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- Facile synthesis of oxo-/thioxopyrimidines and tetrazoles C–C linked to sugars as novel non-toxic antioxidant acetylcholinesterase inhibitorsPublication . Figueiredo, J.A.; Ismael, M.I.; Pinheiro, J.M.; Silva, A.M.S.; Justino, Jorge; Silva, Filipa V.M.; Goulart, Margarida; Mira, D.; Araújo, M.E.M.; Campoy, R.; Rauter, A.P.Microwave-assisted synthesis of oxo-/thioxopyrimidines and tetrazoles linked to furanoses with D-xylo and D-ribo configuration, and to a D-galacto pyranose is reported and compared to conventional methods. Reaction of dialdofuranoses and dialdopyranoses with a b-keto ester and urea or thiourea under micro wave irradiation at 300 W gave in 10 min the target molecules containing the 2-oxo- or 2-thioxo-pyrimidine ring in high yield. The tetrazole-derived compounds were obtained in two steps by reaction of the formyl group with hydroxylamine hydrochloride, copper sulfate, triethylamine and dicyclohexylcarbodiimide to give an intermediate nitrile, which was then treated with sodium azide. The use of microwave irradiation in the latter step also resulted in a considerably shorter reaction time (10 min) compared to hours under conventional heating to obtain a complete starting materials conversion. Acetylcholinesterase inhibition ranged from 20% to 80% for compounds concentration of 100 lg/mL, demonstrating the potential of this family of compounds for the control of Alzheimer’s disease symptoms. Most of the compounds showed antioxidant activity in the b-carotene/linoleic acid assay, some of them exhibiting IC50 values in the same order of magnitude as those of gallic acid. The bioactive compounds did not show cytotoxic effects to human lymphocytes using the MTT method adapted for non-adherent cells, nor geno toxicity determined by the short-term in vitro chromosomal aberration assay.
- Polymerization of ethylene using metallocene and aluminoxane systemsPublication . Justino, Jorge; Dias, A.R.; Ascenso, J.; Marques, M.M.; Tait, P.J.T.This paper describes ethylene polymerization using a number of metal-locene and aluminoxane catalyst systems, Cp2MR2 and methylaluminoxane [M = Zr, W, Nb; R = Cl, CH3]. Two types of methylaluminoxane, MAO (1) and MAO (2), were used as cocatalysts. The polymerization activities of the complexes Cp2WCl2 and Cp2NbCl2 were compared with that of Cp2ZrCl2. The Nb and W complexes were found to be less active than the Zr complex. Polyethylene characterization was also carried out by the following methods: gel permeation chromatography (GPC), differential scanning calorimetry (DSC) and nuclear magnetic resonance (NMR).
- Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones: evaluation of their antimicrobial activity and toxicityPublication . Xavier, N. M.; Goulart, Margarida; Neves, Ana Maria; Justino, Jorge; Chambert, S.; Rauter, A. P.; Queneau, Y.The synthesis of a series of pyranoid derivatives comprising a conjugated carbonyl function and related triazole derivatives, structurally suitable for bioactivity evaluation, was achieved in few steps starting from readily available carboxymethyl glycoside lactones (CMGL). 3-Enopyranosid-2-uloses were generated by oxidation/elimination of tri-O-acylated 2-hydroxy pyranosides. Subsequent Wittig olefination provided stereoselectively 2-C-branched-chain conjugated dienepyranosides with (E)-configuration around the exocyclic double bond. A heterogeneous CuI/Amberlyst-catalyzed 'click' chemistry protocol was used to convert glycosides bearing a propargyl moiety into the corresponding 1,2,3-triazoles. These new molecules were screened for their in vitro antibacterial and antifungal activities and those containing conjugated carbonyl systems demonstrated the best efficacy. (N-Dodecylcarbamoyl)methyl enone glycerosides were the most active ones among the enones tested. The alpha-anomer displayed very strong activities against Bacillus cereus and Bacillus subtilis and strong activity toward Enterococcus faecalis and the fungal pathogen Penicillium aurantiogriseum. The corresponding beta-anomer presented a very strong inhibitory effect against two fungal species (Aspergillus niger and P. aurantiogriseum). (N-Dodecyl-/N-propargyl/or N-benzylcarbamoyl) methyl dienepyranosides exhibited selectively a strong activity toward E. faecalis. Further acute toxicity evaluation indicated low toxic effect of the (N-dodecylcarbamoyl)methyl enone glyceroside alpha-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups
- Homogeneous Ziegler-Natta polymerisation: A kinetic approach .2. Transient-state kineticsPublication . Marques, M.M.; Dias, A.R.; Justino, Jorge; Costa, C.; Lemos, F.; Ribeiro, F.R.An integrated view is presented of several possible mechanisms applicable to the interpretation of homogeneous Ziegler-Natta polymerisation. In this paper, the transient aspects related to the kinetics of Ziegler-Natta polymerisation are investigated. Extensive data are used to construct kinetic profiles (rM vs. t) from a theoretical approach. Special attention is given to the duration of the transient period as a function of the different kinetic parameters. The kinetic models developed are fitted to experimental data, either directly obtained by the authors or published in the literature. These general models have a broad range of application.
