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Volumn 28, Issue 7, 2014, Pages 723-730

A systematic investigation of the fragmentation pattern of two furanoheliangolide C-8 stereoisomers using electrospray ionization mass spectrometry

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; COMPUTATIONAL CHEMISTRY; DISSOCIATION; ELECTROSPRAY IONIZATION; ESTERS; IONS; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE;

EID: 84895153819     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6839     Document Type: Article
Times cited : (14)

References (44)
  • 2
    • 33645667418 scopus 로고    scopus 로고
    • Espectrometria de massas com ionização por "electrospray": processos químicos envolvidos na formação de íons de substâncias orgânicas de baixo peso molecular
    • A. E. M. Crotti, R. Vessechi, J. L. C. Lopes, N. P. Lopes,. Espectrometria de massas com ionização por "electrospray" : processos químicos envolvidos na formação de íons de substâncias orgânicas de baixo peso molecular. Quím. Nova 2006, 29, 287.
    • (2006) Quím. Nova , vol.29 , pp. 287
    • Crotti, A.E.M.1    Vessechi, R.2    Lopes, J.L.C.3    Lopes, N.P.4
  • 3
    • 0005387475 scopus 로고
    • Principles of collisional activation in analytical mass-spectrometry
    • S. A. McLuckey,. Principles of collisional activation in analytical mass-spectrometry. J. Am. Soc. Mass Spectrom. 1992, 3, 599.
    • (1992) J. Am. Soc. Mass Spectrom. , vol.3 , pp. 599
    • McLuckey, S.A.1
  • 4
    • 0034327110 scopus 로고    scopus 로고
    • Applications and mechanisms of charge-remote fragmentation
    • C. Cheng, M. L. Gross,. Applications and mechanisms of charge-remote fragmentation. Mass Spectrom. Rev. 2000, 19, 398.
    • (2000) Mass Spectrom. Rev. , vol.19 , pp. 398
    • Cheng, C.1    Gross, M.L.2
  • 5
    • 77953340995 scopus 로고    scopus 로고
    • Basic rules for the interpretation of atmospheric pressure ionization mass spectra of small molecules
    • M. Holčapek, R. Jirásko, M. Lísa,. Basic rules for the interpretation of atmospheric pressure ionization mass spectra of small molecules. J. Chromatogr. A 2010, 1217, 3908.
    • (2010) J. Chromatogr. A , vol.1217 , pp. 3908
    • Holčapek, M.1    Jirásko, R.2    Lísa, M.3
  • 6
    • 84859376734 scopus 로고    scopus 로고
    • Resolving structural isomers of monosaccharide methyl glycosides using drift tube and traveling wave ion mobility mass spectrometry
    • H. Li, K. Giles, B. Bendiak, K. Kaplan, W. F. Siems, H. H. Hill Jr,. Resolving structural isomers of monosaccharide methyl glycosides using drift tube and traveling wave ion mobility mass spectrometry. Anal. Chem. 2012, 84, 3231.
    • (2012) Anal. Chem. , vol.84 , pp. 3231
    • Li, H.1    Giles, K.2    Bendiak, B.3    Kaplan, K.4    Siems, W.F.5    Hill Jr., H.H.6
  • 7
    • 58149109580 scopus 로고    scopus 로고
    • Mass spectrometry of bis-quinolizidine alkaloids: Differentiation of stereoisomers and metamers using ESI and FAB mass spectrometry
    • B. Jasiewicz, E. Wyrzykiewicz,. Mass spectrometry of bis-quinolizidine alkaloids: differentiation of stereoisomers and metamers using ESI and FAB mass spectrometry. Spectrosc. Lett. 2009, 42, 49.
    • (2009) Spectrosc. Lett. , vol.42 , pp. 49
    • Jasiewicz, B.1    Wyrzykiewicz, E.2
  • 8
    • 79951914577 scopus 로고    scopus 로고
    • Mass spectrometric stereoisomeric differentiation between α- And β-ascorbic acid 2-O-glucosides. Experimental and density functional theory study
    • B. Kanawati, V. Von Saint Paul, C. Herrmann, A. R. Schäffner, P. Schmitt-Kopplin,. Mass spectrometric stereoisomeric differentiation between α- and β-ascorbic acid 2-O-glucosides. Experimental and density functional theory study. Rapid Commun. Mass Spectrom. 2011, 25, 806.
    • (2011) Rapid Commun. Mass Spectrom. , vol.25 , pp. 806
    • Kanawati, B.1    Von Saint Paul, V.2    Herrmann, C.3    Schäffner, A.R.4    Schmitt-Kopplin, P.5
  • 9
    • 84860693452 scopus 로고    scopus 로고
    • Differentiation of underivatized monosaccharides by atmospheric pressure chemical ionization quadrupole time-of-flight mass spectrometry
    • Z. Zhu, L. Song, J. E. Bartmess,. Differentiation of underivatized monosaccharides by atmospheric pressure chemical ionization quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2012, 26, 1320.
