Simone Gabbanini

University of Bologna, Bologna, Emilia-Romagna, Italy

Are you Simone Gabbanini?

Claim your profile

Publications (13)24.77 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Little is known on structure-activity relationships of antioxidant anthocyanins. Raphanus sativus cv Sango sprouts are among the richest sources (270mg/100g fresh weight). We isolated from sprouts' juice 9 acylated anthocyanins, including 4 new compounds. All comprise a cyanidin core bearing 3-4 glucose units, multiply acylated with malonic and phenolic acids (ferulic and sinapic). All compounds were equally effective in inhibiting the autoxidation of linoleic acid in aqueous micelles, with rate constant for trapping peroxyl radicals kinh=(3.8±0.7)×10(4)M(-1)s(-1) at 37°C. In acetonitrile solution kinh varied with acylation: (0.9-2.1)×10(5)M(-1)s(-1) at 30°C. Each molecule trapped a number n of peroxyl radicals ranging from 4 to 7. Anthocyanins bearing sinapic acid were more effective than those bearing the ferulic moiety. Under identical settings, deacylated cyanin, ferulic and sinapic acids had kinh of 0.4×10(5), 0.3×10(5) and 1.6×10(5)M(-1)s(-1) respectively, with n ranging 2-3. Results show the major role of acylation on antioxidant performance.
    Food Chemistry 01/2015; 166:397-406. · 3.33 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Topical bioavailability of lipid- and water-soluble vitamins is a critical issue for protecting or anti-ageing formulations. Using 17-day-old SkinEthic(®) reconstructed human epidermis, we investigated (at 34°C) the role of lemon EO in enhancing the penetration of α-tocopherol (E) and retinyl acetate (A), pyridoxine (B(6)) and ascorbic acid (C), released from O/W or W/O emulsions. D-limonene, α-pinene and p-cymene (65.9, 2.2 and 0.5%w/w of the oil) had skin permeability coefficients Ps (10(-3) cm h(-1)) of 0.56 ± 0.03 (or 0.73 ± 0.02), 0.72 ± 0.05 (or 0.98 ± 0.05) and 0.84 ± 0.04 (or 1.14 ± 0.04), respectively, when incorporated in a W/O (or O/W) emulsion. Vitamins B6, C and A had Ps values of (3.0 ± 0.4) × 10(-3), (7.9 ± 0.6) × 10(-3) and (0.37 ± 0.02) × 10(-5) cm h(-1), respectively, and their flux through the skin was enhanced by a factor of 4.1, 3.4 and 5.8, respectively, in the presence of lemon EO. The penetration of vitamin E was nine-fold enhanced. Lemon EO produced only reversible modification of TEWL, and it is a safe and effective penetration enhancer for topical administration of lipid- and water-soluble vitamins.
    International journal of cosmetic science 04/2012; 34(4):347-56.
  • [Show abstract] [Hide abstract]
    ABSTRACT: The freeze-dried sprouts’ juice of Raphanus sativus (L.) cv. Sango was prepared and analysed for the first time. HPLC analysis of total isothiocyanates, after protein displacement, resulted in 77.8 ± 3.0 lmol/g of dry juice while GC–MS analysis of hexane and acetone extracts showed E- and Z-raphasatin (8.9 and 0.11 lmol/g, respectively) and sulforaphene (11.7 lmol/g), summing up to 20.7 ± 1.7 lmol/g of free isothiocyanates. Sprouts’ juice contained an unprecedented wealth of anthocyanins and a new fractionation methodology allowed us to isolate 34 mg/g of acylated anthocyanins (28.3 ± 1.9 lmol/g), belonging selectively to the cyanidin family. Analysis was performed by HPLC–PDA–ESI–MSn and extended to deacylated anthocyanins and aglycones, obtained, respectively, by alkaline and acid hydrolysis. This study identified 70 anthocyanins, 19 of which have never been described before and 32 of which are reported here in R. sativus for the first time. Sango radish sprouts are exceptional dietary sources of heath-promoting micronutrients.
