• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

通过电喷雾电离串联质谱法区分3,4-和4,15-环氧桉叶烷型倍半萜内酯

Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry.

作者信息

Dias Herbert Júnior, Stefani Ricardo, Tomaz José Carlos, Vessecchi Ricardo, Crotti Antônio Eduardo Miller

机构信息

Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil.

Instituto de Ciências Exatas e da Terra, Universidade Federal do Mato Grosso, Campus Universitário do Araguaia, Araguaia, MT, Brazil.

出版信息

J Anal Methods Chem. 2017;2017:7921867. doi: 10.1155/2017/7921867. Epub 2017 Nov 6.

DOI:10.1155/2017/7921867
PMID:29234552
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5695018/
Abstract

We investigated the fragmentation of the eudesmanolide-type sesquiterpene lactones 1-(4-hydroxymethacryloyloxy)-3,4-epoxy-8-hydroxyeudesm-11(13)-6,12-olide () and 1-(2,3-epoxyangeloyloxy)-4,15-epoxy-8-hydroxyeudesm-11(13)-6,12-olide () by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The elimination of the different ester substituent at C(1) directly from protonated and () led to the formation of two regioisomer product ions ( - RCOH). Further fragmentation of resulted from consecutive eliminations of HO and CO molecules. However, we identified four product ions that allowed for the differentiation between 3,4- and 4,15-epoxyeudesmanolides. The formation of these diagnostic ions was associated with the C(3)-O bond of compound , which propitiates the participation of the lone pair of the oxygen epoxide in the formation of through a Grob-Wharton-type fragmentation, then resulting in an alternative fragmentation pathway. These data can be useful for the fast differentiation between epoxyeudesmanolide regioisomers directly from extracts by liquid chromatography-tandem mass spectrometry (LC-MS/MS), as an alternative to NMR, or even for quantitation studies of these compounds using multiple reaction monitoring (MRM) scan.

摘要

我们通过电喷雾电离串联质谱法（ESI-MS/MS）研究了桉叶烷型倍半萜内酯1-(4-羟基甲基丙烯酰氧基)-3,4-环氧-8-羟基桉叶-11(13)-6,12-内酯（）和1-(2,3-环氧当归酰氧基)-4,15-环氧-8-羟基桉叶-11(13)-6,12-内酯（）的碎片化过程。从质子化的和（）中直接消除C(1)处不同的酯取代基，导致形成两种区域异构体产物离子（-RCOH）。的进一步碎片化是由于HO和CO分子的连续消除。然而，我们鉴定出了四个产物离子，它们可用于区分3,4-和4,15-环氧桉叶烷型倍半萜内酯。这些诊断离子的形成与化合物的C(3)-O键有关，该键通过Grob-Wharton型碎片化促进环氧氧的孤对电子参与形成，进而产生另一种碎片化途径。这些数据可用于通过液相色谱-串联质谱法（LC-MS/MS）直接从提取物中快速区分环氧桉叶烷型倍半萜内酯区域异构体，作为核磁共振（NMR）的替代方法，甚至可用于使用多反应监测（MRM）扫描对这些化合物进行定量研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/42c6946fe7cd/JAMC2017-7921867.sch.005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/ddc5c40c70f6/JAMC2017-7921867.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/ae66b57a7d77/JAMC2017-7921867.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/c97cb1687474/JAMC2017-7921867.sch.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/d64609eb5977/JAMC2017-7921867.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/b599b7abc590/JAMC2017-7921867.sch.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/a4ecde9ef10a/JAMC2017-7921867.sch.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/56f16234f75c/JAMC2017-7921867.sch.004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/42c6946fe7cd/JAMC2017-7921867.sch.005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/ddc5c40c70f6/JAMC2017-7921867.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/ae66b57a7d77/JAMC2017-7921867.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/c97cb1687474/JAMC2017-7921867.sch.001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/d64609eb5977/JAMC2017-7921867.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/b599b7abc590/JAMC2017-7921867.sch.002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/a4ecde9ef10a/JAMC2017-7921867.sch.003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/56f16234f75c/JAMC2017-7921867.sch.004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ae9/5695018/42c6946fe7cd/JAMC2017-7921867.sch.005.jpg

