Band 66, Heft 7-8

Polyacetylenes are known for their biofunctional properties in a wide range of organisms. In the present study, the most frequently occurring polyacetylenes, i.e. falcarinol, falcarindiol, and falcarindiol-3-acetate, were determined in six genera of the Apiaceae family. For this purpose, a straightforward and reliable method for the screening and quantification of the polyacetylenes using high-performance liquid chromatography coupled with diode array and mass spectrometric detection without tedious sample clean-up has been developed. Peak assignment was based on retention times, UV spectra, and mass spectral data. Quantification was carried out using calibration curves of authentic standards isolated from turnip-rooted parsley and Ligusticum mutellina, respectively. The references were unambiguously identified by Fourier transform-IR (FT-IR) spectroscopy, GC-MS, HPLC-MSn in the positive ionization mode, and 1 H NMR and 13 C NMR spectroscopy. To the best of our knowledge, the occurrence of falcarindiol-3-acetate in Anthriscus sylvestris and Pastinaca sativa has been reported for the first time. The data revealed great differences in the polyacetylene contents and varying proportions of individual compounds in the storage roots of Apiaceous plants. The results of the present study may be used as a suitable tool for authenticity control and applied to identify novel sources devoid or particularly rich in polyacetylenes, thus facilitating breeding programs for the selective enrichment and depletion of these plant secondary metabolites, respectively.

Nannochloropsis salina was cultured batch-wise to evaluate the potential of the alga to produce biodiesel. The cells were harvested at the end of the exponential growth phase when the concentration was 18 · 10 6 cells/mL culture. The growth estimated as dry weight from this cell number was (3.8 ± 0.7) mg/L. The lipid and triglyceride contents were 40% and 12% on a dry weight basis, respectively. The amount of the ratio triglycerides/total lipids was approximately 0.3. The composition of triglyceride fatty acid methyl esters (biodiesel) was analysed by gasliquid chromatography and identified as: C14:0, C16:0, C16:1, C18:0, C18:1, C18:2, C18:3, C20:1, and C20:5. The ratio of unsaturated to saturated fatty acid contents was approximately 4.4. Additionally, the characterization of each individual fatty acid ester was discussed with regard to the fuel properties of biodiesel produced by the alga.

2-[(4-Methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetamide derivatives were synthesized and their structures were confirmed by 1 H NMR, IR, and elemental analysis. Cytotoxicity of the compounds towards HEK-293 and GMK cells was evaluated. Moreover, the antiviral and virucidal activities of these compounds against human adenovirus type 5 and ECHO-9 virus were assessed. Some of the newly synthesized derivatives have the potential to reduce the viral replication of both tested viruses.

There has been an increasing importance of drug-resistant pathogens in clinical microbiological and antibacterial research. Indoles and hydrazone-type compounds constitute important classes of compounds in the search for effective agents against multidrug-resistant microbial infections. In this study a series of 1-methylindole-3-carboxaldehyde hydrazone derivatives were evaluated for their in vitro antimicrobial activities using the two-fold serial dilution technique against Staphylococcus aureus, methicillin-resistant S. aureus, methicillinresistant S. aureus isolate, Escherichia coli, Bacillus subtilis, and Candida albicans. The minimum inhibitory concentration (MIC) of the test compounds and the reference standards sultamicillin, ampicillin, fluconazole, and ciprofloxacin was determined. All compounds possessed a broad spectrum of activity having MIC values of 6.25 - 100 μg/ml against the tested microorganisms. Aromaticity and disubstitution of the phenyl ring with especially fluorine and chlorine atoms were found to be significant for the antimicrobial activity

A series of 1,3,5-triazine derivatives that contain 4-amino-2-trifl uoromethyl-benzonitrile, 8-hydroxyquinoline, and different piperazines as substituents at the carbon atoms of the triazine ring have been synthesized by a simple and efficient synthetic protocol. The chemical structures of the compounds were elucidated with the aid of IR, 1 H NMR and 13 C NMR spectroscopy, and elemental analysis. The antimicrobial activity of the compounds was tested against seven bacteria (Staphylococcus aureus MTCC 96, Bacillus cereus MTCC 619, Escherichia coli MTCC 739, Pseudomonas aeruginosa MTCC 741, Klebsiella pneumoniae MTCC 109, Salmonella typhi MTCC 733, Proteus vulgaris MTCC 1771) and four fungi (Aspergillus niger MTCC 282, Aspergillus fumigatus MTCC 343, Aspergillus clavatus MTCC 1323, Candida albicans MTCC 183). The results indicate that some of the novel s-triazines have noteworthy activity in minimum inhibitory concentration as well as agar diffusion tests.

