Papers by Evelyn Bonifazi
Foods, Mar 22, 2024
The total phenolic, flavonoid, and anthocyanin contents were evaluated in 11 cultivars of Argenti... more The total phenolic, flavonoid, and anthocyanin contents were evaluated in 11 cultivars of Argentinian roses of different colors. HPLC-ESI-QTOF/MS was used to identify the components where ellagic and quinic acids, quercetin, and kaempferol glycosylated derivatives were found. The phenolic contents ranged from 78.8 ± 3.2 to 203.4 ± 3.1 mg GAE/g dw, the flavonoid content ranged from 19.1 ± 3.8 to 125.9 ± 6.5 mg QE/g dw, and the anthocyanin content ranged from less than 0.01 to 5.8 ± 0.1 mg CE/g dw. The dark red cultivars exhibited the greatest levels of the analyzed compounds and of the antioxidant activities, even higher than those of certain plants known for their high phenolic contents and antioxidant activity. Moreover, the addition of these extracts decreased the population of L. innocua and P. aeruginosa to undetectable levels 24 h after inoculation. Rose petal extracts, mainly those with a dark red color, can be used as natural additives in food, feed, and cosmetics, as they contain a high proportion of bioactive compounds with antioxidant and antimicrobial effects.
Antioxidants
The effect of freeze and hot air drying methods on the retention of total phenolics, antioxidant ... more The effect of freeze and hot air drying methods on the retention of total phenolics, antioxidant activity (AA), and color of different cultivars of rose petals was analyzed. Both methods similarly preserved the phenolic content and AA, while freeze drying showed better red color retention. Furthermore, the conditions of total phenolics and AA extraction from two rose cultivars, Lovely Red and Malu, were optimized by response surface methodology through a Box–Behnken design. The solvent exhibited a major effect on the total phenolic content (TPC) and AA. The selected parameters were ethanol 38%, 75 °C, and 30 min. Under these conditions, the predicted values for Lovely Red were 189.3 mg GA/g dw (TPC) and 535.6 mg Trolox/g dw (AA), and those for Malu were 108.5 mg GA/g dw (TPC) and 320.7 mg Trolox/g dw (AA). The experimental values were close to the predicted values, demonstrating the suitability of the model. Ultrasound-assisted extraction increased the AA of the extracts but not the...
Journal of Sol-Gel Science and Technology, 2021
Herein, we report on the stabilizing effect of water and the chiral self-assembly mode of a chole... more Herein, we report on the stabilizing effect of water and the chiral self-assembly mode of a cholesterol-based low-molecular-weight supramolecular organogelator. Dynamic rheology experiments performed on gels prepared in methanol and methanol–water mixtures showed an enhanced strength and rigidity in the presence of water, in line with the thermal stability previously observed. Morphological characterization experiments (scanning electron microscopy and X-ray powder diffraction) were performed on aerogels obtained after solvent extraction with supercritical CO2. Concentration- and temperature-dependent proton nuclear magnetic resonance and electronic circular dichroism experiments confirmed that the molecules of gelator self-assemble with a dominant right-handed helicity through intermolecular hydrogen bond interactions between the carbamate groups, and that the addition of water does not affect either the mode of assembly or the chirality of the supramolecular structure. Computational simulation experiments allowed us to propose a mode of self-assembly compatible with the experimental results, which involves a unidimensional head-to-tail stacking of molecules. A methanolic gel was successfully used as a molecular template for the in situ hydrolytic sol-gel polymerization of tetraethyl orthosilicate giving rise to silica nanotubes with an internal diameter of 7 nm. Water effect on a low-molecular-weight gel based on cholesterol and a benzyloxycarbamate group. Water increases the thermostability, strength, and rigidity of a supramolecular organogel. Intermolecular H-bonding interactions are involved in the 1D chiral self-assembly. The organogel was used as a template for in situ sol-gel polymerization of TEOS into silica nanotubes. The presence of water does not affect the mode of self-assembly. Water effect on a low-molecular-weight gel based on cholesterol and a benzyloxycarbamate group. Water increases the thermostability, strength, and rigidity of a supramolecular organogel. Intermolecular H-bonding interactions are involved in the 1D chiral self-assembly. The organogel was used as a template for in situ sol-gel polymerization of TEOS into silica nanotubes. The presence of water does not affect the mode of self-assembly.
