Cytotoxic Compounds Derived from Marine Sponges. A Review (2010-2012).

Abstract: This extensive review covers research published between 2010 and 2012 regarding new compounds derived from marine sponges, including 62 species from 60 genera belonging to 33 families and 13 orders of the Demospongia class (Porifera). The emphasis is on the cytotoxic activity that bioactive metabolites from sponges may have on cancer cell lines. At least 197 novel chemical structures from 337 compounds isolated have been found to support this work. Details on the source and taxonomy of the sponges, their geographical occurrence, and a range of chemical structures are presented. The compounds discovered from the reviewed marine sponges fall into mainly four chemical classes: terpenoids (41.9%), alkaloids (26.2%), macrolides (8.9%) and peptides (6.3%) which, along with polyketides, sterols, and others show a range of biological activities. The key sponge orders studied in the reviewed research were Dictyoceratida, Haplosclerida, Tetractinellida, Poecilosclerida, and Agelasida. Petrosia, Haliclona (Haplosclerida), Rhabdastrella (Tetractinellida), Coscinoderma and Hyppospongia (Dictyioceratida), were found to be the most promising genera because of their capacity for producing new bioactive compounds. Several of the new compounds and their synthetic analogues have shown in vitro cytotoxic and pro-apoptotic activities against various tumor/cancer cell lines, and some of them will undergo further in vivo evaluation.

Synthesis and Antileishmanial Activity of Natural Dehydrodieugenol and Its Mono- and Dimethyl Ethers.

The study of chemistry of naturally occurring compounds and the synthesis of their derivatives is fundamentally important for the development of new drugs. In this work, dehydrodieugenol (DHDE) was obtained through oxidative coupling of eugenol, promoted by an aqueous mixture of potassium ferricyanide (K3 [Fe(CN)6 ]) and NH3  · H2 O. The partial methoxylation of DHDE with MeI and K2 CO3 mainly resulted in the molecular-shaped monomethyl ether (DHDE-1MeO) and its dimethyl ether derivative (DHDE-2MeO). The products from the reactions were characterized by (1) H- and (13) C-NMR spectroscopy. Additionally, these studies have reported the antileishmanial activity of DHDE against Leishmania amazonensis (IC50 value of 42.20 µg ml(-1) ) and shown that partial methoxylation of DHDE results in a significant increase in its antiparasitic activity (IC50 value of 13.68 µg ml(-1) ). Based on in vitro bioassays, DHDE-1MeO has shown the highest leishmanicidal activity in promastigota form. Production by direct one-step synthesis of this monomethoxylated compound can be considered to be a cost-effective and environmentally friendly method with a short reaction time.

The Chemical Diversity of the Ascomycete Fungus Paecilomyces variotii.

Paecilomyces variotii isolated from a broad range of habitats drives the diversification of new high-value-added secondary metabolites that could potentially play an important role in human and animal health. These metabolites include the anhydride metabolite of the nonadride family, as well as the following compounds: naphthopyranone metabolites, sphingofungins, eicosenoic acids, new branched fatty acids, ascofuranone, polyketides, an anacardic acid analogue, straight-chain peptides, and volatile compounds. These natural products show that P. variotii can provide leading compounds for new drug discoveries, which may include herbicide agents, some of which are important in the agrochemical market. Finally, this review outlines recent developments, trends, and prospects for the chemistry of this ascomycete.

Marine sponge lectins: actual status on properties and biological activities.

Marine sponges are primitive metazoans that produce a wide variety of molecules that protect them against predators. In studies that search for bioactive molecules, these marine invertebrates stand out as promising sources of new biologically-active molecules, many of which are still unknown or little studied; thus being an unexplored biotechnological resource of high added value. Among these molecules, lectins are proteins that reversibly bind to carbohydrates without modifying them. In this review, various structural features and biological activities of lectins derived from marine sponges so far described in the scientific literature are discussed. From the results found in the literature, it could be concluded that lectins derived from marine sponges are structurally diverse proteins with great potential for application in the production of biopharmaceuticals, especially as antibacterial and antitumor agents.

Metabolite profiling of Schizochytrium sp. by GC-MS, an oleaginous microbial source of biodiesel.