- Neutron activation analysis of some biological environmental materialsPublication . Freitas, M. C.; Justino, Jorge; Grego, JoséSome biological candidate reference materials were recently or are now being certified for use in quality control of trace element analysis in environmental studies. In this work, the elemental concentration was determined by instrumental neutron activation analysis (INAA) for the materials lichen, poplar leaves, oak tree leaves, eucalyptus leaves and pine needles. As an application of pollution studies, samples of soil and strawberry plants treated with methylbromide as a disinfectant were analysed by INAA. The results evidence contamination with bromide; after several treatments the soil accumulates bromide giving rise to phytoxicity.
- Alkyl deoxy-arabino-hexopyranosides: synthesis, surface properties, and biological activitiesPublication . Silva, Filipa; Goulart, Margarida; Justino, Jorge; Neves, Ana; Santos, F.; Caio, J.; Lucas, S.; Newton, A.; Sacoto, D.; Barbosa, E.; Santos, M. S.; Rauter, A. P.Octyl and dodecyl glycosides possessing 2-deoxy-arabino-hexopyranoside moieties belonging to the D-and L-series in their alpha- and beta-forms were synthesized by reaction of an acetyl protected glycal with octanol or dodecanol, catalyzed by triphenylphosphine hydrobromide, followed by deprotection. Their surface properties were studied and discussed in terms of the adsorption and aggregation parameters, pC(20), CMC, and gamma(CMC). The antimicrobial activities were assessed using the paper disk diffusion and broth dilution methods. Both the octyl and dodecyl 2-deoxy beta-D-glycosides inhibited significantly Enterococcus faecalis, a microbe also highly susceptible to dodecyl 2,6-dideoxy-alpha-L-arabino-hexopyranoside. This compound was particularly active against Bacillus cereus and Bacillus subtilis, presenting for both Bacillus species a minimal inhibitory concentration of the same order of magnitude and a minimal lethal concentration even smaller than that obtained for chloramphenicol, a bioactivity which remained unaltered after 1 year solution storage at 4 degrees C. In addition, activity over Listeria monocytogenes was also observed. Direct cytotoxicity and genotoxicity of the glycosides were determined by proliferative index (mitotic index) evaluation in peripheral human lymphocytes of healthy donors. All compounds induced acute toxicity effects, and the response was dose dependent for the alpha-anomer of both the alkyl 2-deoxy-arabino-hexopyranosides and for the corresponding dodecyl beta-anomer, what suggests that non-toxic but still bioactive concentrations may be found for these compounds
- Phytochemical profile and anticholinesterase and antimicobial activities of supercritical versus conventional extracts of Satureja montanaPublication . Silva, Filipa; Martins, A.; Salta, J.; Neng, N. R.; Nogueira, J.; Mira, Delfina; Gaspar, Natália; Justino, Jorge; Grosso, C.; Urieta, J. S.; Palavra, A. M. S.; Rauter, A. P.Winter savory Satureja montana is a medicinal herb used in traditional gastronomy for seasoning meats and salads. This study reports a comparison between conventional (hydrodistillation, HID, and Soxhlet extraction, SE) and alternative (supercritical fluid extraction, SFE) extraction methods to assess the best option to obtain bioactive compounds. Two different types of extracts were tested, the volatile (SFE-90 bar, second separator vs HID) and the nonvolatile fractions (SFE-250 bar, first and second separator vs SE). The inhibitory activity over acetyl- and butyrylcholinesterase by S. montana extracts was assessed as a potential indicator for the control of Alzheimer's disease. The supercritical nonvolatile fractions, which showed the highest content of (+)-catechin, chlorogenic, vanillic, and protocatechuic acids, also inhibited selectively and significantly butyrylcholinesterase, whereas the nonvolatile conventional extract did not affect this enzyme. Microbial susceptibility tests revealed the great potential of S. montana volatile supercritical fluid extract for the growth control and inactivation of Bacillus subtilis and Bacillus cereus, showing some activity against Botrytis spp. and Pyricularia oryzae. Although some studies were carried out on S. montana, the phytochemical analysis together with the biological properties, namely, the anticholinesterase and antimicrobial activities of the plant nonvolatile and volatile supercritical fluid extracts, are described herein for the first time.
