Stazione Sperimentale per le Industrie Delle Essenze e Dei Derivati Dagli Agrumi SSEA

Reggio Calabria, Italy

Stazione Sperimentale per le Industrie Delle Essenze e Dei Derivati Dagli Agrumi SSEA

Reggio Calabria, Italy
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Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Balestrieri M.L.,The Second University of Naples | Ferrari G.,University of Salerno | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2012

The presence of pipecolic acid and pipecolic acid betaine, also known as homostachydrine, is herein reported for the first time in Citrus genus plants. Homostachydrine was found in fruits, seeds, and leaves of orange, lemon, and bergamot (Citrus bergamia Risso et Poit). As homostachydrine was not commercially available, as a comparative source, extracts of alfalfa leaves (Medicago sativa L.) were used, in which homostachydrine is present at high concentration. Then, the results where confirmed by comparison with an authentic standard synthesized and purified starting from pipecolic acid. The synthesized standard was characterized by a ESI-MS/MS study using a 3D ion-trap mass spectrometer. When subjected to MS/MS fragmentation in positive ion mode, homostachydrine, unlike its lower homologue proline betaine (also known as stachydrine), showed a pattern of numerous ionic fragments that allowed unambiguous identification of the compound. For the quantitation in the plant sources, high sensitivity and specificity were achieved by monitoring the transition (158→72), which is absent in the fragmentation patterns of other major osmolytes commonly used as markers for studies of abiotic stress. As for the metabolic origin of homostachydrine, the occurrence in citrus plants of pipecolic acid leads to the hypothesis that it could act as a homostachydrine precursor through direct methylation. © 2011 American Chemical Society.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Cautela D.,Stazione Sperimentale per le Industrie Delle Essenze e Dei Derivati Dagli Agrumi SSEA | Castaldo D.,Ministero Dello Sviluppo Economico MiSE | And 2 more authors.
Nitric Oxide - Biology and Chemistry | Year: 2013

Endogenous methylarginines, NG,NG-dimethyl-l-arginine (asymmetric dimethylarginine, ADMA), NG-N′G- dimethyl-l-arginine (symmetric dimethylarginine; SDMA), and N G-monomethyl-l-arginine (monomethylarginine; NMMA) are supposed to be produced in human body through the methylation of protein arginine residues by protein arginine methyltransferases (PRMT) and released during proteolysis of the methylated proteins. Micromolar concentration of ADMA and NMMA can compete with arginine for nitric oxide synthase (NOS) reducing nitric oxide (NO) formation, whereas SDMA does not. Indeed, increased ADMA and SDMA plasma levels or a decreased arginine/ADMA ratio is related with risk factors for chronic kidney disease and cardiovascular disease. To the best of our knowledge the exogenous presence of methylarginines, like that in fruits and vegetables, has never been described so far. Here, we report the finding that methylarginines are ubiquitous in vegetables which represent an important part of human daily diet. Some of these vegetables contain discrete amounts of ADMA, SDMA, and NMMA. Specifically, among the vegetables examined, soybean, rye, sweet pepper, broad bean, and potato contain the highest ADMA and NMMA mean levels. Our results establish that the three methylarginines, in addition to being produced endogenously, can also be taken daily through the diet in conspicuous amounts. We propose that the contribution of the methylarginines contained in the vegetables of daily diet should be taken into account when the association between vegetable assumption and their levels is evaluated in clinical studies. Furthermore, a comprehensive understanding on the role of the digestive breakdown process and intestinal absorption grade of the methylarginines contained in vegetables is now needed. © 2013 Elsevier Inc. All rights reserved.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Balestrieri M.L.,The Second University of Naples | Cautela D.,Stazione Sperimentale per le Industrie Delle Essenze e Dei Derivati Dagli Agrumi SSEA | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2012

The occurrence of N-methylated tryptamine derivatives in bergamot plant (Citrus bergamia Risso et Poit) is reported for the first time. Interestingly, the most abundant of these substances is N,N,N-trimethyltryptamine, which has not been previously identified in any citrus plant. The N-methylated tryptamine derivatives were identified and quantitated in leaves, peel, juice, and seeds by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. N,N,N-Trimethyltryptamine was confirmed by MS3 and comparison with the synthesized authentic standard. In addition, the study of the distribution of tryptophan, tryptamine, N-methyltryptamine, N,N-dimethyltryptamine, and N,N,N-trimethyltryptamine indicated that these compounds are differently expressed in the various tissues of the bergamot plant. Intriguingly, chemically synthesized N,N,N-trimethyltryptamine was reported to possess nicotine-like activity being a stimulant of parasympathetic ganglia by exerting its action on acetylcholine receptors. On this basis, the identification of N,N,N-trimethyltryptamine at a relatively high level in leaves suggests a possible role in a physiological mechanism of plant defense. © 2012 American Chemical Society.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Balestrieri M.L.,The Second University of Naples | Casale R.,The Second University of Naples | And 3 more authors.
Journal of Agricultural and Food Chemistry | Year: 2013

