The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin

An efficient synthesis of the marine metabolite 3-bromoverongiaquinol (1) and the first total synthesis of 5-monobromocavernicolin (2), both isolated from the marine sponge Aplysina cavernicola, have been described based on the 1,2 addition of the lithium enolate of N,O-bistrimethylsilylacetamide (BSA, 4) to 1,4-benzoquinone (3). Bromination and purification of the crude product on silica gel chromatography provided 3-bromoverongiaquinol (1) in 50% overall yield. Under alkaline conditions, the crude product of the bromination reaction was converted to 5-monobromocavernicolin (2) in 20% yield which was also obtained in 13% yield (25% yield based on recovered starting material) from 3-bromoverongiaquinol (1).

Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa

Six bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy-O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N-trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents.

Biomolecules produced in liquid-state fermentation by a marine-derived fungus, Penicillium roqueforti

Screening of biomass of a new marine-derived strain of Penicillium roqueforti, as produced by liquid-state fermentation, led to the identification of several volatile organic compounds active in the fatty acid pathway as well as fragments produced by their catabolism, terpenoids, and metabolites from the shikimic acid pathway. In addition, five non-volatile organic compounds, triolein, ergosterol peroxide, 9(11)-dehydroergosterol peroxide, 4-hydroxybenzaldehyde, and d-mannitol, were isolated and identified by spectroscopy. The results showed that this fungal strain did not produce any mycotoxin in the culture conditions applied, and thus is useful for industrial applications, where high value-added biomolecules are generated.

Detection and characterization of fibropapilloma associated herpesvirus of marine turtles in Rio Grande do Sul, Brazil

Fibropapillomatosis (FP) is a benign tumoral disease that affects sea turtles, hampering movement, sight and feeding, ultimately leading to death. In Brazil, the disease was described for the first time in 1986. Research suggests the involvement of a herpesvirus in association with environmental and genetic factors as causal agents of FP. The objective of the present study was to detect and characterize this herpesvirus in sea turtles living in the coast of state Rio Grande do Sul (RS), Brazil. From October 2008 to July 2010, 14 turtles were observed between the beaches of Torres and Tavares, of which 11 were green turtles (Chelonia mydas) and 3 were loggerhead turtles (Caretta caretta). All turtles were young and mean curved carapace length was 37.71±7.82cm, and varied from 31 to 55cm. Only one green turtle presented a 1cm, papillary, pigmented fibropapilloma. Skin and fibropapilloma samples were analyzed by conventional and real time PCR assays to detect and quantify herpesvirus. All skin samples were negative, though the fibropapilloma specimen was positive in both tests. Viral load was 9,917.04 copies of viral genome per milligram of tissue. The DNA fragment amplified from the fibropapilloma sample was sequenced and allocated in the Atlantic phylogeographic group. This study reports the first molecular characterization of herpesvirus associated with fibropapilloma in turtles from the coast of RS.

Monostromatic green algae (Ulvales, Chlorophyta) of São Paulo and Paraná states (Brazil): distribution, growth, and reproduction

(Monostromatic green algae (Ulvales, Chlorophyta) of São Paulo and Paraná states (Brazil): distribution, growth, and reproduction). Culture studies were used for taxa identification and to understand aspects of the biology and physiology of monostromatic green blades growing in various sites along the coast of São Paulo state (23º30'-25ºl2'S, 45º10'-48ºW) and one site in Paraná state (25º35'S, 48º21'W), southeast and south Brazil, respectively. Possible variations of the growth rate, age of reproduction and life history were tested under different conditions of temperature, salinity and day length. Two species were found: Ulvaria oxysperma (Kützing) Bliding and Monostroma sp. The first one has been previously reported for many temperate and tropical estuaries around the world. Green monostromatic blades with the same life-history and ontogeny as Monostroma sp. have been reported so far only for the tropical coast of Brazil. Species are distinct in their ontogeny of the thallus (constant under different conditions) and limiting temperatures of survival. U. oxysperma grows and reproduces from 10 to 25ºC and dies when maintained at 30ºC; Monostroma sp. does not reproduce at 15ºC and survives at 30ºC. The different salinities and day lengths that were tested had no significant effect on either species.

Morphology and reproduction of Predaea feldmannii Børgesen (Nemastomataceae, Rhodophyta), an uncommon species from Brazil

The coast of Espirito Santo State is located in a biogeographic transition zone presenting high diversity. A renewed interest in this region occurred in the 1990s, resulting in various new records and new species descriptions added to the Brazilian marine flora. The study of the infralitoral of this region is just beginning, and a detailed exploration with use of Scuba diving is revealing a flora containing many little-known taxa, particularly of red algae. As a first result, Predaea feldmannii Børgesen is being described for the Brazilian coast. The occurrence of the genus Predaea in Brazil has been considered with restriction since representatives of this genus had been referred only once by Howe & Taylor in 1931, being first considered as Platoma. The occurrence of Predaea in Brazil is now confirmed, and its vegetative and reproductive structures are described in detail. Predaea feldmannii can be recognized by having gonimoblast initial formed on a bulge of the connecting filament, cortical filaments of nearly equal lengths, lack of gland cells, dense clusters of nutritive cells borne only on cells immediatelly contiguous to the auxiliary cell, and a three-celled carpogonial branch.

