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p-Sulfooxyphenylpyruvic acid from the red macro alga Ceratodictyon spongiosum and its sponge symbiont Haliclona cymaeformis.

Investigation of a Philippine specimen of the red alga Ceratodictyon spongiosum and its sponge symbiont Haliclona cymaeformis led to the isolation of p-sulfooxyphenylpyruvic acid, whose structure was elucidated using spectroscopic methods, with the Z-enol geometry determined through analysis of (3)J(C,H) coupling constants. The metabolite was tested for tyrosine kinase inhibition using a (3)H-thymidine incorporation assay, but was found inactive.

Animals↗

Expression of the vanadium-dependent bromoperoxidase gene from a marine macro-alga Corallina pilulifera in Saccharomyces cerevisiae and characterization of the recombinant enzyme.

The vanadium-dependent bromoperoxidase from the marine macro-alga Corallina pilulifera was heterologously expressed in Saccharomyces cerevisiae. The enzyme was purified and crystals in "tear drop" form were obtained. The catalytic properties of the recombinant enzyme were studied and compared with those of the native enzyme purified from C. pilulifera. Differences in thermal stability and chloroperoxidase activity were observed. The recombinant enzyme retained full activity after preincubation at 65 degrees C for 20 min, but the native enzyme was completely inactivated under the same conditions. The chlorinating activity of the native enzyme was more than ten times higher than that of the recombinant enzyme. Other properties, such as K(m) values for KBr and H(2)O(2), and optimal temperature and pH, were similar for each source of C. pilulifera bromoperoxidase.

Bromides↗

Regulation of phytochelatin synthesis by zinc and cadmium in marine green alga, Dunaliella tertiolecta.

Although Cd(2+) is a more effective inducer of phytochelatin (PC) synthesis than Zn(2+) in higher plants, we have observed greater induction of PC synthesis by Zn(2+) than Cd(2+) in the marine green alga, Dunaliella tertiolecta. To elucidate this unique regulation of PC synthesis by Zn(2+), we investigated the effects of Zn(2+) and Cd(2+) on the activities of both phytochelatin synthase (PC synthase) and enzymes in the GSH biosynthetic pathway. PC synthase was more strongly activated by Cd(2+) than by Zn(2+), but the difference was not very big. On the other hand, gamma-glutamylcysteine synthetase (gamma-ECS) and glutathione synthetase (GS) were activated by both heavy metals, but their activities were higher in Zn-treated cells than in Cd-treated cells. Dose-dependent stimulation of intracellular reactive oxygen species (ROS) production was observed with Zn(2+), but not Cd(2+) treatment. These results suggest that Zn(2+) strongly promotes the synthesis of GSH through indirect activation of gamma-ECS and GS by stimulating ROS generation. This acceleration of the flux rate for GSH synthesis might mainly contribute to high level PC synthesis.

Aminoacyltransferases↗

Antibacterial bromophenols from the marine red alga Rhodomela confervoides.

Two bromophenols, together with three known compounds, were isolated from the methanolic extract of the marine alga, Rhodomela confervoides. By means of MS and NMR spectroscopic analyses, they were identified as 3-bromo-4-[2,3-dibromo-4,5-dihydroxyphenyl] methyl-5-(hydroxymethyl) 1,2-benzenediol (1) and 3-bromo-4-[2,3-dibromo-4,5-dihydroxyphenyl] methyl-5- (ethoxymethyl) 1,2-benzenediol (2). Three known compounds were also isolated, namely 3-bromo-4-[2,3-dibromo-4,5-dihydroxyphenyl] methyl-5-(methoxymethyl) 1,2-benzenediol (3), 4,4'- methylenebis [5,6-dibromo-1,2-benzenediol] (4) and bis (2,3-dibromo-4,5-dihydroxybenzyl) ether (5). Compound 5 was the most active against five strains of bacteria with the MIC less than 70 microg/ml, while compounds 2, 3 and 4 exhibited moderate activity.

Anti-Bacterial Agents↗

Nahocols and isonahocols, endothelin antagonists from the brown alga, Sargassum autumnale.

