ABSTRACT
The crude ethanolic extract of leaves, stem-bark and roots of J. flammea were tested for their cytotoxic effect against two mammalian cell lines (HeLa and RAW 264.7) and four bacterial species (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa). When tested at the concentration of 100 microg/mL, the root extract showed the highest cytotoxic activity against mammalian cells followed by the stem-bark extract while the leaves extract did not show significant activity. No antibacterial activity was detected for all extracts when tested up to 500 microg/disc in the disc diffusion assay. The cytotoxic root extract was subjected to fractionation using solvents of ascending polarity: petroleum ether, chloroform, ethylacetate, butanol and water. The water fraction which showed cytotoxic activity was further subjected to routine bioassay-guided fraction to lead to the isolation of sakurasosaponin as the active principle. The recorded IC50 value for sakurasosaponin was 11.3 +/- 1.52 and 3.8 +/- 0.25 microM (n=3) against HeLa and RAW 264.7 respectively. The identification of sakurasosaponin was based on analysis of spectroscopic data.
Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/toxicity , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/toxicity , Plants, Medicinal/chemistry , Saponins/chemistry , Saponins/toxicity , Animals , Bacteria/drug effects , Carbohydrate Sequence , Cell Line, Tumor , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Methanol , Mexico , Mice , Microbial Sensitivity Tests , Molecular Sequence Data , Plant Extracts/chemistry , Plant Extracts/toxicity , Plant Roots/chemistry , SolventsABSTRACT
Chemical investigation of the roots of Diospyros assimilis had led to the isolation and characterization of six naphthalene derivatives, two 2-naphthaldehyes, namely 4-hydroxy-3,5-dimethoxy-2-naphthaldehyde 1, 4-hydroxy-5-methoxy-2-naphthaldehye 2, its related isomer 5-hydroxy-4-methoxy-2-naphthaldehyde 3 and three commonly occurring naphthoquinones, diospyrin 4, 8'-hydroxyisodiospyrin 5 and the simple monomer, plumbagin 6. Their chemical structures were established by detailed NMR investigations including 1H and 13C NMR, HSQC, HMBC and NOESY experiments. In addition, the naphthalene derivatives 1-5 were evaluated for their in vitro antiprotozoal activity against protozoan parasites belonging to the genera Trypanosoma, Leishmania and Plasmodium. Among the tested compounds, naphthaldehyde 1 showed moderate inhibition of the growth of the parasites, T. brucei, T. cruzi, L. donovani with IC50 values of 19.82, 12.28 and 38.78 microM and displayed cytotoxicity towards rat skeletal myoblasts (L-6 cells) with IC50 of 174.94 microM, while 2 and 3 were found to be comparatively less active to 1. The dimeric quinones 4 and 5 exhibited good activity against T. brucei and L. donovani with IC50 of 1.12 and 8.82 microM and 12.94 and 16.66 microM respectively.
Subject(s)
Antiprotozoal Agents/chemistry , Diospyros/chemistry , Naphthalenes/chemistry , Aldehydes/chemistry , Aldehydes/isolation & purification , Aldehydes/pharmacology , Animals , Antiprotozoal Agents/isolation & purification , Antiprotozoal Agents/pharmacology , Cell Survival/drug effects , Cells, Cultured , Inhibitory Concentration 50 , Leishmania donovani/drug effects , Magnetic Resonance Spectroscopy/methods , Molecular Structure , Naphthalenes/isolation & purification , Naphthalenes/pharmacology , Naphthoquinones/chemistry , Naphthoquinones/isolation & purification , Naphthoquinones/pharmacology , Plant Roots/chemistry , Rats , Trypanosoma cruzi/drug effectsABSTRACT
Four phenolic glycosides (1-4), including two new ones (3 and 4), have been isolated from the stems of Casearia multinervosa and identified as arbutin (1), 4-O-E-caffeoylarbutin (2), 4-O-E-coumaroylarbutin (3) and 4-O-E-feruloylarbutin (4), respectively. In addition, the two known phenolic glycosides (1 and 2) were also isolated from the leaves. Structures were elucidated on the basis of spectroscopic evidence. Compounds 1-4 were tested for cytotoxicity against the P388 mouse lympholytic cell line by an ATP Lite-M assay method and showed mild to moderate activity.
Subject(s)
Arbutin/chemistry , Casearia/chemistry , Phenols/isolation & purification , Animals , Arbutin/isolation & purification , Arbutin/pharmacology , Cell Line , Mice , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Phenols/pharmacology , Plant Leaves/chemistry , Plant Stems/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
Three 2-naphthaldehydes, including the novel 4-hydroxy-3,5-dimethoxy-2-naphthaldehyde, the simple naphthoquinone plumbagin and the dimeric naphthoquinones diospyrin and 8'-hydroxyisodiospyrin have been isolated from the roots of Diospyrosassimilis and their structures established by spectroscopic analysis.
Subject(s)
Diospyros/chemistry , Naphthalenes/isolation & purification , Naphthoquinones/isolation & purification , Aldehydes/chemistry , Aldehydes/isolation & purification , India , Molecular Structure , Naphthalenes/chemistry , Naphthoquinones/chemistry , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
Examination of the leaf exudate of the South African species Aloe littoralis by reversed-phase HPLC revealed the presence of two major metabolites. The identification of the two compounds without isolation was attempted by HPLC-NMR based on separation using a C18 column eluting with a deuterium oxide:acetonitrile solvent gradient and an inverse HPLC-NMR probe. For each compound, one-dimensional proton spectra, and two-dimensional homonuclear COSY and TOCSY, and heteronuclear HSQC and HMBC, spectra were collected. On the basis of the data obtained, the metabolites were characterised as 10-hydroxyaloin B and deacetyllittoraloin.
