Synthesis and in vitro biological evaluation of 3, 4-annelated coumarin-pyrimido-pyrimidine systems

3,4-Annelated coumarin-pyrimido-pyrimidine systems (7-imino-8-mercapto-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 2 and 8-hydroxy-7-imino-10-methyl-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 3) were synthesized by the action of 4-amino-2-mercapto-pyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine, respectively, on 4-chlorocoumarin-3-carbonitrile 1. The synthesized compounds were examined for in vitro antibacterial activity against 4 bacterial cultures: Staphylococcus aureus, Streptococcus pneumonia, Escherichia coli, and Aeromonas Salmonicida. The antibacterial activity of synthesized compounds 2 and 3 was compared to antibacterial activity of novobiocin as a standard drug.     

In vitro antioxidant and antibacterial activities of certain 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino}-indolin-2-one derivatives

A new series of 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}-indolin-2-one derivatives were screened for in vitro antioxidant and antimicrobial activities. The results of this study revealed that all synthesized compounds were significantly scavenged DPPH free radicals in a concentration-dependant manner. The IC₅₀ values of all test compounds were found to be between 18.34 and 50.54?µM. All compounds significantly inhibited growth of bacteria and most of the minimum inhibitory concentration values were between 20 and 100?mg?mL^?1 indicating potent to moderate antibacterial activity. In conclusion, 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino)-5 or 7-substituted indolin-2-ones derivatives exhibited moderate antioxidant and antimicrobial activities.     

In vitro microbiological evaluation of novel 2-oxo-2H-chromene-3-carbaldehyde containing 1,3,4-thiadiazole moiety

4-(5-(Methylthio)-1,3,4-thiadiazol-2-ylamino)-2-oxo-2H-chromene-3-carbaldehyde (3) and 4-(5-(ethylthio)-1,3,4-thiadiazol-2-ylamino)-2-oxo-2H-chromene-3-carbaldehyde (4) were prepared. The structures of the newly synthesized compounds were characterized by infrared (IR), nuclear magnetic resonance (NMR) spectral data and elemental analysis. The synthesized compounds were screened in vitro for their antibacterial activities. The synthesized compounds demonstrated moderate antimicrobial activity.     

Synthesis and evaluation of antioxidant activities of some indole-2,3-dione derivatives and analogs

In the present study, a series of novel Schiff bases of isatin were synthesized by condensation of imesatin with different aromatic aldehydes. The imesatins were synthesized by reaction of isatin with p-phenylenediamine. The chemical structures of the synthesized compounds were confirmed by means of IR, 1H-NMR, 13C-NMR, mass spectroscopy, and elemental analysis. These compounds were screened for antioxidant activity by DPPH, nitric oxide and hydrogen peroxide radical scavenging activity. In all the methods, the compound 3-(4-(3,4,5-trimethoxy benzylideneamino)phenylimino) indoline-2-one (5d) showed highest antioxidant activity because of the presence of electron donating groups and the compound 3-(4-(4-nitrobenzylideneamino)phenylimino) indoline-2-one (5f) showed the least activity because of the presence of an electron withdrawing group.     

Pathway and products of CO2-fixation by green prokaryotic algae in the cloacal cavity of Diplosoma virens

Light-dependent ¹⁴CO₂ fixation by the algae of Diplosoma virens (Hartmeyer) ranged between about 3 and 27 moles mg^-1 chlorophyll h^-1. The principal first products of ¹⁴C fixation were 3-phosphoglyceric acid and phosphorylated sugars, indicating that ribulose bisphosphate carboxylase was the primary carboxylation enzyme. The activity of this enzyme in crude extracts of the algae was 4 to 6 moles CO₂ mg^-1 chlorophyll h^-1. The principal end product of ¹⁴C fixation by these algae in the ascidian host was a water-soluble oligosaccharide which was an -1,4-glucan. A maximum of 7% of the ¹⁴C fixed was found in insoluble materials of the algae or its host after 60 min ¹⁴CO₂ fixation. Whether the -1,4-glucan is a product of algal or animal metabolism remains to be determined.     

