Proposed mechanisms for the fragmentation of doubly allylic alkenamides (tingle compounds) by low energy collisional activation in a triple quadrupole mass spectrometer

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 10, 2004, Pages 1462-1470

  Hiserodt, Richard D ^a   Pope, Barry M ^a   Cossette, Michael ^a   Dewis, Mark L ^a  

^a INTERNATIONAL FLAVORS AND FRAGRANCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FRAGMENTATION; TINGLE COMPOUNDS;

CELLS; MASS SPECTROMETRY; NITROGEN COMPOUNDS; POSITIVE IONS; SYNTHESIS (CHEMICAL);

MASS SPECTROMETERS;

ACRYLIC ACID; ALKENAMIDE; ALLYL COMPOUND; AMIDE; PELLITORINE; SPILANTHOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; COLLISIONALLY ACTIVATED DISSOCIATION; FRAGMENTATION REACTION; MASS SPECTROMETER; MASS SPECTROMETRY; MOLECULAR MECHANICS; NONHUMAN; ORGANOLEPTIC PROPERTY; PHYSICAL CHEMISTRY; PHYTOCHEMISTRY;

EID: 4744364017     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2004.06.009     Document Type: Article

References (37)

1. H. Greger Alkamides Structural Relationships, Distribution and Biological Activity Planta Medica 50 1984 366 375
2. Comparative Phytochemistry of the Alkamides J. Iam H. Breteler T. Arnason L. Hansen Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds (NOARC) 1988 Elsevier Amsterdam, The Netherlands 159 178
3. B.P. Bryant, I. Mezine Alkamides that Produce Tingling Parethesia Activate Tactile and Thermal Trigeminal Neurons Brain Res. 842 1999 452 460
4. N. Nakatani, M. Nagashima Pungent Alkamides from Spilanthes acmella L. var. oleracea Clark Biosci. Biotech. Biochem. 56 1992 759 762
5. S.K. Adesina, D.D. Akinwusi New Constituents of Zanthoxylum tessmanii (Engl.) Ayafor Root J. High Res. Chromatogr./Chromatogr. Commun. 9 1986 412 414
6. S.K. Adesina Further New Constituents of Zanthoxylum leprieurii Fitoterapia 58 1987 123 126
7. S.K. Adesina Further Novel Constituents of Zanthoxylum zanthoxyloides Root and Pericarp J. Nat. Prod. 49 1986 715 716
8. B.P. Bryant Trigeminal Sensory Stimuli and Animal Repellants from Plants Int. Pat. Appl. 1999 WO 9921425 A1 19980923
9. M. Nagashima, N. Nakatani LC-MS Analysis and Structure Determination of Pungent Alkamides from Spilanthes acmella L. Flowers Lebensm. Wiss. Technol. 25 1992 417 421
10. X.-G. He, L.-Z. Lin, M.W. Bernart, L.-Z. Lian Analysis of Alkamides in Roots and Achenes of Echinacea purpurea by Liquid-Chromatography Electrospray Mass Spectrometry J. Chromatogr. A 815 1998 205 211
11. V.H. Wysocki, M.M. Ross, S.R. Horning, R.G. Cooks Remote-Site (Charge-Remote) Fragmentation Rapid Commun. Mass Spectrom. 2 1988 214 217
12. J. Adams Charge-Remote Fragmentations Analytical Applications and Fundamental Studies Mass Spectrom. Rev. 9 1990 141 186
13. M. Antoine, J. Adams Implication of the Charge Site in "Charge-Remote" Fragmentations J. Am. Soc. Mass Spectrom. 3 1992 776 778
14. J. Adams, M.J. Songer Charge-Remote Fragmentations for Structural Determination of Lipids Trends Anal. Chem. 12 1993 28 35
15. C. Cheng, E. Pittenauer, M.L. Gross Charge-Remote Fragmentations are Energy-Dependent Processes J. Am. Soc. Mass Spectrom. 9 1998 840 844
16. C. Cheng, M.L. Gross Applications and Mechanisms of Charge-Remote Fragmentation Mass Spectrom. Rev. 19 2000 398 420
17. C. Seto, J.S. Grossert, D.S. Waddell, J.M. Curtis, R.K. Boyd Effects of Ionization Mode on Charge-Site-Remote and Related Fragmentation Reactions of Long-Chain Quaternary Ammonium Ions J. Am. Soc. Mass Spectrom. 12 2001 571 579
18. C. Denekamp, E. Tenetov, Y. Horev Homolytic Cleavages in Pyridinium Ions, an Excited State Process J. Am. Soc. Mass Spectrom. 14 2003 790 801
19. M.J. Contado, J. Adams, N.J. Jensen, M.L. Gross A Charge-Remote Allylic Cleavage Reaction Mechanistic Possibilities J. Am. Soc. Mass Spectrom. 2 1991 180 183
