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The wild mushroom Leucopaxillus candidus (Bres.) Singer was studied for the first time to obtain information about its chemical composition, nutritional value and bioactivity. Free sugars, fatty acids, tocopherols, organic and phenolic acids were analysed by chromatographic techniques coupled to different detectors. L. candidus methanolic extract was tested regarding antioxidant potential (reducing power, radical scavenging activity and lipid peroxidation inhibition). L. candidus was shown to be an interesting species in terms of nutritional value, with high content in proteins and carbohydrates, but low fat levels, with the prevalence of polyunsaturated fatty acids. Mannitol was the most abundant free sugar and β-tocopherol was the main tocopherol isoform. Other compounds detected were oxalic and fumaric acids, p-hydroxybenzoic and cinnamic acids. The methanolic extract revealed antioxidant activity and did not show hepatoxicity in porcine liver primary cells. The present study provides new information about L. candidus.

This study addresses issues regarding chemical and bioactive properties of nine wild edible mushrooms from native Nothofagus forest from Patagonia, Argentina. Macronutrients, sugars, fatty acids, tocopherols, organic acids, phenolic compounds and antioxidant properties were determined. Protein was found in high levels and varied between 3.35 g/100 g dw in Cyttaria hariotii and 22.29 g/100 g dw in Lepista nuda. All of them presented mannitol and trehalose as main sugars. Mannitol was significantly higher in Ramaria patagonica, although absent in Fistulina endoxantha, whereas trehalose predominated in Aleurodiscus vitellinus, Hydropus dusenii, Cortinarius magellanicus, C. hariotii, Grifola gargal and L. nuda, ranging from 1.15 to 10.26 g/100 g dw; it was absent in R. patagonica. The major fatty acid found was linoleic acid, followed by oleic acid and palmitic acid. All species presented oxalic and fumaric acids, while some also had malic, quinic and citric acids. Tocopherols composition was variable. Cortinarius magellanicus presented significantly higher contents of both α-tocopherol and β-tocopherol. R. patagonica presented the best results in all the antioxidant activity assays (EC50 values ≤ 1 mg/mL) and the highest content of phenolic compounds presenting gallic, p-hydroxybenzoic, p-coumaric and cinnamic acids. This study constitutes the first report on chemical composition and nutritional value of most of these edible mushroom species. Furthermore, it provides important information necessary to characterize and define the use of these species as gastronomic delicacies, functional foods and sources of bioactive compounds.

Tocopherols, synthesized by photosynthetic organisms, are micronutrients with antioxidant properties that play important roles in animal and human nutrition. Because of these health benefits, there is considerable interest in identifying the genes involved in tocopherol biosynthesis to allow transgenic alteration of both tocopherol levels and composition in agricultural crops. Tocopherols are generated from the condensation of phytyldiphosphate and homogentisic acid (HGA), followed by cyclization and methylation reactions. Homogentisate phytyltransferase (HPT) performs the first committed step in this pathway, the phytylation of HGA. In this study, bioinformatics techniques were used to identify candidate genes, slr1736 and HPT1, that encode HPT from Synechocystis sp. PCC 6803 and Arabidopsis, respectively. These two genes encode putative membrane-bound proteins, and contain amino acid residues highly conserved with other prenyltransferases of the aromatic type. A Synechocystis sp. PCC 6803 slr1736 null mutant obtained by insertional inactivation did not accumulate tocopherols, and was rescued by the Arabidopsis HPT1 ortholog. The membrane fraction of wild-type Synechocystis sp. PCC 6803 was capable of catalyzing the phytylation of HGA, whereas the membrane fraction from the slr1736 null mutant was not. The microsomal membrane fraction of baculovirus-infected insect cells expressing the Synechocystis sp. PCC 6803 slr1736 were also able to perform the phytylation reaction, verifying HPT activity of the protein encoded by this gene. In addition, evidence that antisense expression of HPT1 in Arabidopsis resulted in reduced seed tocopherol levels, whereas seed-specific sense expression resulted in increased seed tocopherol levels, is presented.