The chemical screening carried out on Schizochytrium sp. biomass led the identification of 24 types of organic compounds belonging to n-alkanes, 1-alkenes, 1-alkanols, free fatty acids, methyl and ethyl esters of saturated and unsaturated fatty acids, saturated tri- and diglycerides, unsaturated monoglycerides, wax esters, sterols, triterpenes, and mono- and sesquiterpenes. Moreover, a sample containing fully saturated ethyl biodiesel was obtained experimentally with a yield of 28.72% w/w of the crude extract, and an average chain length of 15.52 carbons. This strain produced no toxins, but showed important nutrients, making it potentially applicable to the field of functional food, and biodiesel production.

Metabolite profiling of Schizochytrium sp. by GC-MS, an oleaginous microbial source of biodiesel

The chemical screening carried out on Schizochytrium sp. biomass led the identification of 24 types of organic compounds belonging to n-alkanes, 1-alkenes, 1-alkanols, free fatty acids, methyl and ethyl esters of saturated and unsaturated fatty acids, saturated tri- and diglycerides, unsaturated monoglycerides, wax esters, sterols, triterpenes, and mono- and sesquiterpenes. Moreover, a sample containing fully saturated ethyl biodiesel was obtained experimentally with a yield of 28.72% w/w of the crude extract, and an average chain length of 15.52 carbons. This strain produced no toxins, but showed important nutrients, making it potentially applicable to the field of functional food, and biodiesel production.

Metabolite profiling of Schizochytrium sp. by GC-MS, an oleaginous microbial source of biodiesel

The chemical screening carried out on Schizochytrium sp. biomass led the identification of 24 types of organic compounds belonging to n-alkanes, 1-alkenes, 1-alkanols, free fatty acids, methyl and ethyl esters of saturated and unsaturated fatty acids, saturated tri- and diglycerides, unsaturated monoglycerides, wax esters, sterols, triterpenes, and mono- and sesquiterpenes. Moreover, a sample containing fully saturated ethyl biodiesel was obtained experimentally with a yield of 28.72% w/w of the crude extract, and an average chain length of 15.52 carbons. This strain produced no toxins, but showed important nutrients, making it potentially applicable to the field of functional food, and biodiesel production.

ENSAIOS DE INDUÇÃO DE DESOVA DO LINGUADO (Paralichthys orbignyanus VALENCIENNES, 1839) / Induced spawning of the brazilian flounder (paralichthys orbignyanus valenciennes, 1839)

Paralichthys orbignyanus is one of the most valuable flatfish in the southern coast of Brazil, due to its large size and high quality of flesh. So far, biological studies about this species are very rare, and it is not employed for cultivation. This study, undertaken from August 23, 1993 to September 29, 1993, presents the first induced spawning to obtain eggs and larvae of that species in laboratory. Mature adults were caught near Lagoa da Conceição (Florianópolis - SC). Females weighed 1,780 to 3,100 g, and males, 980 to 1,360 g. A total of four couples were injected with Human Chorionic Gonadotropin (HCG): 500 to 1,150 IU/kg for females, and 300 to 400 IU/kg for males. One female did not respond to the treatment and the other ones spawned after a latency period of 46 to 69 hours. Eggs were obtained through artificial fertilization from two females. The total productions of ovulated eggs were 224,000 and 280,000/kg of female, and the larval productions, was 40,500 and 83,200/kg of female, respectively. The best fertilization and hatching rates were 90%. The incubation time varied from 42 to 53 hours. The mean diameter of egg had 790 um, and the unique oil droplet, 116 µm. The mean Total length of hatched larva was 2.0 mm. Experiments of larviculture were not successful, larvae were unable to feed and starved after nine days. The tested hormonal treatment was effective for the