(R)-(+)-Pulegone is a monoterpene found in essential oils from plants of the Labiatae family. This compound is a major constituent of Agastache formosanum oil. In this study, the effect of (R)-(+)-pulegone on the central nervous system was evaluated. (R)-(+)-Pulegone caused a significant decrease in ambulation and an increase in pentobarbital-induced sleeping time in mice, indicating a central depressant effect. (+)-Pulegone also significantly increased the latency of convulsions as assessed by the pentylenetetrazole (PTZ) method. The antinociceptive properties of this monoterpene were studied in chemical and thermal models of nociception. Chemical nociception induced in the first and second phase of the subplantar formalin test was significantly inhibited by (R)-(+)-pulegone and was not blocked by naloxone. Thermal nociception was also significantly inhibited while (R)-(+)-pulegone increased the reaction latency of the mice in the hot plate test. These results suggest that (R)-(+)-pulegone is a psychoactive compound and has the profile of an analgesic drug.

The in vitro activity on Leishmania infantum promastigotes and Trypanosoma cruzi epimastigotes of 25 semisynthetic terpenoid derivatives has been evaluated. These compounds were obtained through chemical modifications of the major components of Euphorbia resinifera (α-euphol and α-euphorbol) and Euphorbia officinarum (obtusifoliol and 31-norlanosterol). Leishmaniasis and Chagas´ disease are major worldwide health problems. The drugs of choice for their treatment are still problematic in both cases, and therefore there is an urgent need to discover new drugs with high activity and low side effects. Natural products have become a key source of new drugs in the last years. The genus Euphorbia has been the subject of abundant phytochemical and pharmacological research because of its potential medical applications, but the antiparasitic effects of derivatives from plants of this genus are still unknown. Our results showed that 76% and 64% of the test compounds had antiparasitic effects on L. infantum and T. cruzi, respectively. The different activities on both parasites, especially their moderate effects on mammalian cells, indicate an interesting selective toxicity.

1 The antitumour activities of extracts from the Red Sea seaweeds Jania rubens, Sargassum subrepandum, and Ulva lactuca were investigated in an in vivo mice model based on intramuscular injection of Ehrlich ascites tumour cells. In parallel, antioxidant activities were measured. Tumour marker levels, liver biochemical parameters, and hepatic oxidant/antioxidant status were measured to prove the anticancer and antioxidant nature of the algal extracts. Significant decreases in carcinoembryonic antigen (CEA) and α-fetoprotein (AFP) levels, activities of liver enzymes, levels of nitric oxide (NO) and malondialdehyde (MDA), and an increase in total antioxidant capacity (TAC) were recorded in groups treated with the algal extracts. Jania rubens was selected for phytochemical screening of its phytoconstituents. In addition, carotenoids, halides, minerals, lipoidal matters, proteins, and carbohydrates were studied. Furthermore, 7-oxo-cholest-5(6)-en-3-ol () and cholesterol ( 2 ) were isolated from the dichloromethane fraction.

Annonaceae aporphine alkaloids, of which liriodenine is the most abundant, have not been extensively studied from a biological standpoint. The goal of this study was to investigate the role of liriodenine in antimicrobial defense during early developmental stages in Annona diversifolia. The fungi Rhizopus stolonifer and Aspergillus glaucus, which are responsible for seed deterioration, were isolated during imbibition, and their antifungal activity was determined by diffusion, macrodilution, and metabolic inhibition assays using purified liriodenine and alkaloid extracts obtained from embryos, radicles, and roots at early developmental stages. The presence of liriodenine in extracts was quantified by high-performance liquid chromatography. Purified liriodenine and alkaloidal extracts inhibited both fungi, and there was a positive relationship between extract activity and amount of liriodenine contained therein. The quantity of liriodenine present in extracts suggests its importance in controlling other phytopathogens.

