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Structure-fragmentation relationship and rapid dereplication of Buxus steroidal alkaloids by electrospray ionization-quadrupole time-of-flight mass spectrometry.
Rapid Commun Mass Spectrom. 2013 Jan 15; 27(1):169-78.RC

Abstract

RATIONALE

Tandem mass spectrometric studies of natural products revealed the identification of key fragments which can be helpful for their rapid dereplication in plant extracts utilizing a liquid chromatography/tandem mass spectrometry (LC/MS/MS) approach, particularly for the thermally labile compounds. The knowledge of the collision-induced dissociation (CID) fragmentation pattern of the molecule is essentially required prior to the analysis by LC/MS/MS.

METHODS

The fragmentation patterns of eleven Buxus steroidal alkaloids were studied by using a positive ion electrospray ionization quadrupole time-of-flight mass spectrometry (ESI-QqTOF-MS/MS) hybrid instrument. Chromatographic separation of a Buxus papillosa extract was achieved using a capillary HPLC system coupled with the mass instrument.

RESULTS

ESI-QqTOF-MS (positive ion mode) showed the presence of several characteristic fragments which can be used to rapidly identify various classes of Buxus steroidal alkaloids. The presence of a cyclopropane ring in the cycloartenol skeleton and the hydroxyl group at C-10 was found to effect on the fragmentation pattern and afford characteristic peaks. This study distinguishes between different types of Buxus steroidal alkaloids based on logical fragmentation pathways. This strategy was successfully applied in LC/ESI-QqTOF-MS/MS analysis of Buxus papillosa extract to investigate and characterize Buxus steroidal alkaloids and 14 compounds were identified as steroidal alkaloids.

CONCLUSIONS

The knowledge of the fragmentation pattern was used for the rapid identification of this bioactive group of biosynthetically unique steroidal alkaloids in complex plant extracts of Buxus species, especially in the absence of any reference material, by combining key fragments, exact mass measurements and relative abundances of diagnostic fragment ions.

Authors+Show Affiliations

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan. musharraf1977@yahoo.comNo 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

23239331

Citation

Musharraf, Syed Ghulam, et al. "Structure-fragmentation Relationship and Rapid Dereplication of Buxus Steroidal Alkaloids By Electrospray Ionization-quadrupole Time-of-flight Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 27, no. 1, 2013, pp. 169-78.
Musharraf SG, Goher M, Shahnaz S, et al. Structure-fragmentation relationship and rapid dereplication of Buxus steroidal alkaloids by electrospray ionization-quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2013;27(1):169-78.
Musharraf, S. G., Goher, M., Shahnaz, S., Choudhary, M. I., & Atta-ur-Rahman, . (2013). Structure-fragmentation relationship and rapid dereplication of Buxus steroidal alkaloids by electrospray ionization-quadrupole time-of-flight mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 27(1), 169-78. https://doi.org/10.1002/rcm.6441
Musharraf SG, et al. Structure-fragmentation Relationship and Rapid Dereplication of Buxus Steroidal Alkaloids By Electrospray Ionization-quadrupole Time-of-flight Mass Spectrometry. Rapid Commun Mass Spectrom. 2013 Jan 15;27(1):169-78. PubMed PMID: 23239331.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure-fragmentation relationship and rapid dereplication of Buxus steroidal alkaloids by electrospray ionization-quadrupole time-of-flight mass spectrometry. AU - Musharraf,Syed Ghulam, AU - Goher,Madiha, AU - Shahnaz,Salma, AU - Choudhary,M Iqbal, AU - Atta-ur-Rahman,, PY - 2012/08/24/received PY - 2012/10/14/revised PY - 2012/10/16/accepted PY - 2012/12/15/entrez PY - 2012/12/15/pubmed PY - 2013/4/30/medline SP - 169 EP - 78 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 27 IS - 1 N2 - RATIONALE: Tandem mass spectrometric studies of natural products revealed the identification of key fragments which can be helpful for their rapid dereplication in plant extracts utilizing a liquid chromatography/tandem mass spectrometry (LC/MS/MS) approach, particularly for the thermally labile compounds. The knowledge of the collision-induced dissociation (CID) fragmentation pattern of the molecule is essentially required prior to the analysis by LC/MS/MS. METHODS: The fragmentation patterns of eleven Buxus steroidal alkaloids were studied by using a positive ion electrospray ionization quadrupole time-of-flight mass spectrometry (ESI-QqTOF-MS/MS) hybrid instrument. Chromatographic separation of a Buxus papillosa extract was achieved using a capillary HPLC system coupled with the mass instrument. RESULTS: ESI-QqTOF-MS (positive ion mode) showed the presence of several characteristic fragments which can be used to rapidly identify various classes of Buxus steroidal alkaloids. The presence of a cyclopropane ring in the cycloartenol skeleton and the hydroxyl group at C-10 was found to effect on the fragmentation pattern and afford characteristic peaks. This study distinguishes between different types of Buxus steroidal alkaloids based on logical fragmentation pathways. This strategy was successfully applied in LC/ESI-QqTOF-MS/MS analysis of Buxus papillosa extract to investigate and characterize Buxus steroidal alkaloids and 14 compounds were identified as steroidal alkaloids. CONCLUSIONS: The knowledge of the fragmentation pattern was used for the rapid identification of this bioactive group of biosynthetically unique steroidal alkaloids in complex plant extracts of Buxus species, especially in the absence of any reference material, by combining key fragments, exact mass measurements and relative abundances of diagnostic fragment ions. SN - 1097-0231 UR - https://www.unboundmedicine.com/medline/citation/23239331/Structure_fragmentation_relationship_and_rapid_dereplication_of_Buxus_steroidal_alkaloids_by_electrospray_ionization_quadrupole_time_of_flight_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.6441 DB - PRIME DP - Unbound Medicine ER -