Direct characterization of isoquinoline alkaloids in a crude plant extract by ion-pair liquid chromatography-electrospray ionization tandem mass spectrometry: example of Eschscholtzia californica.
An ion-pair HPLC-ESI-MS-MS method has been developed for the direct and rapid characterization of isoquinoline alkaloids in a crudely purified extract of the aerial parts of Eschscholtzia californica (Papaveraceae). This plant was chosen because of its increasing use in pharmaceutical industries and because its well known alkaloid composition allows the optimization of the experimental procedure through an on-line analytical sequence. Thus, 14 isoquinoline alkaloids of different types were detected and characterized. The identities of these compounds were confirmed unambigously by their fragmentation and UV spectra obtained by LC-diode-array detection. Various experiments including tandem mass spectrometry and in-orifice collision induced dissociation were performed and prove that MS-MS is a very efficient technique to identify these compounds. An explanation for each isoquinoline alkaloid type MS-MS fragmentation pattern is proposed and indicates similar neutral and/or radical losses. The order of the fragmentation depended on the type of compound but the lost fragments were similar.
Fabre
N
N
Laboratoire Pharmacophores Redox, Phytochimie et Radiobiologie, Université Paul Sabatier, Faculté des Sciences Pharmaceutiques, Toulouse, France. nfabre@cict.fr
Claparols
C
C
Richelme
S
S
Angelin
M L
ML
Fourasté
I
I
Moulis
C
C
D000470:Alkaloids / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007546:Isoquinolines / Q000032:analysis*; D010207:Papaver / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D010946:Plants, Medicinal; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013056:Spectrophotometry, Ultraviolet
D000470:Alkaloids; D007546:Isoquinolines; D010936:Plant Extracts