期刊论文详细信息
Chemistry Central Journal
Use of coupled ion mobility spectrometry-time of flight mass spectrometry to analyze saturated and unsaturated phenylpropanoic acids and chalcones
Mwafaq Ibdah2  David R Gang1 
[1] Institute of Biological Chemistry, Washington State University, PO Box 646340, Pullman, WA 99164-6340, USA
[2] Agriculture Research Organization, Institute of Vegetable and Field Crops, Newe Ya’ar Research Center, P.O. Box 1021, Ramat Yishay 30095, Israel
关键词: Dihydrochalcone;    Chalcone;    Flavonoids;    Phenylpropanoic acids;    Mass spectrometry;    Ion mobility spectrometry;   
Others  :  787773
DOI  :  10.1186/1752-153X-8-38
 received in 2014-02-21, accepted in 2014-06-09,  发布年份 2014
PDF
【 摘 要 】

Background

In metabolite profiling screens or analyses, where generic separation and analysis conditions are used in efforts to measure as many metabolites as possible, overlapping signals from very similar molecules often make it very difficult if not impossible to separate and identify specific molecules of specific classes. The aim of this study was to evaluate the utility of coupling ion mobility spectrometry to UPLC-TOFMS (UPLC-Q-IMS-TOFMS) as a means to separate and identify saturated and unsaturated phenylpropanoic acids and chalcones, phenylpropanoid-acetate pathway derived compounds that are common in plant extracts.

Results

This approach readily separated most of the unsaturated phenylpropanoid acids (t-cinnamate, p-coumarate, caffeate, ferulate) from the corresponding saturated (dihydro-) compounds, and analysis of two dimensional plots of mass/charge ratio values versus ion mobility drift time revealed that the other compounds can indeed be distinguished. However, this approach was less effective for the larger chalcones.

Conclusions

UPLC-Q-IMS-TOFMS is a promising tool to enable the separation, identification and quantification of very similar molecules. Although it has its limitations, as was seen for the chalcones that were not well separated in this investigation, ion mobility spectrometry nevertheless adds an additional level of characterization to large-scale metabolomic screens, which increases the power of such screens without the demand for multiple analyses using very different column chemistries.

【 授权许可】

   
2014 Ibdah and Gang; licensee Chemistry Central Ltd.

【 预 览 】
附件列表
Files Size Format View
20140702191645608.pdf 683KB PDF download
Figure 6. 42KB Image download
Figure 5. 40KB Image download
Figure 4. 44KB Image download
Figure 3. 45KB Image download
Figure 2. 43KB Image download
Figure 1. 47KB Image download
【 图 表 】

Figure 1.

Figure 2.

Figure 3.

Figure 4.

Figure 5.

Figure 6.

【 参考文献 】
  • [1]Leong YW, Harrison LJ, Powell AD: Phenanthrene and other aromatic constituents of Bulbophyllum vaginatum. Phytochemistry 1999, 50:1237-1241.
  • [2]Youn B, Kim SJ, Moinuddin SGA, Lee C, Bedgar DL, Harper AR, Davin LB, Lewis NG, Kang C: Mechanistic and structural studies of apoform, binary, and ternary complexes of the Arabidopsis alkenal double bond reductase At5g16970. J BiolChem 2006, 281:40076-40088.
  • [3]Ordoudi SA, Tsimidou MZ, Vafiadis AP, Bakalbassis EG: Structure-DPPH center dot scavenging activity relationships: parallel study of catechol and guaiacol acid derivatives. J Agric Food Chem 2006, 54:5763-5768.
  • [4]Shimoji Y, Tamura Y, Nakamura Y, Nanda K, Nishidai S, Nishikawa Y, Ishihara N, Uenakai K, Ohigashi H: Isolation and identification of DPPH radical scavenging compounds in Kurosu (Japanese unpolished rice vinegar). J Agric Food Chem 2002, 50:6501-6503.
  • [5]Di Carlo G, Mascolo N, Izzo AA, Capasso F: Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci 1999, 65:337-353.
  • [6]Vogel S, Barbic M, Jurgenliemk G, Heilmann J: Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of a-ring modifications on the pharmacological effect. Eur J Med Chem 2010, 45:2206-2213.
  • [7]Yang WM, Liu JK, Qin XD, Wu WL, Chen ZH: Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus. Z Naturforsch 2004, 59:481-484.
  • [8]Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S, Sauvain M, Valentin A, Moulis C: Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense. Phytochemistry 2007, 68:1312-1320.
  • [9]Amor ECV, Villasenor IM, Nawaz SA, Hussain MS, Choudhary MI: A dihydrochalcone from Syzygium samarangense with anticholinesterase activity. Philipp J Sci 2005, 134:105-111.
  • [10]Shah A, Khan AM, Qureshi R, Ansari FL, Nazar MF, Shah SS: Redox behavior of anticancer chalcone on a glassy carbon electrode and evaluation of its interaction parameters with DNA. Inte J Mol Sci 2008, 9:1424-1434.
  • [11]Szliszka E, Czuba ZP, Mazur B, Paradysz A, Krol W: Chalcones and dihydrochalcones augment TRAIL-mediated apoptosis in prostate cancer cells. Molecules 2010, 15:5336-5353.
  • [12]Quirantes-Piné R, Lozano-Sánchez J, Herrero M, Ibáñez E, Segura-Carretero A, Fernández-Gutiérrez A: HPLC–ESI–QTOF–MS as a powerful analytical tool for characterising phenolic compounds in olive-leaf extracts. Phytochem Anal 2013, 24(3):213-223.
  • [13]Kanu AB, Dwivedi P, Tam M, Matz L, Hill HH: Ion mobility–mass spectrometry. J Mass Spectrom 2008, 43:1-22.
  • [14]Tang XT, Bruce JE, Hill HH: Design and performance of an atmospheric pressure ion mobility fourier transform ion cyclotron resonance mass spectrometer. Rapid Commun Mass Spectrom 2007, 21:1115-1122.
  • [15]Thalassinos K, Grabenauer M, Slade SE, Hilton GR, Bowers MT, Scrivens JH: Characterization of phosphorylated peptides using traveling wave-based and drift cell ion mobility mass spectrometry. Anal Chem 2009, 81:248-254.
  • [16]Li HL, Bendiak B, Siems WF, Gang DR, Hill HH: Carbohydrate structure characterization by tandem ion mobility mass spectrometry (IMMS)(2). Anal Chem 2013, 85:2760-2769.
  • [17]Gonzalez EA, Nazareno MA, Borsarelli CD: Enthalpy-entropy compensation effect in the chalcone formation from naringin in water-ethanol mixtures. J Chem SocPerkin Trans 2002, 2:2052-2056.
  文献评价指标  
  下载次数:107次 浏览次数:34次