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Field Desorption Mass Spectrometry of Physiologically Active Steroid- and Dammarane-Saponins *

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Field Desorption Mass Spectrometry of Physiologically Active Steroid- and Dammarane-Saponins * Field Desorption Mass Spectrometry of Physiologically Active Steroid- and Dammarane-Saponins * T. Komori, M. Kawamura, K. Miyahara, T. Kawasaki, Faculty of Pharmaceutical Sciences, Kyushu University 62, Maedashi 3-1-1, Higashi-ku Fukuoka, 812 Japan O. Tanaka, S. Yahara, Institute of Pharmaceutical Sciences, Hiroshima University, School of Medicine, Kasumi, Hiroshi- ma-shi, 734 Japan and H.-R. Schulten Institute of Physical Chemistry, University of Bonn, Wegelerstr. 12, D-5300 Bonn Z. Naturforsch. 34 c, 1094- 1105 (1979); received July 20, 1979 Natural Products, Physiologically Active Saponins, Sequencing of Underivatized Oligoglycosides, Field Desorption Mass Spectrometry The use of field desorption mass spectrometry is demonstrated not only for molecular weight determination but also for detailed structural analysis of large, underivatized natural products. Owing to cationization by small alkali salt impurities, saponins carrying one to four sugar units gave abundant quasimolecular ions. In addition, the observed sequence-specific fragment ions reflected the complete sequence of the sugar units in the oligoglycosides. This fragmentation of the oligosaccharidic moiety of the natural products was interpreted by analogy with acidic sol- volysis, a mechanism well established in solution chemistry. Of particular interest was a first com­ parison of the field desorption mass spectra obtained from two different commercially available instruments operated by different groups in order to give an estimate of interlaboratory repro­ ducibility in field desorption mass spectrometry. Introduction Electron impact (El)-mass spectrometry (MS) has been shown to be a very useful method [7-10] From the leaves of Lycopersicon pimpinellifolium for identification, determination of purity, and struc­ the fungistatic agent tomatine has been isolated and tural evaluation of saponins. However, for mass spec- crystallized [1] and its structure accurately charac­ trometric investigation volatile derivatives have to be terized as tomatidine 3-0-/?-lycotetraoside [2]. It has produced and often their fragmentation is compli­ also been reported [3] that under natural conditions cated because of the large and complex structure of tomatine may act as an insect repellent rather than the naturally occuring saponins. Moreover, saponins as toxin. Ginseng, the root of Panax ginseng C. A. with more than four sugar do not give molecular Meyer, is one of the most well-known Chinese drugs. ions even when derivatized. In continuation of our It contains characteristically a number of damma- recent reports of field desorption (FD)-MS of na­ rane saponins [4, 5] which are classified into 2 tural products [11 -14] here the results are re­ groups possessing either 20-S-protopanaxadiol or ported of the mass spectrometric studies of physio­ 20-S-protonanaxatriol as the sapogenins. Preliminary, logically active and structurally typical steroid- pharmacological studies of a protopanaxadiol group and dammarane-saponins. In particular, the fission saponin have shown this substance to be a central of terminal sugar units and the sequence-specific nervous system depressing agent, whereas a proto- cleavages in the oligoglycosidic chain(s) have been panaxatriol group saponin has been revealed to be evaluated and compared with data from solution an anti-fatigue and a central nervous system activat­ chemistry. Further, in order to achieve a better un­ ing agent [6]. derstanding of the general fragmentation pattern of * Field Desorption Mass Spectrometry of Natural Prod­ this class o f compound gitogenin- [15] and diosge- ucts Part V, for part IV see ref. [14]. nin- [16] oligoglycosides were recorded by FD-MS Reprint requests to Dr. H.-R. Schulten. as reference substances. The results obtained give a 0341-0382/79/1200-1094 $01.00/0 clear demonstration that FD-MS is not only suitable Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Advancement of Science under a Creative Commons Attribution Creative Commons Namensnennung 4.0 Lizenz. 