Publications by authors named "Cosimo Pizza"

113 Publications

Pulp and Skin: In Depth Chemical Profile and Evaluation of Antioxidant Activity.

Molecules 2021 Aug 29;26(17). Epub 2021 Aug 29.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, 84084 Fisciano, SA, Italy.

Ruiz and Pav., known as the 'Gold of the Incas' or 'lucuma', is a subtropical fruit belonging to the Sapotaceae family, with a very sweet flavor, used to prepare cakes, ice creams as well as in the baking and dairy industries. To date, the content of primary metabolites is known, but little information is reported about the composition in specialized metabolites. Moreover, no study is reported on skin which represent an important agricultural waste due to the high demand for lucuma. In order to have a preliminary metabolite profile of , the extracts of pulp and skin have been analyzed by LC-ESI/LTQOrbitrap/MS/MS in negative ion mode. The careful analysis of the accurate masses, of the molecular formulas and of the ESI/MS spectra allowed to identify specialized metabolites belonging to phenolic, flavonoid and polar lipid classes. The LC-MS/MS analysis guided the isolation of compounds occurring in the pulp extract whose structures have been characterized by spectroscopic methods including 1D- and 2D-NMR experiments and ESI-MS analysis. Furthermore, the phenolic content of the extracts along with the antioxidant activity of extracts and isolated compounds was evaluated.
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http://dx.doi.org/10.3390/molecules26175236DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8434328PMC
August 2021

Antioxidant and In Vitro Preliminary Anti-Inflammatory Activity of (Italian Cultivar "Marrone di Roccadaspide" PGI) Burs, Leaves, and Chestnuts Extracts and Their Metabolite Profiles by LC-ESI/LTQOrbitrap/MS/MS.

Antioxidants (Basel) 2021 Feb 11;10(2). Epub 2021 Feb 11.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, I-84084 Fisciano, SA, Italy.

The Italian "Marrone di Roccadaspide" (), a labeled Protected Geographical Indication (PGI) product, represents an important economic resource for the Italian market. With the aim to give an interesting opportunity to use chestnuts by-products for the development of nutraceutical and/or cosmetic formulations, the investigation of burs and leaves along with chestnuts of , cultivar "Marrone di Roccadaspide", has been performed. The phenolic, tannin, and flavonoid content of the MeOH extracts of "Marrone di Roccadaspide" burs, leaves, and chestnuts as well as their antioxidant activity by spectrophotometric methods (1,1-diphenyl-2-picrylhydrazyl (DPPH), Trolox Equivalent Antioxidant Capacity (TEAC), and Ferric Reducing Antioxidant Power (FRAP) have been evaluated. Furthermore, a cell-based antioxidant in vitro test along with in vitro assays for the evaluation of the ability to reduce nuclear factor-kappa B (NF-κB) activation and nitric oxide (NO) production have been carried out. In order to identify the secondary metabolites responsible for the high phenolic content and the strong antioxidant activity shown by leaves and burs extracts, and to highlight the differences between their chemical composition, the analysis of the metabolite profile of the MeOH extracts obtained from both by-products and chestnuts by liquid chromatography coupled to electrospray ionization and multiple-stage linear ion-trap and Orbitrap high-resolution mass spectrometry (LC-(-)ESI/LTQOrbitrap/MS/MS) has been performed. LC-MS analysis allowed the identification of different classes of specialized metabolites including hydrolyzable tannins, flavonoids, ellagic acid and phenol glucoside derivatives, and triterpenoids as well as polar lipids. Our results show how the antioxidant activity of the extracts can be correlated to their high tannins and flavonoids content while polar lipids occurring in the MeOH extract of the leaves could contribute to determining its higher anti-inflammatory activity.
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http://dx.doi.org/10.3390/antiox10020278DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7917746PMC
February 2021

Giffonins, Antioxidant Diarylheptanoids from , and Their Ability to Prevent Oxidative Changes in Human Plasma Proteins.

J Nat Prod 2021 03 22;84(3):646-653. Epub 2021 Feb 22.

Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II no. 132, 84084 Fisciano (SA), Italy.

With the aim to explore the ability of diarylheptanoids to reduce oxidative changes in human plasma proteins, a phytochemical investigation of the MeOH extract of leaves was perfomed. Analysis by LC-ESI/LTQOrbitrap/MS/MS guided the isolation of two new diarylheptanoid derivatives, giffonins W () and X (). The structures and were assigned by analysis of NMR data combined with a QM (quantum mechanical)/NMR approach. The absolute configurations of and were established by analysis of electronic circular dichroism (ECD) spectra compared with the TDDFT-simulated curves. The antioxidant activity of the new and known giffonins was evaluated by inhibition of human plasma lipid peroxidation. Giffonins with the highest inhibitory activity were tested for their ability to reduce oxidation of thiol groups and carbonylation in plasma proteins, and some of them exhibited higher antioxidant activity than curcumin.
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http://dx.doi.org/10.1021/acs.jnatprod.0c01251DOI Listing
March 2021

Metabolite profiling and antioxidant activity of the polar fraction of Italian almonds (Toritto and Avola): Analysis of seeds, skins, and blanching water.

J Pharm Biomed Anal 2020 Oct 3;190:113518. Epub 2020 Aug 3.