Design,synthesis, antinociceptive,and anti-inflammatory properties of thiazolopyrimidine derivatives

Ten 2-(substituted benzylidene)-7-(4-chlorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one derivatives were synthesized and evaluated. A series of heterocyclic, 2-(substituted benzylidene)-7-(4-chlorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one were synthesized by reaction of 7-(4-chloro phenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one with appropriately substituted aldehydes in the presence of anhydrous sodium acetate and glacial acetic acid. The antinociceptive activity was evaluated by tail-flick technique, anti-inflammatory activity was evaluated by carrageenan-induced paw edema test and their ulcerogenicity index was determined. The para-substituted methyl, hydroxy, fluoro, chloro, bromo, and nitro derivatives showed significant antinociceptive and anti-inflammatory activities. The detailed synthesis, spectroscopic data, and pharmacological screening of the synthesized compounds were reported.     

Studies on the nutritional requirements of the larval stages of Penaeus japonicus using microencapsulated diets

Fatty acid biosynthesis in the larval stages of Penaeus japonicus Bate was examined by feeding microencapsulated diets containing (1-¹⁴C) palmitic acid, and fat-free diets supplemented with defined fatty acids. Highest larval growth rates were achieved on diets containing Tapes philippinarum lipid and, when defined fatty acids were substituted, on diets containing 20:63 fatty acid. The radioactive tracer experiments indicate that 16:17, 18:0 and 18:19 fatty acids may be synthesised from palmitic acid and that P. japonicus larvae may possess the ability to elongate 18:33 to 20:53 and 22:63, and 18:26 to 20:46. However, the rates of these reactions appear to be too slow to meet the larval requirements for essential fatty acids and the 3 series of polyunsaturated fatty acids must be provided in the diet.     

Chemotactic effects of nutrients on spores of the kelps Macrocytis pyrifera and Pterygophora california

Fertile Macrocystis pyrifera (L.) C. Ag. and Pterygophora californica Rupr. were collected in California, USA in 1987 to 1988. Spores of the kelps exhibited both positive and negative chemotaxis to a variety of chemical nutrients. Chemotaxis was measured by counting the number of spores that swam into flattened capillary tubes with the chemical relative to the number that swam into control tubes. Video-motion-analysis also showed that P. californica spores swam towards a nitrogen source more often than they swam away. Similar chemotactic effects were observed in both 2 and 8 h-old preparations. M. pyrifera spores swam towards nitrate, ammonium (1 to 90 M), glycine, aspartate iron (1 m), boron, cobalt, and manganese. Negative chemotaxis was elicited by ammonium (1 000 M) and iron (45 M). Neither phosphate nor zinc had significant effects. P. californica spores were attracted by nitrate, ammonium, phosphate, and boron. Negative chemotactic effects were recorded with iron (45 M) and manganese. Iron (1 M), cobalt, and zinc had no effect. It is suggested that chemotactic behavior is an adaptation which allows the kelp spores to find and settle in microhabitats suitable for gamatophytic growth and reproduction.     

Hydrobiological parameters during an annual cycle in the Arcachon Basin

Temperature, salinity, nutrients and phytoplankton biomass were monitored on a weekly to bimonthly frequency at six stations in the Bay of Arcachon from July 1984 to July 1985. This particular period appears to have differed from the last ten years in displaying higher amplitudes of both temperature and salinity (1.5° to 24.5°C and 20 to 34.5) at high tide. However, although in spring both temperature and salinity were normal (14°C, 28), an important phytoplankton spring bloom occurred, with maximum chlorophyll levels reaching 15 g l^-1 in April. Utilization of nutrients was high, particularly for nitrate and silicate, the concentrations of which decreased, respectively, from 10–15 to 0.1–2 M and 10–20 to 0.25–3 M from February to May. Exhaustion of nitrate was observed in May, except in areas subjected to river input. In contrast, silicate increased throughout the study area from May to July.     

Oxygen and carbon dioxide exchange in the polychaete Nereis virens: influence of ventilation activity and starvation

The influence of ventilation activity and starvation on O₂ uptake and CO₂ production in the polychaete Nereis virens Sars was investigated during September 1986 using worms collected on intertidal flats outside the Nærå Strand estuary, Denmark. The activity level, measured as ventilation rate, , was linearly related to active O₂ uptake, , for worms inhabiting artificial burrows (i.e. tubes) in the laboratory. at 16°C was two and four times the extrapolated standard O₂ uptake ( =0) when was 100 and 500 ml g^-1 h^-1, respectively. The use of tubes had no significant effect on N. viren's temporal ventilation pattern, D_v, compared to natural burrows in sediment. The ventilation rate, , however, was 2 to 3 times higher in tubes than in burrows. Starvation affected both ventilation and gas exchange. increased slightly during the first six days remaining constant thereafter. D_v, on the othe hand, decreased during the first six days followed by a gradual increase to Day 20. The observed decrease in D_v (%) from Day 0 to 1 was attributed to insufficient acclimation of the worms. The time integrated ventilation rate, × D_v, increased gradually throughout the 20 d starvation period. and declined rapidly during the first days of starvation. After 10 d the gas exchange reached steady levels at about 50% of the initial rate. The observed decrease in metabolic rate during starvation was explained by a rapid initial reduction in specific dynamic action (SDA) followed by a gradual exhaustion of readily available metabolic reserves, e.g. glycogen and lipids.     

