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Liquid chromatography/tandem mass spectrometric study and analysis of xanthone and secoiridoid glycoside composition of Swertia chirata , a potent antidiabetic
Author(s) -
Suryawanshi Satyendra,
Mehrotra Nitin,
Asthana R. K.,
Gupta Ram C.
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2795
Subject(s) - chemistry , mangiferin , xanthone , chromatography , aglycone , fragmentation (computing) , tandem mass spectrometry , electrospray ionization , glycoside , mass spectrometry , selected reaction monitoring , glycosidic bond , stereochemistry , organic chemistry , computer science , enzyme , operating system
Abstract Swertia chirata is a bitter plant, used in the Indian system of medicine (Ayurveda) for various human ailments. The bioactive constituents include the xanthone and secoiridoid glycosides consisting of mangiferin, amarogentin, amaroswerin, sweroside and swertiamarin. Methanolic extracts of S . chirata possess constituents with antidiabetic activities, which was investigated by high‐performance liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI‐MS/MS). Preliminary HPLC analyses were performed on a reversed‐phase C18 column using gradient elution. In the LC/ESI‐MS spectra, predominant [M+H] + and [M+Na] + ions were observed in positive ion mode and provided molecular mass information. The five components of S . chirata were structurally correlated and confirmed based on the fragmentation characteristics and information available in the literature. The fragmentation behavior of [M+H] + /[M+Na] + ions of these components were deduced from the collision‐induced dissociation (CID) spectra obtained from the selective on‐column information‐dependant acquisition (IDA) approach. Xanthone‐C‐glycoside showed characteristic fragment ions due to fragmentation in the C‐glycosidic unit while iridoid‐O‐glycosides showed characteristic fragment ions due to cleavage in the glycoside linkage and retro‐Diels‐Alder (RDA) cleavage within an iridoid aglycone. Furthermore, on the basis of this information, an analytical assay was developed and validated to determine relative concentrations of mangiferin, amarogentin, amaroswerin, sweroside and swertiamarin. The detection was carried out using multiple reaction monitoring (MRM) in positive ionization mode with a total analysis time of 3.5 min. The method was successfully applied to standardize four different batches of herbal preparation on the basis of relative concentration of five bioactive components. Copyright © 2006 John Wiley & Sons, Ltd.