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High level expression of histone deacetylase 1 (HDAC1) plays a pivotal role in the pathobiology of cancer [1]. The endogenous fatty acid (9R)-9-hydroxystearic acid, 9R, is a natural HDAC1 inhibitor, which exerts its antiproliferative activity by arresting cancer cells growth in G0/G1 phase [2]. However, one of its major limitations is the unfavorable pharmacokinetic that hampers its therapeutic effectiveness. To overcome this constraint, 9R keratin nanoparticles (9R@Ker) were prepared and described here for the first time. Keratin was selected as carrier because possesses excellent biocompatibility and low toxicity to cells, thus resulting very promising material for drug delivery applications [3]. The formation of 200 nm nanoparticles (NPs) was induced by hydrophobic interactions between 9R and the hydrophobic protein domains, affording water-stable NPs with no need of toxic cross-linking agents. NPs were characterized in terms of particles size distribution, zeta potential, morphology, thermogravimetric behavior and drug release profile. Moreover, in vitro uptake and cytotoxicity was evaluated using human colorectal adenocarcinoma cells (HT29). Our data revealed that 9R@Ker are efficiently internalized by tumor cells, altering membrane lipidic composition. In vitro results demonstrate that the activity of 9R as free or loaded onto NPs is similar in terms of anti-proliferative effect. Remarkably, some significant differences were observed in the cell cycle analysis, showing that while free 9R caused a growth arrest in the G0/G1 phase, 9R@Ker induced a S phase arrest, thus promoting apoptosis (Fig.1). Additional studies are ongoing to better elucidate the underpinning biochemical mechanism of action of our newly developed delivery system.

Recent findings identified a new class of endogenous lipids, branched Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs), able to behave as specific signaling molecules that can regulate the cellular metabolism [1]. Among FAHFAs, the Palmitic-Acid-9-Hydroxy-Stearic Acid (9-PAHSA) seems to exert favorable metabolic effects in obesity-related diseases and type 2 diabetes, causing an increase in insulin sensitivity and glucose uptake. It has been recently reported that the FAHFAs content in human serum of breast cancer patients was significantly decreased compared to healthy controls [2], thus it is very interesting to investigate the possible involvement of these lipid molecules also in cancer transformation and progression. Previous studies of our research group have shown that the administration of 9-hydroxy-stearic acid (9-HSA) to colon carcinoma cells (HT29) induces strong antiproliferative and differentiating effects, with a cell cycle arrest in G0/G1 phase [3]. Since 9-HSA can be produced by the hydrolysis of 9-PAHSA, it is conceivable that also this lipid could act as signaling molecule. Consequently, the aim of this research was the characterization of the glucose metabolism of HT29 cells treated with 9-HSA. As a first step, the effect of 9-HSA on the lipid organization of HT29 cells was studied, showing an increase of the fluidity of plasma membrane. The treatment of HT29 with 9-HSA for 1 h provokes a significant increase of the glucose transporter Glut1 (and in a lesser extent of Glut3) on the plasma membrane, as a result of a translocation from intracellular stores, since the level of expression of the two transporters were unchanged, as determined by RT-PCR. Accordingly, the higher amount of Glut1 on the cell surface caused also an increase in glucose uptake into the cells. RT-PCR analysis showed also a significant increase of MCT1, the monocarboxylate transporter, in HT29 cells treated with 9-HSA. MCT1 is commonly overexpressed by cancer cells to maintain lactate and pH homeostasis [4]. Therefore, lactate production was measured in HT29 cells upon 9-HSA treatment for 1 h. Results show that lactate production was significantly increased, indicating a cellular metabolic shift toward glycolysis. The acute metabolic changes observed in HT29 cells are typical cellular responses to a signal molecule, supporting the hypothesis of a signaling role for 9-HSA in cancer cells. 1. M.M. Yore et al. Cell, 159:318-332, 2014. 2. Q.F. Zhu et al., J. Chromatogr. B, 1061-1062:34-40, 2017. 3. N. Calonghi et al., Biochem. Biophys. Res. Commun., 314:138-142, 2004 4. J. Adijanto and N.J. Philp, Curr. Top. Membr., 70:275-311, 2012.