Dipartimento di Farmacia, University of Salerno, Via Giovanni Paolo II n. 132, 84084, Fisciano, SA, Italy. Electronic address:

The health benefits of almonds along with their ability to prevent atheroschlerosis as well as cardiovascular and diabetes risks are well known. Previous works were focused mainly on the lipid fraction, thus a lack of information about the polar constituents still persists. In order to provide deeper insight into the chemical composition of almond, the polar fraction of Italian almond cultivars (Toritto and Avola) was investigated. The MeOH extract of the Toritto cultivar was submitted to LC-ESI-(HR)MS/MS experiments, highlighting the occurrence of several compounds, mainly cyanogenic glycosides, glycosylated flavonoids, proanthocyanidins, and a diterpene glycoside. EtOH and EtOH:HO solution were also employed for extractions, resulting selective for flavonoids and proanthocyanidins, while cyanogenic glycosides were mainly detected in EtOH:HO extract. Almonds were also blanched to afford skins and blanching water which were analyzed by LC-ESI-(HR)MS/MS experiments in order to establish the source of the identified compounds. Cyanogenic glycosides were detected in the peeled almonds, while flavonoids and proanthocyanidins were detected in almond skins and blanching water. The LC-ESI-(HR)MS/MS analyses of the almonds of the Avola cvs (Fascionello, Pizzuta and Romana) were compared with those of the Toritto cv., showing clear differences in their metabolome, probably due to the different growing conditions. Finally, total phenolic content and radical scavenging activity of the extracts and blanching waters were evaluated by Folin-Ciocalteu assay and by DPPH and ABTS assays, highlighting interesting antioxidant properties possessed by almond skins and blanching water, suggesting their potential employment in pharmaceutical, cosmetic and nutraceutical formulations.
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http://dx.doi.org/10.1016/j.jpba.2020.113518DOI Listing
October 2020

Chestnut shells (Italian cultivar "Marrone di Roccadaspide" PGI): Antioxidant activity and chemical investigation with in depth LC-HRMS/MS rationalization of tannins.

Food Res Int 2020 03 20;129:108787. Epub 2019 Nov 20.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, I-84084 Fisciano (SA), Italy. Electronic address:

In Italy a particularly valuable chestnut is "Marrone di Roccadaspide", a protected geographical indication (PGI) product, deriving from a Castanea sativa cultivar, typical of Salerno province in Campania region. As chestnut industrial processes yield a large amount of shell by-products, in this study the possibility to retrain this waste food as potential source of bioactives was investigated. The ability of "Marrone di Roccadaspide" shell MeOH extract to modulate the pro-inflammatory transcriptional factor NF-κB after LPS stimulation, along with the antioxidant activity by a cell-based in vitro test, were evaluated. To correlate the NF-κB inhibition (67.67% at 5 μg/mL) and the strong antioxidant activity to the chemical composition, an analytical approach based on LC-ESI/LTQOrbitrap/MS/MS along with NMR characterization of isolated compounds was developed. The identification of hydrolysable and condensed tannins, along with flavonoids, phenol glucosides, ellagic acid derivatives, and triterpenoids was accomplished. The most representative compounds were quantitatively analyzed by LC-ESI/QTrap/MS/MS, showing bartogenic acid as the compound occurring in the highest amount (103.08 mg/100 g shells). With the aim to explore the possibility to employ chestnut shells as suitable source of bioactives for the preparation of functional ingredients, the chemical composition and the antioxidant activity of "eco-friendly" extracts (EtOH and EtOH:HO 7:3) was finally evaluated, showing a high superimposability of the EtOH:HO (7:3) extract to the MeOH extract.
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http://dx.doi.org/10.1016/j.foodres.2019.108787DOI Listing
March 2020

HR-LC-ESI-Orbitrap-MS based metabolite profiling of Prunus dulcis Mill. (Italian cultivars Toritto and Avola) husks and evaluation of antioxidant activity.

Phytochem Anal 2019 Jul 14;30(4):415-423. Epub 2019 Feb 14.

Dipartimento di Farmacia, Università degli Studi di Salerno, Fisciano, SA, Italy.

Introduction: Prunus dulcis Mill. is a plant cultivated for the production of its edible seeds, known as sweet almonds. In the last decades almond demand has highly increased due to their wide use in the industrial manufacturing of almond-based foods; this has led to a huge production of waste materials, mainly corresponding to shells and husks.

Objective: To achieve a deeper understanding of the chemical composition of almond husks with the aim of exploring these byproducts as a source of bioactives to be used in nutraceutical and cosmetic formulations.

Methods: Methanol, ethanol and ethanol-water extracts of the almond husks were analysed by high-resolution liquid chromatography electrospray ionisation Orbitrap mass spectrometry (HR-LC-ESI-Orbitrap-MS) in negative ion mode. Tandem mass spectrometry (MS/MS) data were acquired by using the Data-Dependent Scan experiment, allowing the precursor ion to be selected as the most intense peak during LC-MS analyses. Nuclear magnetic resonance (NMR) experiments were performed on a Bruker DRX-600 spectrometer. Folin-Ciocalteu, DPPH (2,2-diphenyl-1-picrylhydrazyl) and TEAC (Trolox equivalent antioxidant capacity) assays were employed to determine the total phenolic content and the radical scavenging activity of the extracts.

Results: The LC-MS/MS analysis of the methanol extract guided the isolation of phloroglucinol derivatives, flavonoids and terpenes. Eco-friendly extraction methods showed to be selective in extracting flavonoids while the comparison of the LC-MS profiles of the Italian cultivars Toritto and Avola showed significant differences, confirming how different growing conditions may influence the metabolome of a plant species.

Conclusion: This study led to a deeper insight into the chemical constituents of almond husks and showed how the eco-friendly extraction resulted in an effective method to obtain extracts rich in antioxidant sources.
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http://dx.doi.org/10.1002/pca.2824DOI Listing
July 2019

Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa.

J Nat Prod 2019 01 10;82(1):74-79. Epub 2019 Jan 10.

Dipartimento di Farmacia , Università degli Studi di Salerno , Via Giovanni Paolo II 132 , 84084 Fisciano , Salerno , Italy.

