Development of a direct headspace collection method from Arabidopsis seedlings using Hs-SPME-GC-TOF-MS analysis

Metabolites

Volumn 3, Issue 2, 2013, Pages 223-242

  Kusano, Miyako ^a,b   Iizuka, Yumiko ^a,b   Kobayashi, Makoto ^a   Fukushima, Atsushi ^a   Saito, Kazuki ^a,c  

^a RIKEN   (Japan)

^b YOKOHAMA CITY UNIVERSITY   (Japan)

^c CHIBA UNIVERSITY   (Japan)

Author keywords

Arabidopsis; HS SPME GC TOF MS; Solid phase microextraction; VOC profiling; Volatile organic compounds

Indexed keywords

VOLATILE ORGANIC COMPOUND;

ARABIDOPSIS; ARTICLE; CHEMICAL ANALYSIS; DATA ANALYSIS; DATA PROCESSING; EXPLANT; GAS CHROMATOGRAPHY; INCUBATION TIME; NONHUMAN; PLANT TISSUE CULTURE; SEEDLING; SOLID PHASE MICROEXTRACTION; TIME OF FLIGHT MASS SPECTROMETRY;

EID: 84902347585     PISSN: None     EISSN: 22181989     Source Type: Journal    
DOI: 10.3390/metabo3020223     Document Type: Article

References (82)