The occurrence and distribution in Citrus genus plants of N-methylated derivatives of tryptamine and their 5-hydroxylated forms are reported. Tryptamine, N-methyltryptamine, N,N-dimethyltryptamine, N,N,N- trimethyltryptamine, 5-hydroxytryptamine (serotonin), 5-hydroxy-N- methyltryptamine, 5-hydroxy-N,N-dimethyltryptamine (bufotenine), and 5-hydroxy-N,N,N-trimethyltryptamine (bufotenidine) were quantitated by LC-ESI-MS/MS. Leaves of all citrus plants examined contained N,N,N-trimethyltryptamine, a compound that we first discovered in the bergamot plant. Interestingly, we also found out that all plants examined contained 5-hydroxy-N,N-dimethyltryptamine and 5-hydroxy-N,N,N-trimethyltryptamine, compounds never described so far in the Citrus genus. As N,N,N- trimethyltryptamine and 5-hydroxy-N,N,N-trimethyltryptamine possess nicotine-like activity by exerting their action on acetylcholine receptors, it is conceivable that both represent the arrival point of a biosynthetic pathway aimed to provide Citrus plants with chemical defense against aggressors. This hypothesis is supported by our finding that leaves and seeds, which are more frequently attacked by biotic agents, are the parts of the plant where the highest levels of those compounds were found. © 2013 American Chemical Society.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Balestrieri M.L.,The Second University of Naples | Bata-Csere A.,The Second University of Naples | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2011

Numerous compounds, many of them osmolytes, were quantified in natural juices and in frozen concentrate juices from fruits of plants of the Citrus genus. l-Proline, N-methyl-l-proline (hygric acid), N,N-dimethyl-l-proline (stachydrine), 4-hydroxy-l-prolinebetaine (betonicine), 4-hydroxy-l-proline, γ-aminobutyric acid (Gaba), 3-carboxypropyltrimethylammonium (GabaBet), N-methylnicotinic acid (trigonelline), and choline in the fruit juices of yellow orange, blood orange, lemon, mandarin, bitter orange (Citrus aurantium), chinotto (Citrus myrtifolia), and grapefruit were analyzed by sensitive HPLC-ESI-tandem mass spectrometry procedure. It was found that the most represented osmolytes in the juices, that is, l-proline, stachydrine, and betonicine, can be quantified with minimal sample preparation and short analysis time (about 1 min) also by flow injection analysis (FIA) ESI-MS/MS with the same results as obtained by HPLC ESI-MS/MS. In all of the juices, discrete amounts of choline and trigonelline were present. Conversely, GabaBet was always below detection limits. Notably, N-methyl-l-proline and 4-hydroxy-l- prolinebetaine, which were discovered for the first time in the juice of bergamot (Citrus bergamia Risso et Poit), are also present in all of the citrus juices examined. © 2011 American Chemical Society.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Cautela D.,Stazione Sperimentale Per le Industrie Delle Essenze e dei Derivati Dagli Agrumi SSEA | Castaldo D.,University of Salerno | Balestrieri M.L.,The Second University of Naples
PLoS ONE | Year: 2014

Nε-trimethyllysine (TML) is a non-protein amino acid which takes part in the biosynthesis of carnitine. In mammals, the breakdown of endogenous proteins containing TML residues is recognized as starting point for the carnitine biosynthesis. Here, we document that one of the main sources of TML could be the vegetables which represent an important part of daily alimentation for most mammals. A HPLC-ESI-MS/MS method, which we previously developed for the analysis of NG-methylarginines, was utilized to quantitate TML in numerous vegetables. We report that TML, believed to be rather rare in plants as free amino acid, is, instead, ubiquitous in them and at not negligible levels. The occurrence of TML has been also confirmed in some vegetables by a HPLC method with fluorescence detection. Our results establish that TML can be introduced as free amino acid in conspicuous amounts from vegetables. The current opinion is that mammals utilize the breakdown of their endogenous proteins containing TML residues as starting point for carnitine biosynthesis. However, our finding raises the question of whether a tortuous and energy expensive route as the one of TML formation from the breakdown of endogenous proteins is really preferred when the substance is so easily available in vegetable foods. On the basis of this result, it must be taken into account that in mammals TML might be mainly introduced by diet. However, when the alimentary intake becomes insufficient, as during starvation, it might be supplied by endogenous protein breakdown. © 2014 Servillo et al.


PubMed | University of Salerno, The Second University of Naples and Stazione Sperimentale per le Industrie delle Essenze e dei derivati dagli Agrumi SSEA
Type: | Journal: Food chemistry | Year: 2016

The occurrence of pipecolic acid betaine (homostachydrine) and its biosynthetic precursor N-methylpipecolic acid was detected for the first time in green coffee beans of Robusta and Arabica species. The analyses were conducted by HPLC-ESI tandem mass spectrometry and the metabolites identified by product ion spectra and comparison with authentic standards. N-methylpipecolic acid was found at similar levels in green coffee beans of Robusta and Arabica, whereas a noticeable difference of homostachydrine content was observed between the two green coffee bean species. Interestingly, homostachydrine content was found to be unaffected by coffee bean roasting treatment because of a noticeable heat stability, a feature that makes this compound a candidate marker to determine the content of Robusta and Arabica species in roasted coffee blends. To this end, a number of certified pure Arabica and Robusta green beans were analyzed for their homostachydrine content. Results showed that homostachydrine content was 1.50.5mg/kg in Arabica beans and 31.010.0mg/kg in Robusta beans. Finally, to further support the suitability of homostachydrine as quality marker of roasted blends of Arabica and Robusta coffee beans, commercial samples of roasted ground coffee blends were analyzed and the correspondence between the derived percentages of Arabica and Robusta beans with those declared on packages by manufacturers was verified.