Cyclooxygenase (COX-1/COX-2)-catalyzed eicosanoid formation plays a key role in inflammation-associated diseases. Natural forms of vitamin E are recently shown to be metabolized to long-chain carboxychromanols and their sulfated counterparts. Here we find that vitamin E forms differentially inhibit COX-2-catalyzed prostaglandin E₂ in IL-1β-stimulated A549 cells without affecting COX-2 expression, showing the relative potency of γ-tocotrienol [almost equal to] δ-tocopherol > γ-tocopherol >> α- or β-tocopherol. The cellular inhibition is partially diminished by sesamin, which blocks the metabolism of vitamin E, suggesting that their metabolites may be inhibitory. Consistently, conditioned media enriched with long-chain carboxychromanols, but not their sulfated counterparts or vitamin E, reduce COX-2 activity in COX-preinduced cells with 5 μM arachidonic acid as substrate. Under this condition, 9'- or 13'-carboxychromanol, the vitamin E metabolites that contain a chromanol linked with a 9- or 13-carbon-length carboxylated side chain, inhibits COX-2 with an IC₅₀ of 6 or 4 μM, respectively. But 13'-carboxychromanol inhibits purified COX-1 and COX-2 much more potently than shorter side-chain analogs or vitamin E forms by competitively inhibiting their cyclooxygenase activity with Ki of 3.9 and 10.7 μM, respectively, without affecting the peroxidase activity. Computer simulation consistently indicates that 13'-carboxychromanol binds more strongly than 9'-carboxychromanol to the substrate-binding site of COX-1. Therefore, long-chain carboxychromanols, including 13'-carboxychromanol, are novel cyclooxygenase inhibitors, may serve as anti-inflammation and anticancer agents, and may contribute to the beneficial effects of certain forms of vitamin E.

The oaks Quercus robur L. and Quercus rubra L. are grown worldwide. The oak fruits (acorns) fallen on the ground during the autumn are usually considered as unusable, although some possible applications have been reported. In the present study, the possible recovery of tocopherols from acorns of two oak species Q. rubra (n = 14) and Q. robur (n = 15) was evaluated. Four tocopherols (Ts) (α-T, β-T, γ-T, and δ-T) in the oak fruits of Q. rubra and Q. robur were identified. The Q. robur acorns had abundant γ-T (28.18 ± 6.7 mg/100 g dw), while in Q. rubra β-T was predominant (17.28 ± 2.91 mg/100 g dw), nearly 95 and 90% of total detected tocopherols, respectively. The variability of tocopherol levels within the same species was lower for Q. rubra (16.5%) and higher for Q. robur (23.4%). The principal component analysis, applied to four tocopherol homologues, confirmed their feasibility to distinguish two strictly separated groups: one for species Q. rubra and the other for Q. robur. The predominance of β-T in Q. rubra acorns is a unique finding in the plant world; therefore, acorns of this oak species can be used as an unconventional natural source of this rare tocopherol homologue.

Apple seeds and their oils from an agro-food waste, derived from the cider industry protected by the Designation of Origin “Sidra de Asturias”, were chemically characterized. The average oil yield was 19.7%. The major fatty acids in apple seed oils are unsaturated fatty acids (90.3 ± 0.3%) belonging to the ω-3, ω-6 and ω-9 series (linolenic acid, 1.2 ± 0.1%; linoleic acid, 55.3 ± 1.2%; oleic acid, 33.4 ± 0.8%). Oils also showed an important antioxidant activity and high levels of tocopherols (total tocopherols 1280 ± 104.8 mg/kg oil) with β-tocopherol (794.5 ± 62.2 mg/kg oil) being most abundant in all cases followed by α-tocopherol (439.2 ± 34.5 mg/kg oil) and these compounds correlate with DPPH radical activity (r = 0.937). In the defatted apple seeds, protein (37.5 ± 1.8%) and fibre (20.3 ± 0.4%) were the major nutritional components detected and other interesting constituents, such as extractable polyphenols and hydrolysable tannins, were also relevant. The results suggest apple seeds from the cider-making industry could be a suitable raw material for food, pharmacological or cosmetic uses.