Lack of social entrainment of free-running circadian activity rhythms in the Australian sugar glider (Petaurus breviceps: Marsupialia)

Summary Social influence on circadian activity rhythms was investigated in the nocturnal Australian marsupial Petaurus breviceps. The activity of two and two was recorded electroacoustically and observed by an IR television camera in LD 12:12 (10¹:10^-1lx) and in LL (10^-1lx) when housed isolated and in pairs (+). In LD-entrained animals the average duration of locomotion, orientation movements, grooming and total activity is influenced by social housing, and individually different activity patterns are harmonized. In constant illumination conditions, however, the members of a pair are not mutually synchronized and free-run with different circadian periodlengths. Therefore social influence on the LD-entrained activity rhythm in Petaurus should be interpreted as social masking rather than direct influence on the circadian system.     

The association of N2-fixing bacteria with sea urchins

Dinitrogen fixation associated with bacteria in the gastrointestinal tract of sea urchins appears to be a widespread phenomenon: sea urchins from the tropics (Diadema antillarum, Echinometra lacunter, Tripneustes ventricosus), the temperature zone (Strongylocentrotus droebachiensis) and the arctic (S. droebachiensis) exhibited nitrogenase activity (C₂H₂ reduction). Pronounced seasonal variation was found in nitrogenase activity of temperate sea urchins feeding on kelp (Laminaria spp.) and eelgrass (Zostera marina). The mean monthly nitrogenase activity was inversely correlated with the nitrogen content of the sea urchin's food, which varied up to fivefold over the course of a year. The highest rate of nitrogenase activity recorded for a temperate sea urchin during the 14 month sampling period was 11.6g N fixed g wet wt^-1 d^-1, with a yearly mean activity of 1.36 g N fixed g wet wt^-1 d^-1. Studies with ¹⁵N confirmed the C₂H₂ reduction results and showed incorporation of microbially-fixed nitrogen into S. droebachiensis demonstrating that N₂ fixation can be a source of N for the sea urchin. Laboratory experiments indicated that part of the sea urchin's (S. droebachiensis) normal gastrointestinal microflora is responsible for the observed nitrogenase activity.     

Antimicrobial activities of marine sponges from French Polynesia and Brittany

Extracts from marine sponges collected in French Polynesia and along the Brittany coast (France) have been tested for antibacterial and antifungal activity. The bioactity is concentrated in Dendrilla sp., Homaxinella trachys, Hyrtios eubamma, Verongia aerophoba and Phakellia ventilabrum. The compound responsible for the activity of H. eubamma has been identified as puupehenone, while that of P. ventilabrum is due to a new sesquiteprenoid isonitrile.This study forms part of the Thèse 3e cycle of Ph. Amade, Université de Bretagne Occidentale     

Temperature and metabolic rate in sedentary fish from the Antarctic,North Sea and Indo-West Pacific Ocean

Resting metabolic rate was measured in demersal stages of the teleostNotothenia neglecta Nybelin from the South Orkney Islands, Antarctica, from 1985 to 1987. The relationship between and body mass (Mb) conformed to the general relationship , wherea is a proportionality constant andb is the scaling exponent. (mg O₂ h^–1) was found to scale toMb ^{(0.82±0.011)} in the summer (November to April, 1.6 to 1 850 g,n=56) and toMb ^{(0.76±0.013)} in the winter (May to October, 0.9 to 1 850 g,n=57) (values ofb are means ± SD). Although the scaling exponents were significantly different (P<0.01), was similar in the juvenile stages of summer- and winter-caught fish matched for body mass. The effects of activity on oxygen consumption was studied using a Brett respirometer. Adult stages had a factorial aerobic scope for activity of 5.7, which is similar to that reported for demersal fish from temperate latitudes. The effects of temperature on resting metabolism was investigated in fish with similar sedentary lifestyles from the North Sea (Agonus cataphractus andMyoxocephalus scorpius) and the Indo-West Pacific (Paracirrhites forsteri, P. arcatus, Neocirrhites armatus andExallias brevis). Extrapolated values of for the tropical species approached zero at 5 to 10°C. For a standard 50 g fish, for the tropical species at 25°C was in the range 3.4 to 4.4 mg O₂ h^–1, compared with 1.3 mg O₂ h^–1 forNotothenia neglecta at its acclimation temperature. Thus, the maximum metabolic rate of sedentary tropical species at 24°C is likely to be 2 to 4 times higher than inN. neglecta at 0°C. This suggests that the energy available for sustained activity is significantly lower in cold- than in warm-water fish.     

