A new ceramide from the leaves of Lannea schimperi (Hochst. ex A.Rich.) Engl.

A new ceramide is being reported herein together with six known compounds from the methanol extract of the leaves of Lannea schimperi (Hochst. ex A.Rich.) Engl. The metabolites were obtained through repeated open column chromatography and were characterized by spectroscopic and spectrometric techniques. The radical-scavenging activity of the crude extract and isolated compounds was evaluated using the DPPH radical. The obtained results suggest the studied species as prominent candidate to fight reactive oxygen species (ROS).

Alkenylbenzoquinones and other compounds from the fruit of Maesa lanceolata exhibited potent cytotoxic, antibacterial, and antiradical scavenging activities§.

A phytochemical study of the methanol extract of the fruit of Maesa lanceolata resulted in the isolation of a new alkenylbenzoquinone (1), alongside the known compounds (Z)-2,5-dihydroxy-6-methyl-3-(pentadec-10'-enyl)-1,4-benzoquinone (2), 2,5-dihydroxy-6-methyl-3-(nonadec-14'-enyl)-1,4-benzoquinone (3), 2,5-dihydroxy-6-methyl-3-(tridecyl)-1,4-benzoquinone (4), (2S,3S,4R,2'R,9E)-[2'-hydroxytetraeicosanoyl]-2-aminooctadec-9-ene-1,3,4-triol (5), monopalmitin (glyceryl palmitate) (6), lupeol (7), and 3-O-(ß-D-glucopyranoside)-ß-sitosterol (8). The structures of the compounds were established by the means of spectroscopic (1 D- and 2 D-NMR) and spectrometric techniques (MS). The isolated compounds were assessed for their antibacterial, cytotoxic, and antiradical activities. Compound 2 showed moderate activity against Staphylococcus warneri (DSMZ 20036), while the other compounds were inactive. The two quinones 1 and 2 were significantly cytotoxic, with IC50 values of 0.005 µM and 12.5 µM respectively, and were weakly active towards DPPH radical (IC50 >250 µg/mL).

A new alkylbenzoquinone from Embelia rowlandii Gilg. (Myrsinaceae).

A new alkylbenzoquinone named embeliquinone (1) together with five known compounds, lupeol (2), 3-O-[6'-O-palmitoyl-ß-d-glucosyl]-spinasta-7,22(23)-diene (3), quercetin (4), (2S,3S,4R,8E)-2-[(2'R)-2'-hydroxy-heneicosanoylamino]-heneicosane-1,3,4-triol-8-ene (5), and ß-sitosterol-3-O-ß-d-glucopyranoside (6) were isolated from the MeOH leaf extract of Embelia rowlandii by using repeated open column chromatography techniques. The structure of the new compound was characterized by analyses of 1D- and 2D-NMR, and MS data. Embeliquinone (1) had moderate anti-cell proliferation activity against A549 cell line with the IC50 value of 21.8 µM. In addition, 1 exhibited weak antibacterial activities against Klebsiella pneumoniae and Staphylococcus aureus with an MIC value of 206.0 µM in both cases.

A naturally occuring triterpene saponin ardisiacrispin B displayed cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death.