    • (2012) Rapid Commun. Mass Spectrom. , vol.26 , pp. 1320
    • Zhu, Z.1    Song, L.2    Bartmess, J.E.3
  • 10
    • 84861632680 scopus 로고    scopus 로고
    • Structure elucidation of new fusarins revealing insights in the rearrangement mechanisms of the fusariummycotoxinfusarin C
    • K. Kleigrewe, F. Aydin, K. Hogrefe, P. Piecuch, K. Bergander, E. U. Wurthwein, H.-U. Humpf,. Structure elucidation of new fusarins revealing insights in the rearrangement mechanisms of the fusariummycotoxinfusarin C. J. Agr. Food Chem. 2012, 60, 5497.
    • (2012) J. Agr. Food Chem. , vol.60 , pp. 5497
    • Kleigrewe, K.1    Aydin, F.2    Hogrefe, K.3    Piecuch, P.4    Bergander, K.5    Wurthwein, E.U.6    Humpf, H.-U.7
  • 11
    • 24644512310 scopus 로고    scopus 로고
    • Triple quadrupole tandem mass spectrometry of sesquiterpene lactones: A study of goyazensolide and its congeners
    • A. E. M. Crotti, J. L. C. Lopes, N. P. Lopes,. Triple quadrupole tandem mass spectrometry of sesquiterpene lactones: a study of goyazensolide and its congeners. J. Mass Spectrom. 2005, 40, 1030.
    • (2005) J. Mass Spectrom. , vol.40 , pp. 1030
    • Crotti, A.E.M.1    Lopes, J.L.C.2    Lopes, N.P.3
  • 15
    • 51649100216 scopus 로고    scopus 로고
    • Further sesquiterpene lactones from Viguierarobusta and the potential anti-inflammatory activity of a heliangolide: Inhibition of human neutrophil elastase release
    • N. S. Arakawa, K. Schorr, S. R. Ambrõsio, I. Merfort, F. B. Da Costa,. Further sesquiterpene lactones from Viguierarobusta and the potential anti-inflammatory activity of a heliangolide: inhibition of human neutrophil elastase release. Z. Naturforsch. C. 2008, 63, 533.
    • (2008) Z. Naturforsch. C. , vol.63 , pp. 533
    • Arakawa, N.S.1    Schorr, K.2    Ambrõsio, S.R.3    Merfort, I.4    Da Costa, F.B.5
  • 16
    • 69849094445 scopus 로고    scopus 로고
    • Budlein A from Viguiera robusta inhibits leukocyte-endothelial cell interactions, adhesion molecule expression and inflammatory mediators release
    • R. Nicolete, N. S. Arakawa, C. Rius, A. Nomizo, P. J. Jose, F. B. Da Costa, M. J. Sanz, L. H. Faccioli,. Budlein A from Viguiera robusta inhibits leukocyte-endothelial cell interactions, adhesion molecule expression and inflammatory mediators release. Phytomedicine 2009, 16, 904.
    • (2009) Phytomedicine , vol.16 , pp. 904
    • Nicolete, R.1    Arakawa, N.S.2    Rius, C.3    Nomizo, A.4    Jose, P.J.5    Da Costa, F.B.6    Sanz, M.J.7    Faccioli, L.H.8
  • 17
    • 80054071903 scopus 로고    scopus 로고
    • Perspectives on sesquiterpene lactones in inflammation and cancer
    • I. Merfort,. Perspectives on sesquiterpene lactones in inflammation and cancer. Curr. Drug Targets 2011, 12, 1560.
    • (2011) Curr. Drug Targets , vol.12 , pp. 1560
    • Merfort, I.1
  • 19
    • 0035955729 scopus 로고    scopus 로고
    • Cysteine 38 in p65/NF-kappa B plays a crucial role in DNA binding inhibition by sesquiterpene lactones
    • A. Garcia-Pineres, V. Castro, G. Mora, T. Schmidt, E. Strunck, H. Pahl, I. Merfort,. Cysteine 38 in p65/NF-kappa B plays a crucial role in DNA binding inhibition by sesquiterpene lactones. J. Biol. Chem. 2001, 276, 39713.