Sulfated bromophenols from Osmundaria obtusiloba (C. Agardh) R. E. Norris (Rhodophyta, Ceramiales)

Two new sulfated oligobromophenols from the marine red algae Osmundaria obtusiloba, 4-(1'-potassium sulfate, 2,3-dibromo, 1',4,5-trihydroxybenzyl) - 4''-(1'''-potassium sulfate, 2'',3''-dibromo, 1''',4'',5''-trihydroxybenzyl) sulfate and 1'-(2, 3-dibromo, 4-potassium sulfate, 1', 4, 5-trihydroxybenzyl) - 4''-(1''' potassium sulfate, 2'', 3''-dibromo, 1''', 4'', 5'' trihydroxybenzyl) sulfate, are herein reported. Besides them it was obtained 2, 2', 3, 3'-tetrabromo-4, 4', 5, 5'-tetrahydroxydiphenylmethane, 2, 3-dibromo-p-hydroxybenzyl methyl ether (methyl lanosol), dipotassium 2,3-dibromo-5-hydroxybenzyl 1',4-disulfate, 24-methylenecolest-5-en-3-beta-ol and alpha-D-mannopyranosyl-(1->2')-glycerate (digeneaside). The structures were determined by analysis of the spectroscopic data (IR, NMR and MS) and comparison with the literature. The 13CNMR data for dipotassium 2,3-dibromo-5hydroxybenzyl-1',4-disulfate are described here for the first time. The present study also suggests a mild method to isolate and to purify sulfated compounds.

First record of Reticulocaulis mucosissimus I. A. Abbott (Naccariaceae, Rhodophyta) for the western Atlantic Ocean

Espírito Santo State lies in the transition region (18°-21° S) between the tropical and subtropical marine-algal provinces and is considered the richest area of the Brazilian flora. The subtidal substratum presents extensive areas of rhodoliths associated with a diversified marine biota. A detailed exploration using Scuba diving technique has revealed many little-known and previously unreported taxa that are new to the Brazilian coast. Among the algae recently discovered, Reticulocaulis mucosissimus I. A. Abbott was found at a depth of 25 meters, thus consisting of the second member of the infrequently encountered family Naccariaceae growing in the same region. This work has revealed additional distribution records of this species not yet reported from the western Atlantic. Description of the morphological and reproductive features of the species as well as illustrations and comments are presented.

Corticolous green algae from tropical forest remnants in the northwest region of São Paulo State, Brazil

The algae inhabit a wide variety of terrestrial environments and substrates; however the taxonomic knowledge for tropical regions is still scarce. This survey was conducted in ten forest remnants in São Paulo State where visible growths of algae and bryophytes were collected and studied for the main algal components of the communities. Results reveal the occurrence of nine species of green algae, distributed through the class Trebouxiophyceae (one species), Charophyceae (one species) and Ulvophyceae (seven species). Desmococcus olivaceus (Persoon ex Archerson) J. R. Laundon and Printzina effusa (Krempelhüber) Thompson & Wujek are new records for Brazil. The most frequent organisms found in the areas pertain to Trentepohliales that is mainly represented by Trentepohlia species. On the basis of results found, it is recommended that such communities receive more attention in future investigations to improve the knowledge about this important group of primary producers.

Antinociceptive activity of sulfated carbohydrates from the red algae Bryothamnion seaforthii (Turner) Kütz. and B. triquetrum (S.G. Gmel.) M. Howe

We report the antinociceptive activity, determined by the writhing, formalin and hot-plate tests in mice, of crude (F0/60), lectin and carbohydrate fractions isolated by ammonium sulfate precipitation (0 to 60%) from Bryothamnion seaforthii and B. triquetrum, species of red algae. Not only fraction F0/60 but also lectins from both species significantly inhibited acetic acid-induced abdominal contractions after intraperitoneal or oral administrations. In the formalin test, lectins (1 and 5 mg/kg, ip, and 5 to 20 mg/kg, po) inhibited the 1st and 2nd phases (5 and 20 min, respectively), but the effect occurred predominantly on the 2nd phase. The effects of the lectins were totally or partially reversed by naloxone (2 mg/kg, sc) in the 1st and 2nd phases, respectively. Experiments performed with lectins in the absence and presence of avidin (1 mg/kg, ip) and D-mannose (1 mg/kg, ip) showed that avidin did not interfere with the effect of B. seaforthii lectin but partially reversed the effect of B. triquetrum lectin. D-Mannose completely reversed the effects of both species. F0/60 fractions from both algae significantly increased the latency time in response to thermal stimuli, and naloxone reversed antinociception, indicating the involvement of the opioid system in both the peripheral and central effects of the fractions. In the writhing test, the carbohydrate fractions were the most active, inhibiting the contractions by 71 and 79% (B. triquetrum) and by 46 and 69% (B. seaforthii) at doses of 1 and 5 mg/kg, ip, respectively. Sulfated carbohydrate fractions of B. seaforthii and B. triquetrum, containing only about 5% protein as contaminants, are probably responsible for the antinociceptive effects of these red algae.

Effects of filtration methods on the neutralization yield of crude marine fish oil

The evaluation of filtration methods on the yield and oleochemicals characteristics on the crude fish oil from the soapstock of marine fish for purposes of nutrition has been conducted in this work. The analytical properties of the crude and the neutralized oil with three excesses of sodium hydroxide (NaOH, 20%, 40% and 60%) were carried out on two different ways with organza and the “glass wool”. The neutralization of the oil brought about a notable improvement in the analytical properties of the oil. Thus, it leads to a high quality fish oil in terms of taste, colour, odours, shelf life and market value. Based on the improved characteristics of the oil, it could be suitable for applications in pharmaceutical and food industries.