1. Hakim, M.; Broza, Y.Y.; Barash, O.; Peled, N.; Phillips, M.; Amann, A.; Haick, H. Volatile Organic Compounds of Lung Cancer and Possible Biochemical Pathways. Chem. Rev. 2012, 112, 5949-5966.
2. Peled, N.; Hakim, M.; Bunn, P.A.; Miller, Y.E.; Kennedy, T.C.; Mattei, J.; Mitchell, J.D.; Hirsch, F.R.; Haick, H. Non-invasive Breath Analysis of Pulmonary Nodules. J. Thorac. Oncol. 2012, 7, 1528-1533.
3. Buszewski, B.; Ligor, T.; Jezierski, T.; Wenda-Piesik, A.; Walczak, M.; Rudnicka, J. Identification of volatile lung cancer markers by gas chromatography-mass spectrometry: comparison with discrimination by canines. Anal. Bioanal. Chem. 2012, 404, 141-146.
4. Phillips, M.; Cataneo, R.N.; Saunders, C.; Hope, P.; Schmitt, P.; Wai, J. Volatile biomarkers in the breath of women with breast cancer. J. Breath Res. 2010, 4.
5. de Gennaro, G.; Dragonieri, S.; Longobardi, F.; Musti, M.; Stallone, G.; Trizio, L.; Tutino, M. Chemical characterization of exhaled breath to differentiate between patients with malignant plueral mesothelioma from subjects with similar professional asbestos exposure. Anal. Bioanal. Chem. 2010, 398, 3043-3050.
6. Abaffy, T.; Duncan, R.; Riemer, D.D.; Tietje, O.; Elgart, G.; Milikowski, C.; DeFazio, R.A. Differential Volatile Signatures from Skin, Naevi and Melanoma: A Novel Approach to Detect a Pathological Process. PLoS One 2010, 5.
7. Barash, O.; Peled, N.; Hirsch, F.R.; Haick, H. Sniffing the unique odor print of non-small-cell lung cancer with gold nanoparticles. Small 2009, 5, 2618-2624.
8. Gordon, S.M.; Szidon, J.P.; Krotoszynski, B.K.; Gibbons, R.D.; Oneill, H.J. Volatile organiccompounds in exhaled air from patients with lung-cancer. Clin. Chem. 1985, 31, 1278-1282.
9. Haick, H.; Hakim, M.; Patrascu, M.; Levenberg, C.; Shehada, N.; Nakhoul, F.; Abassi, Z. Sniffing chronic renal failure in rat model by an array of random networks of single-walled carbon nanotubes. Acs. Nano. 2009, 3, 1258-1266.
10. Peled, N.; Ionescu, R.; Nol, P.; Barash, O.; McCollum, M.; VerCauteren, K.; Koslow, M.; Stahl, R.; Rhyan, J.; Haick, H. Detection of volatile organic compounds in cattle naturally infected with Mycobacterium bovis. Sensor Actuat. B-Chem. 2012, 171, 588-594.
11. Leff, J.W.; Fierer, N. Volatile organic compound (VOC) emissions from soil and litter samples. Soil Biol. Biochem. 2008, 40, 1629-1636.
12. Ryu, C.M.; Farag, M.A.; Hu, C.H.; Reddy, M.S.; Kloepper, J.W.; Pare, P.W. Bacterial volatiles induce systemic resistance in Arabidopsis. Plant Physiol. 2004, 134, 1017-1026.
13. Ryu, C.M.; Farag, M.A.; Hu, C.H.; Reddy, M.S.; Wei, H.X.; Pare, P.W.; Kloepper, J.W. Bacterial volatiles promote growth in Arabidopsis. Proc. Natl. Acad. Sci. USA 2003, 100, 4927-4932.
14. Kai, M.; Haustein, M.; Molina, F.; Petri, A.; Scholz, B.; Piechulla, B. Bacterial volatiles and their action potential. Appl. Microbiol. Biot. 2009, 81, 1001-1012.
15. Weise, T.; Kai, M.; Gummesson, A.; Troeger, A.; von Reuss, S.; Piepenborn, S.; Kosterka, F.; Sklorz, M.; Zimmermann, R.; Francke, W.; Piechulla, B. Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10. Beilstein J. Org. Chem. 2012, 8, 579-596.
16. Knudsen, J.T.; Eriksson, R.; Gershenzon, J.; Stahl, B. Diversity and distribution of floral scent. Botanical Rev. 2006, 72, 1-120.
17. Dudareva, N.; Negre, F.; Nagegowda, D.A.; Orlova, I. Plant volatiles: Recent advances and future perspectives. Crit Rev. Plant Sci. 2006, 25, 417-440.