The LC-MS analysis of the MeOH extract of the aerial parts of Pergularia tomentosa led to the isolation of 23 compounds, of which the structures were elucidated unambiguously by NMR spectroscopic data analysis. Three new doubly linked cardenolides (4, 13, 14) along with several known cardenolides (1-3, 5, 7, 8, 15-23) and flavonol glycosides (6, 9-12) were identified. LC-HRESIMS analysis, in the negative-ionization mode, showed the absence of flavonoids in a methanol extract of the roots of P. tomentosa. On the basis of the antiproliferative activity reported for cardenolides, the isolated compounds were tested for their ability to decrease the cell viability of five different human cancer cell lines, PC3, HeLa, Calu-1, MCF-7, and U251MG, exhibiting IC values ranging from 0.2 to 8.0 μM. Moreover, an S-phase entry assay was performed to investigate if the compounds could affect the cell cycle progression of PC3 prostate carcinoma cells. The results obtained demonstrated that the compounds 4, 7, and 14 at 1 μM considerably reduced the number of cells in the S-phase.
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http://dx.doi.org/10.1021/acs.jnatprod.8b00630DOI Listing
January 2019

In depth LC-ESIMS-guided phytochemical analysis of Ziziphus jujuba Mill. leaves.

Phytochemistry 2019 Mar 4;159:148-158. Epub 2019 Jan 4.

Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II, 84084, Salerno, Italy. Electronic address:

Ziziphus jujuba Mill. leaves are receiving a great attention for their ability to improve sleep, exerting beneficial effects for both the heart and the central nervous system. With the aim to obtain a comprehensive analysis of the specialised metabolites occurring in the leaves of Z. jujuba, a LC-ESI/(HR)Orbitrap/MS profile in negative ion mode of the methanol extract was carried out. The LC-MS profile guided the isolation of 42 compounds, of which the structures were elucidated by 1D and 2D-NMR experiments. Based on this approach, 2 previously unreported dammarane-type saponins have been characterized along with flavonoid derivatives, dammarane-type saponins and triterpenic acids. Dammarane-type saponins were tested for their cytotoxic activity against A549 and HeLa cancer cell lines. None of the tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number. This work provides a deep insight on the chemistry of the leaves of Z. jujuba and could be useful for further biological studies aimed at identifying phytochemicals contributing to the health benefits attributed to this herbal drug.
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http://dx.doi.org/10.1016/j.phytochem.2018.12.014DOI Listing
March 2019

Multi-class polar lipid profiling in fresh and roasted hazelnut (Corylus avellana cultivar "Tonda di Giffoni") by LC-ESI/LTQOrbitrap/MS/MS.

Food Chem 2018 Dec 25;269:125-135. Epub 2018 Jun 25.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, I-84084 Fisciano, SA, Italy. Electronic address:

Hazelnuts are a popular tree nut used whole or as an ingredient in a variety of bakery, candy and chocolate products. Based on the nutritional value and nutraceutical properties, mainly due to the lipid content, US Food and Drug Administration has recognized hazelnut as "heart-healthy" food. "Nocciola di Giffoni" is a Protected Geographical Indication (PGI) Italian hazelnut largely consumed but lacking of a comprehensive lipid profile. To acquire a detailed characterization of the polar lipids in fresh and roasted "Nocciola di Giffoni" hazelnut, an extensive analysis based on high-performance liquid chromatography coupled to multiple-stage linear ion-trap and orbitrap high-resolution mass spectrometry (LC-ESI/LTQOrbitrap/MS/MS) was carried out. This analytical approach (statistically validated) allowed for the detection of a wide range of polar lipids from oxylipins and long chain bases to high molecular weight lipids (phospholipids, sphingolipids, and glycolipids). Most of the polar lipids are here described for the first time in hazelnut.
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http://dx.doi.org/10.1016/j.foodchem.2018.06.121DOI Listing
December 2018

Metabolite profiling of "green" extracts of Corylus avellana leaves by H NMR spectroscopy and multivariate statistical analysis.

J Pharm Biomed Anal 2018 Oct 26;160:168-178. Epub 2018 Jul 26.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, 84084 Fisciano, SA, Italy. Electronic address:

Corylus avellana L. (Betulaceae) leaves, consumed as infusion, are used in traditional medicine, for the treatment of hemorrhoids, varicose veins, phlebitis, and edema due to their astringent, vasoprotective, and antiedema properties. In previous works we reported from the leaves of Corylus avellana cv. "Tonda di Giffoni" diarylheptanoid derivatives, a class of plant secondary metabolites with a wide variety of bioactivities. With the aim to give an interesting and economically feasible opportunity to C. avellana leaves as source of functional ingredients for pharmaceutical and cosmetic formulations, "green" extracts were prepared by employing "eco-friendly" extraction protocols as maceration, infusion and SLDE-Naviglio extraction. Metabolite profiles of the extracts were obtained by H NMR experiments and data were processed by multivariate statistical analysis to highlight differences in the extracts and to evidence the extracts with the highest concentrations of bioactive metabolites. Based on the NMR data, a total of 31 compounds were identified. The metabolite variation among the extracts was evaluated using Principle Component Analysis (PCA) and Partial Least Squares-Discriminant Analysis (PLS-DA). Furthermore, the total phenolic content of the extracts was measured by Folin-Ciocalteu colorimetric assay and the antioxidant activity of extracts was assayed by the spectrophotometric tests DPPH and ABTS and by an in vitro test based on the evaluation of cellular reactive oxygen species production stimulated by pyocyanin.
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http://dx.doi.org/10.1016/j.jpba.2018.07.046DOI Listing
October 2018

Metabolomics and antioxidant activity of the leaves of Prunus dulcis Mill. (Italian cvs. Toritto and Avola).