Bioactive Carbohydrates and Dietary Fibre, 2020
This is a PDF file of an article that has undergone enhancements after acceptance, such as the ad... more This is a PDF file of an article that has undergone enhancements after acceptance, such as the addition of a cover page and metadata, and formatting for readability, but it is not yet the definitive version of record. This version will undergo additional copyediting, typesetting and review before it is published in its final form, but we are providing this version to give early visibility of the article. Please note that, during the production process, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.
Archaeological and Anthropological Sciences, 2020
In this paper, an interdisciplinary investigation was carried out to study if Santa María tricolo... more In this paper, an interdisciplinary investigation was carried out to study if Santa María tricolor style vessels were used as culinary equipment in a 14th century AD domestic cooking space in El Colorado (Yocavil valley, Catamarca, Northwest Argentina) and to question the long-established idea that Santa María vessels were exclusively funerary objects. The combined use of gas chromatography (GC-FID), gas chromatography-mass spectrometry (GC-MS), and high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry (HPLC-ESI-Q-TOF) to study residual lipids from Santa María style vessels provided valuable information on their ancient use. Also, an ordinary striated style ceramic pot with distinct visible soot marks, as well as sediments from the cooking area, was studied for comparative purposes. Fatty acid, sterol, and acylglyceride profiles were characterized, and markers of food sources were searched in the complex mixtures. We identified intact triacylglycerides (TAGs) in the archaeological samples, even unsaturated, indicating exceptional preservation of lipids in the ceramic matrixes. Cholesterol or cholesterol oxidation products were observed in all ceramic containers, as well as plant sterols (stigmasterol, sitosterol) in two containers. Markers for ruminant lipids, such as TAGs that contain odd-chain fatty acids, were found, supported by the identification of odd-chain and branched-chain fatty acids with GC-FID and GC-MS. This evidence contributes to the hypothesis that Santa María vessels were used for culinary purposes in this archaeological domestic cooking space.
Polish Journal of Food and Nutrition Sciences, 2020
The stability of betalains is affected by different factors, such as temperature, pH, water activ... more The stability of betalains is affected by different factors, such as temperature, pH, water activity, light, presence or absence of oxygen, and enzymatic action . Betacyanins in beet extracts have been noted as having pH stability in the range of 3-7 [Mikołajczyk-Bator & Czapski, 2017] and to be readily susceptible to thermal degradation . Temperatures above 50°C are reported to produce the loss of color and antioxidant capacity. In the heat treatment, the betacyanins can be degraded by isomerization and/or decarboxylation . A slight hypsochromic and hypochromic change can occur displacing the maximum absorption in the spectrum, therefore imparting an orange-red color . Also, betanin and isobetanin can be dehydrogenated and hydrolyzed causing the formation of neobetanin (4, 15-dehydrobetanin), which is bright yellow . On the other hand, betaxanthins are also thermally sensitive and have a lower stability than betacyanins do [Pires Goncalves et al., 2013]. In the food area, betalains application is accepted by the European Community [2008] and these pigments (named E162) are used in the production of jellies, jams, strawberry yogurt, ice cream, fruit cocktails, candies, and cookies .
Organic & Biomolecular Chemistry, 2018
A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of ... more A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent.
European Journal of Medicinal Chemistry, 2014
European Journal of Medicinal Chemistry, 2012
Bioorganic & Medicinal Chemistry, 2010
A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their an... more A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI(50) values of 0.42-8.1 and 0.80-2.2microM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity.
The Ugi-Smiles multicomponent reaction is a powerful tool for obtaining N-arylamines from acidic ... more The Ugi-Smiles multicomponent reaction is a powerful tool for obtaining N-arylamines from acidic phenols and has been widely used for gaining access to structurally diverse scaffolds. In this work we demonstrate that this isocyanide-based coupling can be used for the straightforward and efficient synthesis of N,N-disubstituted 3-aminoestrones, steroidal derivatives that usually show interesting biological activities. In this sense, we analyzed the scope and limitations of the reaction when applied to aromatic nitrosteroids and found that the outcome is highly influenced by the steric effects imposed by the steroidal skeleton. After optimization of the reaction conditions a set of thirteen N-substituted 3-aminoestromes were obtained, some of them with interesting antiproliferative and antiviral activities.
