Table of Contents Author Guidelines Submit a Manuscript
Journal of Analytical Methods in Chemistry
Volume 2017 (2017), Article ID 3568621, 18 pages
https://doi.org/10.1155/2017/3568621
Research Article

Changes of Metabolomic Profile in Helianthus annuus under Exposure to Chromium(VI) Studied by capHPLC-ESI-QTOF-MS and MS/MS

1Chemistry Department, University of Guanajuato, L. de Retana 5, 36000 Guanajuato, GTO, Mexico
2Biology Department, University of Guanajuato, L. de Retana 5, 36000 Guanajuato, GTO, Mexico

Correspondence should be addressed to Katarzyna Wrobel

Received 26 June 2017; Revised 4 August 2017; Accepted 13 September 2017; Published 22 November 2017

Academic Editor: Pablo Richter

Copyright © 2017 Alan Alexander Gonzalez Ibarra et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. V. Arbona, M. Manzi, C. de Ollas, and A. Gómez-Cadenas, “Metabolomics as a tool to investigate abiotic stress tolerance in plants,” International Journal of Molecular Sciences, vol. 14, no. 3, pp. 4885–4911, 2013. View at Publisher · View at Google Scholar · View at Scopus
  2. S. C. Booth, M. L. Workentine, A. M. Weljie, and R. J. Turner, “Metabolomics and its application to studying metal toxicity,” Metallomics, vol. 3, no. 11, pp. 1142–1152, 2011. View at Publisher · View at Google Scholar · View at Scopus
  3. T. F. Jorge, J. A. Rodrigues, C. Caldana et al., “Mass spectrometry-based plant metabolomics: Metabolite responses to abiotic stress,” Mass Spectrometry Reviews, vol. 35, no. 5, pp. 620–649, 2016. View at Publisher · View at Google Scholar · View at Scopus
  4. O. A. H. Jones, D. A. Dias, D. L. Callahan, K. A. Kouremenos, D. J. Beale, and U. Roessner, “The use of metabolomics in the study of metals in biological systems,” Metallomics, vol. 7, no. 1, pp. 29–38, 2015. View at Publisher · View at Google Scholar · View at Scopus
  5. K. Král'ová, J. Jampílek, and I. Ostrovský, “Metabolomics - Useful tool for study of plant responses to abiotic stresses,” Ecological Chemistry and Engineering S, vol. 19, no. 2, pp. 133–161, 2012. View at Publisher · View at Google Scholar · View at Scopus
  6. S. Kumar, R. S. Dubey, R. D. Tripathi, D. Chakrabarty, and P. K. Trivedi, “Omics and biotechnology of arsenic stress and detoxification in plants: Current updates and prospective,” Environment International, vol. 74, pp. 221–230, 2015. View at Publisher · View at Google Scholar · View at Scopus
  7. S. Dubey, P. Misra, S. Dwivedi et al., “Transcriptomic and metabolomic shifts in rice roots in response to Cr (VI) stress,” BMC Genomics, vol. 11, no. 1, article no. 648, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. E. Scalabrin, M. Radaelli, G. Rizzato et al., “Metabolomic analysis of wild and transgenic Nicotiana langsdorffii plants exposed to abiotic stresses: Unraveling metabolic responses,” Analytical and Bioanalytical Chemistry, vol. 407, no. 21, pp. 6357–6368, 2015. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Hayat, G. Khalique, M. Irfan, A. S. Wani, B. N. Tripathi, and A. Ahmad, “Physiological changes induced by chromium stress in plants: An overview,” Protoplasma, vol. 249, no. 3, pp. 599–611, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. M. Shahid, S. Shamshad, M. Rafiq et al., “Chromium speciation, bioavailability, uptake, toxicity and detoxification in soil-plant system: A review,” Chemosphere, vol. 178, pp. 513–533, 2017. View at Publisher · View at Google Scholar · View at Scopus