Novel endothelin antagonists, nahocols A, A1, B, C, D1 and D2, and isonahocols D1 and D2, were isolated from the brown alga, Sargassum autumnale. Their structures were determined through detailed analysis of NMR spectra and chemical reactions. Nahocols have an aryl prenyl ether structure, which are speculated to be biogenetic precursors of the ubiquitous prenyl hydroquinones or prenyl benzoquinones in the plant and animal kingdoms.

Endothelin-1↗

A galactose-specific lectin from the red marine alga Ptilota filicina.

A lectin from the red marine alga Ptilota filicina (PFL) was isolated by affinity chromatography on cross-linked guar gum. PFL agglutinated native and papain-treated human erythrocytes with preference for type O erythrocytes. The lectin was inhibited by galactose and its derivatives. The most potent inhibitors were p-Nitrophenyl-N-acetyl-alpha- and beta-D-galactosaminide. Porcine stomach mucin, bovine submaxillary gland mucin and asialo bovine mucin were also inhibitory. The M(r) of PFL, determined by gel filtration, was 56,900. SDS-PAGE gave one band with a subunit M(r) of 19,320, indicating the native protein to be a trimer of apparently identical subunits. PFL was shown to be rich in acidic and hydroxyl amino acids but low in basic amino acids. The ten N-terminal amino acids were Asx-Thr-Lys-Thr-Leu-Leu-Ala-.

Amino Acid Sequence↗

Methoxybifurcarenone: an antifungal and antibacterial meroditerpenoid from the brown alga Cystoseira tamariscifolia.

A meroditerpenoid metabolite has been isolated from the brown alga Cystoseira tamariscifolia and characterized as methoxybifurcarenone, by spectral analysis. Methoxybifurcarenone possesses antifungal activity against three tomato pathogenic fungi: Botrytis cinerea, Fusarium oxysporum sp. mycopersici and Verticillium alboatrum and antibacterial activity against Agrobacterium tumefaciens and Escherichia coli.

Agrobacterium tumefaciens↗

Plocamium hamatum and its monoterpenes: chemical and biological investigations of the tropical marine red alga.

The polyhalogenated monoterpene content of six samples of the tropical marine red alga Plocamium hamatum, collected from the southern, central and northern regions of The Great Barrier Reef, Australia, was assessed. In all but two of the samples, the polyhalogenated monoterpene content was shown to differ markedly. In total, eleven previously reported compounds were isolated and characterised (1-11). Compound 2 was obtained for the first time as a pure natural product. For compound 4 a single crystal X-ray crystallographic analysis was undertaken which established its absolute configuration as (1S,2S,4R,5R,1'E)-2-bromo-1- bromomethyl-1,4-dichloro-5-(2'-chloroethenyl)-5-methylcyclohexa ne. Complete and unambiguous 1H and 13C NMR data are reported for 2 and 4. For 6-8, some prior 13C NMR assignments are revised. The biological activities of compounds 2-8 and 11 were assessed and indicated 4 to have potent antialgal activity towards Chlorella fusca in an agar diffusion bioassay, as well as being moderately antitubercular and cytotoxic. Compound 6 demonstrated moderate cytotoxicity.

Anti-Infective Agents↗

A fibrinolytic enzyme from a marine green alga, Codium latum.

A fibrinolytic enzyme was isolated from a marine green alga, Codium latum, and designated C. latum protease (CLP). It also had fibrinogenolytic activity, hydrolyzing A alpha, B beta and gamma chains with preference in this order. As CLP hydrolyzed oxidized insulin B chain at position Arg22-Gly23, and the peptide map of lysozyme digested with CLP was similar to that with trypsin, CLP would be expected to have a high substrate specificity, similar to that of trypsin. Protease activity peaked at pH 10, and was completely inhibited by diisopropyl fluorophosphate (DFP). Therefore, we conclude that CLP is a trypsin-like serine protease.

Animals↗

5-Lipoxygenase-derived oxylipins from the red alga Rhodymenia pertusa.