PurposeThe purpose of this paper is to serve as an introduction to the usefulness of means‐end chain (MEC) theory and analysis for branding in health tourism.Design/methodology/approachAn online survey was conducted within the transnational EU‐project Alpshealthcomp and with two of the largest public health insurances in Germany. Research design is based on hard laddering according to Walker and Olson. MEC items were derived from Rokeach and from Hiesel and from results of a consumer survey (n=1.607) for Alpine health and wellness tourism.FindingsSeveral research questions are proposed regarding consumer association structures for health tourism using principal component analysis, cluster analysis and t‐test contrast of hypothesis. Personal values have proven to be most valuable for establishing brand associations. Here an identifiable and describable common structure exists for Alpine health tourism. With increasing product experience, consumers concentrate on viewer values closely linked to their personality. If product experience is low, consumers depend on a multitude of values.Research limitations/implicationsThe proportion of female participants in the sample is very high. A more balanced sample and analysis for gender differences could be valuable. Also it should be tried to replicate findings for other types of intangible services.Practical implicationsThe identified value structure can be addressed in brand communication and could complement the concept of brand personality. When shifting emphasis in staging and communicating values according to product experience, tourism managers can establish a stable and strong brand. Behavioral branding can be a useful tool in this context.Originality/valueBranding started to expand into the tourism industry only recently. Specific research work on branding in health tourism is scarce. To the best of the authors' knowledge, there exists no article in which MEC analysis was applied in order to analyze possible carrier of brand associations in health tourism. This work aims to bridge the gap.

The author demonstrates that the phenomenon of acceleration of sexual maturation is more frequent in urban areas. The factors having a part in determining this process are multiple: psychoemotional and audio-visual ones, and have an important role. The acceleration of sexual maturation has rather negative consequences, due to the significant increase of puberal menstrual troubles.

Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas’ rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned.

«MasterLab - Challenge the Science» is a serious video-game designed to help high school students to self-evaluate the adequacy of their educational background in view of a University degree program in Chemistry. The project is developed by a joint working group at the Universities of Bologna and Parma together with a professional videogame producer, in the framework and with the funding of the Italian Scientific Degrees Plan (PLS) – Chemistry. «MasterLab - Challenge the Science» is conceived as a Role Playing Game where the student/player moves throughout different rooms, each containing a different puzzle to solve. The puzzles consist in basic chemistry, mathematics and physics problems at a high school difficulty level and require virtual laboratory operations, measurements and calculations. The puzzles are built up and "gamified" in a modular manner, so they can be quickly written by the experts involved in the project. The game map develops randomly in order to offer to players different kind of problems in each game session. The project is easily expandable, by adding new puzzles, rooms, graphic elements, etc. and could be also extended to other scientific areas. When the player decides to end the game session, she/he will get a score (i.e. a piece of the “seal of science”) depending on the type of skill she/he has demonstrated. Game data will be recorded (according to privacy), in order to obtain accurate and detailed statistics regarding the knowledge of the individual topics useful also for high school teachers. «MasterLab - Challenge the Science» will be free, playable both on mobile devices (smartphone or tablet) and PC/MAC and easily accessible without the need of installation. A collaboration with a Science of Education Department was activated to provide the video-game with validity in term of pedagogical content and approach, to evaluate the effectiveness of the project in term of self-evaluation and to prevent discouraging effects on low score students. A preliminary beta-1 version of the video-game will be presented on the next November to the network of National Scientific Degrees Plan (PLS) – Chemistry. The official release will be delivered and tested in schools starting from spring 2020.

