Optimization and transfer of the mobile phase between various analytical and preparative liquid chromatographic methods
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1 Research Collection Doctoral Thesis Optimization and transfer of the mobile phase between various analytical and preparative liquid chromatographic methods Author(s): Zogg, Georg Christian Publication Date: 1989 Permanent Link: Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library
2 Diss. ETH No [ptqi]aiätra M ä» to^ ffifl@uqi.gi IPMÄ1I GBITWIiM WÄKQ (y)s ÄMÄILWIKBÄIL &» PHIIPÄB&TWII IU@M A dissertation submitted to the SWISS FEDERAL INSTITUTE OF TECHNOLOGY ZÜRICH for the degree of Doctor of Natural Sciences presented by GEORG CHRISTIAN ZOGG eidg. dipl. Apotheker born October 7,1957 Citizen of Grabs, St. Gallen accepted on the recommendation of Prof. Dr. O. Sticher, examiner O. oßc&^r PD Dr. Sz. Nyiredy, co-examiner Zürich 1989 Druck: Zentralstelle der Studentenschaft
3 Summary In the first chapter of this thesis, the theoretical aspeets of the "PRISMA" optimization system are summarized for various analytical and preparative planar and column Chromatographie techniques with special emphasis on the Separation of apolar Compounds. In the subsequent chapters the application of this systematie mobile phase optimization and transfer strategy is described for the Separation of closely related furocoumarins on Normal Phase (NP) Supports. The investigated linear and angular furocoumarins, oecurring in several plant families are typical constituents of many genera in the family Umbelliferae. Mobile phase optimization for some of these potently photosensitizing, mutagenic and carcinogenic Compounds was carried out on TLC plates (Thin Layer Chromatography) in unsaturated Chambers. The elaborated mobile phases were transposed to analytical fully off-line Over-Pressured Layer Chromatography (OPLC) and for Separation of all eight investigated furocoumarin isomers the final optimization Steps were performed on HPTLC plates (High Performance Thin Layer Chromatography), using fully off-line OPLC. The mobile phase obtained was then applied to analytical fully on-line OPLC, a planar-column Chromatographie technique, and to analytical High Performance Liquid Chromatography (HPLC). All three analytical methods gave good separations, but the possibility of analysing many samples ( 18) in parallel favoured the fully off-line OPLC technique. A linear correlation exists between the retention data of these planar, planar-column and column Chromatographie separations. The strategy for transfer of an optimized TLC mobile phase to preparative planar and column liquid chromatography is described for the example of the five main Compounds of Heracleum sphondylium roots as apolar test Compounds. The influence of the main operating parameters on preparative OPLC separations was studied. The solvent strength of the optimized TLC mobile phase had to be reduced due to the larger particie size and the wide particie size distribution of precoated preparative plates. The maximal amount of sample and the flow rate could be directly scaled up from analytical OPLC.
4 Transfer of the optimized TLC mobile phase to Medium Pressure Liquid Chromatography (MPLC) via analytical OPLC was performed for three variants: dry column separations with reduced solvent strength of the mobile phase; separations on columns equilibrated with n-hexane; separations on columns equilibrated with the appropriate mobile phase. Dry-packing procedures for user filling of MPLC columns were developed using silica with an average particie size of 15 pm. The elaborated dry-packing techniques were investigated for further MPLC separations, testing the influence of various operating parameters, such as particie size of the support, solvent strength and flow rate of the mobile phase, capacity and dimensions of the columns. Owing to the experience gained in the study of MPLC, this preparative pressure liquid Chromatographie technique was employed for isolation of the main furocoumarins from a commercially available sample of Pimpinellae radix (Balkan quality). The MPLC separations were compared with the semipreparative HPLC separations of the same eight Compounds from Heraclei mantegazziani radix. Both methods gave chromatograms with practically identical, high resolutions. Finally, analytical Chromatographie forced-flow methods (OPLC and HPLC) were applied for the qualitative and quantitative determination of the investigated furocoumarins in several root extracts of species from the family Umbelliferae. Some commercially available samples were compared with authentic herbal drugs. Typical applications of the elaborated analytical and preparative Chromatographie techniques demonstrate their practical potential for the analysis of plant extracts and the isolation of naturally oecurring Compounds with closely related structures.
