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1.
Inflammopharmacology ; 31(5): 2505-2519, 2023 Oct.
Article in English | MEDLINE | ID: mdl-37639162

ABSTRACT

The aim of this work was to evaluate the anti-inflammatory and antioxidant effects of ethyl acetate extract obtained from the leaves of Brazilian peppertree Schinus terebinthifolius Raddi (EAELSt). Total phenols and flavonoids, chemical constituents, in vitro antioxidant activity (DPPH and lipoperoxidation assays), and cytotoxicity in L929 fibroblasts were determined. In vivo anti-inflammatory and antioxidant properties were evaluated using TPA-induced ear inflammation model in mice. Phenol and flavonoid contents were 19.2 ± 0.4 and 93.8 ± 5.2 of gallic acid or quercetin equivalents/g, respectively. LC-MS analysis identified 43 compounds, of which myricetin-O-pentoside and quercetin-O-rhamnoside were major peaks of chromatogram. Incubation with EAELSt decreased the amount of DPPH radical (EC50 of 54.5 ± 2.4 µg/mL) and lipoperoxidation at 200-500 µg/mL. The incubation with EAELSt did not change fibroblast viability up to 100 µg/mL. Topical treatment with EAELSt significantly reduced edema and myeloperoxidase activity at 0.3, 1, and 3 mg/ear when compared to the vehicle-treated group. In addition, EAELSt decreased IL-6 and TNF-α levels and increased IL-10 levels. Besides, it modulated markers of oxidative stress (reduced total hydroperoxides and increased sulfhydryl contents and ferrium reduction potential) and increased the activity of catalase and superoxide dismutase, without altering GPx activity.


Subject(s)
Anacardiaceae , Antioxidants , Mice , Animals , Antioxidants/pharmacology , Antioxidants/chemistry , Schinus , Quercetin , Brazil , Anacardiaceae/chemistry , Plant Extracts/chemistry , Anti-Inflammatory Agents/pharmacology , Plant Leaves/chemistry
2.
J Pharm Biomed Anal ; 218: 114835, 2022 Sep 05.
Article in English | MEDLINE | ID: mdl-35659659

ABSTRACT

Mangosteen (Garcinia mangostana L.), known as "the queen of fruits", is one of the most praised tropical fruit due to its delicious taste. In the last years, the use of mangosteen in functional products has been increasing, mainly in food beverages and nutraceutical formulations due to its biological activities related to the content of xanthones. The quantitative Nuclear Magnetic Resonance (qNMR) analysis, a rapid and accurate method used for simultaneous quantification of plant metabolites, was here employed to determine the amount of bioactive xanthones in the extracts of G. mangostana arils and shells obtained by using solvent of increasing polarity along with ''eco-friendly'' solvents like ethanol and ethanol-water. Furthermore, the content of xanthones was compared with that occurring in four selected commercial food supplements, among which tablets and capsules, and two fruit juices, based on mangosteen. Quantitative results highlighted a significant variability: the extracts of the shells displayed a higher amount of bioactive xanthones than those of the arils, in particular, of γ-mangostin and α-mangostin, while ß-mangostin, demethylcalabaxanthone, mangostanin, 8-deoxygartanin occurred in higher amounts in arils. A certain variability in the amount of biologically active xanthones (i.e. α-mangostin and γ-mangostin) could be observed in commercial food supplements.


Subject(s)
Garcinia mangostana , Xanthones , Dietary Supplements/analysis , Ethanol/analysis , Fruit/chemistry , Garcinia mangostana/chemistry , Garcinia mangostana/metabolism , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Solvents/analysis , Xanthones/analysis
3.
Molecules ; 27(10)2022 May 22.
Article in English | MEDLINE | ID: mdl-35630805