18. D'Alessandro, M.; Turlings, T.C.J. Advances and challenges in the identification of volatiles that mediate interactions among plants and arthropods. Analyst 2006, 131, 24-32.
19. Loreto, F.; Schnitzler, J.P. Abiotic stresses and induced BVOCs. Trends Plant Sci. 2010, 15, 154-166.
20. Kegge, W.; Pierik, R. Biogenic volatile organic compounds and plant competition. Trends Plant Sci. 2010, 15, 126-132.
21. Dicke, M.; van Loon, J.J.; Soler, R. Chemical complexity of volatiles from plants induced by multiple attack. Nat. Chem. Biol. 2009, 5, 317-324.
22. Tholl, D.; Boland, W.; Hansel, A.; Loreto, F.; Rose, U.S.; Schnitzler, J.P. Practical approaches to plant volatile analysis. Plant J. 2006, 45, 540-560.
23. Badoil, L.; Benanou, D. Characterization of volatile and semivolatile compounds in waste landfill leachates using stir bar sorptive extraction-GC/MS. Anal. Bioanal. Chem. 2009, 393, 1043-1054.
24. Tredoux, A.; de Villiers, A.; Majek, P.; Lynen, F.; Crouch, A.; Sandra, P. Stir bar sorptive extraction combined with GC-MS analysis and chemometric methods for the classification of south African wines according to the volatile composition. J. Agric. Food Chem. 2008, 56, 4286-4296.
25. Ridgway, K.; Lalljie, S.P.D.; Smith, R.M. Comparison of in-tube sorptive extraction techniques for non-polar volatile organic compounds by gas chromatography with mass spectrometric detection. J. Chromatogr. A 2006, 1124, 181-186.
26. Rasanen, I.; Viinamaki, J.; Vuori, E.; Ojanpera, I. Headspace In-Tube Extraction Gas Chromatography-Mass Spectrometry for the Analysis of Hydroxylic Methyl-Derivatized and Volatile Organic Compounds in Blood and Urine. J. Anal. Toxicol. 2010, 34, 113-121.
27. Tisch, U.; Haick, H. Arrays of chemisensitive monolayer-capped metallic nanoparticles for diagnostic breath testing. Rev. Chem. Eng. 2010, 26, 171-179.
28. Tisch, U.; Haick, H. Nanomaterials for cross-reactive sensor arrays. Mrs Bull. 2010, 35, 797-803.
29. Qualley, A.V.; Dudareva, N. Metabolomics of plant volatiles. Methods Mol. Biol. 2009, 553, 329-343.
30. Saito, K.; Matsuda, F. Metabolomics for functional genomics, systems biology, and biotechnology. Annu. Rev. Plant Biol. 2010, 61, 463-489.
31. Roessner, U.; Willmitzer, L.; Fernie, A.R. Metabolic profiling and biochemical phenotyping of plant systems. Plant Cell. Rep. 2002, 21, 189-196.
32. Fiehn, O.; Kopka, J.; Dormann, P.; Altmann, T.; Trethewey, R.N.; Willmitzer, L. Metabolite profiling for plant functional genomics. Nat. Biotechnol. 2000, 18, 1157-1161.
33. Veriotti, T.; Sacks, R. High speed GC/MS of gasoline-range hydrocarbon compounds using a pressure-tunable column ensemble and time-of-flight detection. Anal. Chem. 2000, 72, 3063-3069.
34. Stein, S.E.; Ausloos, P.; Clifton, C.L.; Klassen, J.K.; Lias, S.G.; Mikaya, A.I.; Sparkman, O.D.; Tchekhovskoi, D.V.; Zaikin, V.; Zhu, D. Evaluation of the NIST/EPA/NIH Mass Spectral Library. Abstr. Pap. Am. Chem. Soc. 1999, 218, U368-U368.
35. Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy. 4th ed.; Allured Pub. Corporation: Carol Stream, IL, USA, 2007.
36. Skogerson, K.; Wohlgemuth, G.; Barupal, D.K.; Fiehn, O. The volatile compound BinBase mass spectral database. BMC Bioinformatics 2011, 12, 321.
