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Summary: The present study aimed at understanding the response of dietary fibres and phenolic compounds to apple matrix disintegration and thermal treatment. Apple was processed by mimicking industrial operations of blanching, destructuring by high‐speed homogenisation (HSH) or high‐pressure homogenisation (HPH), and pasteurisation. A viscous puree (0.73 Pa × s), made of juice embedding intact cells and large cell clusters, was obtained by HSH. Conversely, HPH completely disrupted apple tissue leading to a fluid homogenate (0.27 Pa × s) in which the fibrous matrix was suspended. Despite these differences, apple puree and homogenate presented similar content of total and soluble dietary fibre, with no significant differences in the chemical structure of apple pectin, as demonstrated by FT‐IR and NMR analyses. Apple puree and homogenate retained more than 80% of the phenolic content originally present in apple pulp (about 2125 mg/gdw) without detriment to radical scavenging activity. This minor phenolic depletion, regardless of the different extent of mechanical disintegration, was mainly due to the decrease of thermolabile flavanols upon application of analogous heat treatments. [ABSTRACT FROM AUTHOR]

In our previous studies, Prunus spinosa fruit (PSF) ethanol extract was showed to exert antioxidant, antimicrobial, anti-inflammatory and wound healing activities. In the present study, an integrated bioinformatics analysis combined with experimental validation was carried out to investigate the biological mechanism(s) that are responsible for the reported PSF beneficial effects as an antioxidant during a pro-inflammatory TLR4 insult. Bioinformatics analysis using miRNet 2.0 was carried out to address which biological process(es) the extract could be involved in. In addition, Chemprop was employed to identify the key targets of nuclear receptor (NR) signaling and stress response (SR) pathways potentially modulated. The miRNet analysis suggested that the PSF extract mostly activates the biological process of cellular senescence. The Chemprop analysis predicted three possible targets for nine phytochemicals found in the extract: (i) ARE signaling, (ii) mitochondrial membrane potential (MMP) and (iii) p53 SR pathways. The PSF extract antioxidant effect was also experimentally validated in vitro using the human monocyte U937 cell line. Our findings showed that Nrf2 is modulated by the extract with a consequent reduction of the oxidative stress level. This was confirmed by a strong decrease in the amount of reactive oxygen species (ROS) observed in the PSF-treated cells subjected to lipopolysaccharide (LPS) (6 h treatment, 1 µg/mL). No visible effects were observed on p53 and MMP modulation. [ABSTRACT FROM AUTHOR]

The nuclear RNA surveillance mechanism is essential for cancer cell survival and is ensured by the RNA nuclear exosome including some co‐factors, such as the RNA helicase MTR4. Recent studies suggest an involvement of DNA repair proteins such as apurinic/apyrimidinic (AP) endodeoxyribonuclease 1 (APE1), a major endodeoxyribonuclease of Base Excision Repair (BER), in RNA metabolism and RNA decay of oxidized and abasic RNA. Cisplatin (CDDP) and 5‐fluorouracil (5‐FU) are commonly used for the treatment of solid tumours. Whether APE1 is involved in the elimination of CDDP‐ or 5‐FU‐damaged RNA is unknown, as is its possible interaction with the nuclear exosome complex. Here, by using different human cancer cell models, we demonstrated that: (a) APE1 is involved in the elimination of damaged‐RNA, upon CDDP‐ and 5‐FU‐treatments, in a MTR4‐independent manner; (b) the interaction between APE1 and MTR4 is stimulated by CDDP‐ and 5‐FU‐treatments through lysine residues in the APE1 N‐terminal region and is, in part, mediated by nucleic acids and (c) APE1‐ and MTR4‐depletion lead to the generation of R‐loop formation causing the activation of the DNA damage response (DDR) pathway through the ATM‐p53‐p21 axis. Our data demonstrate a role of MTR4 in DDR underpinning the function of APE1 in controlling the RNA quality upon genotoxic treatments with possible implications in chemoresistance. [ABSTRACT FROM AUTHOR]

Cannabis sativa var. Kompolti, a variety routinely used for food production purposes, is characterized by a low concentration of psychoactive molecules, although containing many other biologically attractive metabolites in all parts of the plant, including the roots. In the present work, we evaluate the specific biological activities of the roots' extract from plants cultivated through aeroponics, an affordable and reliable method facilitating the isolation and processing of roots, with the advantage of being suitable for industrial scale-up. Furthermore, aeroponics results in an increased net accumulation of the most biologically attractive constituents (β-sitosterol, friedelin and epi-friedelanol) found in the roots. The ethanolic extract of the aeroponic roots of C. sativa (APEX) and its separate components are studied to evaluate their anti-inflammatory (modulation of the expression level of specific markers upon LPS stimulation in U937 cells, such as IL-6, IL-8, TNF-α, IkB-α, iNOS, IRAK-1 and miR-146a) and antioxidant (in either acellular or cellular settings) activities. The APEX anti-inflammatory and antioxidant capacities are also functionally benchmarked using the wound-healing assay. On the whole, the data obtained show that APEX and its main components showed significant anti-inflammatory and antioxidant activities, which may render the exploitation of roots as a source of natural antioxidants and anti-inflammatory agents highly attractive, with the additional technical and economic advantages of aeroponics compared to soil cultivation. [ABSTRACT FROM AUTHOR]

