Marine Bioactives and Potential Application in Sports

An enriched diet with antioxidants, such as vitamin E, vitamin C, β-carotene and phenolic compounds, has always been suggested to improve oxidative stress, preventing related diseases. In this respect, marine natural product (MNP), such as COX inhibitors, marine steroids, molecules interfering with factors involved in the modulation of gene expression (such as NF-κB), macrolides, many antioxidant agents, thermogenic substances and even substances that could help the immune system and that result in the protection of cartilage, have been recently gaining attention. The marine world represents a reserve of bioactive ingredients, with considerable potential as functional food. Substances, such as chitin, chitosan, n-3 oils, carotenoids, vitamins, minerals and bioactive peptides, can provide several health benefits, such as the reduction of cardiovascular diseases, anti-inflammatory and anticarcinogenic activities. In addition, new marine bioactive substances with potential anti-inflammatory, antioxidant and thermogenic capacity may provide health benefits and performance improvement, especially in those who practice physical activity, because of their increased free radical and Reacting Oxygen Species (ROS) production during exercise, and, particularly, in athletes. The aim of this review is to examine the potential pharmacological properties and application of many marine bioactive substances in sports.     

Protective effect of the phenolic fraction from virgin olive oils against oxidative stress in human cells

This paper reports the protective effect of the phenolic fraction extracted from extra virgin olive oils (OOPEs) against the cytotoxic effects of reactive oxygen species in human erythrocytes and Caco-2 cells, employed as model systems. Pretreatment of cells with various OOPEs, indeed, provides a remarkable protection against oxidative damages: this effect was strictly dependent on the o-diphenolic content of the extracts. Moreover, the protective effects observable in cellular systems were compared with in vitro antioxidant properties, measured by using the FRAP (ferric reducing/antioxidant power) assay; the reducing ability of OOPEs strictly parallels their o-phenolic content. The linear relationship demonstrated between biological effects and antioxidant capacity measured by the FRAP assay allows us to propose the use of this rapid colorimetric method in assessing and certifying the antioxidant power of extra virgin olive oil.     

Marine Antimalarials

Malaria is an infectious disease causing at least 1 million deaths per year, and, unfortunately, the chemical entities available to treat malaria are still too limited. In this review we highlight the contribution of marine chemistry in the field of antimalarial research by reporting the most important results obtained until the beginning of 2009, with particular emphasis on recent discoveries. About 60 secondary metabolites produced by marine organisms have been grouped into three structural types and discussed in terms of their reported antimalarial activities. The major groups of metabolites include isonitrile derivatives, alkaloids and endoperoxide derivatives. The following discussion evidences that antimalarial marine molecules can efficiently integrate the panel of lead compounds isolated from terrestrial sources with new chemical backbones and, sometimes, with unique functional groups.     

Fluorescence properties of humic acid interaction products with s-triazine and bipyridilium herbicides and their Cu complexes: a multivariate approach

Purpose

Excitation–emission matrices spectroscopy (EEMS) of soil humic acids (HAs) contains large amount of information on their properties, as well as on the dynamics related to their intra- and inter-molecular interactions. The objective of this research was (i) to show that EEMS represents a useful tool to investigate the molecular and mechanistic aspects of HA adsorbing capacity towards atrazine (A) and paraquat (P) with or without Cu²⁺ ions and (ii) to evaluate if additional information on these mechanisms can be obtained by combining EEMS with principal component analysis (PCA).

Materials and methods

HAs have been isolated from soil samples collected in a citrus field at three locations, within the plant rows (HAa); between the rows (HAb) and in a adjacent, control soil (HAc). Interaction products were obtained between each HA and A and P, with or without Cu ions. Elemental analysis and Fourier-transorm Infrared Spectroscopy were applied to support fluorescence data. Fluorescence spectra were recorded on aqueous solutions, and fluorescence intensity (FI) values were normalized using a quinine sulphate standard. PCA analysis was performed using the software STATGRAPHICS Centurion XV.I.

Results and discussion

The EEM spectra of the three unreacted HAs are characterized by the presence of two fluorophores α and β, in the region of longer wavelengths pairs (EEWP). The EEM spectra of the HA-A interaction products are featured by the same two fluorophores, with FI values decreased of about 50%, whereas those of the HA-P interaction products show a unique peak, γ, at intermediate EEWP. Finally, the EEM spectra of HA-A-Cu²⁺ show, with respect to HA-A samples, a blue shift of the α peak with an additional decrease of FI values (about 60%) and the disappearance of the peaks β, whereas those of HA-P-Cu²⁺ feature, in comparison with those of HA-P, a small red-shift of the peak γ. PCA data suggest that Cu ions do not affect the interaction mechanism between HA and P, whereas it appears to exercise a strong influence on interaction between HA and A.

Conclusions

The results obtained indicate that EEMS allows direct measurements of the adsorbing capacity of HA towards atrazine and paraquat. Additional information obtained by PCA analysis show that Cu ions behave like a good antagonist in preventing the formation of ionic bonds between HA and atrazine, whereas Cu is not able to affect the prevalent mechanism of HA interaction with paraquat, which is a charge-transfer bond.

