Characterization of the endogenous enzymatic hydrolyses of Petroselinum crispum glycosides: Determined by chromatography upon their sugar and flavonoid products

•Identification and quantification of relevant constituents of Petroselinum crispum.•Analysis of the endogenous enzymatic hydrolysis products of fruit and leaf tissues.•Release of apiose and glucose by the stepwise endogenous enzymatic hydrolysis mechanism.•Mass fragmentation study of the apiosyl-ap...

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Veröffentlicht in:Journal of Chromatography A 2013-06, Vol.1293, p.100-106
Hauptverfasser: Boldizsár, Imre, Füzfai, Zsófia, Molnár-Perl, Ibolya
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Molnár-Perl, Ibolya
description •Identification and quantification of relevant constituents of Petroselinum crispum.•Analysis of the endogenous enzymatic hydrolysis products of fruit and leaf tissues.•Release of apiose and glucose by the stepwise endogenous enzymatic hydrolysis mechanism.•Mass fragmentation study of the apiosyl-apiose and apiosyl-glucose TMS derivatives.•Invertase enzyme activity proved to be independent of parsley tissues. The behavior of the flavonoid diglycosides, relevant constituents of parsley (Petroselinum crispum) fruit (PFr) and leaf (PLe) samples was characterized upon their enzymatic hydrolyses applying complementary liquid chromatography-ultraviolet (LC-UV) and gas chromatography mass selective (GC–MS) detections. Analyses were performed in quantitative manner, from the same extracts as a function of hydrolysis times. Both in fruit and leaf tissue extracts, in intact and in enzyme hydrolyzed ones, apigenin, chrysoeriol, their glycosides, sugars, sugar alcohols, carboxylic acids and phytosterols, in total 17 constituents were identified and quantified. Based primarily on the selective mass fragmentation properties of the trimethylsilyl (oxime) ether/ester derivatives of constituents, we confirmed several novelties to the field. (i) It was shown for the first time that in parsley tissues different types of glycosidase enzyme are active. In PFr samples, both the stepwise and disaccharide specific endogenous mechanisms were certified, quantifying simultaneously the continuous release of apigenin, chrysoeriol, 2-O-apiosyl-apiose, apiose and glucose. (ii) 2-O-Apiosyl-glucose was demonstrated as disaccharide due to its formation under derivatization conditions from parsley glycosides. (iii) Both in PFr and in PLe samples even the invertase enzyme activity was attainable: sucrose decomposition in both tissues was going on with the same intensity. Three different types of enzymatic glycosidase processes were followed with their specific hydrolysis products by means of HPLC-UV and GC–MS, simultaneously.
doi_str_mv 10.1016/j.chroma.2013.03.037
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Psychology ; Gas Chromatography-Mass Spectrometry - methods ; Gas chromatography–mass spectrometry ; glucose ; Glycoside Hydrolases - metabolism ; glycosides ; Glycosides - analysis ; Glycosides - chemistry ; Glycosides - metabolism ; high performance liquid chromatography ; hydrolysis ; leaves ; Other chromatographic methods ; Oximes - chemistry ; parsley ; Pentoses - chemistry ; Petroselinum - chemistry ; Petroselinum - enzymology ; Petroselinum crispum ; phytosterols ; Phytosterols - chemistry ; Plant Extracts - chemistry ; Plant Leaves - chemistry ; sucrose ; sugar alcohols ; tissues ; Trimethylsilyl (oxime) derivatives</subject><ispartof>Journal of Chromatography A, 2013-06, Vol.1293, p.100-106</ispartof><rights>2013 Elsevier B.V.</rights><rights>2014 INIST-CNRS</rights><rights>Copyright © 2013 Elsevier B.V. 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The behavior of the flavonoid diglycosides, relevant constituents of parsley (Petroselinum crispum) fruit (PFr) and leaf (PLe) samples was characterized upon their enzymatic hydrolyses applying complementary liquid chromatography-ultraviolet (LC-UV) and gas chromatography mass selective (GC–MS) detections. Analyses were performed in quantitative manner, from the same extracts as a function of hydrolysis times. Both in fruit and leaf tissue extracts, in intact and in enzyme hydrolyzed ones, apigenin, chrysoeriol, their glycosides, sugars, sugar alcohols, carboxylic acids and phytosterols, in total 17 constituents were identified and quantified. Based primarily on the selective mass fragmentation properties of the trimethylsilyl (oxime) ether/ester derivatives of constituents, we confirmed several novelties to the field. (i) It was shown for the first time that in parsley tissues different types of glycosidase enzyme are active. In PFr samples, both the stepwise and disaccharide specific endogenous mechanisms were certified, quantifying simultaneously the continuous release of apigenin, chrysoeriol, 2-O-apiosyl-apiose, apiose and glucose. (ii) 2-O-Apiosyl-glucose was demonstrated as disaccharide due to its formation under derivatization conditions from parsley glycosides. (iii) Both in PFr and in PLe samples even the invertase enzyme activity was attainable: sucrose decomposition in both tissues was going on with the same intensity. Three different types of enzymatic glycosidase processes were followed with their specific hydrolysis products by means of HPLC-UV and GC–MS, simultaneously.