J Pharm Biomed Anal 2018 Sep 23;158:54-65. Epub 2018 May 23.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, 84084 Fisciano, SA, Italy. Electronic address:

Prunus dulcis leaves have been reported to exert some biological activity, in particular potent free radical-scavenging capacity, but so far there is limited information on their chemical composition. With the aim to achieve deep insight on the chemical constituents of the leaves of P. dulcis cultivars "Toritto" and "Avola", the most appreciated in Italy, an approach based on liquid chromatography-mass spectrometry (LC-MS) combined with isolation and structure elucidation of pure compounds by Nuclear Magnetic Resonance (NMR) analysis was carried out. Results allowed to detect in cv. Toritto leaves phenolics, terpenoids and a cyanogenic glycoside. Successively, various solvent systems were chosen to afford different extracts and an approach based on principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA) from LC-MS data sets highlighted eco-friendly methods as selective in extracting phenolics and glycosides. Comparison of LC-MS profiles of the MeOH extracts of cv. Toritto and cvs. Avola (Pizzuta, Fascionello and Romana) leaves and evaluation of their phenolic contents and antioxidant activity were also carried out.
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http://dx.doi.org/10.1016/j.jpba.2018.05.018DOI Listing
September 2018

In depth chemical investigation of Glycyrrhiza triphylla Fisch roots guided by a preliminary HPLC-ESIMS profiling.

Food Chem 2018 May 9;248:128-136. Epub 2017 Dec 9.

Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II, 84084 Salerno, Italy. Electronic address:

Chemical investigations on Glycyrrhiza spp. have mostly been focused on G. glabra (typically cultivated in Europe, henceforth called European licorice), G. uralensis and G. inflata (known as Chinese licorice) with little information on the constituents of other Glycyrrhiza species. According to the growing interest in further Glycyrrhiza spp. to be used as sweeteners, the roots of G. triphylla have been investigated. The LC-ESI/LTQOrbitrap/MS profile of the methanolic extract of G. triphylla roots guided the isolation of 21 compounds, of which the structures were elucidated by 1D- and 2D-NMR experiments. Based on this approach, 6 previously unreported compounds including two isoflavones 7,5'-dihydroxy-6,3'-dimethoxy-isoflavone-7-O-β-d-glucopyranoside (4) and 7,5'-dihydroxy-6,3'-dimethoxy-isoflavone-7-O-(7,8-dihydro-p-hydroxycinnamoyl)-β-d-glucopyranoside (7) and four saponins, named licoricesaponins M3 (13), N2 (14), O2 (16) and P2 (18), have been characterized. It is to be noted that the accurate masses of some compounds here reported for the first time corresponded to those of compounds previously described in Glycyrrhiza spp. Thus an approach based only on MS analysis could be misleading; only isolation followed by NMR analysis allowed us to unambiguously assign the structures of these previously unreported compounds.
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http://dx.doi.org/10.1016/j.foodchem.2017.12.031DOI Listing
May 2018

Combination of LC-MS based metabolomics and antioxidant activity for evaluation of bioactive compounds in Fragaria vesca leaves from Italy.

J Pharm Biomed Anal 2018 Feb 10;150:233-240. Epub 2017 Dec 10.

Department of Pharmacy, University of Salerno, Via Giovanni Paolo II, 84084, Fisciano, (SA) Italy. Electronic address:

Wild strawberry (Fragaria vesca) is recognized as a traditional food of Campania region (Italy). The vegetative parts have a pharmaceutical interest, being used as decoctions for hypertension treatment due their detoxifying, diuretic, stimulant and dermatological protective properties; leaves, that after collection of fruits are generally thrown away, could be an interesting byproduct, source of bioactive compounds for cosmetic and pharmaceutical industry. In the present work, the metabolite profiles of F. vesca leaves coming from populations spontaneously growing in the underwood (wild) and in crop (cultivated) and from autochthonous and non-autochthonous germplasm of Campania region (Italy) were investigated by LC-ESI/LTQOrbitrap/MS analysis. 27 metabolites mainly belonging to organic acids, flavonoids, catechin and its oligomers, and ellagitannins were putatively identified. Antioxidant activity was tested for each sample, in particular cultivated samples and wild samples with autochthonous germplasm of Campania region showed higher antioxidant activity compared to the non autochthonous ones. Moreover, in this study, it was possible to predict antioxidant metabolites, markers of this species, using LC-MS spectra and multivariate regression data analysis.
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http://dx.doi.org/10.1016/j.jpba.2017.12.005DOI Listing
February 2018

Steroids from Helleborus caucasicus reduce cancer cell viability inducing apoptosis and GRP78 down-regulation.

Chem Biol Interact 2018 Jan 7;279:43-50. Epub 2017 Nov 7.

Department of Pharmacy, University of Salerno, 84084, Fisciano, Italy.

Helleborus caucasicus (Ranunculaceae) is an endemic plant of the Caucasian flora, widely distributed in West Georgia. Biological activities for the extracts of some Helleborus species including H. caucasicus have been reported. In this work we found that butanolic extract of the underground parts of H. caucasicus and isolated compounds decreased cell viability in vitro on cancer cell line of lung origin (Calu-1) in a concentration-dependent manner, compared to the normal cell line. In particular, we identified that furostanol derivative (25S)-22α,25-epoxyfurost-5-ene-3β,11β,26-triol 26-O-β-d-glucopyranoside (5), 20-hydroxyecdysone (6), and 3β,5β,14β-trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-α-l-rhamnopyranoside, known as deglucohellebrin (7) exerted a strong cytotoxic effect on the same cells and on other cancer cell lines (HepG2 and Caco-2) reducing the S-phase entry (compound 6) and inducing cell apoptosis associated with activation of caspase-3 (compound 7). Moreover we demonstrated that 6 and 7 significantly decreased protein expression of GRP78, a general ER-stress marker, suggesting pro-apoptotic functions. These findings indicated that selected compounds from H. caucasicus are potential interesting agents in anti-cancer therapy.
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http://dx.doi.org/10.1016/j.cbi.2017.11.002DOI Listing
January 2018

LC-MS profiling highlights hazelnut (Nocciola di Giffoni PGI) shells as a byproduct rich in antioxidant phenolics.