     

Bromopyrrole Alkaloids as Lead Compounds against Protozoan Parasites

In the present study, 13 bromopyrrole alkaloids, including the oroidin analogs hymenidin (2), dispacamide B (3) and dispacamide D (4), stevensine (5) and spongiacidin B (6), their derivatives lacking the imidazole ring bromoaldisin (7), longamide B (8) and longamide A (9), the dimeric oroidin derivatives sceptrin (10) and dibromopalau’amine (11), and the non-oroidin bromopyrrolohomoarginin (12), manzacidin A (13), and agelongine (14), obtained from marine sponges belonging to Axinella and Agelas genera have been screened in vitro against four parasitic protozoa, i.e., two Trypanosoma species (T. brucei rhodesiense and T. cruzi), Leishmania donovani and Plasmodium falciparum (K1 strain, a chloroquine resistant strain), responsible of human diseases with high morbidity and, in the case of malaria, high mortality. Our results indicate longamide B (8) and dibromopalau’amine (11) to be promising trypanocidal and antileishmanial agents, while dispacamide B (3) and spongiacidin B (6) emerge as antimalarial lead compounds. In addition, evaluation of the activity of the test alkaloids (2–14) against three different enzymes (PfFabI, PfFabG, PfFabZ) involved in the de novo fatty acid biosynthesis pathway of P. falciparum (PfFAS-II) identified bromopyrrolohomoarginin (12) as a potent inhibitor of PfFabZ. The structural similarity within the series of tested molecules allowed us to draw some preliminary structure-activity relationships. Tests against the mammalian L6 cells revealed important clues on therapeutic index of the metabolites. This is the first detailed study on the antiprotozoal potential of marine bromopyrrole alkaloids.     

Properties of humic acids in Mediterranean forest soils (Southern Italy): influence of different plant covering

The chemical and spectroscopic properties of humic acids (HAs) isolated from four litters and their corresponding underlying soils at three depths in a protected forest area in Southern Italy were investigated as a function of four different plant coverings: Quercus ilex L., mixed Carpinus betulus L. and C. orientalis Mill., Pinus halepensis L., and mixed Quercus trojana Webb. and Q. ilex L.. The forested site is a part of a calcareous plateau, characterized by homogeneous soils classified as Eutric Cambisols associated with Calcic Luvisols. The changes in the composition of HAs with soil depth have been evaluated on the basis of chemical (elemental and COOH groups) and spectroscopic analyses (E₄/E₆ ratio and FT IR spectra), and lignin-derived CuO oxidation products. A different distribution of the main elements was found in the various HAs which is apparently related to the type of humic acid-precursor biomolecules in the parent litters. The HAs isolated from soils under Q. ilex and mixed Carpinus species showed a slight increase in the C/H ratio and COOH content downward the soil profile, suggesting increasing aromatic polycondensation and humification degree with depth. On the contrary, no trend was observed for HAs from soils under Pinus halepensis L. and mixed Quercus species, indicating a partial incorporation of residues deriving from litter degradation into these HAs. Further, the content of lignin-derived phenols was higher in Pinus halepensis L. and mixed Quercus species layers, with the same trend measured for the corresponding HAs, thus confirming a lignin contribution related to the lignin type of plant covering.     

Aurantoside J: a new tetramic acid glycoside from Theonella swinhoei. Insights into the antifungal potential of aurantosides

The chemical investigation of an Indonesian specimen of Theonella swinhoei afforded four aurantosides, one of which, aurantoside J (5), is a new compound. The structure of this metabolite, exhibiting the unprecedented N-α-glycosidic linkage between the pentose and the tetramate units, has been determined through detailed spectroscopic analysis. The four obtained aurantosides have been tested against five fungal strains (four Candida and one Fusarium) responsible of invasive infections in immuno-compromised patients. The non-cytotoxic aurantoside I (4) was the single compound to show an excellent potency against all the tested strains, thus providing valuable insights about the antifungal potential of this class of compounds and the structure-activity relationships.     

Diterpenoid (poly)esters and a ring A-seco-phorboid from the aerial parts of Euphorbia macroclada Boiss

Euphorbia macroclada Boiss., a spurge endemic to the Iranian plateau, afforded four pre-myrsinane polyesters, three α-phorboids and one A-seco-phorboid, a type of compound so far unreported within natural products. All new compounds were structurally elucidated by spectroscopic methods, and especially 2D NMR measurements.     

Marine Carotenoids against Oxidative Stress: Effects on Human Health

Carotenoids are lipid-soluble pigments that are produced in some plants, algae, fungi, and bacterial species, which accounts for their orange and yellow hues. Carotenoids are powerful antioxidants thanks to their ability to quench singlet oxygen, to be oxidized, to be isomerized, and to scavenge free radicals, which plays a crucial role in the etiology of several diseases. Unusual marine environments are associated with a great chemical diversity, resulting in novel bioactive molecules. Thus, marine organisms may represent an important source of novel biologically active substances for the development of therapeutics. In this respect, various novel marine carotenoids have recently been isolated from marine organisms and displayed several utilizations as nutraceuticals and pharmaceuticals. Marine carotenoids (astaxanthin, fucoxanthin, β-carotene, lutein but also the rare siphonaxanthin, sioxanthin, and myxol) have recently shown antioxidant properties in reducing oxidative stress markers. This review aims to describe the role of marine carotenoids against oxidative stress and their potential applications in preventing and treating inflammatory diseases.