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Rapid structural determination of alkaloids in a crude extract of Stemona saxorum by high-performance liquid chromatography/electrospray ionization coupled with tandem mass spectrometry.
Rapid Commun Mass Spectrom. 2009 Dec; 23(23):3621-31.RC

Abstract

The electrospray ionization (ESI) mass spectrometric behavior of five Stemona alkaloids, stemokerrin, oxystemokerrin, oxystemokerrilactone, oxystemokerrin N-oxide and stemokerrin N-oxide, was studied using an ESI tandem mass technique (MS(n)). These compounds, isolated from Stemona saxorum endemic in Vietnam, represent a class of alkaloids containing a pyrido[1,2-a]azepine A,B-ring core with a 1-hydroxypropyl side chain attached to C-4. Their fragmentation pathways were elucidated by ESI-MS(n) results and the elemental composition of the major product ions was confirmed by accurate mass measurement. In order to rationalize some fragmentation pathways, the relative Gibbs free energies of some product ions were estimated using the B3LYP/6-31+G(d) method. Based on the ESI-MS(n) results of five reference compounds, a reversed-phase high-performance liquid chromatography with tandem mass spectrometry (RP-HPLC/MS(n)) method was developed for the characterization of Stemona alkaloids with a pyrido[1,2-a]azepine A,B-ring core from the extract of S. saxorum. A total of 41 components were rapidly identified or tentatively characterized, of which 12 compounds were identified as Stemona alkaloids with a pyrido[1,2-a]azepine A,B-ring core, including four new compounds. This method is convenient and sensitive, especially for minor components in complex natural product extracts.

Authors+Show Affiliations

Laboratory of Mass Spectrometry, Department of Analytical Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. 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

Language

eng

PubMed ID

19890955

Citation

Peng, Shu-Ying, et al. "Rapid Structural Determination of Alkaloids in a Crude Extract of Stemona Saxorum By High-performance Liquid Chromatography/electrospray Ionization Coupled With Tandem Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 23, no. 23, 2009, pp. 3621-31.
Peng SY, Shi T, Wang YZ, et al. Rapid structural determination of alkaloids in a crude extract of Stemona saxorum by high-performance liquid chromatography/electrospray ionization coupled with tandem mass spectrometry. Rapid Commun Mass Spectrom. 2009;23(23):3621-31.
Peng, S. Y., Shi, T., Wang, Y. Z., Lin, L. G., Yang, Y. M., Jiang, H. L., & Ye, Y. (2009). Rapid structural determination of alkaloids in a crude extract of Stemona saxorum by high-performance liquid chromatography/electrospray ionization coupled with tandem mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 23(23), 3621-31. https://doi.org/10.1002/rcm.4299
Peng SY, et al. Rapid Structural Determination of Alkaloids in a Crude Extract of Stemona Saxorum By High-performance Liquid Chromatography/electrospray Ionization Coupled With Tandem Mass Spectrometry. Rapid Commun Mass Spectrom. 2009;23(23):3621-31. PubMed PMID: 19890955.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rapid structural determination of alkaloids in a crude extract of Stemona saxorum by high-performance liquid chromatography/electrospray ionization coupled with tandem mass spectrometry. AU - Peng,Shu-Ying, AU - Shi,Ting, AU - Wang,Ya-Zhou, AU - Lin,Li-Gen, AU - Yang,Yi-Ming, AU - Jiang,Hua-Liang, AU - Ye,Yang, PY - 2009/11/6/entrez PY - 2009/11/6/pubmed PY - 2010/2/23/medline SP - 3621 EP - 31 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 23 IS - 23 N2 - The electrospray ionization (ESI) mass spectrometric behavior of five Stemona alkaloids, stemokerrin, oxystemokerrin, oxystemokerrilactone, oxystemokerrin N-oxide and stemokerrin N-oxide, was studied using an ESI tandem mass technique (MS(n)). These compounds, isolated from Stemona saxorum endemic in Vietnam, represent a class of alkaloids containing a pyrido[1,2-a]azepine A,B-ring core with a 1-hydroxypropyl side chain attached to C-4. Their fragmentation pathways were elucidated by ESI-MS(n) results and the elemental composition of the major product ions was confirmed by accurate mass measurement. In order to rationalize some fragmentation pathways, the relative Gibbs free energies of some product ions were estimated using the B3LYP/6-31+G(d) method. Based on the ESI-MS(n) results of five reference compounds, a reversed-phase high-performance liquid chromatography with tandem mass spectrometry (RP-HPLC/MS(n)) method was developed for the characterization of Stemona alkaloids with a pyrido[1,2-a]azepine A,B-ring core from the extract of S. saxorum. A total of 41 components were rapidly identified or tentatively characterized, of which 12 compounds were identified as Stemona alkaloids with a pyrido[1,2-a]azepine A,B-ring core, including four new compounds. This method is convenient and sensitive, especially for minor components in complex natural product extracts. SN - 1097-0231 UR - https://www.unboundmedicine.com/medline/citation/19890955/Rapid_structural_determination_of_alkaloids_in_a_crude_extract_of_Stemona_saxorum_by_high_performance_liquid_chromatography/electrospray_ionization_coupled_with_tandem_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.4299 DB - PRIME DP - Unbound Medicine ER -