Structural characterization of the ligstroside aglycone isoforms in virgin olive oils by liquid chromatography–high‐resolution Fourier‐transform mass spectrometry and H/Dexchange

Abbattista Ramona; Losito Ilario; De Ceglie Cristina; Basile Graziana; Calvano Cosima D.; Palmisano Francesco; Cataldi Tommaso R.I.

摘要

Abstract > A systematic structural characterization of the isomeric forms related to ligstroside aglycone (LA), one of the most relevant secoiridoids contained in virgin olive oils, was performed using reverse phase liquid chromatography with electrospray ionization Fourier‐transform single and tandem mass spectrometry, operated in negative ion mode (RPLC‐ESI(?)‐FTMS and FTMS/MS). The high mass resolution and accuracy provided by the adopted orbital trap mass analyzer enabled the recognition of more than 10 different isomeric forms of LA in virgin olive oil extracts. They were related to four different types of molecular structure, two of which including a dihydropyranic ring bearing one or two aldehydic groups, whereas the others corresponded to dialdehydic open‐structure forms, differing just for the position of a C═C bond. The contemporary presence of enolic or dienolic tautomers associated to most of these compounds, stable at room temperature (23°C), was also assessed through RPLC‐ESI‐FTMS analyses operated under H/D exchange conditions, ie, by using D <sub>2</sub> O instead of H <sub>2</sub> O as co‐solvent of acetonitrile in the RPLC mobile phase. As discussed in the paper, the results obtained for LA indicated a remarkable structural similarity with oleuropein aglycone (OA), the most abundant secoiridoid of olive oil, whose isoforms had been previously characterized using the same analytical approach. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><abstract type=“main”xml:lang=“en”><title type=“main”>abstract>与初榨橄榄油中最相关的裂环烯醚萜类化合物之一狮子甾苷苷配基（LA）相关的异构体的系统结构表征，在负离子模式（RPLC-ESI）下，使用反相液相色谱法和电喷雾电离傅里叶变换单串联质谱法进行分析FTMS和FTMS/MS）。所采用的轨道陷阱质量分析仪提供的高质量分辨率和准确度使其能够识别原始橄榄油提取物中10多种不同的镧异构体形式。它们与四种不同类型的分子结构有关，其中两种包括一个含有一个或两个醛基的二氢吡喃环，而另一种则对应于双醛开放结构形式，只因C的位置不同═邦德。通过在H/D交换条件下进行的RPLC-ESI-FTMS分析，也就是在RPLC流动相中使用D<sub>2</sub>O代替H<sub>2</sub>O作为乙腈的共溶剂，评估了与大多数这些化合物相关的烯酸或二烯醇酸互变异构体在室温（23°C）下稳定的当代存在。正如本文所讨论的，LA的结果表明，其结构与橄榄油中含量最丰富的裂环烯醚萜（OA）具有显著的相似性，其异构体此前已使用相同的分析方法进行了表征 </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-34906/'>《Journal of mass spectrometry: JMS》</a> <b style="margin: 0 2px;">|</b><span>2019年第10期</span><b style="margin: 0 2px;">|</b><span>共13页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Abbattista Ramona&option=202" target="_blank" rel="nofollow">Abbattista Ramona;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Losito Ilario&option=202" target="_blank" rel="nofollow">Losito Ilario;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=De Ceglie Cristina&option=202" target="_blank" rel="nofollow">De Ceglie Cristina;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Basile Graziana&option=202" target="_blank" rel="nofollow">Basile Graziana;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Calvano Cosima D.&option=202" target="_blank" rel="nofollow">Calvano Cosima D.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Palmisano Francesco&option=202" target="_blank" rel="nofollow">Palmisano Francesco;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cataldi Tommaso R.I.&option=202" target="_blank" rel="nofollow">Cataldi Tommaso R.I.;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Dipartimento di ChimicaUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> <p>Dipartimento di ChimicaUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> <p>Dipartimento di ChimicaUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> <p>Dipartimento di ChimicaUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> <p>Centro Interdipartimentale SMARTUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> <p>Dipartimento di ChimicaUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> <p>Dipartimento di ChimicaUniversità degli Studi di Bari “Aldo Moro”Bari Italy;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1187.html" title="分析化学">分析化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=high‐resolution mass spectrometry&option=203" rel="nofollow">high‐resolution mass spectrometry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=H/D exchange&option=203" rel="nofollow">H/D exchange;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ligstroside aglycone&option=203" rel="nofollow">ligstroside aglycone;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=olive oil&option=203" rel="nofollow">olive oil;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=secoiridoids&option=203" rel="nofollow">secoiridoids;</a> </p> <div class="translation"> 机译：None; </div> </li> </ul> </div> </div> <div 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Lakkireddy PRAKASH</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=M HIMAJA&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,M HIMAJA</a> <span> <a href="/journal-cn-14390/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 色谱 </a> </span> <span> . 2016</span><span>,第003期</span> </span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/academic-journal-cn_detail_thesis/0201293802687.html">Online Effective Identification of Glycopeptide Using Liquid Chromatography Combined with Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FTICR-MS)</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ling Xin&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . Ling Xin</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Hou&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Li Hou</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yue Zhou&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Yue Zhou</a> <span> <a href="/journal-cn-56588/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 生命科学与技术进展（英文） </a> </span> <span> . 2015</span><span>,第9期</span> </span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-66778_thesis/020223011486.html">In vitro/in vivo metabolism of ginsenoside Rg5 in rat using ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chao Hong&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . Chao Hong</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ping Yang&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Ping Yang</a> <span> <a href="/conference-cn-66778/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 世界中医药大会第四届夏季峰会暨世界中医药学会体质研究专业委员会第七届学术年会 </a> <span> <span> . 2018</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06130418616612.html">The computer program product which includes the computer program and that computer program which execute method and that method of processing the mass spectrometry data, being the method of processing the mass spectrometry data which possesses the liquid chromatography mass spectrometry machine null periodic signal which includes the fourier transform mass spectrometry machine which includes the data processing expedient which executes</a> <b>[P]</b> . <span> 外国专利：  JP5562933B2 </span> <span> . 2014-07-30</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：包括执行该程序和该处理质谱数据的方法的计算机程序和该计算机程序的计算机程序产品是具有包括傅立叶的液相色谱质谱仪无效周期信号的质谱数据的处理方法。包括执行数据处理权宜之计的变换质谱仪 </span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06130401887461.html">Characterization of crude oil by Fourier transform ion cyclotron resonance mass spectrometry</a> <b>[P]</b> . <span> 外国专利：  US10725013B2 </span> <span> . 2020-07-28</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：傅立叶变换离子回旋共振质谱法表征原油 </span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130401576375.html">CHARACTERIZATION OF CRUDE OIL BY FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRY</a> <b>[P]</b> . <span> 外国专利：  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