Food Res Int 2017 11 1;101:180-187. Epub 2017 Sep 1.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, 84084 Fisciano, SA, Italy. Electronic address:

The Italian "Nocciola di Giffoni", also known as "Tonda di Giffoni", a labelled Protected Geographical Indication (PGI) product, represents an important economic resource for the Italian market. The methanol (MeOH) extract of "Tonda di Giffoni" shells has been investigated for the phenolic content, assayed by the Folin-Ciocalteu method, and for the antioxidant activity by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Trolox Equivalent Antioxidant Capacity (TEAC) assays. In order to achieve deeper insight into the chemical composition of the shells of hazelnut "Nocciola di Giffoni" and to highlight the occurrence of biologically active compounds, a phytochemical investigation was carried out. An initial Liquid Chromatography - Mass Spectrometry (LC-MS) profile of the methanol (MeOH) extract of the shells of C. avellana, cultivar "Tonda di Giffoni" led to the identification of sixteen compounds, of which the structures were elucidated by Nuclear Magnetic Resonance (NMR) spectroscopy. These were identified as a new diarylheptanoid, giffonin V (13), along with fifteen known phenolic compounds belonging to diarylheptanoid, neolignan, phenilpropanoid and flavonoid classes. In order to perform the quantitative determination of the main compounds of MeOH extract of C. avellana L. shells, an analytical method based on liquid chromatography coupled to mass spectrometry (LC-MS) with electrospray ionization source (ESI) and triple quadrupole mass analyzer (QqQ), using multiple reaction monitoring (MRM) scan mode, was developed and validated. The quantitative results highlight that main compounds occurred in the extract in concentration ranging from 6.4 to 83.3 (mg/100g). The antioxidant activity of all the isolated compounds evaluated by TEAC assay showed as the flavonoid derivatives exhibited a higher free-radical-scavenging activity. Moreover, the cytotoxicity of each compound was tested against the cancer cell lines A549 and Hela and against the human skin fibroblasts HaCat. None of tested compounds, in a range of concentrations between 12.5 and 100μM, cause a significant reduction of the cell number.
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http://dx.doi.org/10.1016/j.foodres.2017.08.063DOI Listing
November 2017

Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a preliminary LC-MS profiling.

Phytochemistry 2017 Aug 24;140:45-51. Epub 2017 Apr 24.

Dipartimento di Farmacia, Università degli Studi di Salerno, via Giovanni Paolo II n. 132, 84084, Fisciano, SA, Italy. Electronic address:

The phenolic content of the ethanol extract of the stem bark of the Brazilian plant Schinopsis brasiliensis Engl. (Anacardiaceae) has been evaluated together with the antioxidant activity. The good antioxidant activity exhibited in the Trolox Equivalent Antioxidant Capacity (TEAC) assay (TEAC value = 3.04 mg/mL) encouraged us to investigate its constituents. An analytical approach based on LC-ESIMS was applied to rapidly obtain a metabolite profile of the ethanol extract of the stem bark of S. brasiliensis. Sixteen phenolic compounds, among which five galloyl derivatives, never reported before, have been isolated and their structures have been unambiguously elucidated by extensive spectroscopic methods, including 1D (H, C, TOCSY) and 2D (DQF-COSY, HMBC, and HSQC) NMR experiments. Moreover, the antioxidant activity of all the isolated compounds was evaluated, along with the cytotoxicity against the cancer cell lines A549 (human alveolar basal carcinoma) and Hela (human epitheloid cervix carcinoma). The previously undescribed compounds exhibited a high free-radical-scavenging activity, in the range of 1.10-1.86 mM. None of the tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number.
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http://dx.doi.org/10.1016/j.phytochem.2017.04.008DOI Listing
August 2017

Research survey on iridoid and phenylethanoid glycosides among seven populations of Euphrasia rostkoviana Hayne from the Alps.

Phytochemistry 2017 May 21;137:72-80. Epub 2017 Feb 21.

Laboratory of Bioorganic Chemistry, Department of Physics, Università degli Studi di Trento, 38123 Trento, Italy. Electronic address:

The traditional use of extracts of Euphrasia rostkoviana to relieve ocular inflammation or infections is well documented and supported by clinical studies. Various classes of chemical compounds such as iridoids, phenylethanoids, flavonoids and hydroxycinnamic acids have been reported. The present work aims to assess the chemical diversity among seven populations of Euphrasia rostkoviana found in northern Italy. A meticulous separation of components led to the isolation and structural characterization of two previously unrecorded phenylethanoids methoxycrassifolioside and deoxycrassifolioside and one previously undescribed terpene glucoside (1E,6E)-8-hydroxy-3,7-dimethyl-octa-1,6-dienyl 1-O-β-D-glucopyranoside. We have also identified known phenylethanoids and iridoids that are reported in this genus for the first time. Finally, a targeted quantitative analysis for the standardization of herbal preparations revealed that iridoids occur in all populations whereas the presence and the levels of rutin and phenylethanoids are highly variable.
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http://dx.doi.org/10.1016/j.phytochem.2017.02.013DOI Listing
May 2017

Metabolomics of Healthy Berry Fruits.

Curr Med Chem 2018 ;25(37):4888-4902

Department of Pharmacy, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano (SA), Italy.

