Analysis of the cyanolichen Lichina pygmaea metabolites using in situ DART-MS: From detection to thermochemistry of mycosporine serinol

Journal of Mass Spectrometry

Volumn 50, Issue 3, 2015, Pages 445-462

  Le Pogam, Pierre ^a   Legouin, Béatrice ^a   Le Lamer, Anne Cécile ^a,b   Boustie, Joël ^a   Rondeau, David ^c,d  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

^b UNIVERSITÉ PAUL SABATIER   (France)

^c UNIVERSITÉ DE RENNES 1   (France)

^d UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

Author keywords

Arrhenius plots; DART MS; in situ analysis; lichen metabolites; thermochemistry

Indexed keywords

ARRHENIUS PLOTS; BIOMOLECULES; CHEMICAL ANALYSIS; DEHYDRATION; FUNGI; IONIZATION; IONIZATION OF GASES; IONIZATION OF LIQUIDS; MASS SPECTROMETRY; MOLECULES; THERMOCHEMISTRY;

ACTIVATION ENTHALPIES; DART-MS; DEHYDRATION REACTIONS; DIRECT ANALYSIS IN REAL TIME; ELEMENTAL COMPOSITIONS; IN-SITU ANALYSIS; SECONDARY METABOLITES; THERMODYNAMIC QUANTITIES;

METABOLITES;

ARTICLE; CONTROLLED STUDY; DEHYDRATION; DIRECT ANALYSIS IN REAL TIME MASS SPECTROMETRY; FLOW RATE; LICHEN (DISEASE); LICHEN (ORGANISM); LICHINA PYGMAEA; MASS SPECTROMETRY; METABOLITE; NONHUMAN; PRIORITY JOURNAL; THERMODYNAMICS; TIME OF FLIGHT MASS SPECTROMETRY; ASCOMYCETES; CHEMISTRY; METABOLISM; PROCEDURES;

LICHINA PYGMAEA;

CYCLOHEXANONE DERIVATIVE; MYCOSPORINE-SERINOL; PROPANEDIOL DERIVATIVE;

ASCOMYCOTA; CYCLOHEXANONES; LICHENS; MASS SPECTROMETRY; PROPYLENE GLYCOLS; THERMODYNAMICS;

EID: 84925432532     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3549     Document Type: Article

References (40)