New all-conjugated C-C coupling products bearing both an electron-poor and an electron-rich aromatic moiety have been obtained from the reaction between sym-triaminobenzene derivatives and a series of isomeric chloro-nitrobenzofurazans. The reactions occur under mild reaction conditions, and in some cases a different behaviour depending on the presence, or not, of triethylamine was observed. From 1,3,5-tris(N-morpholinyl) benzene and 5-chloro-4-nitrobenzofurazan in the presence of triethylamine an unexpected product derived from the shift of the nitro group from C-4 to C-5 of the electrophile and bearing the nucleophile at position 4 was obtained. Moreover, from the coupling between 1,3,5-tris(N-pyrrolidinyl) benzene and 4-chloro-7-nitrobenzofurazan a highly stable Wheland intermediate was isolated.

New compounds containing both benzofuroxan and benzothiazole scaffolds were synthesized through electrophile/nucleophile combination of nitrobenzofuroxan derivatives and 2-mercapto- or 2-aminobenzothiazole derivatives and their biological effect on the natural strain Vibrio genus and different bacterial lux-biosensors was studied. Among all the compounds synthesized, that obtained from 2-mercaptobenzothiazole and 7-chloro-4,6-dinitrobenzofuroxan was toxic for bacterial cells, and also able to activated the 1st type Quorum Sensing system. The reaction between 7-chloro-4,6-dinitrobenzofuroxan and 2-aminobenzothiazole derivatives gave two products, one bearing the benzofuroxan moiety linked to the exocyclic amino nitrogen, and the second derived from the attack of two molecules of electrophile to both the nitrogen atoms of the benzothiazole reagent. Their relative ratio is modifiable by tuning the reagents ratio and the reaction time.

The reaction between 1,3,5-tris(N,N-dialkylamino)- benzene derivatives and 2 equiv of p-substituted benzenediazonium salts gives dicationic species which collapse to new benzimidazole derivatives with expulsion of p-substituted anilines. The presence of electron-withdrawing groups on the benzenediazo moiety of the dicationic species plays a key role in this unexpected ring closure reaction. The observed chemical behavior has been rationalized in terms of the already reported reversibility of azo coupling reactions and provided further evidence for it.

The interaction of gliadins with some anthocyanins (e.g. myrtillin, malvin, keracyanin, callistephin) and anthocyanidins (e.g. delphinidin, pelargonidin, cyanidin) has been analysed in aqueous solution at pH condition of the stomach, in which these compounds are initially metabolized. NMR, FT-IR and UV-Vis spectroscopic methods have been employed to determine the anthocyanin binding mode. The spectroscopic data seem to indicate that anthocyans are located along the polypeptide chains of gliadins in a generical molecular interaction between the two moieties. Our data do not exclude that hydrogen bonding interaction too is operating. Anthocyan-gliadins complexes are very soluble in acidic conditions. The results provide new insights into anthocyan-protein interaction and may have relevance to human health.

Asymmetric alkyl phospholanes have been diastereoselectively synthesized by addition of an unsymmetrical bis-Grignard reagent and of a mono-Grignard reagent to benzothiadiphosphole (1) and isolated as sulfides. The relative cis/trans ratio of the products depends on the steric hindrance of the mono-Grignard used. An accurate analysis of NMR and stereoselective data revealed the fundamental role played by hexacoordinated phosphorus intermediates in driving the stereochemical outcome of the reaction. The particular bicyclic and folded structure of reagent 1 strongly stabilizes hypercoordinated phosphorus species involved in the reaction and favors their formation. Pentacoordinate and metastable hexacoordinate phosphorus species have been detected and their evolution studied through (31)P NMR spectroscopy. The diastereoselective outcome of the reaction between reagent 1 and the couple bis-Grignard reagent 5/mono-Grignard reagent has been explained through a pathway involving hexacoordination of the phosphorus as a key step.

