A new biflavanoid, ent-naringeninyl-(I-3alpha,II-8)-4'-O-methylnaringenin (6), along with five known xanthones and two known biflavonoids, was isolated from the root bark of Garcinia livingstonei collected in Tanzania. The absolute configuration of 6 was established by CD spectroscopy. This compound showed moderate activity against P. falciparum (IC(50) 6.7 microM). Antitrypanosomal activity (IC(50) 0.87 microM) was observed for 1,4,5-trihydroxy-3-(3-methylbut-2-enyl)-9H-xanthen-9-one (3). The dimeric xanthone garcilivin A (4) showed a higher and nonselective antiparasitic activity and cytotoxicity (IC(50) 2.0 microM against MRC-5 cells) than its diastereoisomer garcilivin C (5) (IC(50) 52.3 microM).
Chromatographic separation of the roots of a Kenyan medicinal plant, Clerodendrum eriophyllum, led to the isolation of ten abietane diterpenoids (1-10), one of which (1) was isolated for the first time from a natural source. Using spectroscopic data, the structure of 1 was determined to be 12-hydroxy-8,12-abietadiene-3,11,14-trione. Circular dichroism (CD) spectra showed that the stereochemistry of compounds 1, 3, and 6-8 belongs to the normal series of abietane diterpenes, which confirmed the absolute stereochemistry of the isolated compounds. Compounds 2-10 were evaluated for their in vitro antiplasmodial, antileishmanial, antifungal and antibacterial activities. Compounds 3 and 7 exhibited potent antifungal activity (IC50/MIC 0.58/1.25 and 0.96/2.5 µg/mL, respectively) against C. neoformans, whereas 3, 6 and 7 showed strong antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with IC50/MIC values between 1.33–1.75/2.5–5 and 0.96–1.56/2.5 µg/mL, respectively. In addition, compounds 3 and 9 exhibited potent antileishmanial activity (IC50 0.08 and 0.20 µg/mL, respectively) against L. donovani, while 3 and 7 displayed weak antimalarial activity against Plasmodium falciparum, but 9 was inactive.
Phytochemical investigation of the ethyl acetate-soluble fraction of stem bark extract of an African medicinal plant Terminalia brownii led to the isolation of a new oleanane-type triterpenoid, along with seven known triterpenoids, seven ellagic acid derivatives, and 3-O-β-D-glucopyranosyl-β-sitosterol. The new compound was identified using spectroscopic methods, notably 1D- and 2D NMR, as 3β,24-O-ethylidenyl-2α,19α-dihydroxyolean-12-en-28-oic acid. The isolated compounds were evaluated for their antimicrobial and antiplasmodial activities. Two compounds with a galloyl group (4 and 6) were found to be active against chloroquine sensitive (D6) and chloroquine resistant (W2) strains of Plasmodium falciparum, whereas three ellagic acid derivatives (5–7) were found active against three species of fungi and one species of bacteria.
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