Chemical defense: incorporation of diet-derived pyrrolizidine alkaloid into the integumental scales of a moth (<Emphasis Type="Italic">Utetheisa ornatrix</Emphasis>)

Summary. Evidence is presented that pyrrolizidine alkaloid acquired by Utetheisa ornatrix (Lepidoptera, Arctiidae) as a larva from Crotalaria foodplants is incorporated in part into the scales of the adult. A single forewing of a male or female moth may contain in the order of 6 to 13 g monocrotaline in its scale cover or about 1 to 2% of the moths systemic monocrotaline content. Based on estimates of the number of scales per forewing, the monocrotaline content of individual scales is calculated to be in the order of 0.1 and 0.2 ng monocrotaline per male and female scale, respectively. This amounts to concentrations of about 1 and 3%, values roughly at a par with the average systemic concentration (0.5-0.6%) previously determined for monocrotaline in Utetheisa. It is argued that the presence of pyrrolizidine alkaloid in the moths scale coating could account for the promptness with which adult Utetheisa are rejected by spiders. It is suggested further that chemical impregnation of scales with substances deterrent to predators may be more widespread among insects than generally assumed.     

Temperature effects on behavior and survival of marine invertebrates exposed to variations in hydrostatic pressure

Investigation into the pressure resistance of 8 intertidal species belonging to the genera, Uca, Sesurma, Talorchestia and Littorina from the Northern Gulf of Mexico and Panama sheds light on the relationships between temperature and hydrostatic-pressure resistance. Generally, increasing temperature increases the pressure required to elicit reversible reactions such as increased activity and tetany, or paralysis, wheroas increasing temperature generally evokes the irreversible response of death (LD₅₀) at a decreasing pressure. Tropical stenotherms tend to be more sensitive to hydrostatic pressure than eurythermal-temperate species at the same or similar temperatures.     

Performance of IUCN proxies for generation length

One of the criteria used by the International Union for Conservation of Nature (IUCN) to assess threat status is the rate of decline in abundance over 3 generations or 10 years, whichever is longer. The traditional method for calculating generation length (T) uses age‐specific survival and fecundity, but these data are rarely available. Consequently, proxies that require less information are often used, which introduces potential biases. The IUCN recommends 2 proxies based on adult mortality rate, = α + 1/d, and reproductive life span, = α + z^*RL, where α is age at first reproduction, d is adult mortality rate, RL is reproductive life span, and z is a coefficient derived from data for comparable species. We used published life tables for 78 animal and plant populations to evaluate precision and bias of these proxies by comparing and with true generation length. Mean error rates in estimating T were 31% for and 20% for , but error rates for were 16% when we subtracted 1 year ( ), as suggested by theory; also provided largely unbiased estimates regardless of the true generation length. Performance of depends on compilation of detailed data for comparable species, but our results suggest taxonomy is not a reliable indicator of comparability. All 3 proxies depend heavily on a reliable estimate of age at first reproduction, as we illustrated with 2 test species. The relatively large mean errors for all proxies emphasized the importance of collecting the detailed life‐history information necessary to calculate true generation length. Unfortunately, publication of such data is less common than it was decades ago. We identified generic patterns of age‐specific change in vital rates that can be used to predict expected patterns of bias from applying .     