ABSTRACT

Globe artichoke (Cynara cardunculus L. var. scolymus L.), is a perennial plant widely cultivated in the Mediterranean area, known for its edible part named capitula or heads. Its functional properties are related to its high levels of polyphenolic compounds and inulin. "Carciofo di Paestum", an Italian traditional cultivar, is a labeled PGI (Protected Geographical Indication) product of the Campania region, representing an important economic resource. So far, a few chemical investigations were performed on this cultivar, mainly focused on the analysis of methanol extracts. Due to the increasing use of food supplements, in this study, a comprehensive analysis of green extracts of "Carciofo di Paestum" PGI heads was performed. EtOH, EtOH: H2O (80:20, 70:30, 60:40) extracts, as well as infusions and decoctions prepared according to Pharmacopeia XII were analyzed by LC-ESI/QExactive/MS/MS. A total of 17 compounds corresponding to caffeoylquinic acid derivatives, phenolics, flavonoids, and terpenoids were identified. The extracts were further submitted to NMR analysis to highlight the occurrence of primary metabolites. Both LCMS and NMR data were analyzed by Principal Component Analysis (PCA), showing significant differences among the extraction methods. Moreover, 5-caffeoylquinic acid and 1,5-dicaffeoylquinic acid were quantified in the extracts by LC-ESI/QTrap/MS/MS using the Multiple Reaction Monitoring (MRM) method. Furthermore, the phenolic content, antioxidant activity, and α-glucosidase inhibitory activity of C. cardunculus var. scolymus "Carciofo di Paestum" extracts were evaluated.


Subject(s)
Cynara scolymus , Scolymus , Cynara scolymus/chemistry , Metabolomics , Phenols/analysis , Plant Extracts/chemistry , Proton Magnetic Resonance Spectroscopy , Tandem Mass Spectrometry/methods
4.
Molecules ; 26(17)2021 Aug 29.
Article in English | MEDLINE | ID: mdl-34500668

ABSTRACT

Pouteria lucuma 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 Pouteria lucuma, 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.


Subject(s)
Antioxidants/chemistry , Flavonoids/chemistry , Plant Extracts/chemistry , Pouteria/chemistry , Magnetic Resonance Spectroscopy , Tandem Mass Spectrometry
5.
Antioxidants (Basel) ; 10(2)2021 Feb 11.
Article in English | MEDLINE | ID: mdl-33670426

ABSTRACT

The Italian "Marrone di Roccadaspide" (Castanea sativa), 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 C. sativa, 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.

6.
J Nat Prod ; 84(3): 646-653, 2021 03 26.
Article in English | MEDLINE | ID: mdl-33616390

ABSTRACT

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 Corylus avellana leaves was perfomed. Analysis by LC-ESI/LTQOrbitrap/MS/MSn guided the isolation of two new diarylheptanoid derivatives, giffonins W (1) and X (2). The structures 1 and 2 were assigned by analysis of NMR data combined with a QM (quantum mechanical)/NMR approach. The absolute configurations of 1 and 2 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.


Subject(s)
Antioxidants/pharmacology , Corylus/chemistry , Diarylheptanoids/pharmacology , Lipid Peroxidation/drug effects , Antioxidants/isolation & purification , Blood Proteins , Diarylheptanoids/isolation & purification , Humans , Italy , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Leaves/chemistry
7.
J Pharm Biomed Anal ; 190: 113518, 2020 Oct 25.
Article in English | MEDLINE | ID: mdl-32798920

ABSTRACT

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:H2O solution were also employed for extractions, resulting selective for flavonoids and proanthocyanidins, while cyanogenic glycosides were mainly detected in EtOH:H2O 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.


Subject(s)
Antioxidants , Prunus dulcis , Antioxidants/analysis , Flavonoids , Italy , Seeds/chemistry , Tandem Mass Spectrometry , Water
8.
Food Res Int ; 129: 108787, 2020 03.
Article in English | MEDLINE | ID: mdl-32036927

ABSTRACT

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/MSn 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:H2O 7:3) was finally evaluated, showing a high superimposability of the EtOH:H2O (7:3) extract to the MeOH extract.