The consumption of berry-type fruits has become very popular in recent years because of their positive effects on human health. Berries are in fact widely known for their health-promoting benefits, including prevention of chronic disease, cardiovascular disease and cancer. Berries are a rich source of bioactive metabolites, such as vitamins, minerals, and phenolic compounds, mainly anthocyanins. Numerous in vitro and in vivo studies recognized the health effects of berries and their function as bioactive modulators of various cell functions associated with oxidative stress. Plants have one of the largest metabolome databases, with over 1200 papers on plant metabolomics published only in the last decade. Mass spectrometry (MS) and NMR (Nuclear Magnetic Resonance) are the most important analytical technologies on which the emerging ''omics'' approaches are based. They may provide detection and quantization of thousands of biologically active metabolites from a tissue, working in a ''global'' or ''targeted'' manner, down to ultra-trace levels. In the present review, we highlighted the use of MS and NMR-based strategies and Multivariate Data Analysis for the valorization of berries known for their biological activities, important as food and often used in the preparation of nutraceutical formulations.
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http://dx.doi.org/10.2174/0929867323666161206100006DOI Listing
February 2019

Ruscus Genus: A Rich Source of Bioactive Steroidal Saponins.

Planta Med 2016 Dec 8;82(18):1513-1524. Epub 2016 Nov 8.

Dipartimento di Farmacia, Università degli Studi di Salerno, Fisciano (SA), Italy.

The genus (Asparagaceae family) is native to the Mediterranean, Southern and Western Europe and is represented by perennial, rhizomatous, and evergreen shrubs. Among the approximately seven species spread throughout Europe up to Iran, L. (butcher's broom) is the most widely distributed and appreciated. This review provides an overview of the traditional use of spp., the current knowledge of the chemistry of this genus, and the pharmacological studies carried out on spp. extracts. The underground parts of plants are a source of steroidal saponins that can be classified into two structural classes: the hexacyclic spirostanol saponins and the pentacyclic furostanol saponins. The main aglycones are ruscogenin and neoruscogenin. From the pharmacological point of view, the most studied species is undoubtedly , a very ancient phlebotherapeutic agent. Pharmacological investigations since the discovery of the vasoconstrictive and venotonic properties of ruscogenin and neoruscogenin in the underground parts of are discussed. Preparations based on species are currently used for the treatment of chronic venous insufficiency, varicose veins, haemorrhoids, and orthostatic hypotension. Finally, analytical techniques for the quality control of extracts are reported.
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http://dx.doi.org/10.1055/s-0042-119728DOI Listing
December 2016

Oleanane derivatives for pharmaceutical use: a patent review (2000-2016).

Expert Opin Ther Pat 2017 Mar 10;27(3):237-255. Epub 2016 Nov 10.

a Dipartimento di Farmacia , Università degli Studi di Salerno , Fisciano , Italy.

Introduction: Oleanolic acid has been considered a good start molecule for synthetic exploitation. Thus hundreds of oleanane triterpenoids have been synthesized and patented. Also many oleanane saponins have been patented for their biological activities and possible pharmaceutical use. Areas covered: Patents reporting the biological activities of oleanane derivatives and saponins with oleanane-type aglycones were examined. Among the synthesized oleanane derivatives, the most promising seem to be 2-cyano-3,12-dioxoolean-1,9(11)-dien-28-oic acid derivatives which interfere with many pathways involved in inflammation, oxidative stress and cell proliferation. Regarding oleanane-type saponins, several patents claiming their antiproliferative activity or their possible use as adjuvants in vaccines, were reported. Expert opinion: Despite the great number of synthesized oleanane triterpenoids, only CDDO-Me entered clinical development as a possible drug for the treatment of chronic kidney disease (CKD) but a phase 3 clinical trial was terminated due to heart-related adverse effects. Further phase 2 clinical trials of CDDO-Me are in progress for the treatment of CKD and PAH (pulmonary arterial hypertension) patients without heart-related risk factors. Additional investigations leading to compounds with an improved activity/toxicity profile along with well-designed preclinical and clinical trials are needed. Regarding oleanane-type saponins, the real perspective seems to be as adjuvants in vaccines.
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http://dx.doi.org/10.1080/13543776.2017.1253680DOI Listing
March 2017

Quali-quantitative analysis of the phenolic fraction of the flowers of Corylus avellana, source of the Italian PGI product "Nocciola di Giffoni": Isolation of antioxidant diarylheptanoids.

Phytochemistry 2016 Oct 29;130:273-81. Epub 2016 Jun 29.

Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II n. 132, 84084 Fisciano, SA, Italy. Electronic address:

There is only limited information available on the chemical composition of the non-edible parts of Corylus avellana, source of the Italian PGI product "Nocciola di Giffoni" (hazelnut). An initial LC-MS profile of the methanolic extract of the male flowers of C. avellana, cultivar 'Tonda di Giffoni' led to the isolation of 12 compounds, of which the structures were elucidated by NMR spectroscopy. These were identified as three previously undescribed diarylheptanoids, named giffonins Q-S, along with nine known compounds. Furthermore, the quantitative determination of the main compounds occurring in the methanolic extract of C. avellana flowers was carried out by an analytical approach based on LC-ESI(QqQ)MS, using the Multiple Reaction Monitoring (MRM) experiment. In order to explore the antioxidant ability of C. avellana flowers, the methanolic extract and the isolated compounds were evaluated for their inhibitory effects on human plasma lipid peroxidation induced by H2O2 and H2O2/Fe(2+), by measuring the concentration of TBARS.
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http://dx.doi.org/10.1016/j.phytochem.2016.06.007DOI Listing
October 2016

Phenolic Compounds from the Fruits of Medemia argun, a Food and Medicinal Plant of Ancient Egypt.