20. Angle- and Energy-Resolved Fragmentation Spectra from Tandem Mass Spectrometry F.W. McLafferty Tandem Mass Spectrometry 1983 John Wiley and Sons New York 303 320
21. A.G. Harrison Energy-Resolved Mass Spectrometry A Comparison of Quadrupole Cell and Cone-Voltage Collision-Induced Dissociation Rapid Commun. Mass Spectrom. 13 1999 1663 1667
22. A.G. Harrison Fragmentation Reactions of Alkylphenylammonium Ions J. Mass Spectrom. 34 1999 1253 1273
23. D. Lemaire, L. Serani, O. Laprevote, V. Ovcharenko, K. Pihlaja, G. Stajer Energy-Resolved Electrospray Mass Spectrometry of Diexo-Norbornane and Norbornene Derivatives Containing a Fused, Phenyl-Substituted, 1,3-Oxazine Ring Competitive Retro-Diels-Alder Fragmentation Processes Eur. Mass Spectrom. 5 1999 253 257
24. M.W. Wensing, A.P. Snyder, C.S. Harden Energy Resolved Mass Spectrometry of Diethyl Alkyl Phosphonates with an Atmospheric Pressure Ionization Tandem Mass Spectrometer J. Mass Spectrom. 30 1995 1539 1545
25. M.W. Wensing, A.P. Snyder, C.S. Harden Energy Resolved Mass Spectrometry of Dialkyl Methylphosphonates with an Atmospheric Pressure Ionization Tandem Mass Spectrometer Rapid Commun. Mass Spectrom. 10 1996 1259 1265
26. P.J. Dyson, B.F.G. Johnson, J.S. McIndoe, P.R.R. Langridge-Smith Energy-Dependent Electrospray Mass Spectrometry Applications in Transition Metal Carbonyl Chemistry Rapid Commun. Mass Spectrom. 14 2000 311 313
27. D.D. Fetterolf, R.A. Yost Energy-Resolved Collision-nduced Dissociation in Tandem Mass Spectrometry Int. J. Mass Spectrom. Ion Phys. 44 1982 37 50
28. M. Begala, G. Delogu, E. Maccioni, G. Podda, G. Tocco, E. Quezada, E. Uriarte, M.A. Fedrigo, D. Favretto, P. Traldi Electrospray Ionization Iandem Mass Spectrometry in the Characterization of Isomeric Benzofurocoumarins Rapid Commun. Mass Spectrom. 15 2001 1000 1010
29. H.I. Kenttamaa, R.G. Cooks Tautomer Characterization by Energy Resolved Mass Spectrometry. Dimethyl Phosphite and Dimethyl Phosphonate Ions J. Am. Chem Soc. 107 1985 1881 1886
30. W. Weinmann, M. Stoertzel, S. Vogt, J. Wendt Tune Compounds for Electrospray Ionization/In-Source Collision-Induced Dissociation with Mass Spectral Library Searching J. Chromatorg. A 926 2001 199 209
31. W. Weinmann, M. Stoertzel, S. Vogt, M. Svoboda, A. Schreiber Tuning Compounds for Electrospray Ionization/In-Source Collision-Induced Dissociation and Mass Spectra Library Searching J. Mass Spectrom. 36 2001 1013 1023
32. X.-Z. Qin Atmospheric Pressure Ionization Tandem Mass Spectra of Protonated Timolol J. Mass Spectrom. 34 1999 51 59
33. F.-F. Hsu, J. Turk Charge-Remote and Charge-Driven Fragmentation Processes in Diacyl Glycerophosphoethanolamine Upon Low-Energy Collisional Activation A Mechanistic Proposal J. Am. Soc. Mass Spectrom. 11 2000 892 899
34. H. Wang, Y. Wu, Z. Zhao Fragmentation Study of Simvastatin and Lovastatin Using Electrospray Ionization Tandem Mass Spectrometry J. Mass Spectrom. 36 2001 58 70
35. A.W.T. Bristow, K.S. Webb Intercomparison Study of Accurate Mass Measurement of Small Molecules in Mass Spectrometry J. Am. Soc. Mass Spectrom. 14 2003 1086 1098
36. G. Paul, W. Winnik, N. Hughes, H. Schweingruber, R. Heller, A. Schoen Accurate Mass Measurement at Enhanced Mass-Resolution on a Triple Quadrupole Mass-Spectrometer for the Identification of a Reaction Impurity and Collisionally-Induced Fragment Ions of Cabergoline Rapid Commun. Mass Spectrom. 17 2003 561 568
37. N. Hughes, W. Winnik, J.-J. Dunyach, M. Amad, M. Splendore, G. Paul High-Sensitivity Quantitation of Cabergoline and Pergolide Using a Triple-Quadrupole Mass Spectrometer with Enhanced Mass-Resolution Capabilities J. Mass Spectrom. 38 2003 743 751