    Food Chemistry 01/2012; 133:563-572. · 3.33 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: 4-Hydroxynonenal (4-HNE) is a major product of the oxidation of ω-6-polyunstaturated lipids and an effector of radical-mediated oxidative damage, whose analytical determination requires chemical derivatization. In this work, its reactivity with fluorinated phenylhydrazines was explored both under preparative and analytical settings. A five-step synthesis of 4-HNE on gram-scale with an overall yield of 30 % is described. Reaction of 4-HNE with ortho-, meta-, or para-CF3-phenylhydrazine, as well as with the 3,5-di-CF3, 2,4-di-CF3, or pentafluoro analogues, in MeCN with 0.5 mM TFA yields the corresponding hydrazones with rate constants kf of 2.8 ± 0.4, 1.7 ± 0.1, 3.0 ± 0.2, 0.6 ± 0.1, 0.5 ± 0.1, and 3.5 ± 0.5 M–1 s–1, respectively at 298 K. At higher temperatures, the hydrazones undergo intramolecular cyclization to form 1,6-dihydropyridazines that, depending on the solvent and temperature, may further react with the hydrazine to yield tetrahydropyridazine adducts and their oxidation products. Other reaction products were isolated, depending on the reaction conditions, and the complex reactivity of 4-HNE with the above nucleophiles is discussed. Due to the good yield and rate of formation of the hydrazone adducts, their stability and favorable UV absorbance, 2-(trifluoromethyl)phenylhydrazine and 2,3,4,5,6-pentafluorophenylhydrazine are the most interesting candidates for the development of rapid and efficient analytical derivatizations of 4-HNE.
    Annalen der Chemie und Pharmacie 01/2012; 2012(20):3841-3851. · 3.10 Impact Factor
  • Luca Valgimigli, Simone Gabbanini, Riccardo Matera
    [Show abstract] [Hide abstract]
    ABSTRACT: Analysis of lactose and maltose, and their discrimination from other disaccharides such as sucrose, is an important and challenging task in food analysis. ESI-MS and MS/MS are valuable detection methods for underivatized disaccharides, however, the absence of distinctive ions and CID fragmentation patterns does not allow discrimination of stereoisomers without good chromatographic resolution. Among the many chromatographic approaches, reverse-phase elution on porous graphitic carbon (PGC) appears to be the most performing and suited to ESI-MS spectrometry. After an overview on LC-MS analysis of oligosaccharides, in this chapter, we focus on a recently developed U-HPLC-ESI-MS/MS approach, on PGC columns, able to separate and detect the disaccharides (lactose and maltose) in their anomeric forms, as formate adducts obtained directly in-column. By using a Paul-ion-trap to monitor adduct [M+HCOO]- at m/z 387 in ESI negative mode (MS1), and CID fragment ion [M-H]- at m/z 341 (MS2), the method offers low pg sensitivity in complex vegetable matrices.
    01/2012: pages 443-463; , ISBN: 9781849733700
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Solvent extracts from the aerial and root parts and seed oil from E. sativa (rocket salad) were assayed for anticancer activity against melanoma cells. The seed oil (isothiocyanates rich) significantly (p<0.01) reduced the tumor growth comparable to the control. Remarkably, the seed oil inhibited melanoma growth and angiogenesis in mice without any major toxicity. The findings qualify seed oil for further investigations in the real of cancer prevention and treatment.
    Fitoterapia 02/2011; 82(4):647-53. · 2.23 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Lactose intolerance is a common condition caused by intestinal lactase deficiency, and a lactose-free diet represents the simplest way to avoid gastrointestinal symptoms. The emerging use of dietary supplements requires analytical tools that are capable of assessing these analytes, particularly for those based on dry herbal extracts that contain lactose together with maltose and sucrose, because of cross-contamination and/or deliberate addition as excipient. Electrospray ionization mass spectrometry (ESI-MS) and MS/MS are valuable detection methods for underivatized disaccharides; however, the absence of distinctive ions and collision-induced dissociation (CID) fragmentation patterns does not allow discrimination of stereoisomers without good chromatographic resolution. We developed an ultrahigh performance liquid chromatography-ESI (U-HPLC-ESI) approach, based on porous graphitic carbon (PGC) columns, working at 5 °C to separate and detect the disaccharides in their anomeric forms as formate adducts obtained directly in-column by eluting with formate buffer/acetonitrile gradient mixtures. Using a Paul trap, we monitored the adducts [M + HCOO](-) at m/z 387 in ESI negative mode (MS(1)) as well as the CID fragment ion [M - H](-) at m/z 341 (MS(2)) and used MS(3) fragment ions at m/z 178 and 161 to confirm disaccharides identity in complex vegetable matrices. Complete resolution of lactose α- and β-anomers, maltose α- and β-anomers, and sucrose was obtained with R ≥ 2.0 for all peaks and selectivity α = 1.2 between α- and β-anomers of lactose. The limits of detection were in the range of 3-7 µg/l (ppb) for the target disaccharides. Because of the rapidity and good anomeric discrimination, the described method represents an alternative tool to investigate the mutarotation phenomenon for reducing disaccharides.