Abstract: The reaction of formaldehyde with enantiomerically pure α-N-protected amino acid hydrazides is described. The system has been investigated in different solvents, including both aqueous formaldehyde and paraformaldehyde, with the [...]

[alpha]-Amino acids and [alpha]-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the [alpha]-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride. Key words: [alpha]-amino acid, [alpha]-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

Conventional (CB) and apple-pomace-reformulated (RB) biscuits were administered to healthy rats. Although the areas under curve (AUC) of glucose concentration were comparable between samples, differences in the glycaemic profile of CB and RB were observed. RB caused an initial steeper increase in glycaemia but a shift in the glycaemic peak from 45 to 60 min, as compared to CB. When CB or RB was ingested with apple juice (AJ) no differences were observed as compared to their ingestion with a soft drink (SD) simulating AJ sugar content, indicating that reformulation, more than the presence of AJ, was crucial in affecting the glycaemic response. Consumer acceptability towards reformulation was assessed through conjoint analysis, by simulating labels reporting information on reformulation. Consumers preferred information generally referring to the health-promoting effect (i.e. "low sugar" and "high fibre" contents), despite directly relating to a specific disease (i.e. "suitable for diabetics" and "low glycaemic index"). [ABSTRACT FROM AUTHOR]

• ESI-MS/MS fragmentation pattern of the [M+Na]+ ion of PEs was studied. • Fragment ions useful to detect known and new PEs in J. curcas seed oil were found. • Method is useful to detect PEs contamination of derivatives for food use. • Use of MeOH/H 2 O (85:15) in HPLC-ESI-MS/MS analysis enhanced the [M+Na]+ ion signal. Jatropha curcas L. is an inedible plant whose seed oil is an interesting source for biodiesel production. Seed cake, the main byproduct remaining (about 70% w/w) after the oil extraction process, has a high nutritional value but the presence in Jatropha curcas seed of phorbol esters (PEs), a family of toxic compounds with a tigliane skeleton, prevents application of seed cake and other byproducts (e.g. glycerin) in animal feed without an efficient detoxification. Considering the high toxicity of PEs, it is important to have a sensitive analytical method to evaluate the presence of these compounds in Jatropha curcas derivatives. In this paper we present the study of the ESI-MS/MS fragmentation pattern of the [M+Na]+ ion at m / z 733.5 of the six known PEs, namely Jatropha factors (JFs) C 1 -C 6 , which allowed to tentatively identify a series of characteristic and specific fragment ions useful to reveal the presence of JFs in Jatropha curcas seed oil, distinguish them from each other, and identify new PEs (J1-J4). Moreover, the substitution of the usual acetonitrile/water as mobile phase with a mixture of methanol/water (85:15, v/v) allowed to increase the signal of the sodium adduct of about 50-fold during the HPLC-ESI-MS/MS analysis. [ABSTRACT FROM AUTHOR]

Abstract The aim of this work was the study of the best conditions for obtaining a callus culture from the pulp of Acca sellowiana , and to perform a quali-quantitative analysis of the secondary metabolites yielded by the in vitro callus culture. To this end, callus was induced on both Murashige and Skoog and Gamborg B5 media containing various combinations of growth regulators. Three previously undescribed ursane-type triterpenoids, 2α,3β,6α,23-tetrahydroxy-18α,19α-urs-20-en-28-oic acid, 2α,3β,23-trihydroxy-18α,19α-urs-20-en-28-oic acid and 2α,3β,6β,23-tetrahydroxy-18α,19α-urs-20-en-28-oic acid were isolated from the methanolic extract of A. sellowiana culture and characterized by 1D and 2D NMR experiments. Moreover, the quali-quantitative analysis (ESI-MSn and GC–MS) also showed the presence of β-sitosterol, phloridzin, oleanolic, ursolic, 3β-hydroxy-18α,19α-urs-20-en-28-oic, maslinic, corosolic, 2α,3β-dihydroxy-18α,19α-urs-20-en-28-oic, and tormentic acid. Graphical abstract Unlabelled Image Highlights • Optimal conditions to obtain callus cultures from A. sellowiana pulp were studied. • High content of triterpenic acids was found in A. sellowiana fruit pulp culture. • Three undescribed triterpenoids were characterized by 1D and 2D NMR spectra. • The in vitro production of triterpenic acids was higher than in vivo. [ABSTRACT FROM AUTHOR]