相似文献

1
Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry.通过电喷雾电离串联质谱法区分3,4-和4,15-环氧桉叶烷型倍半萜内酯
J Anal Methods Chem. 2017;2017:7921867. doi: 10.1155/2017/7921867. Epub 2017 Nov 6.
2
Analysis and fragmentation mechanisms of hirsutinolide-type sesquiterpene lactones by ultra-high-performance liquid chromatography/electrospray ionization linear ion trap Orbitrap mass spectrometry.采用超高效液相色谱/电喷雾电离线性离子阱轨道阱质谱法分析和研究去氢木香内酯型倍半萜内酯的裂解机制
Rapid Commun Mass Spectrom. 2016 Mar 15;30(5):569-80. doi: 10.1002/rcm.7473.
3
Characterization of tanshinones in the roots of Salvia miltiorrhiza (Dan-shen) by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry.采用高效液相色谱-电喷雾电离串联质谱法对丹参根中丹参酮进行表征分析。
Rapid Commun Mass Spectrom. 2006;20(8):1266-80. doi: 10.1002/rcm.2447.
4
Electrospray ionization tandem mass spectrometry analysis of isopimarane diterpenes from Velloziaceae.维洛西亚科异海松烷二萜的电喷雾电离串联质谱分析
Rapid Commun Mass Spectrom. 2016 Jan 15;30(1):61-8. doi: 10.1002/rcm.7411.
5
A fragmentation-based method for the differentiation of glutathione conjugates by high-resolution mass spectrometry with electrospray ionization.基于碎片的方法，通过电喷雾电离高分辨质谱法对谷胱甘肽缀合物进行区分。
Anal Chim Acta. 2013 Jul 25;788:89-98. doi: 10.1016/j.aca.2013.06.022. Epub 2013 Jun 20.
6
Gas-phase fragmentation study of novel synthetic 1,5-benzodiazepine derivatives using electrospray ionization tandem mass spectrometry.使用电喷雾电离串联质谱法对新型合成1,5-苯二氮䓬衍生物进行气相裂解研究。
Rapid Commun Mass Spectrom. 2008 Jul;22(14):2253-68. doi: 10.1002/rcm.3612.
7
Gas-phase fragmentation reactions of protonated benzofuran- and dihydrobenzofuran-type neolignans investigated by accurate-mass electrospray ionization tandem mass spectrometry.通过精确质量电喷雾电离串联质谱法研究质子化苯并呋喃和二氢苯并呋喃型新木脂素的气相裂解反应。
J Mass Spectrom. 2019 Jan;54(1):35-46. doi: 10.1002/jms.4304.
8
Analysis of furo[3,2-c]tetrahydroquinoline and pyrano[3,2-c]tetrahydroquinoline derivatives as antitumor agents and their metabolites by liquid chromatography/electrospray ionization tandem mass spectrometry.采用液相色谱/电喷雾串联质谱法分析呋[3,2-c]四氢喹啉和吡喃[3,2-c]四氢喹啉衍生物作为抗肿瘤药物及其代谢物。
Rapid Commun Mass Spectrom. 2013 Jun 15;27(11):1222-30. doi: 10.1002/rcm.6562.
9
New features on the fragmentation patterns of homoisoflavonoids in Ophiopogon japonicus by high-performance liquid chromatography/diode-array detection/electrospray ionization with multi-stage tandem mass spectrometry.高效液相色谱/二极管阵列检测/电喷雾电离多阶段串联质谱法分析麦冬中异黄酮类化合物碎片模式的新特征。
Rapid Commun Mass Spectrom. 2010 Aug 15;24(15):2193-206. doi: 10.1002/rcm.4608.
10
Are benzoylium and nitrilium ions produced from substituted 2-arene-2-oxazolines during mass spectrometry? A study based on density functional theory calculations, quantum theory of atoms in molecules, and electrospray ionization tandem mass spectrometry.取代的 2-芳基-2-恶唑啉在质谱中是否会产生苯甲鎓离子和腈鎓离子？基于密度泛函理论计算、原子分子量子理论和电喷雾串联质谱的研究。
Rapid Commun Mass Spectrom. 2023 Feb 28;37(4):e9449. doi: 10.1002/rcm.9449.

