Synthesis of a simplified triazole analogue of pateamine A.

Pateamine A is a naturally occurring metabolite extracted from the marine sponge Mycale hentscheli. It exhibits potent cytotoxicity towards cancer cell lines and has been shown to target protein translation initiation via inhibition of the function of eukaryotic initiation factor 4A proteins. We have synthesised a simplified analogue of pateamine A, consisting of the skeletal core of the natural product but with the thiazole heterocycle replaced by a triazole. The convergent design of the synthesis features a base-induced opening of a δ-valerolactone to access the Z,E-dienoate moiety, Julia-Kocienski olefination and copper-catalysed azide-alkyne cycloaddition. Bioactivity testing of the simplified pateamine A analogue (3) indicated a significant reduction in cytotoxicity, compared to natural pateamine A. We propose that this reduced activity is due mainly to the substitution of the thiazole for the triazole heterocycle. This supports the hypothesis that the thiazole of pateamine A is important for binding to its biological target.

Photoredox synthesis of 6- and 7-membered ring scaffolds via N-centered radicals.

N-Containing heterocycles are important scaffolds due to their ubiquitous presence in bioactive compounds. Their synthesis has been considered as an important research field. In this work we report the access to 6- and 7-membered rings via a photoinduced strategy. To our knowledge, this work represents the first exemple of photo-induced 7-endo-trig cyclization with N-centered radicals.

An Overview of Traditional Uses, Phytochemical Compositions and Biological Activities of Edible Fruits of European and Asian Cornus Species.

Cornus species are widely distributed in central and southern Europe, east Africa, southwest Asia, and America. Several species are known for edible fruits, especially Cornus mas and Cornus officinalis. These delicious fruits, characterized by their remarkable nutritional and biological values, are widely used in traditional medicine. In contrast to the other edible Cornus species, C. mas and C. officinalis are the most studied for which little information is available on the main phytochemicals and their biological activities. Fruits are characterised by several classes of secondary metabolites, such as flavonoids, phenolic acids, lignans, anthocyanins, tannins, triterpenoids, and iridoids. The available phytochemical data show that the different classes of metabolites have not been systematically studied. However, these edible species are all worthy of interest because similarities have been found. Thus, this review describes the traditional uses of Cornus species common in Europe and Asia, a detailed classification of the bioactive compounds that characterize the fruits, and their beneficial health effects. Cornus species are a rich source of phytochemicals with nutritional and functional properties that justify the growing interest in these berries, not only for applications in the food industry but also useful for their medicinal properties.

Thermal Stress in Melon Plants: Phytoprostanes and Phytofurans as Oxidative Stress Biomarkers and the Effect of Antioxidant Supplementation.

The extreme temperatures generated in the melon crop, early harvest, induce an increase in reactive oxygen species (ROS) plant levels leading to oxidative stress. Phytoprostanes (PhytoPs) and phytofurans (PhytoFs) are plant metabolites derived from α-linolenic acid oxidation induced by ROS. The aims of this work were to evaluate PhytoPs and PhytoFs as oxidative stress biomarkers in leaves of melon plants thermally stressed. In addition, to fortify melon plant antioxidant defenses, foliar spraying was assayed using salicylic and gallic acid solutions and Ilex paraguariensis extract. PhytoP and PhytoF concentration ranges were 109-1146 and 130-4400 ng/g, respectively. Their levels in stressed plants were significantly higher than in nonstressed samples. In stressed samples treated with I. paraguariensis, PhytoP and PhytoF levels were significantly lower than in stressed samples without antioxidants. PhytoPs and PhytoFs represent relevant oxidative stress biomarkers in melon leaves. The use of natural antioxidants could reduce plant oxidative stress.

The novelty of phytofurans, isofurans, dihomo-isofurans and neurofurans: Discovery, synthesis and potential application.

Polyunsaturated fatty acids (PUFA) are oxidized in vivo under oxidative stress through free radical pathway and release cyclic oxygenated metabolites, which are commonly classified as isoprostanes and isofurans. The discovery of isoprostanes goes back twenty-five years compared to fifteen years for isofurans, and great many are discovered. The biosynthesis, the nomenclature, the chemical synthesis of furanoids from α-linolenic acid (ALA, C18:3 n-3), arachidonic acid (AA, C20:4 n-6), adrenic acid (AdA, 22:4 n-6) and docosahexaenoic acid (DHA, 22:6 n-3) as well as their identification and implication in biological systems are highlighted in this review.