4.0 International License. T. Komori et al. ■ Field Desorption Mass Spectrometry of Natural Products 1095 for molecular weight determination but is a powerful valley definition) which is partly due to the higher tool for structural investigation of these underivat- ion source potentials of + 6 kV/— 4 kV employed for ized oligoglycosides. the Varian instrument. All FD spectra were recorded As the free steroid- and dammarane-saponins were electrically (scantimes between 4 and 8 s/decade). studied by two different analytical groups and with Data processing was performed by the Spectrosys- different commercially available instruments it was tem MAT 200. Alternatively, the signals were accu­ of interest to investigate whether a preliminary, qual­ mulated by a multichannel analyzer (Varian CAT- itative comparison of the FD results was possible 1024) which was triggered by the cyclic magnetic and obtain for the first time information about in­ scan of the mass spectrometer. An example of an terlaboratory reproducibility. original plot of the multichannel analyzer output is shown in Fig. 2. Methods Results and Discussion JEOL D-300 instrument, Kyushu University Our previous FD investigations of oligoglycosidic The FD spectra were produced on a commercial natural products indicated that the process respon­ JEOL D-300 instrument (combined EI/FD ion sible for the cleavage of sugar units at the glycosidic source). All spectra were recorded electrically (scan oxygen could be explained by analogy with the well speed: 120 s or 300 s/full range). The resolution ob­ established mechanism of acidic hydrolysis in solu­ tained was R = 1200 (10% valley definition) and the tion chemistry. Proton transfer reactions in the ad­ average accuracy in the mass determination was sorbed sample on the surface of the FD emitter ±0.3 mass unit (m.u.). For accurate mass measurements lead, for instance, to a preferential loss of terminal ar- reference masses were taken from the El mass spectra rhamnose in comparison with aglycone-linked ß- of perfluorokerosene. Field desorption emitters, used glucose [12]. In order to evaluate the more general in all experiments, were prepared by high temperature validity of this concept the FD mass spectrum of activation of 10 |im diam. tungsten wires. FD emit­ tomatine (1) was recorded (Fig. 1). The character­ ters with an average length of 30 |im for the carbon istic signals obtained can be described as follows: microneedles were used as standards. The ionization 1. The FD spectrum of 1 shows the [M + Na]+ efficiency and the adjustment of the FD emitter ion at m /z 1056 as the base peak. The correspond­ were determined by means of m /z 58 of acetone in ing cation complexes of potassium are not observ­ the field ionization mode. All FD spectra were pro­ ed. The [M -I- H]+ ion is recorded with 86% rel. duced at an ion source pressure of 3 x 10-7 Torr, abundance. and ion source temp, between 60 °C and 70 °C, the 2. In the FD-spectra o f steroid tri- and tetra-gly- ion source potentials were + 3 or + 2 kV for the field cosides [11, 12] the glucosidic bond cleavage at C-3 anode and — 5 kV for the slotted cathode plate. The of the aglycone was not observed. Consistently also samples were desorbed by direct heating (emitter the FD-spectrum of 1 did not show the galactosidic heating current) without emission control. MeOH bond cleavage at C-3 of the aglycone. was used as solvent for all compounds. In general, 3. In general, /?-D-xylosides are hydrolyzed about lxlO -5# was applied as sample to the standard 4.8 times faster than /?-D-glucosides in solution chem­ emitter via the syringe technique. The substances 2, istry [17]. In the FD spectrum o f 1 which is averaged 3, 7, 8, and 9 were recorded by the D-300 instru­ from 5 consecutive magnetic scans in the mass range ment. from m /z 100 to m /z 1100 the loss of the terminal xylose unit (C5H90 4 , 133 m. u.) leads to the [(M + Varian MAT 731 instrument, University of Bonn Na)-132]+ ion at m /z 924, and the [(M + H)-132]+ The same sample amount, same solvent, and the ion at m /z 902. Loss of the glucose unit (C6Hn0 5, same type of FD emitter was used including the 163 m. u.) gives the [(M + Na)-162]+ ion at m /z 894 procedure for control of the ionization efficiency. and [(M + H)-162]+ ion at m /z 872, respectively. In Similar ion source pressure and ion source tempera­ this case, cleavage of the terminal xylopyranosyl ture were maintained as described above. The ob­ bond does indeed give the more intense fragment tained mass resolution was higher (R = 2000, 10% ions than that of the glucopyranosyl bond. 1096 T. Komori et al. • Field Desorption Mass Spectrometry of Natural Products m/z ---------------------------------• Fig. 1. FD mass spectrum of 1. Electrical recording (Methods, B), between 30 and 35 mA emitter heating current using the Varian MAT 200 data system; detection threshold 500 counts. The ratio for the loss of glucose: xylose is about 1 : 3.6. However, due to the relatively short time for the two sequence-specific fragment ions in FD. These magnetic scan covering the whole mass range, the are produced by the elimination of terminal xylose at small number of spectra which were recorded and m /z 924 and terminal glucose at m /z 894 from the averaged by the data system and the narrow interval high molecular weight natural product 1. of 30 to 35 mA emitter heating current (close to the Using repetitive magnetic scans in the mass range best anode temperature (BAT)), only a rough esti­ from m /z 890 to m /z 931 a sample o f 1 was com ­ mate of the prevailing cleavage of the terminal ß- pletely desorbed and the FD ions were recorded in D-xylose can be made.
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