本文引用的文献

1
Precursor Ion Scan Mode-Based Strategy for Fast Screening of Polyether Ionophores by Copper-Induced Gas-Phase Radical Fragmentation Reactions.基于前体离子扫描模式的策略，通过铜诱导的气相自由基断裂反应快速筛选聚醚离子载体。
Anal Chem. 2017 Apr 4;89(7):3929-3936. doi: 10.1021/acs.analchem.6b02855. Epub 2017 Mar 22.
2
A new antifungal eudesmanolide glycoside isolated from Sphaeranthus indicus Linn. (Family Compositae).从印度香须树（菊科）中分离得到的一种新的抗真菌桉烷型倍半萜内酯糖苷。
Nat Prod Res. 2016 Dec;30(24):2770-2776. doi: 10.1080/14786419.2016.1155575. Epub 2016 Mar 8.
3
Fragmentation reactions using electrospray ionization mass spectrometry: an important tool for the structural elucidation and characterization of synthetic and natural products.
电喷雾电离质谱的碎片化反应：一种用于合成和天然产物结构阐明和表征的重要工具。
Nat Prod Rep. 2016 Mar;33(3):432-55. doi: 10.1039/c5np00073d. Epub 2015 Dec 16.
4
Isolation, Characterization, and Antiproliferative Activities of Eudesmanolide Derivatives from the Flowers of Inula japonica.旋覆花中桉烷型倍半萜内酯衍生物的分离、表征及抗增殖活性
J Agric Food Chem. 2015 Oct 21;63(41):9006-11. doi: 10.1021/acs.jafc.5b03075. Epub 2015 Oct 13.
5
The eudesmanolide tanapsin from Tanacetum oshanahanii and its acetate induce cell death in human tumor cells through a mechanism dependent on reactive oxygen species.来自山艾蒿的桉烷倍半萜 Tanapsin 及其乙酸酯通过依赖于活性氧的机制诱导人肿瘤细胞死亡。
Phytomedicine. 2015 Mar 15;22(3):385-93. doi: 10.1016/j.phymed.2015.01.008. Epub 2015 Feb 16.
6
Dereplication of Streptomyces sp. AMC 23 polyether ionophore antibiotics by accurate-mass electrospray tandem mass spectrometry.通过精确质量电喷雾串联质谱法对链霉菌属AMC 23聚醚离子载体抗生素进行去重复化分析。
J Mass Spectrom. 2014 Nov;49(11):1117-26. doi: 10.1002/jms.3432.
7
Gas-phase basicities of polyfunctional molecules. Part 4: Carbonyl groups as basic sites.多官能团分子的气相碱度。第 4 部分：羰基作为碱性基团。
Mass Spectrom Rev. 2015 Sep-Oct;34(5):493-534. doi: 10.1002/mas.21416. Epub 2014 Jan 7.
8
Principles of collisional activation in analytical mass spectrometry.分析质谱中碰撞激活的原理。
J Am Soc Mass Spectrom. 1992 Sep;3(6):599-614. doi: 10.1016/1044-0305(92)85001-Z.
9
Quantitative analysis of peptides and proteins in biomedicine by targeted mass spectrometry.靶向质谱法在生物医学中对肽和蛋白质的定量分析。
Nat Methods. 2013 Jan;10(1):28-34. doi: 10.1038/nmeth.2309.
10
Gas-phase reactivity of protonated 2-oxazoline derivatives: mass spectrometry and computational studies.质子化 2-噁唑啉衍生物的气相反应性：质谱和计算研究。
Rapid Commun Mass Spectrom. 2012 May 15;26(9):1061-9. doi: 10.1002/rcm.6182.