37. Wagner, C.; Sefkow, M.; Kopka, J. Construction and application of a mass spectral and retention time index database generated from plant GC/EI-TOF-MS metabolite profiles. Phytochemistry 2003, 62, 887-900.
38. Aprea, E.; Gika, H.; Carlin, S.; Theodoridis, G.; Vrhovsek, U.; Mattivi, F. Metabolite profiling on apple volatile content based on solid phase microextraction and gas-chromatography time of flight mass spectrometry. J. Chromatogr. A 2011, 1218, 4517-4524.
39. Tikunov, Y.; Lommen, A.; de Vos, C.H.; Verhoeven, H.A.; Bino, R.J.; Hall, R.D.; Bovy, A.G. A novel approach for nontargeted data analysis for metabolomics. Large-scale profiling of tomato fruit volatiles. Plant Physiol. 2005, 139, 1125-1137.
40. Tikunov, Y.M.; de Vos, R.C.; Gonzalez Paramas, A.M.; Hall, R.D.; Bovy, A.G. A role for differential glycoconjugation in the emission of phenylpropanoid volatiles from tomato fruit discovered using a metabolic data fusion approach. Plant Physiol. 2010, 152, 55-70.
41. Roze, L.V.; Chanda, A.; Laivenieks, M.; Beaudry, R.M.; Artymovich, K.A.; Koptina, A.V.; Awad, D.W.; Valeeva, D.; Jones, A.D.; Linz, J.E. Volatile profiling reveals intracellular metabolic changes in Aspergillus parasiticus: veA regulates branched chain amino acid and ethanol metabolism. BMC Biochem. 2010, 11, 33.
42. Abel, C.; Clauss, M.; Schaub, A.; Gershenzon, J.; Tholl, D. Floral and insect-induced volatile formation in Arabidopsis lyrata ssp petraea, a perennial, outcrossing relative of A.thaliana. Planta 2009, 230, 1-11.
43. Aharoni, A.; Giri, A.P.; Deuerlein, S.; Griepink, F.; de Kogel, W.J.; Verstappen, F.W.; Verhoeven, H.A.; Jongsma, M.A.; Schwab, W.; Bouwmeester, H.J. Terpenoid metabolism in wild-type and transgenic Arabidopsis plants. Plant Cell. 2003, 15, 2866-2884.
44. Chen, F.; Tholl, D.; D'Auria, J.C.; Farooq, A.; Pichersky, E.; Gershenzon, J. Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell. 2003, 15, 481-494.
45. Salas, J.J.; Garcia-Gonzalez, D.L.; Aparicio, R. Volatile compound biosynthesis by green leaves from an Arabidopsis thaliana hydroperoxide lyase knockout mutant. J. Agric. Food Chem 2006, 54, 8199-8205.
46. Huang, M.S.; Abel, C.; Sohrabi, R.; Petri, J.; Haupt, I.; Cosimano, J.; Gershenzon, J.; Tholl, D. Variation of Herbivore-Induced Volatile Terpenes among Arabidopsis Ecotypes Depends on Allelic Differences and Subcellular Targeting of Two Terpene Synthases, TPS02 and TPS03. Plant Physiol 2010, 153, 1293-1310.
47. Lee, S.; Badieyan, S.; Bevan, D.R.; Herde, M.; Gatz, C.; Tholl, D. Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis. Proc. Natl. Acad. Sci. USA 2010, 107, 21205-21210.
48. Snoeren, T.A.; Kappers, I.F.; Broekgaarden, C.; Mumm, R.; Dicke, M.; Bouwmeester, H.J. Natural variation in herbivore-induced volatiles in Arabidopsis thaliana. J. Exp. Bot. 2010, 61, 3041-3056.
49. Huang, M.; Sanchez-Moreiras, A.M.; Abel, C.; Sohrabi, R.; Lee, S.; Gershenzon, J.; Tholl, D. The major volatile organic compound emitted from Arabidopsis thaliana flowers, the sesquiterpene (E)-β-caryophyllene, is a defense against a bacterial pathogen. New Phytologist 2012, 193, 997-1008.
50. Farag, M.A.; Ryu, C.M.; Sumner, L.W.; Pare, P.W. GC-MS SPME profiling of rhizobacterial volatiles reveals prospective inducers of growth promotion and induced systemic resistance in plants. Phytochemistry 2006, 67, 2262-2268.
