 9R, 10S, 13Z, 17S)-7,8:7,17:16,17-triepoxy-7,8-seco-cassa-13-ene (niloticane B, 2). The previously reported (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-diene-7,17-diol (3), (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-dien-7-ol-17-al (4), and (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-dien-7-ol (5) a, mixture of stigmasterol (6a) and sitosterol (6b), and lupeol (7) were also isolated. Several column fractions displayed significant activity against a panel of Trypanosoma and Leishmania spp., and from the most active fraction, compound 4 was isolated with high purity. The compound displayed high activity, particularly against T. brucei, T. evansi, and L. mexicana (0.88–11.7 µM) but only a modest effect against human embryonic kidney cells and no cross-resistance with the commonly used melaminophenyl arsenical and diamidine classes of trypanocides. The effect of compound 4 against L. mexicana promastigotes was irreversible after a 5-h exposure, leading to the sterilization of the culture between 24 and 48 h. Frontiers Media S.A. 2021-04-21 /pmc/articles/PMC8097170/ /pubmed/33968894 http://dx.doi.org/10.3389/fchem.2021.624741 Text en Copyright © 2021 Anyam, Daikwo, Ungogo, Nweze, Igoli, Gray, De Koning and Igoli. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Anyam, John V.
Daikwo, Priscilla E.
Ungogo, Marzuq A.
Nweze, Nwakaego E.
Igoli, Ngozichukwuka P.
Gray, Alexander I.
De Koning, Harry P.
Igoli, John O.
Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica
title Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica
title_full Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica
title_fullStr Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica
title_full_unstemmed Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica
title_short Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica
title_sort two new antiprotozoal diterpenes from the roots of acacia nilotica
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8097170/
https://www.ncbi.nlm.nih.gov/pubmed/33968894
http://dx.doi.org/10.3389/fchem.2021.624741
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