Nat Prod Commun 2016 Mar;11(3):279-82

Medemia argun is a mysterious and little known monotypic fan palm from the Nubian Desert Oases of southern Egypt and northern Sudan. Its fruits have been found in the tombs from the 5th Dynasty (ca. 2500 BC) to Roman times (6-7th century AD), including the celebrated tomb of Tutankhamun. In ancient Egypt, the fruits of this palm were widely distributed and were highly valued, as confirmed by their frequent occurrence in offerings in the tombs. In order to elucidate the chemical composition of the phenolic fraction, phytochemical investigation of the BuOH extract of fruits was carried out to afford eight compounds (1-8), among which was the new 2,4-dihydroxy-6-methylacetophenone 2-0-β-D-glucopyranoside (1). With the aim to investigate if the high shelf life of M argun fruits could be related to the occurrence of antioxidant principles that were able to prevent oxidative reactions, the evaluation was carried out of the in vitro antioxidant activity by Trolox equivalent antioxidant capacity (TEAC) assay of the extract and isolated compounds.
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March 2016

Antioxidant activity, cytotoxic activity and metabolic profiling of juices obtained from saffron (Crocus sativus L.) floral by-products.

Food Chem 2016 May 26;199:18-27. Epub 2015 Nov 26.

Department of Pharmacy, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano (SA), Italy.

Juices obtained from cold-pressed saffron (Crocus sativus L.) floral by-products were evaluated as a potential source of compounds with antioxidant and cytotoxic activities. Floral by-products were split in two batches for extraction 24 and 48h after flower harvesting, respectively. The in vitro anti-oxidant activity of these extracts was tested using the FRAP and DPPH assays, and two biological models of lipid oxidation (activity in preventing cholesterol degradation and protection against Cu(2+)-mediated degradation of the liposomal unsaturated fatty acids). The cytotoxic activity was evaluated using the MTT assay. The results show that extracts obtained 48h post-harvest contained higher levels of total polar phenols and had the highest antioxidant activity in all of the performed assays. The LC-DAD and LC-ESI-(HR)MS(n) metabolic profiles showed high levels of kaempferol derivatives and anthocyanins. This study suggests that juices from saffron floral by-products could potentially be used to develop new products for the food and health industry.
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http://dx.doi.org/10.1016/j.foodchem.2015.11.115DOI Listing
May 2016

Giffonins J-P, Highly Hydroxylated Cyclized Diarylheptanoids from the Leaves of Corylus avellana Cultivar "Tonda di Giffoni".

J Nat Prod 2015 Dec 25;78(12):2975-82. Epub 2015 Nov 25.

Dipartimento di Farmacia, Università degli Studi di Salerno , Via Giovanni Paolo II 132, 84084 Fisciano, Salerno, Italy.

Two new diaryl ether heptanoids, giffonins J and K (1 and 2), along with five new diarylheptanoids, giffonins L-P (3-7), were isolated from a methanol extract of the leaves of Corylus avellana cultivar "Tonda di Giffoni". These compounds were identified as highly hydroxylated cyclized diarylheptanoids by 1D- and 2D-NMR experiments. The relative configurations of giffonins J-P (1-7) were established by a combined QM (quantum mechanical)/NMR approach, comparing the experimental (13)C/(1)H NMR chemical shift data and the related predicted values. The cytotoxic activities of giffonins J-P (1-7) were evaluated against the human osteosarcoma U2Os and SAOs cell lines.
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http://dx.doi.org/10.1021/acs.jnatprod.5b00695DOI Listing
December 2015

Can Small Chemical Modifications of Natural Pan-inhibitors Modulate the Biological Selectivity? The Case of Curcumin Prenylated Derivatives Acting as HDAC or mPGES-1 Inhibitors.

J Nat Prod 2015 Dec 20;78(12):2867-79. Epub 2015 Nov 20.

Department of Pharmacy, University of Salerno , Via Giovanni Paolo II 132, 84084 Fisciano (SA), Italy.

Curcumin, or diferuloylmethane, a polyphenolic molecule isolated from the rhizome of Curcuma longa, is reported to modulate multiple molecular targets involved in cancer and inflammatory processes. On the basis of its pan-inhibitory characteristics, here we show that simple chemical modifications of the curcumin scaffold can regulate its biological selectivity. In particular, the curcumin scaffold was modified with three types of substituents at positions C-1, C-8, and/or C-8' [C5 (isopentenyl, 5-8), C10 (geranyl, 9-12), and C15 (farnesyl, 13, 14)] in order to make these molecules more selective than the parent compound toward two specific targets: histone deacetylase (HDAC) and microsomal prostaglandin E2 synthase-1 (mPGES-1). From combined in silico and in vitro analyses, three selective inhibitors by proper substitution at position 8 were revealed. Compound 13 has improved HDAC inhibitory activity and selectivity with respect to the parent compound, while 5 and 9 block the mPGES-1 enzyme. We hypothesize about the covalent interaction of curcumin, 5, and 9 with the mPGES-1 binding site.
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http://dx.doi.org/10.1021/acs.jnatprod.5b00700DOI Listing
December 2015

Steviol glycosides targeted analysis in leaves of Stevia rebaudiana (Bertoni) from plants cultivated under chilling stress conditions.

Food Chem 2016 Jan 29;190:572-580. Epub 2015 May 29.

Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, via Giovanni Paolo II, 132, 84084 Fisciano, SA, Italy. Electronic address:

Stevia rebaudiana is an important agricultural crop for the production of a high-potency natural sweetener, sensitive to low temperature during the developmental stage. Stimulation of chilling stress with a pre-treatment with endogenous signalling components and in particular with salicylic acid (SA), hydrogen peroxide (H2O2), 6-benzylaminopurine (BAP) and calcium chloride (CaCl2) could induce tolerance to chilling and could constitute a suitable way to maintain quality and quantity of steviol glycosides under controlled artificial environment. In the present work the effects of different putative signalling molecules on the morpho-physiological parameters were evaluated, and a specific method for the quali-quantitative analysis of steviol glycosides in S. rebaudiana plants cultivated under controlled conditions was developed, by using LC-ESI-FT (Orbitrap) MS, LC-ESI-QqQ-MS/MS and multivariate data analysis. This approach underlined that the pre-treatment has influence on the production of secondary metabolites. In particular Stevia plants characterised by higher contents of rebaudioside A and stevioside, were identified.
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http://dx.doi.org/10.1016/j.foodchem.2015.05.116DOI Listing
January 2016

Structure and cytotoxic activity of sesquiterpene glycoside esters from Calendula officinalis L.: Studies on the conformation of viridiflorol.