1. C. Roullier, M. Chollet-Krugler, E.-M. Pferschy-Wenzig, A. Maillard, G. N. Rechberger, B. Legouin-Gargadennec, R. Bauer, J. Boustie,. Characterization and identification of mycosporines-like compounds in cyanolichens. Isolation of mycosporine hydroxyglutamicol from Nephroma laevigatum Ach. Phytochemistry 2011, 72, 1348.
2. J. Boustie, M. Grube,. Lichens-a promising source of bioactive secondary metabolites. Plant Genet. Resour.-C 2005, 3, 273.
3. S. Huneck, I. Yoshimura,. Identification of lichen substances. Springer: Berlin, 1996.
4. S. La Barre, C. Roullier, J. Boustie,. In Outstanding marine molecules, S. La Barre, M. Kornprobst, (Eds). Wiley: New-York, 2014, 333.
5. K. H. Nguyen, M. Chollet-Krugler, N. Gouault, S. Tomasi,. UV-protectant metabolites from lichens and their symbiotic partners. Nat. Prod. Rep. 2013, 30, 1490.
6. Y. V. Yuan, Y. Athukorala,. Marine cosmeceuticals: trends and prospects, S. K. Kim, (Ed.). Taylor and Francis: Boca Raton, Florida, USA, 2011, 143.
7. A. Oren, N. Gunde-Cimerman,. Mycosporines and mycosporine-like amino acids: UV protectants or multipurpose secondary metabolites? FEMS Microbiol. Lett. 2007, 269, 1.
8. W. Van Roy, A. Mathey, L. Van Vaeck,. In situ analysis of lichen pigments by Fourier Transform Laser Microprobe Mass Spectrometry with external ion source. Rapid Commun. Mass Spectrom. 1996, 10, 562.
9. C. Liao, M. D. Piercey-Normore, J. L. Sorensen, K. Gough,. In situ imaging of usnic acid in selected Cladonia spp. by vibrational spectroscopy. Analyst 2010, 135, 3242.
10. P. Ozenda, G. Clauzade,. Les lichens: étude biologique et flore illustrée. Masson: Paris, 1970.
11. J. Hajslova, T. Cajka, L. Vaclavik,. Challenging applications offered by direct analysis in real time (DART) in food-quality and safety analysis. TrAC Trends Anal. Chem. 2011, 30, 204.
12. L.-P. Li, B.-S. Feng, J.-W. Yang, C.-L. Chang, Y. Bai, H.-W. Liu,. Applications of ambient mass spectrometry in high-throughput screening. Analyst 2013, 138, 3097.
13. E. Esquenazi, Y.-L. Yang, J. Watrous, W. H. Gerwick, P. C. Dorrestein,. Imaging mass spectrometry of natural products. Nat. Prod. Rep. 2009, 26, 1521.
14. N. Bjarnholt, B. Li, J. D'Alvise, C. Janfelt,. Mass spectrometry imaging of plant metabolites-principles and possibilities. Nat. Prod. Rep. 2014, 31, 818.
15. P. Nemes, A. A. Barton, A. Vertes,. Three-dimensional imaging of metabolites in tissues under ambient conditions by Laser Ablation Electrospray Ionization mass spectrometry. Anal. Chem. 2009, 81, 6668.
16. R. A. Musah, M. A. Domin, M. A. Walling, J. R. E. Shepard,. Rapid identification of synthetic cannabinoids in herbal samples via direct analysis in real time mass spectrometry: Identification of synthetic cannabinoids via DART-MS. Rapid Commun. Mass Spectrom. 2012, 26, 1109.
17. D. J. Weston,. Ambient ionization mass spectrometry: current understanding of mechanistic theory, analytical performance and application areas. Analyst 2010, 135, 661.
18. R. B. Cody, J. A. Laramée, H. D. Durst,. A Versatile new ion source for the analysis of materials in open air under ambient conditions. Anal. Chem. 2005, 77, 2297.
19. E. S. Chernetsova, G. E. Morlock, I. A. Revelsky,. DART mass spectrometry and its applications in chemical analysis. Russ. Chem. Rev. 2011, 80, 235.
20. L. Song, S. C. Gibson, D. Bhandari, K. D. Cook, J. E. Bartmess,. Ionization mechanism of positive-ion direct analysis in real time: a transient microenvironment concept. Anal. Chem. 2009, 81, 10080.
21. G. A. Harris, C. E. Falcone, F. M. Fernández,. Sensitivity "hot spots" in the direct analysis in real time mass spectrometry of nerve agent simulants. J. Am. Soc. Mass Spectrom. 2012, 23, 153.
22. M. Zhou, J. F. McDonald, F. M. Fernández,. Optimization of a direct analysis in real time/time-of-flight mass spectrometry method for rapid serum metabolomic fingerprinting. J. Am. Soc. Mass Spectrom. 2010, 21, 68.
23. S. D. Maleknia, T. M. Vail, R. B. Cody, D. O. Sparkman, T. L. Bell, M. A. Adams,. Temperature-dependent release of volatile organic compounds of eucalypts by direct analysis in real time (DART) mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23, 2241.
24. C. Roullier, M. Chollet-Krugler, A. Bernard, J. Boustie,. Multiple dual-mode centrifugal partition chromatography as an efficient method for the purification of a mycosporine from a crude methanolic extract of Lichina pygmaea. J. Chromatogr. B 2009, 877, 2067.
25. C. Roullier, M. Chollet-Krugler, P. van de Weghe, F. Lohézic-Le Dévéhat, J. Boustie,. A novel aryl-hydrazide from the marine lichen Lichina pygmaea: Isolation, synthesis of derivatives, and cytotoxicity assays. Bioorg. Med. Chem. Lett. 2010, 20, 4582.
26. G. A. Harris, D. M. Hostetler, C. Y. Hampton, F. M. Fernández,. Comparison of the internal energy deposition of direct analysis in real time and electrospray ionization time-of-flight mass spectrometry. J. Am. Soc. Mass Spectrom. 2010, 21, 855.
27. W. F. K. Wynne-Jones, H. Eyring,. Absolute rate of reactions in condensed phases. J. Chem. Phys. 1935, 3, 492.
28. Y. Abe, M. Yamaguchi, M. Mutsuga, Y. Hirahara, M. Kawamura, R. Kikura-Hanajiri, Y. Goda, Y. Kawamura,. Discrimination of plasticizers and screening of phthalates in polyvinyl chloride using DART-TOF/MS. Shokuhin Eiseigaku Zasshi J. Food Hyg. Soc. Jpn. 2009, 51, 160.
29. K. Fouyer, O. Lavastre, D. Rondeau,. Direct Monitoring of the Role Played by a Stabilizer in a Solid Sample of Polymer Using Direct Analysis in Real Time Mass Spectrometry: The Case of Irgafos 168 in Polyethylene. Anal. Chem. 2012, 84, 8642.
30. J. H. Gross,. Direct analysis in real time-a critical review on DART-MS. Anal. Bioanal. Chem. 2014, 406, 63.
31. K. N. Marsh,. Recommended reference materials for the realization of physicochemical properties. Blackwell Scientific Publications: Oxford, UK, 1987.
32. J. Tirkey, S. P. Adhikary,. Cyanobacteria in biological soil crusts of India. Curr. Sci. 2005, 89, 515.
33. A. A. Gorbushina, K. Whitehead, T. Dornieden, A. Niesse, A. Schulte, J. I. Hedges,. Black fungal colonies as units of survival: hyphal mycosporines synthesized by rock-dwelling microcolonial fungi. Can. J. Bot. 2003, 81, 131.
34. H. Jiang, K. Gao, E. W. Helbling,. UV-absorbing compounds in Porphyra haitanensis (Rhodophyta) with special reference to effects of desiccation. J. Appl. Phycol. 2008, 20, 387.
35. M. G. Evans, M. Polanyi,. Application of the transition-state method to the calculation of reaction velocities, especially in solution. Trans. Faraday Soc. 1935, 31, 875.
36. H. Eyring,. Activated complex in chemical reactions. J. Chem. Phys. 1935, 3, 107.
37. K. J. Laidler,. Chemical kinetics. McGraw-Hill: New-York, 1965.
38. R. B. Hall, A. M. DeSantolo, S. J. Bares,. Time resolved measurements of methanol decomposition on Ni (100) utilizing laser induced desorption. Surf. Sci. Lett. 1985, 161, 533.
39. P. J. Robinson, K. A. Holbrook,. Unimolecular reactions. Wiley-Interscience: New York, 1972.
40. P. Le Pogam, B. Legouin, J. Boustie, D. Rondeau,. Detection and chemical reactivity of lichen secondary metabolites using in situ DART-MS. Proceedings of the EuPA 2013 congress, Saint-Malo, France, 2013.