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Alternative Green Extraction Methods for Natural Products Dissertation zur Erlangung des Grades Doktor der Naturwissenschaften (Dr. rer. nat.) der Fakultät für Chemie und Pharmazie Universität Regensburg vorgelegt von Theresa Höß Binswangen, Januar 2018 Promotionsausschuss 1. Gutachter Prof. Dr. Werner Kunz, Institut für Physikalische und Theoretische Chemie, Universität Regensburg (Deutschland) 2. Gutachter Prof. Dr. Jörg Heilmann, Lehrstuhl für Pharmazeutische Biologie, Universität Regensburg (Deutschland) 3. Prüfer Apl. Prof. Dr. Rainer Müller, Institut für Physikalische und Theoretische Chemie, Universität Regensburg (Deutschland) Vorsitzender Prof. Dr. Henri Brunner Promotionsgesuch eingereicht am: 31.01.2018 Datum der mündlichen Prüfung: 22.03.2018 Diese Doktorarbeit entstand in der Zeit von November 2014 bis Januar 2018 am Institut für Physikalische und Theoretische Chemie der Universität Regensburg unter der Betreuung von Prof. Dr. Werner Kunz. Acknowledgment An dieser Stelle möchte ich mich herzlich bei allen bedanken, die mich während der Anfertigung dieser Arbeit unterstützt haben. Zuerst möchte ich Herrn Prof. Dr. Werner Kunz danken. Vielen Dank für das wirklich sehr interessante Thema und dafür, dass Sie mir die Möglichkeit gegeben haben, diese Arbeit bei Ihnen am Lehrstuhl anfertigen zu dürfen. Außerdem möchte ich mich dafür bedanken, dass Sie mir es ermöglicht haben, meine Ergebnisse auf diversen Konferenzen vorstellen zu dürfen sowie dafür, dass Sie die Zusammenarbeit mit international wichtigen Firmen in der Parfüm- und Duftstoffindustrie realisiert haben. Im Gegenzug habe ich auch gerne auf dem Feld Unkraut gejätet! Außerdem möchte ich mich bei Herrn Prof. Dr. Jörg Heilmann bedanken. Ohne Ihre Hilfe und die Bereitstellung Ihrer analytischen Geräte wäre die Anfertigung dieser Arbeit nicht möglich gewesen. Vielen Dank auch, dass Sie die Aufgabe als Zweitgutachter übernehmen. Besonderer Dank geht an meine Laborkollegen und Freunde Dr. Alexander Wollinger und Dr. Marcel Flemming. Vielen Dank für die tolle gemeinsame Zeit im Labor und die nicht zu vergessenen Dienstreisen! Dankeeeeé für die Korrektur meiner Arbeit und Eure alltägliche Diskussions- und Hilfsbereitschaft! Des Weiteren möchte ich Dr. Didier Touraud für seine guten und zahlreichen Ideen für diese Doktorarbeit danken! Merci! Vielen Dank an all meine Kollegen am Lehrstuhl für die schöne Zeit und wissenschaftliche Unterstützung! Spezieller Dank geht dabei an meine Bürokollegin und langjährige Freundin Lydi! Danke, dass du mich immer bei Laune gehalten hast! Außerdem möchte ich meinen Studenten Stefanie Ritter, Stefanie Fischer, Magdalena Luger, Benjamin Ciszek, Robert Eckl, Lisa-Marie Altmann, Maximilian Dehmel, Julia I Märsch, Meike Bauer, Manuel Rothe und Chantal Walser danken, die mich im Rahmen ihrer Forschungsarbeiten im Labor unterstützt haben. Bei der Firma Phytotagante S.A.S. (Frankreich), insbesondere bei Jamal Chahboun, bedanke ich mich für die Bereitstellung der Irisrhizome sowie der Möglichkeit, ein Up- Scale meiner mizellaren Extraktion durchzuführen. Ein großes Dankeschön auch an unseren Industrie-Partner, für die Chance unsere Extraktionsmethode auf Rosen zu übertragen. Vielen Dank für die tolle Zeit inmitten der Rosenfelder in Südfrankreich. Vielen Dank auch an Prof. Dr.-Ing. Jochen Strube an der TU Clausthal und insbesondere seinem Doktoranden Leon Klepzig für die Durchführung der Rektifikation-Destillationen an dem Institut für Thermische Verfahrens- und Prozesstechnik. Zu guter Letzt: Danke Mama & Papa, dass Ihr mich nonstop unterstützt und ich sicher gehen kann, dass Ihr das auch noch Euer ganzes Leben lang tun werdet! Und danke Caro, dass Du mir vom ersten Tag an zur Seite gestanden bist! Theresa Höß II Abstract The aim of this thesis was the invention of alternative green extraction methods for the isolation of fragrance compounds from plants paying particular attention to the concepts and principles of Green Chemistry. Conventional extraction methods, such as hydro distillation and solvent extraction, exhibit several drawbacks such as long process duration, high energy consumption and the use of flammable and toxic solvents like hexane. Therefore, a simple, efficient and mild extraction method for fragrance compounds with natural, biocompatible and biodegradable soap solutions was developed and patented (EP 3 130 655 A1, 2017). Iris butter obtained from iris rhizomes (Iris germanica L. and Iris pallida Lam.) is one of the most luxurious raw materials for the perfume industry. The attractive violet-like fragrance is due to irones, i.e., terpenoids formed by oxidative degradation of iridals during rhizome aging. By using aqueous soap solutions, especially a myristate solution, an almost complete extraction of the desired irones was possible within a short time and at moderate temperatures. This gentle method prevents the degradation and volatilization of the fragrances at high temperatures, which are disadvantages of conventional extraction methods. Furthermore, various fatty acids, particularly myristic acid, are naturally occurring