Phytochemistry 2015 Sep 7;117:1-9. Epub 2015 Jun 7.

Laboratory of Pharmacognosy, Department of Pharmacological and Biomolecular Sciences, Università degli Studi di Milano, 20133 Milan, Italy.

Topic applications of Calendula officinalis L. lipophilic extracts are used in phytotherapy to relieve skin inflammatory conditions whereas infusions are used as a remedy for gastric complaints. Such a different usage might be explained by some cytotoxicity of lipophilic extracts at gastric level but little is known about this. Therefore, we screened the CH2Cl2 extract from the flowers of C. officinalis by MTT and LDH assays in human epithelial gastric cells AGS. This bioassay-oriented approach led to the isolation of several sesquiterpene glycosides which were structurally characterized by spectroscopic measurements, chemical reactions and MM calculations. The conformational preferences of viridiflorol fucoside were established and a previously assigned stereochemistry was revised. The compounds 1a, 2a and 3f showed comparably high cytotoxicity in the MTT assays, whereas the effect on LDH release was lower. Our study provides new insights on the composition of C. officinalis extracts of medium polarity and identifies the main compounds that could be responsible for cytotoxic effects at gastric level.
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http://dx.doi.org/10.1016/j.phytochem.2015.05.005DOI Listing
September 2015

Medicinal plants in the treatment of women's disorders: Analytical strategies to assure quality, safety and efficacy.

J Pharm Biomed Anal 2015 Sep 28;113:189-211. Epub 2015 Mar 28.

Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II n. 132, 84084 Fisciano (SA), Italy. Electronic address:

During last decades an increasing number of herbal products specifically targeting women's disorders has appeared in the worldwide marketplace. This growth highlights the need for a critical evaluation of quality, safety and efficacy of these products. Analytical techniques applied to the quality control of the main medicinal plants used for women health (relief of menopause and menstrual related symptoms) have been reviewed. Thanks to the innovation in analytical technology, identification and detection of secondary metabolites dramatically improved. In particular, hyphenated techniques have proved to be the most suitable for the rapid identification of compounds in plant matrix. Moreover, taking into account that differences in sample quality are not only found in the main compounds or in the chemical markers but also in the low-concentration compounds, fingerprint analysis might be a simple way for identification and quality control of herbal products containing a large number of low amounts of unknown compounds. Furthermore in several papers the informations obtained from the analysis of a plant have been processed by statistical elaborations. Medicinal plants here discussed are classified on the basis of the chemical markers used for their quality control.
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http://dx.doi.org/10.1016/j.jpba.2015.03.020DOI Listing
September 2015

Giffonins A-I, antioxidant cyclized diarylheptanoids from the leaves of the hazelnut tree (Corylus avellana), source of the Italian PGI product "Nocciola di Giffoni".

J Nat Prod 2015 Jan 24;78(1):17-25. Epub 2014 Nov 24.

Dipartimento di Farmacia, Università degli Studi di Salerno , Via Giovanni Paolo II n. 132, 84084 Fisciano, Salerno, Italy.

Eight new diaryl ether heptanoids, giffonins A-H (1-8), and one diaryl heptanoid, giffonin I (9), were isolated from the methanol extract of the leaves of Corylus avellana. Its hazelnut is the PGI product of the Campania region (Italy) known as "Nocciola di Giffoni". The MeOH extract of C. avellana leaves and giffonins A-I (1-9) were evaluated for their inhibitory effects on human plasma lipid peroxidation induced by H2O2 and H2O2/Fe(2+), by measuring the concentration of TBARS (thiobarbituric acid reactive substances). Compounds 4 and 8 at 10 μM reduced both H2O2- and H2O2/Fe(2+)-induced lipid peroxidation by more than 60% and 50%, respectively, indicating higher activity than curcumin used as reference compound.
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http://dx.doi.org/10.1021/np5004966DOI Listing
January 2015

Metabolic profiling of Vitex agnus castus leaves, fruits and sprouts: analysis by LC/ESI/(QqQ)MS and (HR) LC/ESI/(Orbitrap)/MS n.

J Pharm Biomed Anal 2015 Jan 28;102:215-21. Epub 2014 Sep 28.

Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II, 84084 Fisciano, Salerno, Italy. Electronic address:

Food supplements based on Vitex agnus castus L. (Verbenaceae) fruits, also known as chasteberry, are routinely used by women against somatic and psychic premenstrual symptoms such as depression, sadness or irritability. With the aim of highlighting the differences in the chemical profiles of cultivated fruits and different parts of wild plants (fruits, leaves and sprouts) of V. agnus castus, a method concerning with the quali-quantitative study of the derived hydroalcoholic extracts was carried out by using high-performance liquid chromatography coupled to electrospray negative ionization Orbitrap multicollisional high resolution mass spectrometry (LC/ESI/(Orbitrap)MS(n)) and high-performance liquid chromatography coupled to electrospray negative ionization triple quadrupole tandem mass spectrometry (LC/ESI/(QqQ)MS) in multiple reaction monitoring (MRM) mode.
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http://dx.doi.org/10.1016/j.jpba.2014.09.018DOI Listing
January 2015
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