Tropane alkaloids spectrometry

Lawson, G., Ostah, N., and Woolley, J.G., MS/MS smdies of tropane alkaloids Detection and determination of stmctnre, m Applications of Modem Mass Spectrometry in Plant Science Research, Newton, R.P. and Walton, T.J., Eds., Clarendon Press, New York, 1996, chap. 16. 

Only H NMR, 13C NMR, and mass spectrometry, the three most important spectroscopic methods for the tropane alkaloids, will be treated here. 

Mateus, L., Cherkaoui, S., Christen, R, and Veuthey, J. L. (1999). Capillary electrophoresis-diode array detection-electrospray mass spectrometry for the analysis of selected tropane alkaloids in plant extracts. Electrophoresis 20, 3402—3409. 

Fig. 5 Statistical evaluation of LC-MS-based methods for tropane alkaloids referred in this chapter. (a) Relative frequency of ionization methods. +APCI positive atmospheric pressure chemical ionization, +ESI positive electrospray ionization, FAB fast atom bombardment, +TSP positive thermospray, (b) Relative frequency of scan modes used. MS full scan MS, MS/MS tandem mass spectrometry (product ion scan), MRM multiple reaction monitoring, SIM selected ion monitoring, (c) Relative frequency of mass analysers used. EBQtQ2 double focusing sector field mass spectrometer, IT ion trap, QqQ triple quadrupole, SQ single quadrupole. Considered publications were found by PubMed data-based search and references cited in these articles...

Auriola S, Martinsen A, Oksman-Caldentey KM, Naaranlahti T (1991) Analysis of tropane alkaloids with thermospray high-performance liquid chromatography-mass spectrometry. J Chromatogr 562 737-744... 

As already reported by Drager in 2002 [45], the low UV absorption of tropane alkaloids means that other detection modes have been investigated. Besides mass spectrometry, electrochemical detection was tested by different authors, but sensitivity was not significantly improved since tropane alkaloids are only moderately... 

Analyses of tropane alkaloids are mainly carried out by GC and HPLC and to a lesser extent by CE. This review describes recent applications developed for the analysis of this class of compounds in plant materials and biological matrices. Of course, mass spectrometry is generally used as the detection technique because of its high sensitivity and selectivity, but other techniques such as UV, fluorescence, flame ionization detection, nuclear magnetic resonance, among others have also been investigated. Finally, desorption electrospray ionization mass spectrometry is reported as a new interesting detection technique for the rapid analysis of samples without any sample preparation. 

Carbon-13 n.m.r. and mass spectrometry have become essential methods in quantitative analysis of alkaloid mixtures extracted from plants, in addition to g.l.c. and photometry. Study of the mechanism of fragmentation of 3-substi-tuted tropanes is a useful tool for analysis of mixtures of tropane alkaloids. A comprehensive study on the n.m.r. spectroscopy of tropane alkaloids included most major representatives of this class. Other papers deal with the n.m.r. spectra of cocaine metabolites and derivatives. A radioimmunassay of atropine and benzoylecgonine in urine was published. Photometric determination of tropane derivatives in chloroform extracts was done via colorimetry of the bromocresol purple complex.Adsorption chromatography methods have been used with different resins. ... 

El Bazoui A, Bellimam MA, Lancar 1, Soulaymani A. Gas-liquid chromatography-mass spectrometry investigation of tropane alkaloids in Hyoscyamus albus L. from Morocco. Z Naturforsch C 2012 67(9 - 10) 461-5. 

Namera A, Yashdd M, Hirose Y, Yamaji S, Tani T, Kojima T (2002) Quantitative analysis of tropane alkaloids in biological materials by gas chromatography-mass spectrometry. Forensic Sci Int 130(l) 34- 3. doi 10.1016/s0379-0738(02)00302-x... 

The use of detectors other than UV for the analysis of tropane alkaloids has been reviewed previously [15, 24, 27]. In contrast to conventional detectors such as UV, RI, fluorescence, and ELSD coupled with LC, the MS detector provides information on the molecular structure of the separated compotmds (Fig. 31.3). Over the past decade, liquid chromatography coupled with mass spectrometry (LC-MS) has undergone tremendous technological improvement and is now one of the most powerful tools for the investigation of natural compotmds. 

NACE appears to be ideally suited for online coupling with mass spectrometry due to high volatility and surface tension of most of the organic solvents used [ 114]. Carefully optimized NACE-MS method was applied to a very large number of alkaloids in different psychoactive plant extracts, as demonstrated by Posch et al. [115]. The method allowed the separation of structurally closely related substances, such as diastereomers and other isobaric compounds, as well as to separate members of different alkaloid classes including tropane alkaloids without modification of the procedure. 

Blossey EC, Budzikiewicz H, Ohashi M, Fodor G, Djerassi C (1964) Mass spectrometry in structural and stereochemical problems. XXXIX. Tropane alkaloids. Tetrahedron 20 (Copyright (C) 2012 American Chemical Society (ACS). All Rights Reserved.) 585-595. doi 10.1016/s0040-4020(01)98621-l... 

Blossey, E.C., Budzikiewicz, H., Ohashi M., et al Mass spectrometry in structural and stereochemical problems—XXXIX. Tropane alkaloids. 

The on-line coupling of CE with electrospray ionization mass spectrometry (CE-ESI-MS) allows high separation efficiency together with high sensitivity and selectivity as well as molecular structural information. A CE-UV-ESI-MS method was developed for the analysis of hoscyamine, scopolamine, and other tropane derivatives [131]. The differentiation of hyoscyamine from littorine, commonly encountered in plant material, was demonstrated using in-source collision-induced dissociation. The developed method was applied to the analysis of these alkaloids in Belladonna leaf extract and in Datura Candida x D. awreahairy root extract. Recently, CE coupled with electrochemiluminescence detection has been used for the determination of atropine and scopolamine in Flos daturae [132]. 

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