Aggregation pheromone ofCarpophilus freemani (Coleoptera: Nitidulidae): A blend of conjugated triene and tetraene hydrocarbons

Summary Males ofCarpophilus freemani Dobson (Coleoptera: Nitidulidae) produce an aggregation pheromone to which both sexes fly in a wind-tunnel bioassay. The major pheromone component (ca. 30 ng per male per day in volatile collections) was identified as (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene. A minor component, (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-undecatetraene, was 3–10% as abundant as the major triene and was 5–20% as active when compared at relative doses ranging from natural proportions to 1:1. These compounds act synergistically: a mixture of major and minor components in natural proportions attracted more than twice as many beetles as the major component alone, and the mixture fully accounted for the activity of male-derived volatile collections. Six other male-derived conjugated hydrocarbons, ranging from 2% down to 0.04% as abundant as the major component, were also identified. These are (in order of decreasing bioassay activity when compared on an equal-weight basis): (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene, (2E,4E,6E)-5-ethyl-3-me-thyl-2,4,6-octatriene, (3E,5E,7E,9E)-8-ethyl-4,6-dimethyl-3, 5,7,9-dodecatetraene, (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6, 8-undecatetraene, (3E,5E,7E)-5-ethyl-7-methyl-3,5,7-undecatriene, and (2E,4E,6E)-3,5-dimethyl-2,4,6-nonatriene. All structure identifications were confirmed by synthesis. In the wind tunnel, the pheromone acted synergistically with host-type volatiles such as propyl acetate, valeric acid, and ethanol. This concept was verified by fields tests in California, in which there was dramatic synergism between the pheromone and fermenting host materials. Pheromone biosynthesis is discussed.     

The ecotoxicology of titanium dioxide nanoparticles,an important engineering nanomaterial

Abstract

Titanium dioxide nanoparticles (nano-TiO₂) are useful because of their unique physicochemical properties. The wide application of nano-TiO₂ has raised concerns regarding its potential threat to organisms and the environment. Therefore, the production and application of nano-TiO₂ in the global market is summarized in this paper. This review presents the adverse effects of nano-TiO₂ in vivo, including potential exposure routes such as transdermal, oral and inhalative exposure, risk evaluation of nanotoxicity in vitro using bacteria, microorganisms, cells and biological molecules), physicochemical characterization of nano-TiO₂ regarding crystal structure, size, shape, surface characteristics and coatings, and the mechanisms of toxicity of nano-TiO₂ based on environmentally relevant test species and cells. This review aims to fill deficiencies in toxicological research and to facilitate the assessment of the environmental risks by nano-TiO₂ which is conducive to designing safer nanoproducts in our daily life.

• Highlights

• Presented the possible human health hazards related to nano-TiO2 exposure.

• Identified the current research deficiencies in this area.

• Summarized the underlying toxicity mechanisms.

• Summarized the compound toxicity of NPs.

     

Carotenoids in the tiger prawn Penaeus esculentus during ovarian maturation

Female Penaeus esculentus Haswell were collected by 15 to 20 min duration trawls during 1990. Carotenoids were analysed in the digestive gland, abdominal muscle, the remainder of the body (hereafter called integument) and ovary of prawns in Stage 2 through Stage 4 (fully mature) of maturation. The only oxycarotenoids (xanthophylls) identified were astaxanthins or astaxanthin esters; occasionally low levels of -carotene were detected in the digestive gland. The concentrations of astaxanthin monoesters (AM) and diesters (AD) were highest, with only minor amounts of free astaxanthins (Ast), except in the maturing ovaries, where free astaxanthins predominated (up to 80% of the total carotenoid). Of the total carotenoid, 82 to 94% was in the integument, but at maturity the digestive gland contained 10.7±3.4% and the ovary 5.6±0.9% of the total carotenoid. Only the ovary increased in mass during maturation, reaching up to 5.2% of total prawn mass. During this period, digestive gland concentrations of AM, AD and Ast all increased (tota 20 to 120 g g^-1); levels in the muscle and integument varied little throughout maturation (total 0.4 and 100 g g^-1, respectively); ovary AM levels remained low throughout (1.5 to 1.2 g g^-1), AD increased from only 2 to 5 g g^-1, but Ast increased from 2 to 34 g g^-1. Apart from the ovary, AM concentrations were the most variable. In common with other decapod Crustacea, the maturing ovary of P. esculentus contained high levels of carotenoids, indicating that these may have an important role in early development. The natural diet of P. esculentus includes a variety of carotenoids, but except for a little -carotene, the digestive gland, where absorption occurs, contained astaxanthins, with only an occasional trace of -carotene. This suggests that the conversion of dietary carotenoids to astaxanthin occurs soon after ingestion.