INTRODUCTION: Multidrug resistance of cancer cells constitutes a serious problem in chemotherapy and a challenging issue in the discovery of new cytotoxic drugs. Many saponins are known to display anti-cancer effects. In this study, the cytotoxicity and the modes of action of a naturally occuring oleanane-type tritepene saponin, ardisiacrispin B isolated from the fruit of Ardisia kivuensis Taton (Myrsinaceae) was evaluated on a panel of 9 cancer cell lines including various sensitive and drug-resistant phenotypes. METHODS: Resazurin reduction assay was used to evaluate cytotoxicity and ferroptotic cell death of samples; caspase-Glo assay was used to detect the activation of caspases in CCRF-CEM leukemia cells. Flow cytometry was used for cell cycle analysis and detection of apoptotic cells by annexin V/PI staining, analysis of mitochondrial membrane potential (MMP) and measurement of reactive oxygen species (ROS). RESULTS: Ardisiacrispin B displayed significant cytotoxic effects in the 9 tested cancer cell lines with IC50 values below 10 µM. The IC50 values ranges were 1.20 µM (towards leukemia CCRF-CEM cells) to 6.76 µM [against heptocarcinoma HepG2 cells] for ardisiacrispin B and 0.02 µM (against CCRF-CEM cells) to 122.96 µM (against resistant CEM/ADR5000 leukemia cells) for doxorubicin. Collateral sensitivity of resistant HCT116p53-/- colon adenocarcinoma cells to ardisiacripsin B was observed. Ardisiacrispin B induced apoptosis in CCRF-CEM cells via activation of inititator caspases 8 and 9 and effector caspase 3/7, alteration of MMP and increase in ROS production. Ferroptosis also contributed to the cytotoxicity of ardisiacrispin B. CONCLUSIONS: The studied oleanane-type triterpene saponin is a good cytotoxic molecule that deserve more detailed exploration in the future, to develop novel cytotoxic drugs to combat both sensitive and drug-resistant cancers.

A New Alkenylmethylresorcinol from the Fruits of Ardisia kivuensis.

The phytochemical study of the MeOH extract from the fruits of Ardisia kivuensis was carried out using repeated silica gel column chromatography followed by Sephadex LH-20 to afford a new alkenylmethylresorcinol, ardisinol III (1) along with three known compounds, oleanolic acid, ß-sitosterol and pentacosanoic acid. The structure of 1 was elucidated using spectroscopic analysis (NMR and MS), and comparison with published data. Compound 1 had weak antioxidant activity (IC50 109.8 µg/mL) while other compounds were not active as compared to L-ascorbic acid (IC50 3.9 µg/mL).

Antimicrobial activity and cytotoxicity of the ethanol extract, fractions and eight compounds isolated from Eriosema robustum (Fabaceae).

BACKGROUND: The aim of this study was to evaluate the antimicrobial activity and the cytotoxicity of the ethanol crude extract, fractions and isolated compounds from the twigs of Eriosema robustum, a plant used for the treatment of coughs and skin diseases. METHODS: Column chromatographic and spectroscopic techniques were used to isolate and identify eight compounds, robusflavones A (1) and B (2), orostachyscerebroside A (3), stigmasterol (4), 1-O-heptatriacontanoyl glycerol (5), eicosanoic acid (6), 3-O-ß-D-glucopyranoside of sitosterol (7) and 6-prenylpinocembrin (8), from E. robustum. A two-fold serial microdilution method was used to determine the minimum inhibitory concentration (MIC) against fungi and bacteria, and the 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide reduction assay was used to evaluate the cytotoxicity. RESULTS: Fraction B had significant antimicrobial activity against Aspergillus fumigatus and Cryptoccocus neoformans (MIC 0.08 mg/ml), whilst the crude extract and fraction A had moderate activity against A. fumigatus and Candida albicans (MIC 0.16 mg/ml). Fraction A however had excellent activity against Staphylococcus aureus (MIC 0.02 mg/ml), Enterococcus faecalis and Escherichia coli (MIC 0.04 mg/ml). The crude extract had significant activity against S. aureus, E. faecalis and E. coli. Fraction B had good activity against E. faecalis and E. coli (MIC 0.08 mg/ml). All the isolated compounds had a relatively weak antimicrobial activity. An MIC of 65 µg/ml was obtained with robusflavones A (1) and B (2) against C. albicans and A. fumigatus, orostachyscerebroside A (3) against A. fumigatus, and robusflavone B (2) against C. neoformans. Compound 8 had the best activity against bacteria (average MIC 55 µg/ml). The 3 fractions and isolated compounds had LC50 values between 13.20 to > 100 µg/ml against Vero cells yielding selectivity indices between 0.01 and 1.58. CONCLUSION: The isolated compounds generally had a much lower activity than expected based on the activity of the fractions from which they were isolated. This may be the result of synergism between different compounds in the complex extracts or fractions. The results support the traditional use of E. robustum to treat infections. The crude extract had a good activity and low preparation cost, and may be useful in topical applications to combat microbial infections.