Subject(s)
Antioxidants/analysis , Nuts/chemistry , Rationalization , Tannins/analysis , Calibration , Cell Proliferation , Ellagic Acid/analysis , Evaluation Studies as Topic , Fagaceae/chemistry , Flavonoids/analysis , Glucosides/analysis , Humans , Hydrolyzable Tannins/analysis , Italy , NF-kappa B/metabolism , Phenols/analysis , Plant Extracts/analysis , Proanthocyanidins/analysis , Reactive Oxygen Species , Tandem Mass Spectrometry , Triterpenes/analysis
9.
Phytochem Anal ; 30(4): 415-423, 2019 Jul.
Article in English | MEDLINE | ID: mdl-30762260

ABSTRACT

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.


Subject(s)
Antioxidants/analysis , Flavonoids/analysis , Phenols/analysis , Phytochemicals/analysis , Plant Extracts/chemistry , Prunus dulcis/chemistry , Chromatography, Liquid , Free Radical Scavengers/analysis , Magnetic Resonance Spectroscopy , Plant Extracts/isolation & purification , Seeds/chemistry , Spectrometry, Mass, Electrospray Ionization , Tandem Mass Spectrometry
10.
J Nat Prod ; 82(1): 74-79, 2019 01 25.
Article in English | MEDLINE | ID: mdl-30629433

ABSTRACT

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 IC50 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.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Apocynaceae/chemistry , Cardenolides/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cardenolides/chemistry , Cardenolides/pharmacology , Cell Cycle/drug effects , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Plant Components, Aerial/chemistry
11.
Phytochemistry ; 159: 148-158, 2019 Mar.
Article in English | MEDLINE | ID: mdl-30616145

ABSTRACT

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.


Subject(s)
Chromatography, High Pressure Liquid/methods , Phytochemicals/analysis , Plant Extracts/chemistry , Plant Leaves/chemistry , Spectrum Analysis/methods , Ziziphus/chemistry , A549 Cells , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Methanol/chemistry , Plant Extracts/pharmacology
12.
Food Chem ; 269: 125-135, 2018 Dec 15.
Article in English | MEDLINE | ID: mdl-30100414

ABSTRACT

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/MSn) 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.


Subject(s)
Corylus/chemistry , Lipids/analysis , Tandem Mass Spectrometry/methods , Corylus/metabolism , Food Analysis , Italy , Nuts
13.
J Pharm Biomed Anal ; 160: 168-178, 2018 Oct 25.
Article in English | MEDLINE | ID: mdl-30096647

ABSTRACT

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 1H 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.


Subject(s)
Corylus/metabolism , Free Radical Scavengers/analysis , Green Chemistry Technology/methods , Phenols/analysis , Plant Extracts/analysis , Corylus/chemistry , Free Radical Scavengers/pharmacology , Humans , Metabolomics/methods , Nuclear Magnetic Resonance, Biomolecular/methods , Phenols/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Proton Magnetic Resonance Spectroscopy/methods , Pyocyanine/pharmacology , Reactive Oxygen Species/metabolism , THP-1 Cells
14.
J Pharm Biomed Anal ; 158: 54-65, 2018 Sep 05.
Article in English | MEDLINE | ID: mdl-29860179

ABSTRACT

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.


Subject(s)
Free Radical Scavengers/pharmacology , Green Chemistry Technology/methods , Plant Extracts/pharmacology , Prunus dulcis/chemistry , Chemistry, Pharmaceutical/instrumentation , Chemistry, Pharmaceutical/methods , Chromatography, High Pressure Liquid/instrumentation , Chromatography, High Pressure Liquid/methods , Free Radical Scavengers/chemistry , Free Radical Scavengers/isolation & purification , Green Chemistry Technology/instrumentation , Italy , Magnetic Resonance Spectroscopy/instrumentation , Magnetic Resonance Spectroscopy/methods , Metabolomics/instrumentation , Metabolomics/methods , Phenols/analysis , Plant Extracts/analysis , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/chemistry , Plant Leaves/metabolism , Prunus dulcis/metabolism , Tandem Mass Spectrometry/instrumentation , Tandem Mass Spectrometry/methods
15.
Food Chem ; 248: 128-136, 2018 May 15.
Article in English | MEDLINE | ID: mdl-29329835

ABSTRACT

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-ß-d-glucopyranoside (4) and 7,5'-dihydroxy-6,3'-dimethoxy-isoflavone-7-O-(7,8-dihydro-p-hydroxycinnamoyl)-ß-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.