    Biological Mass Spectrometry 09/2010; 45(9):1012-8. · 3.41 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The present study investigates the antimicrobial activity of various solvent extracts of Eruca sativa (aerial and root) and seed oil against-antibiotic resistant Gram-negative (Escherichia coli, Pseudomoms aeruginosa and Shigella flexneri) and Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacteria. Among the various preparations, seed oil was the most active, exhibiting a maximum zone inhibition of 97% for Gram-positive bacteria and of 74–97% for Gram-negative bacteria. The MIC of the seed oil was found to be 65–75 and 60–70 $mu$g/ml for Gram-negative and Gram-positive bacteria, respectively. Analytical investigation on main volatile and non-volatile components was performed on seed oil. Among the formers allyl isothiocyanate (40 $mu$g/g), 3-butenyl isothiocyanate (260 $mu$g/g), 4-methylsulfinybutyl isothiocyanate (sulforaphane 743 $mu$g/g), 2-phenylethyl isothiocyanate (159 $mu$g/g) and bis(isothiocyanatobutyl)disulphide (∼5000 $mu$g/g) were determined by head space/SPME/GC–MS analysis. Free fatty acids were 1.6% w/w of the oil and overall 25 fatty acids were identified. Erucic and oleic acids were the main fatty acids both in the free (7.8 and 2.1 mg/ml) and esterified forms (50.6% w/w and 14.9% w/w of total fatty acids). Unsaponifiable fraction was 1.8% w/w. Seed oil of E. sativa has promising pharmacological efficacies and ensures the presence of bio-active components responsible for the observed beneficial effects. Our findings support its use in traditional medicine as antimicrobial bioagent and highlight the potential of this food plant for its possible clinical use.
    Food Chemistry. 01/2010; 120(1):217-224.
  • [Show abstract] [Hide abstract]
    ABSTRACT: A convenient method for in vitro investigation of the release of lipid- and water-soluble vitamins from cosmetic formulations was developed. The permeation of (d)-alpha-tocopherol (vitamin E), retinyl acetate (pro-vitamin A), ascorbic acid (vitamin C) and pyridoxine (vitamin B6) through SkinEthic reconstructed human epidermis (RHE), and synthetic polyethersulfone and polycarbonate membranes was studied in vitro using a Franz-type diffusion apparatus, coupled either to a spectrophotometer for continuous reading (dynamic setting) or to HPLC-DAD analysis of the receptor medium (static setting). O/W and W/O emulsions were compared with simple aqueous solutions for their kinetic of vitamins release, to evaluate the influence of the cosmetic formulation on the bioavailability of active ingredients. Results indicate that synthetic membranes offer a limited barrier to the diffusion of vitamins, but may provide information on the release ability of the formulation. Penetration was more effective when water was the external phase of the formulation, i.e. W/O emulsions were less effective in the release of vitamins than O/W emulsion or aqueous solutions. RHE (17 days old) offered a significantly higher barrier to penetration of vitamins, as expected for native human epidermis. The relative ranking in coefficient of permeability (Ps (cm/h)) was: ascorbic acid>pyridoxine>retinyl acetate>alpha-tocopherol approximately 0, the absolute values depending on the formulation. The method herein described showed to be a practical and convenient tool for the quality-control and efficacy evaluation of cosmetic formulations.
    Journal of pharmaceutical and biomedical analysis 01/2010; 52(4):461-7. · 2.45 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Foot malodor is mostly due to short-chain fatty acids produced by bacterial metabolism of eccrine sweating. We aimed to develop a protocol for an objective (instrumental) efficacy evaluation of foot deodorant formulations. Head-space solid-phase microextractions of target fatty acids from the feet of six healthy volunteers were analyzed by GC-MS. A comparative analysis of the treated vs. the untreated foot was performed in each subject after washing the feet with a physiologic solution and incubating at 36 degrees C for 24-72 h in tryptic soy agar growth medium. Acetic, butyric, isobutyric and isovaleric acids were identified as the main contributors to foot malodor in the majority of volunteers. Propionic, valeric and isocaproic acids were also detected in some subjects. Comparative analysis according to the protocol developed showed a statistically significant (P<0.01) reduction of target fatty acids ranging from -26.6% to -77.0%. The protocol developed is a convenient, sensitive and non-invasive method to test the efficacy of foot deodorant formulations in human volunteers.