  11. D. Mani, B. Sharma, C. Kumar, N. Pathak, and S. Balak, “Phytoremediation potential of Helianthus annuus l in sewage-irrigated Indo-Gangetic alluvial soils,” International Journal of Phytoremediation, vol. 14, no. 3, pp. 235–246, 2012. View at Publisher · View at Google Scholar · View at Scopus
  12. G. de la Rosa, H. Castillo-Michel, G. Cruz-Jiménez et al., “Cr Localization and Speciation in Roots of Chromate Fed Helianthus annuus L. Seedlings Using Synchrotron Techniques,” International Journal of Phytoremediation, vol. 16, no. 11, pp. 1073–1086, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. T. Kind and O. Fiehn, “Seven Golden Rules for heuristic filtering of molecular formulas obtained by accurate mass spectrometry,” BMC Bioinformatics, vol. 8, article no. 105, 2007. View at Publisher · View at Google Scholar · View at Scopus
  14. L. Yi, N. Dong, Y. Yun et al., “Chemometric methods in data processing of mass spectrometry-based metabolomics: A review,” Analytica Chimica Acta, vol. 914, pp. 17–34, 2016. View at Publisher · View at Google Scholar · View at Scopus
  15. M. Ernst, D. B. Silva, R. R. Silva, R. Z. N. Vêncio, and N. P. Lopes, “Mass spectrometry in plant metabolomics strategies: From analytical platforms to data acquisition and processing,” Natural Product Reports, vol. 31, no. 6, pp. 784–806, 2014. View at Publisher · View at Google Scholar · View at Scopus
  16. L. Perez de Souza, T. Naake, T. Tohge, and A. R. Fernie, “From chromatogram to analyte to metabolite. How to pick horses for courses from the massive web resources for mass spectral plant metabolomics,” GigaScience, vol. 6, no. 7, pp. 1–20, 2017. View at Publisher · View at Google Scholar
  17. C. A. Smith, E. J. Want, G. O'Maille, R. Abagyan, and G. Siuzdak, “XCMS: processing mass spectrometry data for metabolite profiling using nonlinear peak alignment, matching, and identification,” Analytical Chemistry, vol. 78, no. 3, pp. 779–787, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. N. G. Mahieu, J. L. Genenbacher, and G. J. Patti, “A roadmap for the XCMS family of software solutions in metabolomics,” Current Opinion in Chemical Biology, vol. 30, pp. 87–93, 2016. View at Publisher · View at Google Scholar · View at Scopus
  19. T. Kind and O. Fiehn, “Metabolomic database annotations via query of elemental compositions: Mass accuracy is insufficient even at less than 1 ppm,” BMC Bioinformatics, vol. 7, article no. 234, 2006. View at Publisher · View at Google Scholar · View at Scopus
  20. H. Tsugawa, T. Kind, R. Nakabayashi et al., “Hydrogen Rearrangement Rules: Computational MS/MS Fragmentation and Structure Elucidation Using MS-FINDER Software,” Analytical Chemistry, vol. 88, no. 16, pp. 7946–7958, 2016. View at Publisher · View at Google Scholar · View at Scopus
  21. S. Böcker, M. C. Letzel, Z. Lipták, and A. Pervukhin, “SIRIUS: Decomposing isotope patterns for metabolite identification,” Bioinformatics, vol. 25, no. 2, pp. 218–224, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. E. Y. Barrientos, C. R. Flores, K. Wrobel, and K. Wrobel, “Impact of cadmium and selenium exposure on trace elements, fatty acids and oxidative stress in Lepidium sativum,” Journal of the Mexican Chemical Society, vol. 56, no. 1, pp. 3–9, 2012. View at Google Scholar · View at Scopus
  23. F. J. A. Aguilar, K. Wrobal, K. Lokits et al., “Analytical speciation of chromium in in-vitro cultures of chromate-resistant filamentous fungi,” Analytical and Bioanalytical Chemistry, vol. 392, no. 1-2, pp. 269–276, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. ICH Harmonized Tripartite Guideline, Validation of analytical procedures: text and methodology (Q2/R1), 2012, http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf.