The lipid extract of the temperate red alga Rhodymenia pertusa has yielded four eicosanoid metabolites, three of which are new natural products. Using principally NMR and MS techniques, their structures were deduced as 5R,6S-dihydroxy-7(E),9(E),11(Z),14(Z)-eicosatetraenoic acid (5R,6S-diHETE), 5R*,6S*-dihydroxy-7(E),9(E),11(Z),14(Z),17(Z)-eicosapentaenoic acid (5R*,6S*-diHEPE), 5-hydroxy-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid (5-HETE), 5-hydroxy-6(E),8(Z),11(Z),14(Z),17(Z)-eicosapentaenoic acid (5-HEPE). The co-occurrence of these metabolites strongly suggests that R. pertusa contains a unique 5R-lipoxygenase system acting on both arachidonic and eicosapentaenoic acids.

Arachidonate 5-Lipoxygenase↗

Purification and characterisation of vanadium haloperoxidases from the brown alga Pelvetia canaliculata.

Two enzymes characterised as iodoperoxidases (PcI and PcII), with vanadium-dependent activity, have been purified from the brown alga Pelvetia canaliculata (L.) Decne et Thur. (Fucaceae, Phaeophyceae), collected in the Northern Portuguese coast, at Viana do Castelo. The relative molecular masses were 166 kDa for PcI and 416 kDa for PcII, as determined by gel filtration. SDS-PAGE shows that PcI has just one band corresponding to a subunit of 66 kDa, while PcII shows four bands (66, 72, 157 and 280 kDa). The following kinetic parameters have been determined from a steady-state analysis of the oxidation of iodide by H2O2: PcI, pHopt = 6.0, KM(I-) = 2.1 mM, KM(H2O2) = 110 microM, Ki(I-) = 127 mM; and PcII, pHopt = 6.5, KM(I-) = 2.4 mM, KM(H2O2) = 20 microM and Ki(I-) = 69 mM. These iodoperoxidases are thermostable, as also observed for vanadium bromo- and chloroperoxidases.

Catalytic Domain↗

Two new isomers of domoic acid from a red alga, Chondria armata.

Isodomoic acids G and H, two new isomers of the neurotoxin domoic acid, along with isodomoic acids A, B, E and F, were isolated from a red alga, Chondria armata, collected at the southern tip of Kyushu Island. The structures of two of these were deduced to be (E, E) and (Z, E) isomers of 2-carboxy-4-(5-carboxy-l-methyl-2-hexenylidene)-3-pyrro- lidineacetic acid, based on electrospray ionization mass and [1H]nuclear magnetic resonance spectral analyses including [1H-1H]correlation spectroscopy and nuclear Overhauser effect correlation spectroscopy.

Chromatography, High Pressure Liquid↗

Morphological observations of diarrhea in mice caused by aplysiatoxin, the causative agent of the red alga Gracilaria coronopifolia poisoning in Hawaii.

Diarrhea caused by the red alga Gracilaria coronopifolia poisoning was investigated in mice. The target site of a lethal dose was the whole small intestine where the toxin caused bleeding, resulting in hemorrhagic shock. With a sublethal dose, diarrhea appeared about 4.5 h after i.p. injection and continued for about 4 h intermittently. The site of diarrhea was the large intestine, where the submucosa first accumulated fluid from edema. Then the fluid moved into the lamina propria, the surface epithelial cells were broken and the fluid flowed into the lumen. Finally, diarrheic components apparently originating from capillaries were secreted directly into the lumen. The cecum was the main target of the diarrhea. After the diarrhea ended, the number of goblet cells was increased remarkably and many fine cracks were left on the surface of the epithelium.

Administration, Oral↗

Biosorption of chromium(VI) from aqueous solutions by green algae Spirogyra species.

Biosorption of heavy metals is an effective technology for the treatment of industrial wastewaters. Results are presented showing the sorption of Cr(VI) from solutions by biomass of filamentous algae Spirogyra species. Batch experiments were conducted to determine the adsorption properties of the biomass and it was observed that the adsorption capacity of the biomass strongly depends on equilibrium pH. Equilibrium isotherms were also obtained and maximum removal of Cr(VI) was around 14.7 x 10(3) mg metal, kg of dry weight biomass at a pH of 2.0 in 120 min with 5 mg/l of initial concentration. The results indicated that the biomass of Spirogyra species is suitable for the development of efficient biosorbent for the removal and recovery of Cr(VI) from wastewater.

Adsorption↗

Derivation and application of a new model for heavy metal biosorption by algae.

