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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Frontiers Media S.A.
2021-04-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2021.624741/full |
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| author | John V. Anyam Priscilla E. Daikwo Marzuq A. Ungogo Marzuq A. Ungogo Nwakaego E. Nweze Ngozichukwuka P. Igoli Alexander I. Gray Harry P. De Koning John O. Igoli |
| author_facet | John V. Anyam Priscilla E. Daikwo Marzuq A. Ungogo Marzuq A. Ungogo Nwakaego E. Nweze Ngozichukwuka P. Igoli Alexander I. Gray Harry P. De Koning John O. Igoli |
| author_sort | John V. Anyam |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-17T03:42:08Z |
| format | Article |
| id | doaj.art-51a6d047a8324de680e843bc78838c3e |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-17T03:42:08Z |
| publishDate | 2021-04-01 |
| publisher | Frontiers Media S.A. |
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| series | Frontiers in Chemistry |
| spelling | doaj.art-51a6d047a8324de680e843bc78838c3e2022-12-21T22:04:59ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-04-01910.3389/fchem.2021.624741624741Two New Antiprotozoal Diterpenes From the Roots of Acacia niloticaJohn V. Anyam0Priscilla E. Daikwo1Marzuq A. Ungogo2Marzuq A. Ungogo3Nwakaego E. Nweze4Ngozichukwuka P. Igoli5Alexander I. Gray6Harry P. De Koning7John O. Igoli8Phytochemistry Research Group, Department of Chemistry, University of Agriculture, Makurdi, NigeriaPhytochemistry Research Group, Department of Chemistry, University of Agriculture, Makurdi, NigeriaInstitute of Infection, Immunity and Inflammation, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow, United KingdomDepartment of Veterinary Pharmacology and Toxicology, Ahmadu Bello University, Zaria, NigeriaDepartment of Veterinary Medicine, Faculty of Veterinary Medicine, University of Nigeria, Nsukka, NigeriaCentre for Food Technology and Research, Benue State University, Makurdi, NigeriaStrathclyde Institute of Pharmacy and Biomedical Science, University of Strathclyde, Glasgow, United KingdomInstitute of Infection, Immunity and Inflammation, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow, United KingdomPhytochemistry Research Group, Department of Chemistry, University of Agriculture, Makurdi, NigeriaThe 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.https://www.frontiersin.org/articles/10.3389/fchem.2021.624741/fullNigeriaspectroscopyAcacia niloticaditerpenesseco-oxocassanestrypanosomiasis |
| spellingShingle | John V. Anyam Priscilla E. Daikwo Marzuq A. Ungogo Marzuq A. Ungogo Nwakaego E. Nweze Ngozichukwuka P. Igoli Alexander I. Gray Harry P. De Koning John O. Igoli Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica Frontiers in Chemistry Nigeria spectroscopy Acacia nilotica diterpenes seco-oxocassanes trypanosomiasis |
| 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 | Nigeria spectroscopy Acacia nilotica diterpenes seco-oxocassanes trypanosomiasis |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2021.624741/full |
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