Crude petroleum ether extract from the bark of Poulsenia armata showed antimicrobial activity. Activity-guided fractionation led to the isolation and structure elucidation of two active new triterpene derivatives, the stearate of glut-5-en-3beta-ol (1) and 3beta,28-diacetoxyurs-12-ene (4), for the first time as naturally occurring compounds. Compound 4 has previously been synthesized. The structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry and chemical transformations. This is the first report on the chemistry and pharmacology of the genus.
The marine soft corals Sarcophyton trocheliophorum crude extracts possessed antimicrobial activity towards pathogenic bacterial strains, i.e. Bacillus cereus, Salmonella typhi, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. Bioassay-guided fractionation indicated that the antimicrobial effect was due to the presence of terpenoid bioactive derivatives. Further biological assays of the n-hexane fractions were carried out using turbidity assay, inhibition zone assay and minimum inhibitory concentration for investigating the growth-inhibition effect towards the Gram-positive and Gram-negative bacteria. The fractions were screened and the structure of the isolated compound was justified by interpretation of the spectroscopic data, mainly mass spectrometry (GC-MS). The structure was assigned as (5S)-3-[(3E,5S)-5-hydroxy-3-hepten-6-yn-1-yl]-5-methyl-2(5H)-furanone and was effective at concentrations as low as 0.20mg/mL. The above findings, in the course of our ongoing research on marine products, may implicate that the profound anti-microbial activity of the S. trocheliophorum soft corals, inhabiting the red sea reefs, is attributed to the presence of growth-inhibiting secondary metabolites mainly terpenoids.
Three phenolic compounds cosmosiin, caffeic acid, and p-coumaric acid were isolated for the first time from the leaves of Cupressus sempervirens L., together with cupressuflavone, amentoflavone, rutin, quercitrin, quercetin, myricitrin. The isolated compounds were identified using (1)H- and (13)C-NMR spectra. The hepatoprotective activity of the MeOH extract was carried out in liver homogenate of normal and CCl(4)-treated rats; a significant decrease in glutamate oxaloacetate transaminase, glutamate pyruvate transaminase, cholesterol level, and triglycerides, while a significant increase in the total protein level, was observed after the oral administration of MeOH extract. The free radical scavenging activity against stable 2,2-diphenyl-2-picrylhydrazyl (DPPH*) was measured for MeOH extract and some of the isolated phenolic compounds in comparison with alpha-tocopherol and butylated hydroxy toluene as standard antioxidants using ESR technique, showed high antioxidant activity for quercetin, rutin, caffeic acid, and p-coumaric acid.
The fungus Aspergillus amoenus Roberg strain UP197 was shown to produce antibacterial tetramic acid based alkaloids. Two new compounds, pyranterreone I and J (1 and 2), were isolated and characterized, in addition to the known compounds cordylactam, 7-hydroxycordylactam, pyranterreone C, D, F and G. Neither the pyranterreones nor the cordylacctams had previously been tested for antimicrobial activity. Thus, all isolated compounds were tested against a panel of clinically important bacteria and fungi. Pyranterreone C was active against Gram-positive and Gram-negative bacteria, with minimal inhibitory concentrations (MIC) between 1 and 8 mu g/mL, whereas the MICs for all other compounds were >32 mu g/mL. Pyranoterreone C was cytotoxic towards HepG2 cells, and since pyranterreone C reacted rapidly with the nucleophile cysteine, it is likely that the observed antibacterial activity is due to the chemical reactivity rather than enzymatic affinity, making it unsuitable for development as an antibacterial drug.