5 Zusammenfassung Im ersten Kapitel dieser Arbeit werden die theoretischen Aspekte des "PRISMA'-Optimierungssystems für die verschiedenen analytischen und präparativen, planar- und säulenchromatographischen Techniken dargestellt. Der Schwerpunkt wird dabei auf die Trennung apolarer Substanzen mittels Normal-Phasen (NP) Chromatographie gerichtet. In den folgenden Kapiteln wird die praktische Anwendung des "PRISMA"- Systems, zur Optimierung und Übertragung der mobilen Phase, anhand analytischer und präparativer Trennungen von Furanocumarinen sehr ähnlicher Struktur beschrieben. Die, als apolare Testsubstanzen eingesetzten, linearen und angularen Furanocumarine kommen in zahlreichen Pflanzenfamilien vor, sind aber vor allem typische Inhaltsstoffe verschiedener Umbelliferen. Die Optimierung der mobilen Phase für diese photosensibilisierenden, mutagenen und cancerogenen Substanzen erfolgte auf NP-TLC-Platten (Thin Layer Chromatography) in ungesättigten Kammern. Die optimierten mobilen Phasen wurden auf die analytische off-line OPLC (Over-Pressured Layer Chromatography) übertragen und für die Trennung aller acht eingesetzten Furanocumarine erfolgten die letzten Optimierungs schritte auf HPTLC-Platten (High Performance Thin Layer Chromatography) unter Verwendung dieser Forced-Flow Technik. Anschliessend wurde die optimierte mobile Phase auf die analytische on-line OPLC, eine planar-säulenchromatographische Technik, und auf die analytische HPLC (High Performance Liquid Chromatography) übertragen. Alle drei Systeme ergaben gute Trennungen, wobei der Vorteil mehrere Proben ( 18) gleichzeitig zu analysieren, die fully off-line OPLC favorisiert. Beim Vergleich dieser drei Trenntechniken konnte ein linearer Zusammen hang zwischen den jeweiligen Retentionszeiten beobachtet werden. Anhand der Trennung der fünf apolaren Hauptkomponennten der Bärenklauwurzeln wird die Strategie zur Optimierung und Übertragung der mobilen Phase auf präparative planar- und säulenchromatographische Methoden beschrieben. Für die präparativen OPLC Trennungen wurden die wichtigsten Bedienungs parameter getestet. Aufgrund der grösseren Teilchengrösse und Teilchen-
6 grössenverteilung in den PSC-Platten (Präparative Schicht Chromato graphie) musste die Lösungsmittelstärke der optimierten mobilen Phase reduziert werden. Die maximale Probenmenge und die Flussrate konnten im entsprechenden Verhältnis von der analytischen OPLC übernommen werden. Die Übertragung der optimierten mobilen Phase auf die Mitteldruckflüssigkeitschromatographie (Medium Pressure Liquid Chromatography: MPLC) erfolgte auf drei verschiedene Arten: Trockensäulentrennungen mit reduzierter Lösungsmittelstärke der mobilen Phase; Trennungen auf mit n-hexan äquilibrierten Säulen; Trennungen auf mit der mobilen Phase equilibrierten Säulen. Die Beurteilung, welche der drei Varianten eingesetzt werden kann, erfolgte mit Hilfe der analytischen OPLC. Zur Verwendung von Kieselgel mit einer durchschnittlichen Teilchengrösse von 15 pm wurden geeignete Techniken zur Trockenfüllung von MPLC-Säulen entwickelt. Unter Verwendung dieser Trockenfüllmethoden können MPLC-Säulen problemlos durch den jeweiligen Anwender mit dem entsprechenden Kieselgel gepackt werden. So vorbereitete Chromatographie-Säulen wurden für die Überprüfung verschiedener MPLC- Bedienungsparameter, wie Teilchengrösse der stationären Phase, Lösungsmittelstärke und Flussrate der mobilen Phase, Kapazität und Grösse der Säulen verwendet. Basierend auf den Erfahrungen aus den zahlreichen MPLC-Trennungen wurde diese präparative Forced-Flow Technik zur Isolierung der acht Furanocumarine aus einem Handelsmuster von Pimpinellae radix (Balkan- Qualität) eingesetzt. Diese MPLC-Trennungen und die semipräparativen HPLC-Trennungen derselben acht Furanocumarine aus den Wurzeln von Heracleum mantegazzianum zeigten praktisch identische Auflösungen. Unter Verwendung der analytischen, chromatographischen Forced-Flow Techniken konnten die acht Furanocumarine in den Wurzeln verschiedener Umbelliferen qualitativ und quantitativ bestimmt werden. Einige Handels drogen wurden mit authentischen Mustern verglichen. Die Applikationsbeispiele der ausgearbeiteten planar- und säulenchromatographischen Forced-Flow Methoden illustrieren deren praktische Einsatzmöglichkeiten für die Analyse von Pflanzenextrakten und die Isolierung von Pflanzeninhaltsstoffen mit sehr ähnlichen Strukturen.
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