TY - JOUR
T1 - Antimicrobial and in silico studies of the triterpenoids of Dichapetalum albidum
AU - Chama, Mary A.
AU - Dziwornu, Godwin A.
AU - Popli, Elizabeth
AU - Mas-Claret, Eduard
AU - Egyir, Beverly
AU - Ayine-Tora, Daniel M.
AU - Owusu, Kofi B.A.
AU - Reid, David G.
AU - Osei-Safo, Dorcas
AU - Duer, Melinda
AU - Mulholland, Dulcie
AU - Bender, Andreas
N1 - Publisher Copyright:
© 2023
PY - 2023/7
Y1 - 2023/7
N2 - 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.
AB - 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.
KW - 2β, 6β, 21α-trihydroxyfriedelan-3-one
KW - 3β-acetoxy-2α,19β-dihydroxy-urs-12-en-28-oic acid
KW - Dichapetalum albidum
KW - Glucose-6-phosphate dehydrogenase
KW - Leishmania donovani
KW - Trypanosoma brucei brucei
UR - http://www.scopus.com/inward/record.url?scp=85166654458&partnerID=8YFLogxK
U2 - 10.1016/j.heliyon.2023.e18299
DO - 10.1016/j.heliyon.2023.e18299
M3 - Article
AN - SCOPUS:85166654458
SN - 2405-8440
VL - 9
JO - Heliyon
JF - Heliyon
IS - 7
M1 - e18299
ER -