51. Kusano, M.; Fukushima, A.; Arita, M.; Jonsson, P.; Moritz, T.; Kobayashi, M.; Hayashi, N.; Tohge, T.; Saito, K. Unbiased characterization of genotype-dependent metabolic regulations by metabolomic approach in Arabidopsis thaliana. BMC Syst. Biol. 2007, 1, 53.
52. Scheible, W.R.; Morcuende, R.; Czechowski, T.; Fritz, C.; Osuna, D.; Palacios-Rojas, N.; Schindelasch, D.; Thimm, O.; Udvardi, M.K.; Stitt, M. Genome-wide reprogramming of primary and secondary metabolism, protein synthesis, cellular growth processes, and the regulatory infrastructure of Arabidopsis in response to nitrogen. Plant Physiol. 2004, 136, 2483-2499.
53. Verdonk, J.C.; Ric de Vos, C.H.; Verhoeven, H.A.; Haring, M.A.; van Tunen, A.J.; Schuurink, R.C. Regulation of floral scent production in petunia revealed by targeted metabolomics. Phytochemistry 2003, 62, 997-1008.
54. Mandelli, J.; Wajner, A.; Pires, R.; Giugliani, R.; Coelho, J.C. Effect of CuCl2, NaCl and EDTA on the enzyme alpha-L-iduronidase in the plasma of normal individuals and heterozygotes for MPS I. Clinica Chimica Acta 2002, 318, 83-89.
55. Yang, W.C.; Schultz, R.D. Inhibitory Effect of Ethylenediaminetetraacetate (Edta) on the Porcine Lymphocyte-Response to Mitogens and Reversal of the Effect with Metal-Ions. Biol. Trace Elem. Res. 1982, 4, 175-182.
56. Ortiz-Serrano, P.; Gil, J.V. Quantitation of free and glycosidically bound volatiles in and effect of glycosidase addition on three tomato varieties (Solanum lycopersicum L.). J. Agric. Food Chem. 2007, 55, 9170-9176.
57. Obara, N.; Hasegawa, M.; Kodama, O. Induced volatiles in elicitor-treated and rice blast fungusinoculated rice leaves. Biosci. Biotechnol. Biochem. 2002, 66, 2549-2559.
58. Rohloff, J.; Bones, A.M. Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication. Phytochemistry 2005, 66, 1941-1955.
59. Agger, S.A.; Lopez-Gallego, F.; Hoye, T.R.; Schmidt-Dannert, C. Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120. J. Bacteriol. 2008, 190, 6084-6096.
60. Quintana, A.; Reinhard, J.; Faure, R.; Uva, P.; Bagneres, A.G.; Massiot, G.; Clement, J.L. Interspecific variation in terpenoid composition of defensive secretions of European Reticulitermes termites. J. Chem. Ecol. 2003, 29, 639-652.
61. Bylesjo, M.; Rantalainen, M.; Cloarec, O.; Nicholson, J.K.; Holmes, E.; Trygg, J. OPLS discriminant analysis: combining the strengths of PLS-DA and SIMCA classification. J. Chemom. 2006, 20, 341-351.
62. Trygg, J.; Holmes, E.; Lundstedt, T. Chemometrics in metabonomics. J. Proteome Res. 2007, 6, 469-479.
63. Vercammen, J.; Pham-Tuan, H.; Arickx, I.; Van der Straeten, D.; Sandra, P. Monitoring of isothiocyanates emanating from Arabidopsis thaliana upon paraquat spraying. J. Chromatogr. A 2001, 912, 127-134.
64. Lambrix, V.; Reichelt, M.; Mitchell-Olds, T.; Kliebenstein, D.J.; Gershenzon, J. The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory. Plant Cell 2001, 13, 2793-2807.
65. Simkin, A.J.; Schwartz, S.H.; Auldridge, M.; Taylor, M.G.; Klee, H.J. The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles beta-ionone, pseudoionone, and geranylacetone. Plant J. 2004, 40, 882-892.
66. Caja, M.D.; Preston, C.; Kempf, M.; Schreier, P. Flavor authentication studies of alpha-ionone, beta-ionone, and alpha-ionol from various sources. J. Agr. Food Chem. 2007, 55, 6700-6704.
67. Prochazkova, D.; Haisel, D.; Wilhelmova, N. Content of carotenoids during ageing and senescence of tobacco leaves with genetically modulated life-span. Photosynthetica 2009, 47, 409-414.
