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.

Extraction of nutraceuticals from Spirulina (blue-green alga): A bioorganic chemistry practice using thin-layer chromatography.

Spirulina is a blue-green alga (cyanobacteria) with high nutritive value. This work provides an innovative and original approach to the consideration of a bioorganic chemistry practice, using Spirulina for the separation of phytochemicals with nutraceutical characteristics via thin-layer chromatography (TLC) plates. The aim is to bring together current research, theory, and practice, and always in accordance with pedagogical ideas.

Chemical constituents of the fermentation broth of the marine-derived fungus Penicillium roqueforti / / Componentes químicos del caldo de fermentación del hongo de origen marino Penicillium roqueforti

Background. The filamentous fungus Penicillium roqueforti is a well-known multifunctional cell factory of high added-value biomolecules. Aims. The objective of this work was to carry out a detailed analysis of the metabolites present in the culture broth of a new marine-derived Penicillium roqueforti strain isolated in the Canary Islands, Spain. Methods. The fungal biomass production was carried out in liquid-state fermentation, and after 10-12 days of incubation at 22-25 °C, the supernatant mycelia was separated by filtration, and the culture broth (12 l) was stored in a refrigerator at 4 °C for a subsequent liquid–liquid extraction with dichloromethane (3×), in accordance with the modified Kupchan method. The volatile and semi-volatile organic compounds were separated by chromatography and analyzed using GC–MS and NMR spectroscopy analyses. Results. Several volatile organic compounds involved in the fatty acid pathway were identified: a terpenoid, a cyclic dipeptide, phthalates, and an alkyl adipate. In addition, three categories of non-volatile compounds (alkanes, fatty acids and 1-alkanols) were identified by spectroscopy. The results show that the fermented broth of this fungal strain has no mycotoxins under the culture conditions applied.Conclusions. It is hoped that this chemo-specific information will offer critical input for improving the biotechnological applications of this filamentous fungus (AU)

Antecedentes. El hongo filamentoso Penicillium roqueforti es una fábrica celular multifuncional de biomoléculas de alto valor añadido. Objetivos. El objetivo de este trabajo fue realizar un estudio minucioso de los metabolitos presentes en el caldo de cultivo de una nueva cepa de Penicillium roqueforti de origen marino aislada en las Islas Canarias, España. Métodos. La producción de biomasa fúngica se llevó a cabo por fermentación en estado líquido. Tras 10-12 días de incubación a 22-25 °C se separó el micelio sobrenadante por filtración y el caldo de cultivo (12 l) se almacenó en un frigorífico a 4 °C hasta su posterior extracción líquido-líquido con diclorometano (×3) de acuerdo con el método modificado de Kupchan. Los compuestos orgánicos volátiles y semi-volátiles se caracterizaron por GC-MS y análisis espectroscópico (NMR). Resultados. Se identificaron varios compuestos orgánicos volátiles implicados en la ruta de los ácidos grasos, un terpeno, un dipéptido cíclico, varios ftalatos y un adipato de alquilo. Además, fueron identificados por espectroscopía tres tipos de compuestos no volátiles: alcanos, ácido grasos y 1-alcanoles. Los resultados mostraron que el caldo fermentado de esta cepa fúngica no presenta micotoxinas en las condiciones de cultivo empleadas. Conclusiones. Es de esperar que esta información quimio-específica aporte datos críticos para el progreso de las aplicaciones biotecnológicas de este hongo filamentoso (AU)

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.

Chemical constituents of the fermentation broth of the marine-derived fungus Penicillium roqueforti.

BACKGROUND: The filamentous fungus Penicillium roqueforti is a well-known multifunctional cell factory of high added-value biomolecules. AIMS: The objective of this work was to carry out a detailed analysis of the metabolites present in the culture broth of a new marine-derived Penicillium roqueforti strain isolated in the Canary Islands, Spain. METHODS: The fungal biomass production was carried out in liquid-state fermentation, and after 10-12 days of incubation at 22-25°C, the supernatant mycelia was separated by filtration, and the culture broth (12l) was stored in a refrigerator at 4°C for a subsequent liquid-liquid extraction with dichloromethane (3×), in accordance with the modified Kupchan method. The volatile and semi-volatile organic compounds were separated by chromatography and analyzed using GC-MS and NMR spectroscopy analyses. RESULTS: Several volatile organic compounds involved in the fatty acid pathway were identified: a terpenoid, a cyclic dipeptide, phthalates, and an alkyl adipate. In addition, three categories of non-volatile compounds (alkanes, fatty acids and 1-alkanols) were identified by spectroscopy. The results show that the fermented broth of this fungal strain has no mycotoxins under the culture conditions applied. CONCLUSIONS: It is hoped that this chemo-specific information will offer critical input for improving the biotechnological applications of this filamentous fungus.

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.

Evidence of a new intermediate compound of the chitin biogenesis found in a marine-derived fungus.

The chemical screening of the biomass of a new marine-derived strain of Penicillium roqueforti, produced by liquid-state fermentation, led to the identification of several volatile and nonvolatile compounds. As a result of previous studies, we have isolated and characterized a new molecule. The chemical structure of 2-deoxy-2-phosphamino-α-D-glucopyranose isolated was elucidated on the basis of 1D and 2D NMR studies together with other instrumental techniques. As a result of this discovery, a biogenetic route has been proposed to explain its formation as an intermediary component of the chitin biosynthesis.

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.