An extensive phytochemical investigation of the EtOH/H2O (7:3) extracts of Sida rhombifolia L. and Sida acuta Burm. f., yielded a previously undescribed ceramide named rhombifoliamide (1) and a xylitol dimer (2), naturally isolated here for the first time, as well as the thirteen known compounds viz, oleanolic acid (3), β-amyrin glucoside (4), ursolic acid (5), β-sitosterol glucoside (6), tiliroside (7), 1,6-dihydroxyxanthone (8), a mixture of stigmasterol (9) and β-sitosterol (10), cryptolepine (11), 20-Hydroxyecdysone (12), (E)-suberenol (13), thamnosmonin (14) and xanthyletin (15). Their structures were elucidated by the analyses of their spectroscopic and spectrometric data (1 D and 2 D NMR, and HRESI-MS) and by comparison with the previously reported data. The crude extracts, fractions, and some isolated compounds were tested against chloroquine-sensitive (3D7) and chloroquine-resistant (Dd2) Plasmodium falciparum strains. All the tested samples demonstrated moderate and/or significant activities against 3D7 (IC50 values: 0.18―20.11 µg/mL) and Dd2 (IC50 values: 0.74―63.09 µg/mL).
30 January 2018 in BMC Complementary and Alternative Medicine
Despite the remarkable progress in cancer therapy in recent years, this disease still remains a serious public health concern. The use of natural products has been and continues to be one of the most effective ways to fight malignancies. The cytotoxicity of 14 compounds from African medicinal plants was evaluated in four human carcinoma cell lines and normal fibroblasts. The tested samples included: β-spinasterol (1), friedelanone (2), 16β-hydroxylupeol (3), β-amyrin acetate (4), lupeol acetate (5), sequoyitol (6), rhamnitrin (7), europetin 3-O-rhamnoside (8), thonningiol (9), glyasperin F (10), seputhecarpan B (11), seputhecarpan C (12), seputhecarpan D (13) and rheediaxanthone A (14). The neutral red uptake (NR) assay was used to evaluate the cytotoxicity of samples; caspase-Glo assay, flow cytometry for cell cycle analysis and mitochondrial membrane potential (MMP) as well as spectrophotometry to measure levels of reactive oxygen species (ROS) were performed to detect the mode of action of compounds 9 and 13 in MCF-7 breast adenocarcinoma cells. Compounds 3, 9–13 displayed cytotoxic effects against the four tested cancer cell lines with IC50 values below 85 μM. Compounds 9 and 13 had IC50 values below 10 μM in 4/4 and 3/4 tested cell lines respectively. The IC50 values varied from 0.36 μM (against MCF7 cells) to 5.65 μM (towards colon carcinoma DLD-1 cells) for 9, from 9.78 μM (against MCF7 cells) to 67.68 μM (against HepG2 cells) for 13 and 0.18 μM (towards HepG2 cells) to 72 μM (towards Caco-2 cells) for the reference drug, doxorubicin. Compounds 9 and 13 induced cell cycle arrest in Go/G1 whilst doxorubicin induced arrest in G2/M. The two molecules (9 and 13) also induced apoptosis in MCF-7 cells through activation of caspases 3/7 and 9 as well as enhanced ROS production. Compounds 9 and 13 are good cytotoxic phytochemicals that should be explored more in future to develop a cytotoxic drug to fight human carcinoma.
Ozoroa insignis Del. is an ethnobotanical plant widely used in traditional medicine for various ailments, including schistosomiasis, tapeworm, and hookworm infections. From the so far not investigated fruits of Ozoroa insignis, the anthelmintic principles could be isolated through bioassay-guided isolation using Caenorhabditis elegans and identified by NMR spectroscopic analysis and mass spectrometric studies. Isolated 6-[8(Z)-pentadecenyl] anacardic (1), 6-[10(Z)-heptadecenyl] anacardic acid (2), and 3-[7(Z)-pentadecenyl] phenol (3) were evaluated against the 5 parasitic organisms Schistosoma mansoni (adult and newly transformed schistosomula), Strongyloides ratti, Heligmosomoides polygyrus, Necator americanus, and Ancylostoma ceylanicum, which mainly infect humans and other mammals. Compounds 1–3 showed good activity against Schistosoma mansoni, with compound 1 showing the best activity against newly transformed schistosomula with 50% activity at 1µM. The isolated compounds were also evaluated for their cytotoxic properties against PC-3 (human prostate adenocarcinoma) and HT-29 (human colorectal adenocarcinoma) cell lines, whereby compounds 2 and 3 showed antiproliferative activity in both cancer cell lines, while compound 1 exhibited antiproliferative activity only on PC-3 cells. With an IC50 value of 43.2 µM, compound 3 was found to be the most active of the 3 investigated compounds.
The chemical investigation of Anonidium mannii root extract by column chromatography techniques led to the isolation of eight compounds among which two previously unreported compounds; a lanostane-type triterpene, lanosta-7,9(11),23-triene-3β,15α-diol 1 and an alkaloid, 9-hydroxy-8-methoxyphenanthridin-6(5H)-one 2 along with six known compounds: lanosta-7,9(11),24-triene-3β,21-diol 3, oxoanolobine 4, 3, 4-dihydroxybenzoic acid 5, stigmasterol 6, β-sitosterol 7 and 3-O-β-D-glucopyranosyl-β-stigmasterol 8. Their structures were established from spectral data, mainly HR-ESIMS, 1 D and 2 D NMR and by comparison with literature data. The crude root and stem bark extracts (AMR and AMB) and the isolated compounds (1–8) were tested against nine Gram-negative bacteria using rapid p-iodonitrotetrazolium chloride ≥97% (INT) microdilution technique. It was found that AMR, AMB and compound 5 were active against the nine tested bacteria with MIC values ranging from 64 to 1024 µg/mL. Compounds 1–4 had selective antibacterial activities whilst 6–8 were not active.