68. Thomas, H.; deVilliers, L. Gene expression in leaves of Arabidopsis thaliana induced to senesce by nutrient deprivation. J. Exp. Bot. 1996, 47, 1845-1852.
69. Al-Shwyeh, H.A.; Mirghani, M.E.S.; Jamal, P. Antibacterial activity of Malaysian mango kernel. Afr J. Biotechnol. 2011, 10, 18739-18748.
70. Miklosy, E.; Kerenyi, Z. Comparison of the volatile aroma components in noble rotted grape berries from two different locations of the Tokaj wine district in Hungary. Anal. Chim. Acta 2004, 513, 177-181.
71. Nikbakhtzadeh, M.R.; Tirgari, S.; Fakoorziba, M.R.; Alipour, H. Two volatiles from the venom gland of the Samsum ant, Pachycondyla senaarensis. Toxicon. 2009, 54, 80-82.
72. Sathya, A.; Ramasubramaniaraja, R.; Brindha, P. Pharmacognostical, phytochemical and GC-MS investigation of successive extracts of Gymnema syvestre R.Br. J. Pharm. Res. 2010, 3, 984-987.
73. Maggi, F.; Lucarini, D.; Tirillini, B.; Vittori, S.; Sagratini, G.; Papa, F. Essential oil composition of Ephedra nebrodensis Tineo ex Guss. subsp. nebrodensis from central Italy. J. Essent. Oil Res. 2010, 22, 354-357.
74. Velasco-Negueruela, A.; Perez-Alonso, M.J.; Perez de Paz, P.L.; Pala-Paul, J.; Sanz, J. Analysis by gas chromatography-mass spectrometry of the volatiles from the fruits of Ammodaucus leucotrichus subsp. leucotrichus and subsp. nanocarpus grown in North Africa and the Canary Islands, respectively. J. Chromatogr. A 2006, 1108, 273-275.
75. Radulovic, N.; Dekic, M.; Stojanovic-Radic, Z.; Palic, R. Volatile constituents of Erodium cicutarium (L.) L' H,rit. (Geraniaceae). Centr Eur J. Biol. 2009, 4, 404-410.
76. Silva, D.R.; Endo, E.H.; Dias, B.P.; Nakamura, C.V.; Svidzinski, T.I.E.; de Souza, A.; Young, M.C.M.; Ueda-Nakamura, T.; Cortez, D.A.G. Chemical Composition and Antimicrobial Properties of Piper ovatum Vahl. Molecules 2009, 14, 1171-1182.
77. Chaverri, C.; Diaz, C.; Ciccio, J.F. Chemical Analysis of Essential Oils from Ocotea gomezii WC Burger and Ocotea morae Gomez-Laur. (Lauraceae) Collected at Reserva Biologica Alberto M. Brenes in Costa Rica and their Cytotoxic Activity on Tumor Cell Lines. J. Braz Chem. Soc. 2011, 22, S1-S4.
78. Fiehn, O.; Robertson, D.; Griffin, J.; van der Werf, M.; Nikolau, B.; Morrison, N.; Sumner, L.W.; Goodacre, R.; Hardy, N.W.; Taylor, C.; Fostel, J.; Kristal, B.; Kaddurah-Daouk, R.; Mendes, P.; van Ommen, B.; Lindon, J.C.; Sansone, S.A. The metabolomics standards initiative (MSI). Metabolomics 2007, 3, 175-178.
79. Jonsson, P.; Johansson, E.S.; Wuolikainen, A.; Lindberg, J.; Schuppe-Koistinen, I.; Kusano, M.; Sjostrom, M.; Trygg, J.; Moritz, T.; Antti, H. Predictive metabolite profiling applying hierarchical multivariate curve resolution to GC-MS data--a potential tool for multi-parametric diagnosis. J. Proteome Res. 2006, 5, 1407-1414.
80. Redestig, H.; Kusano, M.; Fukushima, A.; Matsuda, F.; Saito, K.; Arita, M. Consolidating metabolite identifiers to enable contextual and multi-platform metabolomics data analysis. BMC Bioinformatics 2010, 11, 214.
81. Smyth, G.K. Linear models and empirical bayes methods for assessing differential expression in microarray experiments. Stat. Appl Genet. Mol. Biol. 2004, 3, Article 3.
82. Eriksson, L.; Trygg, J.; Wold, S. CV-ANOVA for significance testing of PLS and OPLS (R) models. J. Chem. 2008, 22, 594-600.