An equilibrium model for describing the relationships between important parameters for heavy metal sorption by algae was derived through a thermodynamics approach. In this model, both the removal efficiency of heavy metal and metal adsorption per unit algal biomass are considered to be simple functions of the ratio of algal biomass concentration to the initial metal concentration for selected conditions, i.e. as at constant pH and temperature. The model was found to fit the experimental results well (judged by the correlation-regression coefficient, R2), for the adsorption of cadmium, copper, lead and zinc by two algal species, Oocystis sp. (both living and non-living) and Chlorococcum sp. The applicability of the model was also supported by the reprocessed results of experimental data given in the literature, i.e. for the metal species, Cd, Pb, Cu and Ag, the algal species, Chlorella vulgaris, Scenedesmus quadricauda and Cladophora crispata, and both batch and continuous fixed-bed reactors. It was also demonstrated that the model could be applied over a broad range of pH for cadmium and copper adsorption by Oocystis sp. However, the model was not applicable at very low and high pH levels, due to negligible adsorption and precipitation, respectively.

Adsorption↗

Bioconcentration of the insecticide pyridaphenthion by the green algae Chlorella saccharophila.

A study was undertaken to examine the uptake of the organophosphate insecticide pyridaphenthion in the chlorophyta Chlorella saccharophila. Algae cultures were exposed to the initial nominal concentration 10.0 mg l(-1) pyridaphention during seven days. The insecticide bioconcentrates in the biomass to the highest level of 441.5 +/- 25.9 mg kg(-1) on the fifth day of exposure and was followed by a decrease to 76.6 +/- 5.1 mg kg(-1) on the seventh day. A model was constructed to describe the dynamic process, which estimated a bioconcentration factor (BCF) equal to 28. The study demonstrates the potential of accumulation of pyridaphenthion in aquatic organisms and helps to expand the pyridaphenthion toxicity database. The replacement of fenitrothion by pyridaphenthion concerning their use in rice flooded cultures is discussed.

Absorption↗

QSAR study on the toxicity of substituted benzenes to the algae (Scenedesmus obliquus).

50% effective inhibition concentration 48h-EC50 of 40 substituted benzenes to the algae (Scenedesmus obliquus) was determined. The energy of the lowest unoccupied molecular orbital (E(LUMO)) was calculated by the quantum chemical method MOPAC6.0-AM1. By using E(LUMO) and the hydrophobicity parameter log K(OW) the quantitative structure-activity relationship model (QSAR) was developed: log1/EC50=0.272 logK(OW) - 0.659E(LUMO) + 2.54, R2 = 0.793, S.E. = 0.316, F = 71.07, n = 40. A series of equations were obtained about the measured EC50 values of different subclasses of compounds. For those compounds containing double -NO2, their toxicity may be related chiefly to the intracellular reduction of -NO2 obtaining electron, while for anilines and phenols, K(OW) contributes most to the QSAR and E(LUMO) very little.

Benzene Derivatives↗

Microbiological reduction of chromium(VI) in presence of pyrolusite-coated sand by Shewanella alga Simidu ATCC 55627 in laboratory column experiments.

Hexavalent chromium (Cr(VI)) was reduced to non-toxic trivalent chromium (Cr(III)) by a dissimilatory metal reducing bacteria, Shewanella alga Simidu (BrY-MT) ATCC 55627. A series of dynamic column experiments were conducted to provide an understanding of Cr(VI) reduction by the facultative anaerobe BrY-MT in the presence of pyrolusite (beta-MnO(2)) coated sand and uncoated-quartz sand. All dynamic column experiments were conducted under growth conditions using Cr(VI) as the terminal electron acceptor and lactate as the electron donor and energy source. Reduction of Cr(VI) was rapid (within 8 h) in columns packed with uncoated quartz sand and BrY-MT, whereas Cr(VI) reduction by BrY-MT was delayed (57 h) in the presence of beta-MnO(2)-coated sand. The role of beta-MnO(2) in this study was to provide oxidation of trivalent chromium (Cr(III)). BrY-MT attachment was higher on beta-MnO(2)-coated sand than on uncoated quartz sand at 10, 60, and 85.5 h. Results have shown that this particular strain of Shewanella did not appreciably reduce Mn(IV) to Mn(II) species nor biosorbed Cr and Mn during its metabolic activities.

Adsorption↗