Abstract The in vitro α-glucosidase inhibitory activity of raw, mildly (F 71.7 5 = 0.4 min, 5 Log reductions of Cryptosporidium parvum) and intensively ( F 90 12 =14.8 min, 2 Log reductions of Alicyclobacillus acidoterrestris) pasteurized apple juice was studied. Raw apple juice (23 mg dw /mL) caused 90% α-glucosidase inhibition. Analogous results were obtained for the mildly treated sample. The most intense treatment reduced by 35% the α-glucosidase inhibition. However, such a decrease was associated with an increase in the phenolic content, suggesting that α-glucosidase inhibition might not rely on these compounds, but depend on more complex mechanisms. Apple juice was combined with acarbose to investigate their interaction towards α-glucosidase inhibition. A synergistic behavior was observed for concentrations <2 mg/mL. Increasing the concentration of the combined system (up to 9 mg/mL) produced an antagonistic effect, while a further increase (<9 mg/mL) allowed approaching an addictive behavior. Highlights • Apple juice inhibited α -glucosidase in a concentration-dependent way. • Conventional pasteurization did not affect the α -glucosidase inhibitory capacity of apple juice. • Severe pasteurization reduced by 35% the apple juice inhibitory capacity. • Apple juice-acarbose system played a synergistic effect up to 40% α -glucosidase inhibition. [ABSTRACT FROM AUTHOR]

Introduction Very rarely fruit pulp has been used in in vitro culture to produce secondary metabolites useful in promoting health. Objectives The aims of this work were the study of the best conditions to obtain the callus cultures from the pulp of two varieties of apples, Golden Delicious (GD) and 'Mela Rosa Marchigiana' (MRM), and the quali-quantitative analysis of secondary metabolites produced by the two in vitro callus cultures. Methodology Callus was induced on both Murashige and Skoog and Gamborg B5 media containing various combinations of supplements. To achieve the maximum recovery of secondary metabolites produced, preliminary extraction tests were carried out on GD apple culture using two different organic solvents (MeOH and EtOAc). The quali-quantitative analysis of the methanolic extract of both cultures was carried out by ESI-MS n and GC-MS techniques. Results The GC-MS analysis revealed the presence of triterpenic acids, in particular, oleanolic, ursolic, maslinic, pomolic, tormentic, corosolic and annurcoic acid along with a phytosterol, β-sitosterol. In addition, GD callus culture produced phloridzin, absent in the MRM culture. In this last culture, however, the total amount of secondary metabolites was markedly higher. The in vivo production of these bioactive compounds were also quantified in the GD and MRM apple pulps. Conclusion Apple pulps produced higher amounts of triterpenic acids in vitro than in vivo. The present work can be considered a method to amplify the production of important secondary metabolites which exert beneficial effects on human health. Copyright © 2016 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

A simple, efficient two-step synthesis of N-protected N′-formyl- gem-diaminoalkyl derivatives is reported. The procedure involves the unprecedented reduction of the carbamoyl azide of α- N-Boc/Fmoc/Z-protected amino acids and dipeptides (Boc = tert-butoxycarbonyl, Fmoc = 9-fluorenylmethoxycarbonyl, Z = benzyloxycarbonyl) by treatment with NaBH4 at room temperature. The reaction proceeds rapidly (45 min) without detectable epimerization (by HPLC-ESI-MS analysis) and is not influenced by the nature of the starting carbamoyl azide. The 1H and 13C NMR analyses of the synthesized N-protected N′-formamides were carried out in [D6]DMSO. The spectra exhibited the presence of two rotameric forms in solution as a result of the restricted rotation around the N-CO formyl bond. The integration of the N-CH-N protons of the two isomers showed that the cis isomer (rotamer B) was the more abundant conformer by 60 to 78 %. The reported synthesis represents the potential value of carbamoyl azides as versatile chiral starting materials for many synthetic purposes. [ABSTRACT FROM AUTHOR]