Column chromatography of the dichloromethane fraction from an aqueous methanolic extract of fruit peel of Citrus pyriformis Hassk. (Rutaceae) resulted in the isolation of seven compounds including one coumarin (citropten), two limonoids (limonin and deacetylnomilin), and four sterols (stigmasterol, ergosterol, sitosteryl-3-β-D-glucoside, and sitosteryl-6ʹ- O-acyl-3-β-D-glucoside). From the ethyl acetate fraction naringin, hesperidin, and neohesperidin were isolated. The dichloromethane extract of the defatted seeds contained three additional compounds, nomilin, ichangin, and cholesterol. The isolated compounds were identified by MS (EI, CI, and ESI), 1 H, 13 C, and 2D-NMR spectral data. The limonoids were determined qualitatively by LC-ESI/MS resulting in the identification of 11 limonoid aglycones. The total methanolic extract of the peel and the petroleum ether, dichloromethane, and ethyl acetate fractions were screened for their antioxidant and anti-inflammatory activities. The ethyl acetate fraction exhibited a significant scavenging activity for DPPH· free radicals (IC 50 = 132.3 μg/mL). The petroleum ether fraction inhibited 5-lipoxygenase with IC 50 = 30.6 μg/mL indicating potential anti-inflammatory properties. Limonin has a potent cytotoxic effect against COS7 cells [IC 50 = (35.0 ± 6.1) μ M ] compared with acteoside as a positive control [IC 50 = (144.5 ± 10.96) μ M ]

Pseudomonas aeruginosa BN10 isolated from hydrocarbon-polluted soil was found to produce rhamnolipids when cultivated on 2% glycerol, glucose, n-hexadecane, and n-alkanes. The rhamnolipids were partially purified on silica gel columns and their chemical structures elucidated by combination of one- and two-dimensional 1 H and 13 C NMR techniques and ESI-MS analysis. Eight structural rhamnolipid homologues were identified: Rha-C 10 - C 8 , Rha-C 10 -C 10 , Rha-C 10 -C 12:1 , Rha-C 10 -C 12 , Rha 2 -C 10 -C 8 , Rha 2 -C 10 -C 10 , Rha 2 -C 10 -C 12:1 , and Rha 2 -C 10 -C 12 . The chemical composition of the rhamnolipid mixtures produced on different carbon sources did not vary with the type of carbon source used. The rhamnolipid mixture produced by Pseudomonas aeruginosa BN10 on glycerol reduced the surface tension of pure water from 72 to 29 mN m -1 at a critical micellar concentration of 40 mg l -1 , and the interfacial tension was 0.9 mN m -1 . The new surfactant product formed stable emulsions with hydrocarbons and showed high antimicrobial activity against Gram-positive bacteria. The present study shows that the new strain Pseudomonas aeruginosa BN10 demonstrates enhanced production of the di-rhamnolipid Rha 2 -C 10 -C 10 on all carbon sources used. Due to its excellent surface and good antimicrobial activities the rhamnolipid homologue mixture from Pseudomonas aeruginosa BN10 can be exploited for use in bioremediation, petroleum and pharmaceutical industries.

The effect of a traditional Ethiopian lupin processing method on the chemical composition of lupin seed samples was studied. Two sampling districts, namely Mecha and Sekela, representing the mid- and high-altitude areas of north-western Ethiopia, respectively, were randomly selected. Different types of traditionally processed and marketed lupin seed samples (raw, roasted, and finished) were collected in six replications from each district. Raw samples are unprocessed, and roasted samples are roasted using firewood. Finished samples are those ready for human consumption as snack. Thousand seed weight for raw and roasted samples within a study district was similar (P > 0.05), but it was lower (P < 0.01) for finished samples compared to raw and roasted samples. The crude fibre content of finished lupin seed sample from Mecha was lower (P < 0.01) than that of raw and roasted samples. However, the different lupin samples from Sekela had similar crude fibre content (P > 0.05). The crude protein and crude fat contents of finished samples within a study district were higher (P < 0.01) than those of raw and roasted samples, respectively. Roasting had no effect on the crude protein content of lupin seed samples. The crude ash content of raw and roasted lupin samples within a study district was higher (P < 0.01) than that of finished lupin samples of the respective study districts. The content of quinolizidine alkaloids of finished lupin samples was lower than that of raw and roasted samples. There was also an interaction effect between location and lupin sample type. The traditional processing method of lupin seeds in Ethiopia has a positive contribution improving the crude protein and crude fat content, and lowering the alkaloid content of the finished product. The study showed the possibility of adopting the traditional processing method to process bitter white lupin for the use as protein supplement in livestock feed in Ethiopia, but further work has to be done on the processing method and animal evaluation.