    • (2001) J. Biol. Chem. , vol.276 , pp. 39713
    • Garcia-Pineres, A.1    Castro, V.2    Mora, G.3    Schmidt, T.4    Strunck, E.5    Pahl, H.6    Merfort, I.7
  • 20
    • 2942618506 scopus 로고    scopus 로고
    • Role of cysteine residues of p65/NF-kappa B on the inhibition by the sesquiterpene lactone parthenolide and-N-ethyl maleimide, and on its transactivating potential
    • A. Garcia-Pineres, M. Lindenmeyer, I. Merfort,. Role of cysteine residues of p65/NF-kappa B on the inhibition by the sesquiterpene lactone parthenolide and-N-ethyl maleimide, and on its transactivating potential. Life Sci. 2004, 75, 841.
    • (2004) Life Sci. , vol.75 , pp. 841
    • Garcia-Pineres, A.1    Lindenmeyer, M.2    Merfort, I.3
  • 23
    • 0019307324 scopus 로고
    • Mode of action of sesquiterpene lactones as anti-inflammatory agents
    • I. Hall, C. Starnes, K. Lee, T. Waddell,. Mode of action of sesquiterpene lactones as anti-inflammatory agents. J. Pharm. Sci. 1980, 69, 537.
    • (1980) J. Pharm. Sci. , vol.69 , pp. 537
    • Hall, I.1    Starnes, C.2    Lee, K.3    Waddell, T.4
  • 24
    • 84864408810 scopus 로고    scopus 로고
    • Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase I metabolism of bioactive compounds
    • M. Niehues, V. P. Barros, F. D. S. Emery, M. Dias-Baruffi, M. D. D. Assis, N. P. Lopes,. Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase I metabolism of bioactive compounds. Eur. J. Med. Chem. 2012, 54, 804.
    • (2012) Eur. J. Med. Chem. , vol.54 , pp. 804
    • Niehues, M.1    Barros, V.P.2    Emery, F.D.S.3    Dias-Baruffi, M.4    Assis, M.D.D.5    Lopes, N.P.6
  • 25
    • 77954466059 scopus 로고    scopus 로고
    • Fragmentation studies and electrospray ionization mass spectrometry of lapachol: Protonated, deprotonated and cationized species
    • R. Vessecchi, F. S. Emery, S. E. Galembeck, N. P. Lopes,. Fragmentation studies and electrospray ionization mass spectrometry of lapachol: protonated, deprotonated and cationized species. Rapid Commun. Mass Spectrom. 2010, 24, 2101.
    • (2010) Rapid Commun. Mass Spectrom. , vol.24 , pp. 2101
    • Vessecchi, R.1    Emery, F.S.2    Galembeck, S.E.3    Lopes, N.P.4
  • 26
    • 84871833964 scopus 로고    scopus 로고
    • Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: A computational and mass spectrometry study of lapachol congeners
    • R. Vessecchi, F. S. Emery, S. E. Galembeck, N. P. Lopes,. Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: a computational and mass spectrometry study of lapachol congeners. J. Mass Spectrom. 2012, 47, 1648.
    • (2012) J. Mass Spectrom. , vol.47 , pp. 1648
    • Vessecchi, R.1    Emery, F.S.2    Galembeck, S.E.3    Lopes, N.P.4
  • 27
    • 84876234443 scopus 로고    scopus 로고
    • A predictive science approach to aid understanding of electrospray ionisation tandem mass spectrometric fragmentation pathways of small molecules using density functional calculations
    • A. Galezowska, M. W. Harrison, J. M. Herniman, C.-K. Skylaris, G. J. Langley,. A predictive science approach to aid understanding of electrospray ionisation tandem mass spectrometric fragmentation pathways of small molecules using density functional calculations. Rapid Commun. Mass Spectrom. 2013, 27, 964.
    • (2013) Rapid Commun. Mass Spectrom. , vol.27 , pp. 964
    • Galezowska, A.1    Harrison, M.W.2    Herniman, J.M.3    Skylaris, C.-K.4    Langley, G.J.5
  • 28
    • 21844444320 scopus 로고    scopus 로고
    • Internal energy and fragmentation of ions produced in electrospray sources
    • V. Gabelica, E. De Pauw,. Internal energy and fragmentation of ions produced in electrospray sources. Mass Spectrom. Rev. 2005, 24, 566.
    • (2005) Mass Spectrom. Rev. , vol.24 , pp. 566
    • Gabelica, V.1    De Pauw, E.2
  • 29
    • 85153548439 scopus 로고    scopus 로고
    • Using multiple mass defect filters and higher energy collisional dissociation on an LTQ orbitrap XL for fast, sensitive and accurate metabolite ID
    • accessed June 2013
    • Y. Huang, S. Liu, S. Miao, P.M. Jeanville,. Using multiple mass defect filters and higher energy collisional dissociation on an LTQ orbitrap XL for fast, sensitive and accurate metabolite ID. Thermo Fisher Scientific-Application Note 417. Available: http://www.thermoscientific.com/ecomm/servlet/ techresource?productId=11962157&taxonomy=4&resourceId= 89747&contentType=Application%20Notes&storeId=11152 (accessed June 2013).