Hazelnuts are a well-known source of different healthy molecules. However, only few studies have investigated deeply their amounts considering simultaneously the contribution of the cultivar, the pellicle and the effect of roasting. For such purpose, peeled/unpeeled and raw/toasted samples of “Nocchione”, “Tonda di Giffoni”, “Tonda Gentile delle Langhe” and “Tonda Gentile Romana” hazelnuts were investigated as regards to their fatty acid composition, tocopherols and total phenolic compounds. Our results indicate that all four cultivars contain a high fraction of mono- and poly-unsaturated fatty acids, about 110–210 mg/kg of tocopherols and, when unpeeled, 1250–2100 mg/kg of phenolic compounds. In particular, unpeeled and toasted “Tonda Gentile delle Langhe” hazelnuts contain more than 2 g/kg dry weight of hydrophilic phenolics and more than 200 mg/kg dry weight of tocopherols. The study confirms that the highest concentration of bioactive compounds is contained in hazelnut’s pellicle. Accordingly, a principal component analysis (PCA) demonstrates that removal of the pellicle is associated with reduced amounts of phenolic compounds and α- and γ-tocopherols. The PCA also indicates that β-tocopherol, together with total fat, are the variables that most characterize the cultivar. Toasting, on the other hand, induces the oxidation of monounsaturated fatty acids, but does not influence the presence of tocopherols and has a positive impact on the presence of phenolic compounds whose concentration significantly increased regardless of kernel’s pellicle.

Six Amaranthus species (A. cruentus, A. hybridus, A. hypochondriacus, A. muricatus, A. tuberculatus, and A. viridis) were collected in Italy (wild habitats) from crops and roadsides. Amaranth seed oil was extracted to obtain fractions rich in squalene. Squalene, free fatty acid, tocopherol, and sterol composition and content were investigated in detail. An analysis of variance and principal components was performed. The oil content in the seed ranged from 5.17% (A. muricatus) to 12.20% (A. tuberculatus). The quantity of squalene in the oil varied from 3.43% (A. muricatus) to 6.09% (A. hypochondriacus). The primary sterols were beta-sitosterol, brassicasterol, campesterol, and stigmasterol. The main tocopherols in all the samples were alfa-tocopherol, beta-tocopherol, and delta-tocopherol. Our results exhibited that the smallest seeds (A. tuberculatus) have the highest percentages of oil and squalene, whereas the largest seeds size (A. muricatus) show the lowest percentages. There is also evidence that the samples growing at lower altitudes show the highest concentration of fatty acids. According to our results, the six wild Amaranthus species exhibited similar characteristics to commercial species. This study confirms that the site of the collection has an impact on the oil and squalene content of the Amaranthus species.

The main objective of this study was to evaluate the feasibility of developing multivariate models to estimate physico-chemical characteristics and antioxidant content of extra virgin olive oil from fluorescence spectra obtained at specific excitation wavelengths. Six replicates of each extra virgin olive oil sample were contained in clear glass bottles. Two replicates were subjected to four weeks of natural indirect light; two bottles for two days; and the third couple were kept it in darkness as a control. For each pair, one bottle was used for spectroscopic measurements and the other was sent to an accredited external laboratory to obtain physico-chemical measurements: acidity, peroxide index, K270, K232, total tocopherols, α-tocopherol, β-tocopherol and γ-tocopherol. Fluorescence emission spectra were acquired at different excitation wavelengths: 326 nm, 350 nm and 365 nm and partial least squares regression (PLSR) models were developed. The highest R2 values were found for excitation at 350 nm, reaching almost 0.9 in most of the parameters.

The objective of this study was to use accelerated-solvent-extraction to achieve antioxidant extracts from chia seeds oils, enriched in tocopherols and tocotrienols, namely tocochromanols. Nanotechnology applications have been also incorporated to develop an innovative formulation of chia seeds oil nanoemulsion that preserve its antioxidant potential after conditions of oxidative stress. Chia seeds oils proved to be a valuable source of tocochromanols, from 568.84 to 855.98 μg g−1, depending on the geographical provenance. Quantitative data obtained by LC-DAD-ESI-MS/MS showed outstanding levels of γ-Tocopherol, over 83%, followed far behind by Tocopherols-(α, β, δ) and Tocotrienols-(α, β, δ, γ)-tocotrienols. The characteristic tocochromanols fingerprint of chia seeds oils was positively correlated with the FRAP and DPPH antioxidant activity of the extracts (between 18.81 and 138.48 mg Trolox/g). Formulation of the Chia seeds oils as nanoemulsions did not compromised the antioxidant properties of fresh extracts. Interestingly, nanoemulsions retained about the 80% of the initial antioxidant capacity after UV-induced stress, where the non-emulsified oils displayed a remarkable reduction (50–60%) on its antioxidant capacity under the same conditions. These antioxidant chia seeds formulations can constitute a promising strategy to vectorizing vitamin E isomers, in order to be used for food fortification, natural additives and to increase the self-life of food products during packing.Graphic abstract