The reaction of 1,2-diaza-1,3-butadienes with dibenzyl diisopropylphosphoramidite, methyl tetraisopropylphosphorodiamidite or tris(dimethylamino)phosphane under solvent-free conditions gave stable α-phosphoranylidene-hydrazones that, in turn, were transformed into the corresponding 5-oxo-4-phosphoranylidene-4,5-dihydro-1H-pyrazoles. X-ray diffraction analysis of one of these derivatives is reported. α-Phosphoranylidene-hydrazones, derived from the reaction between 1,2-diaza-1,3-butadienes with dibenzyl diisopropylphosphoramidite, were converted by hydrolytic cleavage into (E)-hydrazono-phosphonates, which are useful for the preparation of the corresponding (3-oxo-2,3-dihydro-1H-pyrazol-4-yl)phosphonamidates.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

The reaction between tert-butylmagnesium chloride (or tert-pentylmagnesium chloride) and the particular phosphorus–sulfur bond of a benzothiadiphospholic system showed, for the first time, evidence of formation of intermediates with a four-center structure. The possibility, for the phosphorus atom, to have very stable hypervalent coordinations makes it possible to observe its hypervalent states during the course of a reaction. The benzothiadiphosphole, with its bicyclic folded structure, further stabilizes the hypervalent coordinations thus making the intermediates sufficiently stable to be detected during the course of the reaction by 31P NMR spectroscopy, which revealed the nature and the stability of the species involved in this reaction, carried out also using other Grignard reagents.

The reactions between strongly electron-rich aromatic substrates (1,3,5-tris(N,N-dialkylamino)benzenes, neutral carbon super nucleophiles) and diazonium salts produce moderately stable sigma complexes (Wheland complexes). The reactivity of Wheland complexes with electrophiles (other diazonium salts, or 4,7-dinitrobenzofuroxan) produces exchange reactions in the electrophilic part: the better electrophile replaces the less powerful electrophile. In the same way, in Wheland complexes with the 1,3,5-tris(morpholinyl)benzene, the 1,3,5-tris(piperidinyl)benzene replaces the less powerful nucleophile 1,3,5-tris(morpholinyl)benzene. Evidence is reported here indicating that for the title system the reaction of the attack of the electrophilic reagent producing Wheland complexes is a reversible process. The final products of the diazo-coupling reactions undergo a further attack of some diazonium salts. From the final products of the double diazo-coupling reactions (diazo compounds), we collected evidence that is a clear instance of complete reversibility of the diazo-coupling reaction.

The usual idea on the two-steps mechanism of aromatic electrophilic substitution reactions is that the first step (the attack of the electrophilic reagent on the activated substrate) is rate limiting, while the driving force of the reaction is the fast proton departure to recover the resonance energy of the aromatic substrate. The now examined systems allow the formation of stable σ cationic complexes (Wheland intermediates) which may be investigated by simple procedures. Data here reported represent a clear and simple instance of a measurement of the rate of the proton abstraction from a Wheland intermediate and they indicate that this proton abstraction occurs by base catalysis in a rate determining step. Probably, this feature is more frequent than that usually conceived in the mechanism of electrophilic aromatic substitution reactions, because these reactions are often carried out in reaction mixtures containing large amounts of proton acceptor species which might mask the possible base catalysis. Copyright © 2007 John Wiley & Sons, Ltd.

Recent studies have shown that an endogenous lipoperoxidation product, 9-hydroxystearic acid (9-HSA), acts in colon carcinoma cells (HT29) as a growth inhibitor by inducing p21 WAF1 in an immediate-early, p53-independent manner and that p21 WAF1 is required for 9-HSA-mediated growth arrest in HT29 cells. It is conceivable, therefore, to hypothesize that the cytostatic effect induced by this agent is at least partially associated with a molecular mechanism that involves histone deacetylase 1 (HDAC1) inhibition, as demonstrated for sodium butyrate and other specific inhibitors, such as trichostatin A and hydroxamic acids. Here, we show that, after administration, 9-HSA causes an accumulation of hyperacetylated histones and strongly inhibits the activity of HDAC1. The interaction of 9-HSA with the catalytic site of the enzyme has been highlighted by computational modeling of the human HDAC1, using its homolog from the hyperthermophilic Aquifex aeolicus as a template. Consistent with the experimental data, we find that 9-HSA can bind to the active site of the protein, showing that the inhibition of the enzyme can be explained at the molecular level by the ligand-protein interaction.