    • Thermo Fisher Scientific - Application Note , vol.417
    • Huang, Y.1    Liu, S.2    Miao, S.3    Jeanville, P.M.4
  • 31
    • 0032770285 scopus 로고    scopus 로고
    • Energy-resolved mass spectrometry: A comparison of quadrupole cell and cone-voltage collision-induced dissociation
    • A. G. Harrison,. Energy-resolved mass spectrometry: a comparison of quadrupole cell and cone-voltage collision-induced dissociation. Rapid Commun. Mass Spectrom 1999, 13, 1663.
    • (1999) Rapid Commun. Mass Spectrom , vol.13 , pp. 1663
    • Harrison, A.G.1
  • 33
    • 35448946869 scopus 로고    scopus 로고
    • Gas-phase basicities of polyfunctional molecules. Part 1: Theory and methods
    • G. Bouchoux,. Gas-phase basicities of polyfunctional molecules. part 1: theory and methods. Mass Spectrom. Rev. 2007, 26, 775.
    • (2007) Mass Spectrom. Rev. , vol.26 , pp. 775
    • Bouchoux, G.1
  • 35
    • 47049091460 scopus 로고    scopus 로고
    • Evaluation of the enthalpy of formation, proton affinity, and gas-phase basicity of gamma-butyrolactone and 2-pyrrolidinone by isodesmic reactions
    • R. Vessecchi, S. E. Galembeck,. Evaluation of the enthalpy of formation, proton affinity, and gas-phase basicity of gamma-butyrolactone and 2-pyrrolidinone by isodesmic reactions. J. Phys. Chem. A 2008, 112, 4060.
    • (2008) J. Phys. Chem. A , vol.112 , pp. 4060
    • Vessecchi, R.1    Galembeck, S.E.2
  • 36
    • 0842341771 scopus 로고
    • The development and use of quantum-mechanical molecular-models.76. AM1 - A new general-purpose quantum-mechanical molecular-model
    • M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart,. The development and use of quantum-mechanical molecular-models.76. AM1-A new general-purpose quantum-mechanical molecular-model. J. Am. Chem. Soc. 1985, 107, 3902.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 37
    • 0345491105 scopus 로고
    • Development of the colle-salvetti correlation-energy formula into a functional of the electron-density
    • C. T. Lee, W. T. Yang, R. G. Parr,. Development of the colle-salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B. 1988, 37, 785.
    • (1988) Phys. Rev. B. , vol.37 , pp. 785
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 38
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. 3. The role of exact exchange
    • A. D. Becke,. Density-functional thermochemistry. 3. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 40
    • 46149091762 scopus 로고    scopus 로고
    • Application of computational quantum chemistry to chemical processes involved in mass spectrometry
    • R. Vessecchi, S. E. Galembeck, N. P. Lopes, P. G. B. D. Nascimento, A. E. M. Crotti,. Application of computational quantum chemistry to chemical processes involved in mass spectrometry. Quím. Nova 2008, 31, 840.
    • (2008) Quím. Nova , vol.31 , pp. 840
    • Vessecchi, R.1    Galembeck, S.E.2    Lopes, N.P.3    Nascimento, P.G.B.D.4    Crotti, A.E.M.5
  • 41
    • 85153552272 scopus 로고    scopus 로고
    • NIST-National Institute of Standards and Technology. Available: webbook.nist.gov/chemistry
    • NIST-National Institute of Standards and Technology. Available: webbook.nist.gov/chemistry.
  • 42
    • 84876269476 scopus 로고    scopus 로고
    • From the mobile proton to wandering hydride ion: Mechanistic aspects of gas-phase ion chemistry
    • G. Bouchoux,. From the mobile proton to wandering hydride ion: mechanistic aspects of gas-phase ion chemistry. J. Mass Spectrom. 2013, 48, 505.
    • (2013) J. Mass Spectrom. , vol.48 , pp. 505
    • Bouchoux, G.1
  • 44
    • 0006250854 scopus 로고    scopus 로고
    • Structural effects on the intrinsic basicities of alpha,beta-unsaturated lactones and ketones
    • G. Bouchoux, D. Leblanc, O. Mõ, M. Yañez,. Structural effects on the intrinsic basicities of alpha,beta-unsaturated lactones and ketones. J. Org. Chem. 1997, 62, 8439.
    • (1997) J. Org. Chem. , vol.62 , pp. 8439
    • Bouchoux, G.1    Leblanc, D.2    Mõ, O.3    Yañez, M.4


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