- New In Vitro studies on the bioprofile of Genista tenera antihyperglycemic extractPublication . Batista, D.; Falé, P.L.; Serralheiro, M.L.; Araújo, M.E.; Madeira, P.J.A.; Borges, C.; Torgal, Isabel; Goulart, Margarida; Justino, Jorge; Martins, A.; Rauter, A.P.The inhibition of a-glucosidase and glucose-6-phosphatase, two enzymes involved in the carbohydrate metabolism, is an important target to control glycaemia on individuals with type 2 diabetes. In this work we report for the first time the inhibition of both enzymes by the antihyperglycemic n-butanol extract from Genista tenera (Fabaceae). This extract decreased a-glucosidase and glucose-6-phosphatase activities to 0.97 and 80.25 %, respectively, being more effective than acarbose, and phlorizin, the positive controls, which reduced enzymes activities only to 17.39 and 96.06 %. Once inflammation and oxidative stress are related to diabetic impairments, the anti-inflammatory activity of the extract was also evaluated, through its inhibitory activity over COX-1 enzyme (47.5 % inhibition). Moreover, after induction of oxidative stress by UV radiation, the viability of irradiated rat liver hepatoma cells exposed to the extract was significantly higher (67.82 %) than that promoted by ascorbic acid, the positive control (45.05 %). In addition, the stability of the extract under gastrointestinal conditions was evaluated by HPLC–DAD-ESI–MS/MS. Flavonoid diglycosides were identified as the main constituents of the extract, and no alterations in the chemical composition nor in the antioxidant activity were observed after in vitro digestion with artificial gastric and pancreatic juices.
- Phenolic composition and antioxidant activity of Rocha pear and other pear cultivars: a comparative studyPublication . Salta, J.; Martins, A.; Santos, R. G.; Neng, N. R.; Nogueira, J. M.; Justino, Jorge; Rauter, A. P.The phenolic profile and the antioxidant activity of Rocha pear, a Portuguese pear cultivar, were determined and compared with the commercially available pear varieties Cornice, Abate, General Leclerc and Passe Crassane. Phenolic composition of the methanolic extracts of these pears was determined by high performance liquid chromatography with diode array detection (HPLC-DAD), while antioxidant activities were evaluated using three complementary test systems: DPPH radical scavenging activity, ferric reducing power capacity and beta-carotene/linoleic acid bleaching assay. When compared to the studied varieties, Rocha pear (peel and flesh) presented the highest content of total phenolics. Among them, chlorogenic, syringic, ferulic and coumaric acids, arbutin and (-)-epicatechin were detected as major components. In addition, among the tested varieties, Rocha pear presented the best antioxidant activities in the DPPH and ferric reducing power assays.
- A novel pentacyclic triterpene from Leontodon filiiPublication . Tostão, Z.; Noronha, J.P.; Cabrita, E.J.; Medeiros, J.; Justino, Jorge; Bermejo, J.; Rauter, A. P.A novel oleanene triterpenetetrol was isolated from the chloroform extract of the aerial parts of Leontodon filii. Its structure was shown to be 2β,3β,15α,21β-olean-12-ene-2,3,15,21-tetrol by chemical and spectroscopic methods. The fungicidal efficacy of the chloroform and methanol extracts of the plant was also evaluated, a protective effect being found against Plasmopara viticola, Botrytis cinerea, particularly powerful against Pyricularia oryzae.