Proposal accepted: NMR experiments have shown unequivocally that the previously only proposed zwitterionic carbon-carbon Meisenheimer-Wheland complexes are formed in the reaction of 4,6-dinitrobenzofuroxan (DNBF) with 1,3,5-tris(N,N-dialkylamino)benzenes. Increasing the temperature results in a rapid exchange between three homomeric forms of the complex (see scheme; NR2=piperidyl, morpholinyl, pyrrolidinyl).

The reaction of benzothiadiphosphole 1 with an equimolar mixture of R 1 MgBr and R 2 MgBr gave intermediate A¢, which, after only 4-5 min, was treated with an equimolar amount of R 3 MgBr, giving the asymmetric phosphine PR 1 R 2 R 3 in 45% overall yield (75-80% yield when R 1 ) R 2 and 85-90% yield when R 1 ) R 2 ) R 3 ) and the byproduct 6 in 90% yield. The treatment of 6 with PCl3 quantitatively regenerates the starting reagent 1. Treatment of the phosphines with elemental sulfur gave the corresponding sulfides.

Different strategies are presented to conjugate a fluorescein moiety to 9- and 10-hydroxystearic acids (HSAs). 5-Amino-fluorescein (5-AF) was used as a starting reagent. When reacted with acyl-chloride-modified HSAs, 5-AF gave rise to stable amide derivatives with a 75% reaction yield. These products exhibited the typical steady-state and time-resolved fluorescence properties of the fluorescein chromophore with absorption at 494 nm and emission at 519 nm. Flow cytometry studies confirmed the distinct proapoptotic effect of underivatized 9-HSA on Jurkat cells and revealed a comparable ability of its amide derivative. Confocal microscopy imaging studies showed that green fluorescence could stain intracellular membranous structures. Moreover, dual-dye labeling with Mito Tracker Red, followed by colocalization analysis, revealed that HSA can move to the mitochondria. Thus, fluorescent derivatives of HSA can be used to monitor the localization of these biologically active molecules in living cells and can provide a useful tool for linking biochemical investigation with optical visualization methods. In contrast, when unmodified HSAs were used, the reaction gave monoesterified and diesterified fluorescein derivatives. These products exhibited unusual steady-state and time-resolved fluorescence properties with the excitation wavelength at 342 nm and the emission wavelength at 432 nm. It is shown that the synthesized HSA amides of fluorescein provide all of the typical photophysical and instrumental advantages of this popular dye, whereas the unusual luminescence and excitation properties of the monoester and diester of the 5-aminofluorescein would make these dyes interesting to explore as potential candidates for two photon excitation applications.

An overview discussing the main methods to obtain hair shape modification is presented, beginning from historically well known and traditional procedures to obtain waving to newest systems for hair straightening.