  25. B. Mei, J. D. Puryear, and R. J. Newton, “Assessment of Cr tolerance and accumulation in selected plant species,” Plant and Soil, vol. 247, no. 2, pp. 223–231, 2002. View at Publisher · View at Google Scholar · View at Scopus
  26. M. E. Palm-Espling, M. S. Niemiec, and P. Wittung-Stafshede, “Role of metal in folding and stability of copper proteins in vitro,” Biochimica et Biophysica Acta (BBA) - Molecular Cell Research, vol. 1823, no. 9, pp. 1594–1603, 2012. View at Publisher · View at Google Scholar · View at Scopus
  27. P. C. Nagajyoti, K. D. Lee, and T. V. M. Sreekanth, “Heavy metals, occurrence and toxicity for plants: a review,” Environmental Chemistry Letters, vol. 8, no. 3, pp. 199–216, 2010. View at Publisher · View at Google Scholar · View at Scopus
  28. A. Ramakrishna and G. A. Ravishankar, “Influence of abiotic stress signals on secondary metabolites in plants,” Plant Signaling and Behavior, vol. 6, no. 11, pp. 1720–1731, 2011. View at Publisher · View at Google Scholar · View at Scopus
  29. J. Kováčik, P. Babula, J. Hedbavny, and B. Klejdus, “Hexavalent chromium damages chamomile plants by alteration of antioxidants and its uptake is prevented by calcium,” Journal of Hazardous Materials, vol. 273, pp. 110–117, 2014. View at Publisher · View at Google Scholar · View at Scopus
  30. P. Babula, V. Adam, R. Opatrilova, J. Zehnalek, L. Havel, and R. Kizek, “Uncommon heavy metals, metalloids and their plant toxicity: A review,” Environmental Chemistry Letters, vol. 6, no. 4, pp. 189–213, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. D. Selmar and M. Kleinwächter, “Stress enhances the synthesis of secondary plant products: The impact of stress-related over-reduction on the accumulation of natural products,” Plant & Cell Physiology (PCP), vol. 54, no. 6, pp. 817–826, 2013. View at Publisher · View at Google Scholar · View at Scopus
  32. M.-C. Gutierrez, A. Parry, M. Tena, J. Jorrin, and R. Edwards, “Abiotic elicitation of coumarin phytoalexins in sunflower,” Phytochemistry, vol. 38, no. 5, pp. 1185–1191, 1995. View at Publisher · View at Google Scholar · View at Scopus
  33. A. Saeed, “Isocoumarins, miraculous natural products blessed with diverse pharmacological activities,” European Journal of Medicinal Chemistry, vol. 116, pp. 290–317, 2016. View at Publisher · View at Google Scholar · View at Scopus
  34. D. Engelmeier, F. Hadacek, O. Hofer et al., “Antifungal 3-Butylisocoumarins from Asteraceae-Anthemideae,” Journal of Natural Products, vol. 67, no. 1, pp. 19–25, 2004. View at Publisher · View at Google Scholar · View at Scopus
  35. J. L. Hartwell and B. J. Abbott, “Antineoplastic Principles in Plants: Recent Developments in the Field,” vol. 7 of Advances in Pharmacology, pp. 117–209, Elsevier, 1970. View at Publisher · View at Google Scholar
  36. M. T. Scotti, M. B. Fernandes, M. J. P. Ferreira, and V. P. Emerenciano, “Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity,” Bioorganic & Medicinal Chemistry, vol. 15, no. 8, pp. 2927–2934, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. J. R. Prasifka, O. Spring, J. Conrad, L. W. Cook, D. E. Palmquist, and M. E. Foley, “Sesquiterpene lactone composition of wild and cultivated sunflowers and biological activity against an insect pest,” Journal of Agricultural and Food Chemistry, vol. 63, no. 16, pp. 4042–4049, 2015. View at Publisher · View at Google Scholar · View at Scopus