Paralichthys orbignyanus é um dos linguados com maior interesse comercial no litoral sudeste-sul do Brasil, por seu tamanho e qualidade da carne. Até o momento foi pouco estudado, não sendo aproveitado em cultivo. Neste trabalho, desenvolvido entre 23/8/1993 e 29/9/1993, fizeram-se as primeiras induções de desova para obtenção de ovos e larvas desta espécie em laboratório. Indivíduos maduros foram capturados nas imediações da Lagoa da Conceição (Florianópolis - SC). As fêmeas tinham peso entre 1780 e 3100 g e os machos, entre 980 e 1360 g, formando quatro casais. Foram injetados com gonadotrofina coriônica humana (HCG), em doses únicas de 500 a 1150 UI/kg para fêmeas, e 300 a 400 UI/kg para machos. Uma fêmea não respondeu ao tratamento e as demais ovularam após um período de 46 a 69 horas, obtendo-se ovos, através de desova artificial, com duas fêmeas. A produção total de óvulos foi de 224.000 e 280.000/kg de fêmea, e a de larvas, de 40.500 e 83.200/kg de fêmea, respectivamente. As maiores taxas de fecundação e de eclosão foram de 90%. O tempo de incubação dos ovos foi de 42 a 53 horas. O diâmetro médio dos ovos embrionados foi de 790 µm e o da gota de óleo, única, de 116 µm. Ao eclodir, a larva tinha um comprimento médio de 2,0 mm. Nos cultivos, as larvas não conseguiram se alimentar e sobreviveram apenas nove dias. O tratamento hormonal proposto foi efetivo na indução do ling

INDUCED SPAWNING OF THE BRAZILIAN FLOUNDER (PARALICHTHYS ORBIGNYANUS VALENCIENNES, 1839) / ENSAIOS DE INDUÇÃO DE DESOVA DO LINGUADO (Paralichthys orbignyanus VALENCIENNES, 1839)

Paralichthys orbignyanus is one of the most valuable flatfish in the southern coast of Brazil, due to its large size and high quality of flesh. So far, biological studies about this species are very rare, and it is not employed for cultivation. This study, undertaken from August 23, 1993 to September 29, 1993, presents the first induced spawning to obtain eggs and larvae of that species in laboratory. Mature adults were caught near Lagoa da Conceição (Florianópolis - SC). Females weighed 1,780 to 3,100 g, and males, 980 to 1,360 g. A total of four couples were injected with Human Chorionic Gonadotropin (HCG): 500 to 1,150 IU/kg for females, and 300 to 400 IU/kg for males. One female did not respond to the treatment and the other ones spawned after a latency period of 46 to 69 hours. Eggs were obtained through artificial fertilization from two females. The total productions of ovulated eggs were 224,000 and 280,000/kg of female, and the larval productions, was 40,500 and 83,200/kg of female, respectively. The best fertilization and hatching rates were 90%. The incubation time varied from 42 to 53 hours. The mean diameter of egg had 790 um, and the unique oil droplet, 116 µm. The mean Total length of hatched larva was 2.0 mm. Experiments of larviculture were not successful, larvae were unable to feed and starved after nine days. The tested hormonal treatment was effective for the

Paralichthys orbignyanus é um dos linguados com maior interesse comercial no litoral sudeste-sul do Brasil, por seu tamanho e qualidade da carne. Até o momento foi pouco estudado, não sendo aproveitado em cultivo. Neste trabalho, desenvolvido entre 23/8/1993 e 29/9/1993, fizeram-se as primeiras induções de desova para obtenção de ovos e larvas desta espécie em laboratório. Indivíduos maduros foram capturados nas imediações da Lagoa da Conceição (Florianópolis - SC). As fêmeas tinham peso entre 1780 e 3100 g e os machos, entre 980 e 1360 g, formando quatro casais. Foram injetados com gonadotrofina coriônica humana (HCG), em doses únicas de 500 a 1150 UI/kg para fêmeas, e 300 a 400 UI/kg para machos. Uma fêmea não respondeu ao tratamento e as demais ovularam após um período de 46 a 69 horas, obtendo-se ovos, através de desova artificial, com duas fêmeas. A produção total de óvulos foi de 224.000 e 280.000/kg de fêmea, e a de larvas, de 40.500 e 83.200/kg de fêmea, respectivamente. As maiores taxas de fecundação e de eclosão foram de 90%. O tempo de incubação dos ovos foi de 42 a 53 horas. O diâmetro médio dos ovos embrionados foi de 790 µm e o da gota de óleo, única, de 116 µm. Ao eclodir, a larva tinha um comprimento médio de 2,0 mm. Nos cultivos, as larvas não conseguiram se alimentar e sobreviveram apenas nove dias. O tratamento hormonal proposto foi efetivo na indução do ling