Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum
Here we report a new polyhydroxylated triterpene, 2β,6β,21α-trihydroxyfriedelan-3-one (4) isolated from the root and stem bark of Dichapetalum albidum A. Chev (Dichapetalaceae), along with six known triterpenoids (1–3, 5, 6, 8), sitosterol-3β-O-D-glucopyranoside (9), a dipeptide (7), and a tyramine...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-07-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S240584402305507X |
| _version_ | 1797771439504359424 |
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| author | Mary A. Chama Godwin A. Dziwornu Elizabeth Popli Eduard Mas-Claret Beverly Egyir Daniel M. Ayine-Tora Kofi B-A. Owusu David G. Reid Dorcas Osei-Safo Melinda Duer Dulcie Mulholland Andreas Bender |
| author_facet | Mary A. Chama Godwin A. Dziwornu Elizabeth Popli Eduard Mas-Claret Beverly Egyir Daniel M. Ayine-Tora Kofi B-A. Owusu David G. Reid Dorcas Osei-Safo Melinda Duer Dulcie Mulholland Andreas Bender |
| author_sort | Mary A. Chama |
| collection | DOAJ |
| description | Here we report a new polyhydroxylated triterpene, 2β,6β,21α-trihydroxyfriedelan-3-one (4) isolated from the root and stem bark of Dichapetalum albidum A. Chev (Dichapetalaceae), along with six known triterpenoids (1–3, 5, 6, 8), sitosterol-3β-O-D-glucopyranoside (9), a dipeptide (7), and a tyramine derivative of coumaric acid (10). Friedelan-3-one (2) showed an antimicrobial activity (IC50) of 11.40 μg/mL against Bacillus cereus, while friedelan-3α-ol (1) gave an IC50 of 13.07 μg/mL against Staphylococcus aureus with ampicillin reference standard of 19.52 μg/mL and 0.30 μg/mL respectively. 3β-Acetyl tormentic acid (5) showed an IC50 of 12.50 μg/mL against Trypanosoma brucei brucei and sitosterol-3β-O-d-glucopyranoside (9) showed an IC50 of 5.06 μg/mL against Leishmania donovani with respective reference standards of IC50 5.02 μg/mL for suramin and IC50 0.27 μg/mL for amphotericin B. Molecular docking of the isolated compounds on the enzyme glucose-6-phosphate dehydrogenase (G6PDH) suggested 3β-acetyl tormentic acid (5) and sitosterol-3β-O-D-glucopyranoside (9) as plausible inhibitors of the enzyme in accordance with the experimental biological results observed. |
| first_indexed | 2024-03-12T21:36:34Z |
| format | Article |
| id | doaj.art-87c5e08070e249ea81ae8b796b7763b2 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-03-12T21:36:34Z |
| publishDate | 2023-07-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-87c5e08070e249ea81ae8b796b7763b22023-07-27T05:59:12ZengElsevierHeliyon2405-84402023-07-0197e18299Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidumMary A. Chama0Godwin A. Dziwornu1Elizabeth Popli2Eduard Mas-Claret3Beverly Egyir4Daniel M. Ayine-Tora5Kofi B-A. Owusu6David G. Reid7Dorcas Osei-Safo8Melinda Duer9Dulcie Mulholland10Andreas Bender11Department of Chemistry, SPMS, CBAS, University of Ghana, Ghana; Corresponding author.Department of Chemistry, SPMS, CBAS, University of Ghana, GhanaYusuf Hamied Department of Chemistry, University of Cambridge, United KingdomRoyal Botanic Gardens, Kew, Richmond, TW9 3AQ, United KingdomDepartment of Bacteriology, Noguchi Memorial Institute for Medical Research, College of Health Sciences, University of Ghana, GhanaDepartment of Chemistry, SPMS, CBAS, University of Ghana, GhanaDepartment of Parasitology, Noguchi Memorial Institute for Medical Research, College of Health Sciences, University of Ghana, GhanaYusuf Hamied Department of Chemistry, University of Cambridge, United KingdomDepartment of Chemistry, SPMS, CBAS, University of Ghana, GhanaYusuf Hamied Department of Chemistry, University of Cambridge, United KingdomDepartment of Chemistry, University of Surrey, Guildford, United KingdomYusuf Hamied Department of Chemistry, University of Cambridge, United KingdomHere we report a new polyhydroxylated triterpene, 2β,6β,21α-trihydroxyfriedelan-3-one (4) isolated from the root and stem bark of Dichapetalum albidum A. Chev (Dichapetalaceae), along with six known triterpenoids (1–3, 5, 6, 8), sitosterol-3β-O-D-glucopyranoside (9), a dipeptide (7), and a tyramine derivative of coumaric acid (10). Friedelan-3-one (2) showed an antimicrobial activity (IC50) of 11.40 μg/mL against Bacillus cereus, while friedelan-3α-ol (1) gave an IC50 of 13.07 μg/mL against Staphylococcus aureus with ampicillin reference standard of 19.52 μg/mL and 0.30 μg/mL respectively. 3β-Acetyl tormentic acid (5) showed an IC50 of 12.50 μg/mL against Trypanosoma brucei brucei and sitosterol-3β-O-d-glucopyranoside (9) showed an IC50 of 5.06 μg/mL against Leishmania donovani with respective reference standards of IC50 5.02 μg/mL for suramin and IC50 0.27 μg/mL for amphotericin B. Molecular docking of the isolated compounds on the enzyme glucose-6-phosphate dehydrogenase (G6PDH) suggested 3β-acetyl tormentic acid (5) and sitosterol-3β-O-D-glucopyranoside (9) as plausible inhibitors of the enzyme in accordance with the experimental biological results observed.http://www.sciencedirect.com/science/article/pii/S240584402305507XDichapetalum albidum2β, 6β, 21α-trihydroxyfriedelan-3-one3β-acetoxy-2α,19β-dihydroxy-urs-12-en-28-oic acidLeishmania donovaniTrypanosoma brucei bruceiGlucose-6-phosphate dehydrogenase |
| spellingShingle | Mary A. Chama Godwin A. Dziwornu Elizabeth Popli Eduard Mas-Claret Beverly Egyir Daniel M. Ayine-Tora Kofi B-A. Owusu David G. Reid Dorcas Osei-Safo Melinda Duer Dulcie Mulholland Andreas Bender Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum Heliyon Dichapetalum albidum 2β, 6β, 21α-trihydroxyfriedelan-3-one 3β-acetoxy-2α,19β-dihydroxy-urs-12-en-28-oic acid Leishmania donovani Trypanosoma brucei brucei Glucose-6-phosphate dehydrogenase |
| title | Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum |
| title_full | Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum |
| title_fullStr | Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum |
| title_full_unstemmed | Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum |
| title_short | Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum |
| title_sort | antimicrobial and in silico studies of the triterpenoids of dichapetalum albidum |
| topic | Dichapetalum albidum 2β, 6β, 21α-trihydroxyfriedelan-3-one 3β-acetoxy-2α,19β-dihydroxy-urs-12-en-28-oic acid Leishmania donovani Trypanosoma brucei brucei Glucose-6-phosphate dehydrogenase |
| url | http://www.sciencedirect.com/science/article/pii/S240584402305507X |
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