SynopsisOBJECTIVE: Formaldehyde is an effective and popular semiperma-nent hair straightener, but the severe consequences for humanhealth due to its toxicity have prompted the search for saferalternatives. Different carbonyl compounds, including glyoxylicacid, have recently been proposed as promising candidates. Despitethe interest in this topic, there is a lack of information about theinteractions between hair keratin and straightener agents. Thisstudy addresses this issue to gain new insights useful in the devel-opment of new products for safe, semipermanent hair deformation.METHODS: The possible reactions occurring between carbonylgroups and nucleophilic sites on amino acid residues belonging tothe keratin were investigated using as model compounds somealdehydes and amino acid derivatives. Raman and IR analyses onyak hair subjected to the straightening treatment with glyoxylicacid in different conditions were carried out. Scanning electronmicroscope (SEM) analyses were carried out on yak and curlyhuman hair after each step of the straightening procedure.RESULTS: The reactions between aldehydes and N-a-acetyl-L-lysine revealed the importance of the carbonyl electrophilicity andtemperature to form imines. Raman and IR analyses on yak hairsubjected to the straightening treatment evidenced rearrangementsin the secondary structure distribution, conformational changes tothe disulphide bridges, a decrease of the serine residues and forma-tion of imines. It was also indicated that straightening producedmajor conformational rearrangements within the hair fibre ratherthan on the cuticle.CONCLUSION: This investigation revealed the role played by theelectrophilicity of the carbonyl on the straightener agent and of thetemperature, closely related to the dehydration process. Raman andIR studies indicated the involvement of imine bonds and the occur-rence of a sequence of conformational modifications during thestraightening procedure. SEM analyses showed the effectiveness ofthe treatment at the cuticular level.ResumeOBJECTIF: Le formaldehyde est un agent defrisant semi-permanentpour cheveux efficace et populaire, defriser mais les graves con-sequences de son utilisation sur la sante de l’homme dues a sa toxi-cite ont stimule la recherche pour de plus s^ures alternatives.Different composes carbonyles, y compris l’acide glyoxylique, onteterecemment propose comme candidats prometteurs. Malgrel’inter^et pour ce sujet, il y a un manque d’information sur les inter-actions entre la keratine des cheveux et les agents defrisant. Cetteetude aborde cette question dans le but d’acquerir de nouvellesconnaissances utiles al’elaboration de produits plus s^urs qui serontutilisees pour obtenir la deformation semi-permanente des cheveux.METHODES: Les possible reactions entre les groupes carbonyles etles sites nucleophiles des residus d’acides amines appartenant alakeratine ont ete etudiees en utilisant pour modeles des aldehydes etdes derives d’acides amines. Des analyses Raman et IR sur des poilsde yack soumis au traitement de defrisage avec l’acide glyoxyliquedans differentes conditions ont eterealisees. Des analyses parmicroscope electronique a balayage (SEM) ont ete effectuees sur despoils de yak et des cheveux boucles humains apres chaque etape dela procedure de defrisage.RESULTATS: Les reactions entre des aldehydes et des N-a-acetyl-lysine ont revele l’importance de l’electrophilicite du carbonyl et dela temperature pour former des imines. Les analyses Raman et IRsur les poils de yak soumis a un traitement de defrisage ont mis enevidence des rearrangements dans la distribution de la structuresecondaire, des changements conformationnels de ponts disulfures,une diminution des residus de serine et la formation d’imines. Il aegalement ete indique que le defrisage produit des rearrangementsconformationnels majeurs au sein de la fibre capillaire plut^ot quesur la cuticule.CONCLUSION: Cette etude a reveleler^ole jou e par l’electrophilic-ite du groupe carbonyle sur l’agent defrisant et par la temperature,etroitement lie au processus de deshydratation. Etudes Raman et IRont indique l’implication des liaisons imines et la presence d’unesequence de les modifications conformationelles au cours de laprocedure de defrisage. Les analyses SEM ont montre l’efficacitedutraitement au niveau de la cuticule.IntroductionSince the first decade of the last century, the permanent deformationof human hair has been achieved with the use of chemical agents.In fact, due to the elastic properties of hair [1], when both wavingand straightening are obtained by thermal treatment, only a tempo-rary deformation that lasts only until the next wash is obtained [2]

The reaction between tris(N-piperidinyl)benzene and 4-methoxybenzenediazonium tetrafluoroborate afforded a Wheland intermediate (W) that was isolated and crystallized at low temperature. This permitted to obtain, for the first time, the X-ray structure analysis of a s- complex in the diazo coupling reaction. In solution, W slowly evolves to the rearomatized product PH+ (as salt). The single crystal X-ray diffraction determination of the neutral azo compound P is also reported.