</description><subject>2-O-Apiosyl-apiose</subject><subject>2-O-Apiosyl-glucose</subject><subject>Analytical chemistry</subject><subject>apigenin</subject><subject>Aroma and flavouring agent industries</subject><subject>beta-fructofuranosidase</subject><subject>Biological and medical sciences</subject><subject>carboxylic acids</subject><subject>Chemistry</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>derivatization</subject><subject>Endogenous enzymatic hydrolysis</subject><subject>enzyme activity</subject><subject>Exact sciences and technology</subject><subject>Flavonoids</subject><subject>Flavonoids - analysis</subject><subject>Flavonoids - chemistry</subject><subject>Flavonoids - metabolism</subject><subject>Food industries</subject><subject>Fruit - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas Chromatography-Mass Spectrometry - methods</subject><subject>Gas chromatography–mass spectrometry</subject><subject>glucose</subject><subject>Glycoside Hydrolases - metabolism</subject><subject>glycosides</subject><subject>Glycosides - analysis</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - metabolism</subject><subject>high performance liquid chromatography</subject><subject>hydrolysis</subject><subject>leaves</subject><subject>Other chromatographic methods</subject><subject>Oximes - chemistry</subject><subject>parsley</subject><subject>Pentoses - chemistry</subject><subject>Petroselinum - chemistry</subject><subject>Petroselinum - enzymology</subject><subject>Petroselinum crispum</subject><subject>phytosterols</subject><subject>Phytosterols - chemistry</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Leaves - chemistry</subject><subject>sucrose</subject><subject>sugar alcohols</subject><subject>tissues</subject><subject>Trimethylsilyl (oxime) derivatives</subject><issn>0021-9673</issn><issn>1873-3778</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kd-K1TAQxoso7tnVNxDNjeBNj0mTNqdeLMhx_QMLCq7XYZpM2xzapibtQvdpfFRTetQ7YWAC-c18M_MlyQtG94yy4u1pr1vvethnlPE9XUM-SnbsIHnKpTw8TnaUZiwtC8kvkssQTpQySWX2NLnIeJFxXshd8uvYggc9obcPMFk3EFeTqUWCg3ENDm4O8fmw9PFTk3Yx3nVLwLBi33DyLmBnh7kn2tswxtx0i3bBGgzvyAeMfXs7oCHVQrZxJ9d4GNuFzGMUi0rWkzA34AkMhtQd3LvBWUNG78ysp_AseVJDF_D5OV8ldx9v7o6f09uvn74c39-mWohySmVdUgGmqKEsSjjUTIAo6jKrkGZg8qqSOdWG58xw0KWWWSFohblhBnMGnF8lb7a2UffnjGFSvQ0auw4GjDdQLM-EoCIeMKJiQ3XcPnis1ehtD35RjKrVGnVS265qtUbRNWQse3lWmKsezd-iP15E4PUZgKChqz0M2oZ_nORSlHLlXm1cDU5BE--ufnyPSnn0t2RMHiJxvREYD3Zv0augLQ4ajfWoJ2Wc_f-svwGhfr1M</recordid><startdate>20130607</startdate><enddate>20130607</enddate><creator>Boldizsár, Imre</creator><creator>Füzfai, Zsófia</creator><creator>Molnár-Perl, Ibolya</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QH</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H96</scope><scope>H97</scope><scope>L.G</scope></search><sort><creationdate>20130607</creationdate><title>Characterization of the endogenous enzymatic hydrolyses of Petroselinum crispum glycosides: Determined by chromatography upon their sugar and flavonoid products</title><author>Boldizsár, Imre ; Füzfai, Zsófia ; Molnár-Perl, Ibolya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c449t-7f904ad6fa969a8f14a46f92be02ad5bb750cd351d3ac9c72640be5d1de51a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>2-O-Apiosyl-apiose</topic><topic>2-O-Apiosyl-glucose</topic><topic>Analytical chemistry</topic><topic>apigenin</topic><topic>Aroma and flavouring agent industries</topic><topic>beta-fructofuranosidase</topic><topic>Biological and medical sciences</topic><topic>carboxylic acids</topic><topic>Chemistry</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>derivatization</topic><topic>Endogenous enzymatic hydrolysis</topic><topic>enzyme activity</topic><topic>Exact sciences and technology</topic><topic>Flavonoids</topic><topic>Flavonoids - analysis</topic><topic>Flavonoids - chemistry</topic><topic>Flavonoids - metabolism</topic><topic>Food industries</topic><topic>Fruit - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas Chromatography-Mass Spectrometry - methods</topic><topic>Gas chromatography–mass spectrometry</topic><topic>glucose</topic><topic>Glycoside Hydrolases - metabolism</topic><topic>glycosides</topic><topic>Glycosides - analysis</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - metabolism</topic><topic>high performance liquid chromatography</topic><topic>hydrolysis</topic><topic>leaves</topic><topic>Other chromatographic methods</topic><topic>Oximes - chemistry</topic><topic>parsley</topic><topic>Pentoses - chemistry</topic><topic>Petroselinum - chemistry</topic><topic>Petroselinum - enzymology</topic><topic>Petroselinum crispum</topic><topic>phytosterols</topic><topic>Phytosterols - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Leaves - chemistry</topic><topic>sucrose</topic><topic>sugar alcohols</topic><topic>tissues</topic><topic>Trimethylsilyl (oxime) derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Boldizsár, Imre</creatorcontrib><creatorcontrib>Füzfai, Zsófia</creatorcontrib><creatorcontrib>Molnár-Perl, Ibolya</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aqualine</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science &amp; Fisheries Abstracts (ASFA) 2: Ocean Technology, Policy &amp; Non-Living Resources</collection><collection>Aquatic Science &amp; Fisheries Abstracts (ASFA) 3: Aquatic Pollution &amp; Environmental Quality</collection><collection>Aquatic Science &amp; Fisheries Abstracts (ASFA) Professional</collection><jtitle>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Boldizsár, Imre</au><au>Füzfai, Zsófia</au><au>Molnár-Perl, Ibolya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of the endogenous enzymatic hydrolyses of Petroselinum crispum glycosides: Determined by chromatography upon their sugar and flavonoid products</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2013-06-07</date><risdate>2013</risdate><volume>1293</volume><spage>100</spage><epage>106</epage><pages>100-106</pages><issn>0021-9673</issn><eissn>1873-3778</eissn><coden>JOCRAM</coden><abstract>•Identification and quantification of relevant constituents of Petroselinum crispum.•Analysis of the endogenous enzymatic hydrolysis products of fruit and leaf tissues.•Release of apiose and glucose by the stepwise endogenous enzymatic hydrolysis mechanism.•Mass fragmentation study of the apiosyl-apiose and apiosyl-glucose TMS derivatives.•Invertase enzyme activity proved to be independent of parsley tissues. The behavior of the flavonoid diglycosides, relevant constituents of parsley (Petroselinum crispum) fruit (PFr) and leaf (PLe) samples was characterized upon their enzymatic hydrolyses applying complementary liquid chromatography-ultraviolet (LC-UV) and gas chromatography mass selective (GC–MS) detections. Analyses were performed in quantitative manner, from the same extracts as a function of hydrolysis times. Both in fruit and leaf tissue extracts, in intact and in enzyme hydrolyzed ones, apigenin, chrysoeriol, their glycosides, sugars, sugar alcohols, carboxylic acids and phytosterols, in total 17 constituents were identified and quantified. Based primarily on the selective mass fragmentation properties of the trimethylsilyl (oxime) ether/ester derivatives of constituents, we confirmed several novelties to the field. (i) It was shown for the first time that in parsley tissues different types of glycosidase enzyme are active. In PFr samples, both the stepwise and disaccharide specific endogenous mechanisms were certified, quantifying simultaneously the continuous release of apigenin, chrysoeriol, 2-O-apiosyl-apiose, apiose and glucose. (ii) 2-O-Apiosyl-glucose was demonstrated as disaccharide due to its formation under derivatization conditions from parsley glycosides. (iii) Both in PFr and in PLe samples even the invertase enzyme activity was attainable: sucrose decomposition in both tissues was going on with the same intensity. Three different types of enzymatic glycosidase processes were followed with their specific hydrolysis products by means of HPLC-UV and GC–MS, simultaneously.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>23623367</pmid><doi>10.1016/j.chroma.2013.03.037</doi><tpages>7</tpages></addata></record>
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subjects 2-O-Apiosyl-apiose
2-O-Apiosyl-glucose
Analytical chemistry
apigenin
Aroma and flavouring agent industries
beta-fructofuranosidase
Biological and medical sciences
carboxylic acids
Chemistry
Chromatographic methods and physical methods associated with chromatography
derivatization
Endogenous enzymatic hydrolysis
enzyme activity
Exact sciences and technology
Flavonoids
Flavonoids - analysis
Flavonoids - chemistry
Flavonoids - metabolism
Food industries
Fruit - chemistry
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry - methods
Gas chromatography–mass spectrometry
glucose
Glycoside Hydrolases - metabolism
glycosides
Glycosides - analysis
Glycosides - chemistry
Glycosides - metabolism
high performance liquid chromatography
hydrolysis
leaves
Other chromatographic methods
Oximes - chemistry
parsley
Pentoses - chemistry
Petroselinum - chemistry
Petroselinum - enzymology
Petroselinum crispum
phytosterols
Phytosterols - chemistry
Plant Extracts - chemistry
Plant Leaves - chemistry
sucrose
sugar alcohols
tissues
Trimethylsilyl (oxime) derivatives
title Characterization of the endogenous enzymatic hydrolyses of Petroselinum crispum glycosides: Determined by chromatography upon their sugar and flavonoid products
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