Subject(s)
Glycyrrhiza/chemistry , Isoflavones/chemistry , Plant Roots/chemistry , Chromatography, High Pressure Liquid , Iran , Isoflavones/analysis , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Extracts/chemistry , Saponins/analysis , Saponins/chemistry , Spectrometry, Mass, Electrospray Ionization
16.
Curr Med Chem ; 25(37): 4888-4902, 2018.
Article in English | MEDLINE | ID: mdl-27924727

ABSTRACT

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.


Subject(s)
Fruit/metabolism , Functional Food , Metabolomics , Biomarkers/metabolism , Body Fluids/metabolism , Database Management Systems , Databases, Factual , Food Handling , Fruit/chemistry , Fruit/classification , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Oxidative Stress
17.
Chem Biol Interact ; 279: 43-50, 2018 Jan 05.
Article in English | MEDLINE | ID: mdl-29126784

ABSTRACT

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-3ß,11ß,26-triol 26-O-ß-d-glucopyranoside (5), 20-hydroxyecdysone (6), and 3ß,5ß,14ß-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.


Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Apoptosis/drug effects , Cell Survival/drug effects , Heat-Shock Proteins/metabolism , Helleborus/chemistry , Steroids/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Down-Regulation , Endoplasmic Reticulum Chaperone BiP , Gene Expression Regulation/drug effects , Heat-Shock Proteins/genetics , Humans , Plant Roots/chemistry , Rhizome/chemistry , Steroids/chemistry
18.
J Pharm Biomed Anal ; 150: 233-240, 2018 Feb 20.
Article in English | MEDLINE | ID: mdl-29253779

ABSTRACT

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.


Subject(s)
Antioxidants/analysis , Chromatography, High Pressure Liquid , Fragaria/metabolism , Metabolomics/methods , Plant Extracts/analysis , Plant Leaves/metabolism , Spectrometry, Mass, Electrospray Ionization , Tandem Mass Spectrometry , Fragaria/growth & development , Humans , Italy , Least-Squares Analysis , Multivariate Analysis , Phytotherapy , Plant Leaves/growth & development , Plants, Medicinal , Principal Component Analysis
19.
Food Res Int ; 101: 180-187, 2017 11.
Article in English | MEDLINE | ID: mdl-28941682

ABSTRACT

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.


Subject(s)
Antioxidants/analysis , Chromatography, Liquid/methods , Corylus/chemistry , Phenols/analysis , Tandem Mass Spectrometry/methods , A549 Cells , Antioxidants/isolation & purification , Biphenyl Compounds/analysis , Cell Line/drug effects , Cell Survival/drug effects , Free Radical Scavengers , HeLa Cells/drug effects , Humans , Italy , Phenols/isolation & purification , Phytochemicals/analysis , Picrates/analysis , Plant Extracts/chemistry , Plant Extracts/isolation & purification
20.
Phytochemistry ; 140: 45-51, 2017 Aug.
Article in English | MEDLINE | ID: mdl-28448799

ABSTRACT

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-ESIMSn 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 (1H, 13C, 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.


Subject(s)
Anacardiaceae/chemistry , Antioxidants/chemistry , Phenols/chemistry , A549 Cells , Antioxidants/isolation & purification , Brazil , Chromatography, Liquid , HeLa Cells , Humans , Mass Spectrometry , Phenols/isolation & purification , Plant Bark/chemistry , Plant Extracts/chemistry
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