N-Boc/Fmoc/Z- N′-formyl- gem-diaminoalkyl derivatives, intermediates particularly useful in the synthesis of partially modified retro-inverso peptides, have been characterized by both positive and negative ion electrospray ionization (ESI) ion-trap multi-stage mass spectrometry (MSn). The MS2 collision induced dissociation (CID) spectra of the sodium adduct of the formamides derived from the corresponding N-Fmoc/Z-amino acids, dipeptide and tripeptide acids show the [M + Na-NH2CHO]+ ion, arising from the loss of formamide, as the base peak. Differently, the MS2 CID spectra of [M + Na]+ ion of all the N-Boc derivatives yield the abundant [M + Na-C4H8]+ and [M + Na-Boc + H]+ ions because of the loss of isobutylene and CO2 from the Boc protecting function. Useful information on the type of amino acids and their sequence in the N-protected dipeptidyl and tripeptidyl- N′-formamides is provided by MS2 and subsequent MSn experiments on the respective precursor ions. The negative ion ESI mass spectra of these oligomers show, in addition to [M-H]−, [M + HCOO]− and [M + Cl]− ions, the presence of in-source CID fragment ions deriving from the involvement of the N-protecting group. Furthermore, MSn spectra of [M + Cl]− ion of N-protected dipeptide and tripeptide derivatives show characteristic fragmentations that are useful for determining the nature of the C-terminal gem-diamino residue. The present paper represents an initial attempt to study the ESI-MS behavior of these important intermediates and lays the groundwork for structural-based studies on more complex partially modified retro-inverso peptides. Copyright © 2013 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

[image omitted] A simple and mild one-pot synthesis of potentially bioactive α-N-protected dipeptidyl ureas is reported. The procedure involves the reaction between the carbamoyl azide of an α-N-protected amino acid and an α-amino acid methyl ester. The reaction is fast (3 h at 45 °C), regardless of the nature of both the reagents, and racemization free. The reported protocol represents a valid alternative to existing methods. [ABSTRACT FROM AUTHOR]

Abstract: The aim of this work was to investigate the products of the reactions between isoeugenol and eugenol with the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and their role in the radical scavenging mechanism. The reaction of isoeugenol and eugenol with the DPPH radical produced, as evidenced by GC–MS and HPLC–MS, a complex mixture of dimeric species in which dehydrodiisoeugenol and its adducts with methanol (reaction solvent) and dehydrodieugenol were the main reaction products, respectively. The antioxidant activity of dehydrodiisoeugenol, determined by the DPPH method, resulted lower than that of isoeugenol considering both the parameters Effective Concentration (EC50) and Antiradical Efficiency (AE). In particular, due to its very slow kinetic behaviour (), the possible contribution of dehydrodiisoeugenol to the DPPH radical scavenging activity of isoeugenol () was practically negligible. On the contrary, dehydrodieugenol had an antioxidant activity higher than that of eugenol and its lower (85min with respect to 126min) made it possible to contribute to the DPPH radical scavenging activity of eugenol. [Copyright &y& Elsevier]

In this paper we describe the unprecedented reaction between α-diazo esters 1 and iodine. The reaction, carried out in the presence of aqueous NaHCO3, afforded the Z-isomer of the corresponding unsaturated-2-iodo ester 8. The configuration of compounds 8 was determined using the 3JC&bond;H coupling between carbonyl carbon atom and alkene proton. Mechanistic considerations accounting for the observed phenomena and including quantum chemical calculations are proposed. Copyright © 2008 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

A rapid and efficient method for the synthesis of N-carbamoyl-L-amino acids is reported. The procedure, involving the reaction between urea and α-amino acids sodium salts, was performed under microwave conditions using an unmodified domestic microwave oven. A careful study of the operative conditions indicated proline (1d) as the less reactive substrate and phenylglycine (1e) as the more reactive one among all the α-amino acids tested. Substitution of urea with potassium cyanate produced a low conversion into the corresponding N-carbamoyl derivative, and a possible explanation of this result is reported. [ABSTRACT FROM AUTHOR]

The nitration of diphenylmethane to three main isomeric dinitro derivatives, performed with nitric acid in dichloromethane, is proposed as an organic laboratory experiment showing a number of advantages over typical aromatic nitrations in sulfuric acid. [ABSTRACT FROM AUTHOR]

Cannabis sativa L. has been used for a long time to obtain food, fiber, and as a medicinal and psychoactive plant. Today, the nutraceutical potential of C.sativa is being increasingly reappraised; however, C. sativa roots remain poorly studied, despite citations in the scientific literature. In this direction, we identified and quantified the presence of valuable bioactives (namely, β-sitosterol, stigmasterol, campesterol, friedelin, and epi-friedelanol) in the root extracts of C. sativa, a finding which might pave the way to the exploitation of the therapeutic potential of all parts of the C. sativa plant. To facilitate root harvesting and processing, aeroponic (AP) and aeroponic-elicited cultures (AEP) were established and compared to soil-cultivated plants (SP). Interestingly, considerably increased plant growth—particularly of the roots—and a significant increase (up to 20-fold in the case of β-sitosterol) in the total content of the aforementioned roots' bioactive molecules were observed in AP and AEP. In conclusion, aeroponics, an easy, standardized, contaminant-free cultivation technique, facilitates the harvesting/processing of roots along with a greater production of their secondary bioactive metabolites, which could be utilized in the formulation of health-promoting and health-care products. [ABSTRACT FROM AUTHOR]