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Liquid chromatography/electrospray ionization mass spectrometry for the characterization of twenty-three flavonoids in the extract of Dalbergia odorifera.
Rapid Commun Mass Spectrom. 2005; 19(11):1557-65.RC

Abstract

A method incorporating high-performance liquid chromatography (HPLC) with electrospray ionization and tandem mass spectrometry, with parallel analysis by HPLC with UV detection using a diode-array detector, was developed for the qualitative characterization of flavonoids in D. odorifera. Twenty-three flavonoids, including six isoflavones, six neoflavones, four isoflavanones, three flavanones, two chalcones, one isoflavanonol and one pterocarpan, were unambiguously identified by comparing their retention times, UV and MS spectra with those of authentic compounds. Furthermore, the collision-induced dissociations of the [M-H]- ions were studied to clarify the MS behavior of the different types of flavonoids. In negative ion ESI-MS all the flavonoids yielded prominent [M-H]- ions in the first order mass spectra. Fragments involving losses of CH3*, H2O, CO, C2H2O, and CO2 were observed in the MS/MS spectra. Each of the seven types of flavonoid showed characteristic MS/MS fragmentation patterns. The isoflavanones, flavanones and chalcones were observed to undergo retro-Diels-Alder fragmentations. The spectra of almost all the neoflavonoids unexpectedly exhibited only [M-H-CH3]-* radical anions as base peaks without any further fragmentation. Substitution positions also remarkably influenced the fragmentation behavior, which could assist in distinction among the flavonoid isomers. The fragmentation rules deduced here could aid in the characterization of other flavonoids of these types.

Authors+Show Affiliations

School of Pharmaceutical Sciences, Peking University, Beijing 100083, PR China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15880612

Citation

Liu, Rongxia, et al. "Liquid Chromatography/electrospray Ionization Mass Spectrometry for the Characterization of Twenty-three Flavonoids in the Extract of Dalbergia Odorifera." Rapid Communications in Mass Spectrometry : RCM, vol. 19, no. 11, 2005, pp. 1557-65.
Liu R, Ye M, Guo H, et al. Liquid chromatography/electrospray ionization mass spectrometry for the characterization of twenty-three flavonoids in the extract of Dalbergia odorifera. Rapid Commun Mass Spectrom. 2005;19(11):1557-65.
Liu, R., Ye, M., Guo, H., Bi, K., & Guo, D. A. (2005). Liquid chromatography/electrospray ionization mass spectrometry for the characterization of twenty-three flavonoids in the extract of Dalbergia odorifera. Rapid Communications in Mass Spectrometry : RCM, 19(11), 1557-65.
Liu R, et al. Liquid Chromatography/electrospray Ionization Mass Spectrometry for the Characterization of Twenty-three Flavonoids in the Extract of Dalbergia Odorifera. Rapid Commun Mass Spectrom. 2005;19(11):1557-65. PubMed PMID: 15880612.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Liquid chromatography/electrospray ionization mass spectrometry for the characterization of twenty-three flavonoids in the extract of Dalbergia odorifera. AU - Liu,Rongxia, AU - Ye,Min, AU - Guo,Hongzhu, AU - Bi,Kaishun, AU - Guo,De-An, PY - 2005/5/10/pubmed PY - 2005/7/23/medline PY - 2005/5/10/entrez SP - 1557 EP - 65 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 19 IS - 11 N2 - A method incorporating high-performance liquid chromatography (HPLC) with electrospray ionization and tandem mass spectrometry, with parallel analysis by HPLC with UV detection using a diode-array detector, was developed for the qualitative characterization of flavonoids in D. odorifera. Twenty-three flavonoids, including six isoflavones, six neoflavones, four isoflavanones, three flavanones, two chalcones, one isoflavanonol and one pterocarpan, were unambiguously identified by comparing their retention times, UV and MS spectra with those of authentic compounds. Furthermore, the collision-induced dissociations of the [M-H]- ions were studied to clarify the MS behavior of the different types of flavonoids. In negative ion ESI-MS all the flavonoids yielded prominent [M-H]- ions in the first order mass spectra. Fragments involving losses of CH3*, H2O, CO, C2H2O, and CO2 were observed in the MS/MS spectra. Each of the seven types of flavonoid showed characteristic MS/MS fragmentation patterns. The isoflavanones, flavanones and chalcones were observed to undergo retro-Diels-Alder fragmentations. The spectra of almost all the neoflavonoids unexpectedly exhibited only [M-H-CH3]-* radical anions as base peaks without any further fragmentation. Substitution positions also remarkably influenced the fragmentation behavior, which could assist in distinction among the flavonoid isomers. The fragmentation rules deduced here could aid in the characterization of other flavonoids of these types. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/15880612/Liquid_chromatography/electrospray_ionization_mass_spectrometry_for_the_characterization_of_twenty_three_flavonoids_in_the_extract_of_Dalbergia_odorifera_ DB - PRIME DP - Unbound Medicine ER -