  38. O. Spring, J. Pfannstiel, I. Klaiber et al., “The nonvolatile metabolome of sunflower linear glandular trichomes,” Phytochemistry, vol. 119, pp. 83–89, 2015. View at Publisher · View at Google Scholar · View at Scopus
  39. F. M. Raupp and O. Spring, “New sesquiterpene lactones from sunflower root exudate as germination stimulants for Orobanche cumana,” Journal of Agricultural and Food Chemistry, vol. 61, no. 44, pp. 10481–10487, 2013. View at Publisher · View at Google Scholar · View at Scopus
  40. R. E. Minto and B. J. Blacklock, “Biosynthesis and function of polyacetylenes and allied natural products,” Progress in Lipid Research, vol. 47, no. 4, pp. 233–306, 2008. View at Publisher · View at Google Scholar · View at Scopus
  41. P. Proksch and E. Rodriguez, “Chromenes and benzofurans of the asteraceae, their chemistry and biological significance,” Phytochemistry, vol. 22, no. 11, pp. 2335–2348, 1983. View at Publisher · View at Google Scholar · View at Scopus
  42. G. Yang, W. Zhao, T. Zhang et al., “Chromone derivatives from the leaves of Nicotiana Tabacum and their anti-tobacco mosaic virus activities,” Heterocycles, vol. 89, no. 1, pp. 183–188, 2014. View at Publisher · View at Google Scholar · View at Scopus
  43. L. G. Korkina, “Phenylpropenoids as naturally occurring antioxidants: from plant defense to human health,” Cellular and Molecular Biology TM, vol. 53, no. 1, pp. 15–25, 2007. View at Google Scholar
  44. M. Chadwick, H. Trewin, F. Gawthrop, and C. Wagstaff, “Sesquiterpenoids lactones: benefits to plants and people,” International Journal of Molecular Sciences, vol. 14, no. 6, pp. 12780–12805, 2013. View at Publisher · View at Google Scholar · View at Scopus
  45. L. A. Richards, A. E. Glassmire, K. M. Ochsenrider et al., “Phytochemical diversity and synergistic effects on herbivores,” Phytochemistry Reviews, vol. 15, no. 6, pp. 1153–1166, 2016. View at Publisher · View at Google Scholar · View at Scopus
  46. Y. Shikishima, Y. Takaishi, G. Honda et al., “Chemical constituents of Prangos tschimganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity,” Chemical & Pharmaceutical Bulletin, vol. 49, no. 7, pp. 877–880, 2001. View at Publisher · View at Google Scholar · View at Scopus
  47. J. C. T. Elguera, E. Y. Barrientos, K. Wrobel, and K. Wrobel, “Effect of cadmium (Cd(II)), selenium (Se(IV)) and their mixtures on phenolic compounds and antioxidant capacity in Lepidium sativum,” Acta Physiologiae Plantarum, vol. 35, no. 2, pp. 431–441, 2013. View at Publisher · View at Google Scholar · View at Scopus
  48. J. Kováčik, J. Grúz, B. Klejdus, F. Štork, R. Marchiosi, and O. Ferrarese-Filho, “Lignification and related parameters in copper-exposed Matricaria chamomilla roots: Role of H2O2 and NO in this process,” Journal of Plant Sciences, vol. 179, no. 4, pp. 383–389, 2010. View at Publisher · View at Google Scholar · View at Scopus
  49. P. Ahmad, S. Rasool, A. Gul et al., “Jasmonates: Multifunctional roles in stress tolerance,” Frontiers in Plant Science, vol. 7, no. 2016, article no. 813, 2016. View at Publisher · View at Google Scholar · View at Scopus
  50. B. Singh and R. A. Sharma, “Plant terpenes: defense responses, phylogenetic analysis, regulation and clinical applications,” 3 Biotech, vol. 5, no. 2, pp. 129–151, 2015. View at Publisher · View at Google Scholar