    Skin Research and Technology 11/2009; 15(4):503-10. · 1.41 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: The permeation of essential oils through SkinEthic® reconstructed human epidermis, (RHE), was studied in vitro to establish a convenient tool to monitor the kinetics of release of active principles from cosmetic formulations. Twelve days old human epidermis held on polycarbonate disks was revitalized by addition of growth medium and incubated at 37 °C in 5% CO2 atmosphere for five days prior to investigation. A system of six custom designed glass Franz-type diffusion cells were used for the permeation studies at 34 °C. The diffusion kinetic for 8 selected terpenes (camphor, carvone, 1,8-cineole, linalool, menthol, α-thujone, menthone, t-anethole), chosen as analytical markers of a mixture of plant essential oils contained in a cosmetic formulation, was probed by HS/SPME–GC–MS analysis and elaborated according to Fick's first law to obtain skin permeability coefficients (PS = 1.51, 1.47, 1.36, 0.80, 0.62, 0.40 and 0.14 × 10−3 cm/h, respectively). The method proved to be sensitive, simple and reproducible, and RHE represents a convenient model for safety/quality assessment of cosmetic formulations.
    Journal of Pharmaceutical and Biomedical Analysis. 01/2009;
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Brassica vegetables are attracting major attention as healthy foods because of their content of glucosinolates (GLs) that release the corresponding isothiocyanates (ITCs) upon myrosinase hydrolysis. A number of studies have so far documented the chemopreventive properties of some ITCs. On the other hand, single nutrients detached from the food itself risk being somewhat "reductive", since plants contain several classes of compounds endowed with a polyhedral mechanism of action. Our recent finding that 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) and 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC), released by the GLs purified from Japanese (Kaiware) Daikon (Raphanus sativus L.) seeds and sprouts, had selective cytotoxic/apoptotic activity on three human colon carcinoma cell lines prompted further research on the potential chemopreventive role of a standardized Kaiware Daikon extract (KDE), containing 10.5% w/w GRH and 3.8% w/w GRE, compared to its isolated components. KDE administered in combination with myrosinase at doses corresponding to 50 microM GRH-ITC plus 15 microM GRE-ITC (50 microM KDE-ITC) to three human cancer cell lines (LoVo, HCT-116 and HT-29) significantly reduced cell growth by 94-96% of control in six days (p < 0.05), outperforming pure GRH-ITC or GRE-ITC at the same dose. On the other hand, the same treatment had no significant toxicity on normal human T-lymphocytes. A 50 microM concentration of KDE-ITC had relevant apoptosis induction in all tested cancer cell lines, as confirmed by annexin V assay (e.g., 33% induction in LoVo compared to control, p < 0.05), Bax protein induction (e.g., +20% in HT-29, p < 0.05), and Bcl2 downregulation (e.g.-20% in HT-29, p < 0.05), and induced caspase-1 and PARP-1 activation in all cancer cells as shown by Western blot analysis. Unlike pure GRH or GRH-ITC, KDE also had significant chain-breaking antioxidant activity, retarding the AAPH-initiated autoxidation of methyl linoleate in SDS micelles at concentrations as low as 4.4 ppm (-50% in oxygen consumption rate), as monitored by Clark-type microelectrode oxygen-uptake kinetics, and induced very fast quenching of DPPH. radical in methanol with t(1/2) (s) = (1.47 +/- 0.25) x 10(-2)/[KDE; (g/L)], measured by stopped-flow UV-vis kinetics at 298 K. The potential chemopreventive role of KDE is discussed.
    Journal of Agricultural and Food Chemistry 10/2008; 56(17):7823-30. · 2.91 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Liquid chromatographic (HPLC) and GC-MS methods were developed to confirm the unusual presence of trans-anethole in Salvia sclarea essential oil. The selectivity of the HPLC method with a diode array detector (DAD) was enhanced by a post-column on-line photochemical derivatization. When a photoreactor (equipped with a 254 nm UV lamp) was arranged between the analytical column and the DAD, photoinduced modification of the anethole chromophore resulted in modified spectral properties. Therefore, two UV spectra (photoreactor Off and On) were achieved for the photoreactive trans-anethole, providing an information rich detection system. Using both HPLC and GC-MS approaches the unambiguous confirmation of the occurrence of trans-anethole in some commercial samples of S. sclarea oil was obtained. Genuine samples of S. sclarea essential oil were also prepared from the “drug” by each of the following techniques: steam-distillation, Soxhlet extraction in n-hexane, cold extraction in diethyl ether. GC-MS analysis of all the above extracts revealed the presence of trans-anethole. Although not previously recognized, trans-anethole is to be considered a “normal” component of S. sclarea essential oil.
    Journal of Separation Science 01/2002; 25:703-709. · 2.59 Impact Factor