The linalool dehydratase-isomerase from Castellaniella defragrans strain 65Phen catalyzes in the thermodynamically unfavourable direction the hydration of β-myrcene to linalool and further the isomerization to geraniol, the initial steps in anaerobic β-myrcene biodegradation. We have now investigated the stereochemistry of this reaction. (S)-(+)-Linalool is formed with an enantiomeric excess of at least 95.4%. (R)-(-)-Linalool was not detected. This indicates an introduction of the hydroxy group on the si-face of β-myrcene.

Salicylic acid (SA) is a naturally produced compound and has been implicated to play important roles in defense of plants against diverse biotic and abiotic stresses. To understand how SA functions in the tolerance of cucumber (Cucumis sativus) to chilling stress, endogenous SA levels in two different cultivars with opposite chilling responsiveness were quantified. Membrane integrity, including malondialdehyde (MDA) content and leakage of electrolyte, was also examined in SA-pretreated cucumber plants under chilling conditions. In addition, activities of the two antioxidant enzymes peroxidase (POD) and catalase (CAT) were quantified, and hydrogen peroxide (H2O2) production was investigated histochemically in SA-treated leaves under chilling temperature. Chilling stress resulted in greater induction of SA levels in the chilling-tolerant cultivar Changchun mici in both leaves and seeds compared to the chilling-sensitive one Beijing jietou, while the former one contained higher levels of SA than the latter one in the seeds under normal conditions. Pretreatment with SA diminished the increased electrolyte leakage and MDA content caused by chilling in the leaves of both cultivars, while much less MDA and electrolyte leakage were produced in Changchun mici compared to Beijing jietou. Moreover, exogenous application of SA increased significantly the POD and CAT activities and soluble protein content. Most importantly, exogenous SA treatment could eliminate the accumulation of H2O2 in leaves and cotyledons of both cultivars caused by chilling stress. The data clearly demonstrated that the chilling-tolerant cultivar displays a higher SA level than the chilling-sensitive one, and that exogenous SA can enhance the chilling tolerance ability, which might be achieved through modulating the antioxidant system in cucumber.

Hairy roots were induced by infecting stems and leaves of Glycyrrhiza inflata with Agrobacterium rhizogenes ATCC 15834. The optimization of growth and glycyrrhizin accumulation of G. infl ata hairy roots was studied. Sucrose (6%, w/v) was optimal for growth and glycyrrhizin accumulation in G. infl ata hairy roots. Effects of elicitors like chitosan, methyl jasmonate, and yeast extract on glycyrrhizin production were studied. Methyl jasmonate (100 μM) was most efficient in enhancing glycyrrhizin production up to almost 109 μg/g dry weight on day 5 of elicitation. These results indicate that application of elicitors can enhance the capacity of G. inflata hairy roots to produce glycyrrhizin.

A method was developed for rapid screening and isolation of eicosapentaenoic acid (EPA)-producing soil fungi through polymerase chain reaction (PCR) amplification. Genes coding for Δ6 fatty acid desaturase and Δ5 fatty acid desaturase were used as molecular markers for screening these EPA-producing fungi from soil. Three out of 65 soil fungi gave positive results through PCR amplification. Two out of these three strains were found to produce EPA when they had grown in 80 ml potato/dextrose liquid medium at (25 ± 1) °C for 144 h. The EPA yields were 215.81 mg l-1 and 263.80 mg l-1, respectively. The other positive strain was detected to produce arachidonic acid (AA). This study indicates that molecular detection of genes encoding Δ6 and Δ5 desaturases is an efficient method for primary screening of EPA- or its related polyunsaturated fatty acids (PuFAs)-producing fungi, which can improve the screening efficiency prominently

In spite of the importance of chemical signals (pheromones) in the reproductive behaviour of lizards, the chemical compounds secreted by their femoral glands, which may be used as sexual signals, are only known for a few lizard species. Based on mass spectra, obtained by GC-MS, we found 49 lipophilic compounds in femoral gland secretions of male tegu lizards (Tupinambis merianae) (fam. Teiidae), including a very high proportion of carboxylic acids and their esters ranging between n-C 8 and n-C 20 (mainly octadecanoic and 9,12-octadecadienoic acids), with much less proportions of steroids, tocopherol, aldehydes, and squalene. We discuss the potential function of these compounds in secretions, and compare the compounds found here with those documented for other lizard species.