Francisco Javier Toledo Marante

Structural characterization and metabolite profiling of the facultative marine fungus Paecilomyces variotii

A new Paecilomyces variotii strain was isolated from the marine habitat. The fungal biomass necessary for the chemical study was produced with success, at a laboratory scale. A total of 28 structural groups were identified from volatile compounds that, in the main, are normal lipid compounds involved in the fatty acid pathway, fragments from their catabolism, terpenoids, and a metabolite from the shikimic acid route. In addition, two non-volatile compounds, triolein and ergosterol peroxide, were isolated and identified by spectroscopy. This is the first report to describe these compounds for the species P. variotii, suggesting its potential use as a natural source to produce nutraceuticals and functional foods.

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.

Química de productos naturales aplicada a la acuicultura: una revisión interdisciplinar

This review sought to highlight the importance of natural products versus synthetic products, as bioactive molecules, towards the development of better management practices in aquaculture. The nature, structure, activity, and applications of these naturally-occurring high value-added compounds are described, as well as the methodology used for their study. Examples include the well-known rotenone, eugenol, forskolin, isatin, malyngamide, chlorodesmine, pachydictyol, fimbrolide, and other potentially active molecules in aquaculture.

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

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.

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.

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.

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.

Actividad antioxidante de los polifenoles de HYPOGYMNIA TAVARESII D. HAWKSW. & P. JAMES

Lichen substances have more than one phenolic hydroxyl group attached to one or more benzene rings, thus qualifying them as polyphenols. The secondary metabolites isolated from the lichen H. tavaresii have been studied in a bid to find compounds protective against oxidative stress and free radical-induced damage. The compounds were identified based on their MS and 1H-NMR spectra as well as retention factors of TLC analysis. In addition to the previously described metabolites (atranorin, chloroatranorin, physodic and physodalic acids) of H. tavaresii, a further three were identified in its thalli: 2´-O-methylphysodone, isophysodic and ursolic acids. The newly identified compounds of H. tavaresii thalli may be useful in the chemotaxonomic classification of this species. Antioxidant effectiveness of the acetone extracts fractions was measured. The compounds of the active fractions were purified and exhibited 180-800 fold less radical scavenging activity than the reference substance α-(+)-tocopherol in a DPPH• model expressed by IC50 values.

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.

CHEMICAL CONSTITUENTS DERIVED FROM THE CANARIES MARINE SPONGE Myxilla sp.

The authors would like to thank the Canary government (Agencia Canaria de Investigacion, Innovacion y Sociedad de la Informacion, ACIISI) for the PhD fellowship granted to Pere Ferriol, and the financial support given to the project SI-697 (ULPAPD-08/01-5).