The reaction of a series of symmetric and unsymmetric triaminobenzene derivatives with proton as electrophile has been studied. The formation of both Wheland complex (C-H salt) and N-H salt in relative amount depending on the experimental conditions has been observed. In the case of the attack of the proton on the nitrogen atom, the 1H and 13C NMR spectra showed the equivalence of three aromatic protons (and related carbon atoms) of the adduct thus indicating that salification occurs on a non-defined nitrogen atom. This behavior can be explained hypothesizing motion of the proton from a nitrogen atom to another in a motion that could not permit to define the protonation site. On the contrary, X-ray diffraction analysis on crystals of the NH salts reveals that in the solid state the proton is situated in a well-defined position.

Deuterium labelled compounds possess a wide range of applications in pharmaceuticals, environmental, materials and chemical sciences. They are useful in the investigation of bio-active molecules, giving detailed insights into the mechanism of chemical reactions. The deuteration of fatty acids, including stearic acid and its derivatives, permits to obtain reference or standard compounds for many purposes, including studies on metabolic pathways and analytical determinations. This paper refers to hydroxystearic acids, a class of compounds of interest in many applied fields focusing particular attention on the most used deuterium-labelling methodologies and related problems. An outline on the main applications of deuterated hydroxystearic acids is also done, critically discussing the examples taken from the literature. Furthermore, new results are presented concerning a simple protocol for obtaining D2 ‘in situ’: using the seeds of Dimorphoteca sinuata L. as natural precursor, and a lab-scale apparatus developed by us, we have verified the possibility to obtain deuterium-pluri-labelled 9-hydroxystearic acid.

Organic compounds present in plants have been used in various experimental conditions for dyeing tests aimed to develop safe and environmentally friendly temporary and semipermanent hair dyes. Yak hairs were used as a model for the colorimetric evaluation of red, yellow, blue, and brown shades conferred to hair by selected natural compounds. Two different sources for red, yellow, blue and brown shades were tested. Anthocyanins from mulberry fruits and alizarin emerged as promising candidates for red shades, anthocyanin-blue and curcumin for blue and yellow, respectively, and p-benzoquinone and juglone for browns. The influence of pH, dye concentration, soaking time, and medium in which the dyes have been dissolved or dispersed has been studied.

The reactions between 2,4-dipyrrolidin-1-yl-1,3-thiazole, a supernucleophilic reagent, and 4,6-dinitrobenzofuroxan (DNBF) or 4,6-dinitrotetrazolopyridine (DNTP), two superelectrophilic reagents, afforded new covalent complexes that are contemporaneously intermediates of an SNAr reaction (a Meisenheimer complex) and of an SEAr reaction (a Wheland complex). These compounds belong to a new class of covalent complexes, which we have named Wheland–Meisenheimer complexes (WM). The high stability of the complexes reported herein allowed the first X-ray diffraction analyses ofWMcomplexes. In addition, the reactions are diastereoselective, probably because of the specific approach of the two starting partners. The WM complex obtained with DNBF unexpectedly evolved to a neutral substitution product, a furazan derivative. Probably, the protons bonded to two sp3 carbon atoms are lost together with the oxygen atom of the furoxan moiety to form water. This represents a unique example of the formation of a neutral substitution compound from a C–C WM complex. Finally, exchange of the DNBF moiety in WM8 with DNTP in a solution of CD3CN was observed; the formation of the WM9 complex provided further evidence for the reversibility of the formation of the WM complexes.

A decoction of Capparis spinosa L. roots, widely used in the traditional folk medicine of southern Italy, was prepared and submitted to antibacterial activity tests, which showed an interesting bacteriostatic activity on the growth of Deinococcus radiophilus. Heterocyclic compounds were also recovered from the chloroformic extract of the roots.