Servillo L.,The Second University of Naples | D'Onofrio N.,The Second University of Naples | Longobardi L.,University of North Carolina at Chapel Hill | Sirangelo I.,The Second University of Naples | And 6 more authors.
Journal of Cellular Biochemistry | Year: 2013

Hyperglycaemia, a characteristic feature of diabetes mellitus, induces endothelial dysfunction and vascular complications by accelerating endothelial cell (EC) senescence and limiting the proliferative potential of these cells. Here we aimed to investigate the effect of stachydrine, a proline betaine present in considerable quantities in juices from fruits of the Citrus genus, on EC under high-glucose stimulation, and its underlying mechanism. The senescence model of EC was set up by treating cells with high-glucose (30 mM) for different times. Dose-dependent (0.001-1 mM) evaluation of cell viability revealed that stachydrine does not affect cell proliferation with a similar trend up to 72 h. Noticeable, stachydrine (0.1 mM) significantly attenuated the high-glucose induced EC growth arrest and senescence. Indeed, co-treatment with high-glucose and stachydrine for 48 h kept the percentage of EC in the G 0/G1 cell cycle phase near to control values and significantly reduced cell senescence. Western blot analysis and confocal-laser scanning microscopy revealed that stachydrine also blocked the high-glucose induced upregulation of p16INK4A and downregulation of SIRT1 expression and enzyme activity. Taken together, results here presented are the first evidence that stachydrine, a naturally occurring compound abundant in citrus fruit juices, inhibits the deleterious effect of high-glucose on EC and acts through the modulation of SIRT1 pathway. These results may open new prospective in the identification of stachydrine as an important component of healthier eating patterns in prevention of cardiovascular diseases. © 2013 Wiley Periodicals, Inc.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | Casale R.,The Second University of Naples | Cautela D.,Stazione Sperimentale per le Industrie delle Essenze e dei derivati dagli Agrumi SSEA | And 3 more authors.
LWT - Food Science and Technology | Year: 2016

Green beans of Robusta and Arabica coffee species were examined by HPLC-ESI-MS2 analysis for the content of glycosylated forms of serotonin and its N-methylated derivatives. The results showed for the first time the occurrence of serotonin 5-O-β-glucoside and tryptophan-N1-glucoside in coffee beans. Both substances were identified by their product ion spectra and by comparison with synthesized authentic standards. Interestingly, serotonin 5-O-β-glucoside occurs at similar levels in beans of all varieties of Robusta and Arabica coffee species, whereas tryptophan-N1-glucoside is present at high levels in beans of Robusta and at much lower levels in those of Arabica species. This striking difference in the content of tryptophan-N1-glucoside could afford a new tool to discriminate between beans of Arabica and Robusta coffee species. © 2016 Elsevier Ltd.


Servillo L.,The Second University of Naples | Giovane A.,The Second University of Naples | D'Onofrio N.,The Second University of Naples | Casale R.,The Second University of Naples | And 3 more authors.
International Journal of Molecular Sciences | Year: 2013

NG,NG-dimethyl-L-arginine (ADMA) and NG-methyl-L-arginine (NMMA) are endogenous inhibitors of nitric oxide synthase (NOS). In contrast, NG,N'G-dimethyl-Larginine (SDMA) possesses only a weak inhibitory potency towards neuronal NOS and it is known to limit nitric oxide (NO) production by competing with L-arginine for cellular uptake. The inhibition of NOS is associated with endothelial dysfunction in cardiovascular diseases as well in chronic renal failure. L-Homoarginine (HArg), a structural analog of L-arginine (Arg), is an alternative but less efficient substrate for NOS. Besides, it inhibits arginase, leading to an increased availability of L-arginine for NOS to produce NO. However, its relation with cardiovascular disease remains unclear. To date, several analytical methods for the quantitative determination of Arg, HArg, NMMA, AMDA, and SDMA in biological samples have been described. Here, we present a simple, fast, and accurate HPLC-ESI-MS/MS method which allows both the simultaneous determination and quantification of these compounds without needing derivatization, and the possibility to easily modulate the chromatographic separation between HArg and NMMA (or between SDMA and ADMA). Data on biological samples revealed the feasibility of the method, the minimal sample preparation, and the fast run time which make this method very suitable and accurate for analysis in the basic and clinical settings. © 2013 by the authors; licensee MDPI, Basel, Switzerland.

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