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Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry.
J Chromatogr A. 2010 Nov 05; 1217(45):7109-22.JC

Abstract

Liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (LC/ESI-QTOF-MS/MS) was performed to study the fragmentation behaviors of steroidal alkaloids from Fritillaria species, the antitussive and expectorant herbs widely used in traditional Chinese medicine. We propose, herein, a strategy that combining key diagnostic fragment ions and the relative abundances and amounts of major fragment ions (the ions exceeding 10% in abundance) to distinguish different sub-classes of Fritillaria alkaloids (FAs). It was found that hydrogen rearrangement and induction effects result in ring cleavage of the basic skeletons occurred in the MS/MS process and produced characteristic fragment ions, which are useful for structural elucidation. This method was finally used to investigate the primary steroidal alkaloids in the extracts of eight major Fritillaria species. As a result, 41 steroidal alkaloids (29 cevanine type, 1 jervine type, 6 veratramine type and 5 secosolanidine type alkaloids) were selectively identified in these Fritillaria species. Twenty-six compounds were unambiguously identified by comparing with the reference compounds and 15 compounds were tentatively identified or deduced according to their MS/MS data. Logical fragmentation pathways for different types of FAs have been proposed and are useful for the identification of these types of steroidal alkaloids in natural products especially when there are no reference compounds available.

Authors+Show Affiliations

Key Laboratory of Modern Chinese Medicines (China Pharmaceutical University), Ministry of Education, Nanjing 210009, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20926090

Citation

Zhou, Jian-Liang, et al. "Characterization and Identification of Steroidal Alkaloids in Fritillaria Species Using Liquid Chromatography Coupled With Electrospray Ionization Quadrupole Time-of-flight Tandem Mass Spectrometry." Journal of Chromatography. A, vol. 1217, no. 45, 2010, pp. 7109-22.
Zhou JL, Xin GZ, Shi ZQ, et al. Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Chromatogr A. 2010;1217(45):7109-22.
Zhou, J. L., Xin, G. Z., Shi, Z. Q., Ren, M. T., Qi, L. W., Li, H. J., & Li, P. (2010). Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of Chromatography. A, 1217(45), 7109-22. https://doi.org/10.1016/j.chroma.2010.09.019
Zhou JL, et al. Characterization and Identification of Steroidal Alkaloids in Fritillaria Species Using Liquid Chromatography Coupled With Electrospray Ionization Quadrupole Time-of-flight Tandem Mass Spectrometry. J Chromatogr A. 2010 Nov 5;1217(45):7109-22. PubMed PMID: 20926090.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. AU - Zhou,Jian-Liang, AU - Xin,Gui-Zhong, AU - Shi,Zi-Qi, AU - Ren,Mei-Ting, AU - Qi,Lian-Wen, AU - Li,Hui-Jun, AU - Li,Ping, Y1 - 2010/09/16/ PY - 2010/03/31/received PY - 2010/08/16/revised PY - 2010/09/07/accepted PY - 2010/10/8/entrez PY - 2010/10/12/pubmed PY - 2011/1/22/medline SP - 7109 EP - 22 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1217 IS - 45 N2 - Liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (LC/ESI-QTOF-MS/MS) was performed to study the fragmentation behaviors of steroidal alkaloids from Fritillaria species, the antitussive and expectorant herbs widely used in traditional Chinese medicine. We propose, herein, a strategy that combining key diagnostic fragment ions and the relative abundances and amounts of major fragment ions (the ions exceeding 10% in abundance) to distinguish different sub-classes of Fritillaria alkaloids (FAs). It was found that hydrogen rearrangement and induction effects result in ring cleavage of the basic skeletons occurred in the MS/MS process and produced characteristic fragment ions, which are useful for structural elucidation. This method was finally used to investigate the primary steroidal alkaloids in the extracts of eight major Fritillaria species. As a result, 41 steroidal alkaloids (29 cevanine type, 1 jervine type, 6 veratramine type and 5 secosolanidine type alkaloids) were selectively identified in these Fritillaria species. Twenty-six compounds were unambiguously identified by comparing with the reference compounds and 15 compounds were tentatively identified or deduced according to their MS/MS data. Logical fragmentation pathways for different types of FAs have been proposed and are useful for the identification of these types of steroidal alkaloids in natural products especially when there are no reference compounds available. SN - 1873-3778 UR - https://www.unboundmedicine.com/medline/citation/20926090/Characterization_and_identification_of_steroidal_alkaloids_in_Fritillaria_species_using_liquid_chromatography_coupled_with_electrospray_ionization_quadrupole_time_of_flight_tandem_mass_spectrometry_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(10)01239-2 DB - PRIME DP - Unbound Medicine ER -