Este trabajo de tesis describe la sintesis de naftoquinonas relacionadas a las quinonas naturales... more Este trabajo de tesis describe la sintesis de naftoquinonas relacionadas a las quinonas naturales lapachol y β-lapachona, que presentan una amplia variedad de actividades biologicas entre las cuales se destaca su actividad antitumoral. El fin fue lograr compuestos con accion citotoxica mejorada y poder determinar los requerimientos estructurales de este tipo de quinonas, para facilitar asi el racional desarrollo de nuevos compuestos especificos. Se llevo a cabo la sintesis de 1,2 y 1,4-naftoquinonas dihidropirano y dihidrofurano con modificaciones en el anillo aromatico, principalmente con la introduccion de un grupo hidroxilo. En primer lugar se obtuvieron derivados hidroxilados de lapachol y dunniol, para luego mediante reacciones de ciclacion adecuadas obtener las naftoquinonas triciclicas deseadas. Se exploraron distintas metodologias para lograr una sintesis mas eficiente de los hidroxilapacholes de interes. Con el fin de sintetizar el derivado 10-hidroxi-β-lapachona mediante l...
ChemInform, 2012
β-Lapachone Analogues with Enhanced Antiproliferative Activity. -Selective acid-promoted cyclizat... more β-Lapachone Analogues with Enhanced Antiproliferative Activity. -Selective acid-promoted cyclization of lapachols (I) affords the α-(III) and β-lapachones (II), respectively. This method constitutes the first synthesis of β-lapachone analogues (IIa) and (IIb). Evaluation of antiproliferative activity in human solid tumor cell lines provides β-lapachone (IIc) as the lead. ROS formation and DNA damage are critical factors in the cellular toxicity of cells exposed to (IIc), and this might be the leading mechanism of action of (IIc). -(RIOS-LUCI, C.; BONIFAZI, E. L.; LEON, L. G.; MONTERO, J. C.; BURTON, G.; PANDIELLA, A.; MISICO, R. I.; PADRON*, J. M.; Eur. J. Med. Chem. 53 (2012) 264-274, http://dx.
ACS Applied Materials & Interfaces, 2014
In this communication, we report on a novel and versatile low-molecular-weight organogelator. The... more In this communication, we report on a novel and versatile low-molecular-weight organogelator. The methanolic gel exhibits an exceptional water-enhanced stability as evidenced by a 30 °C increase in Tg with up to 10%v/v of water. This atypical property not observed with other solvents makes of this supramolecular gel a highly stable matrix compatible with aqueous interfaces. As a proof of principle we present the sensing performance of a symmetric tricarbocyanine fluorophore bearing a Zn(II)chelator unit. The system retained its remarkable physical integrity for a long period of time opening new possibilities for other organic-aqueous interface applications.
European Journal of Medicinal Chemistry, 2012
Structureeactivity relationships a b s t r a c t
Bioorganic & Medicinal Chemistry, 2010
A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their an... more A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI(50) values of 0.42-8.1 and 0.80-2.2microM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity.
European Journal of Medicinal Chemistry, 2014
The antiproliferative activities of a series of 36 naphthoquinone derivatives were subjected to a... more The antiproliferative activities of a series of 36 naphthoquinone derivatives were subjected to a Quantitative Structure-Activity Relationships (QSAR) study. For this purpose a panel of four human cancer cell lines was used, namely HBL-100 (breast), HeLa (cervix), SW-1573 (non-small cell lung) and WiDr (colon). A conformation-independent representation of the chemical structure was established in order to avoid leading with the scarce experimental information on X-ray crystal structure of the drug interaction. The 1179 theoretical descriptors derived with E-Dragon and Recon software were simultaneously analyzed through linear regression models based on the Replacement Method variable subset selection technique. The established models were validated and tested through the use of external test sets of compounds, the Leave-One-Out Cross Validation method, Y-Randomization and Applicability Domain analysis.
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Papers by Evelyn Bonifazi