in the rhizomes. Thus, this extraction method uses an intrinsic plant substance as a highly efficient extraction medium and solubilizer. After the removal of the rhizomes from the aqueous soap solution, myristic acid containing the desired nonpolar fragrance molecules was precipitated by neutralization and separated from the remaining aqueous phase. Excess myristic acid can be recovered by crystallization in cold ethanol or by molecular distillation. As myristic acid is already a frequent ingredient of formulations like crèmes, lotions, or perfumes, the final extract with its remaining fatty acid represents an ideal basic raw material. In a second part, this newly invented extraction method was transferred to rose blossoms to evaluate its extraction power and applicability. The most important ingredient in roses is the essential oil, which contains around 400 substances such as citronellol, geraniol, and III 2-phenylethanol. Rose oil obtained by steam distillation is a key ingredient in cosmetics and fine fragrances. Since 2-phenylethanol is soluble in water, its content in the distillate is very low. Consequently, the rose absolute, which is obtained by solvent extraction commonly with hexane, is of high interest for perfume industry due to its fragrance composition similar to the rose petals. Extracting rose blossoms with an aqueous soap solution prevents the risk of handling large quantities of flammable and toxic solvents as well as the danger of potential petrochemical residues in the extract. In collaboration with a major international perfume company, it could be demonstrated that the experimental procedure of the micellar extraction of Rosa x centifolia L. is less complicated compared to iris rhizomes due to the different nature of the plant material. The odoriferous extract is completely soluble in ethanol and with its remaining fatty acid an ideal basic raw material for cosmetics or perfumes. However, compared to the extraction of the non- water-soluble irones, the addition of an inorganic salt to the aqueous extraction solution is necessary to decrease the solubility of partially water-soluble substances such as 2- phenylethanol but also geraniol. Adding a harmless salt, for instance potassium carbonate or sodium chloride, is still in accordance with the principles of Green Chemistry. As a result, an extract with a scent similar to the pure rose blossoms is achieved, but without toxic residues as obtained by the production of rose absolute. In a third part, the extraction of plant material solely with the pure fatty acids without using water was examined. The direct extraction of the fragrances, which are located on the surface of the rose petals, should be possible with a liquid mixture of lipophilic fatty acids. Therefore, a ternary mixture of lauric acid, myristic acid, and palmitic acid was used as extraction solution since a low melting system with a melting point around 30 °C is formed. Thereby, the advantages of classical enfleurage and solvent extraction can be combined. Also, the extraction of plants respectively plant materials, which continue their physiological activities after picking, is conceivable under these mild conditions. The focus of this study was mainly the isolation of the fragrance compounds from the fatty acid mixture. Therefore, molecular distillation, which is a continuous thermal separation process with only short exposure to increased temperature and decreased pressure, was investigated. In contrast to solvent extraction, not the extraction medium but the fragrance compounds were distilled. As a result, a product free of toxic residues with a IV composition similar to the origin was obtained, which was not feasible applying simple vacuum distillation. Moreover, the separated extraction medium can be reused for further extraction cycles due to the chemical and thermal stability of fatty acids. For the recycling of the extraction medium, the solution does not even have to be purified or saponified in contrast to micellar extraction. Instead, the solution can be reused directly. So far, a proof of concept regarding the isolation of the fragrance compounds was accomplished. The aim is to continue the investigation of the extraction power of the fatty acid mixture in future. With the approach “modern enfleurage” a solvent-free, non-toxic and sustainable extraction process for fragrances from plant material is possible without thermal degradation of sensitive
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  • Peroxisomal Trans-2-Enoyl-Coa Reductase Is Involved in Phytol Degradation

    Peroxisomal Trans-2-Enoyl-Coa Reductase Is Involved in Phytol Degradation

    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Elsevier - Publisher Connector FEBS Letters 580 (2006) 2092–2096 Peroxisomal trans-2-enoyl-CoA reductase is involved in phytol degradation J. Gloerich, J.P.N. Ruiter, D.M. van den Brink, R. Ofman, S. Ferdinandusse, R.J.A. Wanders* Laboratory Genetic Metabolic Diseases (F0-224), Departments of Clinical Chemistry and Pediatrics, Emma’s Children’s Hospital, Academic Medical Center, University of Amsterdam, Meibergdreef 9, 1105 AZ Amsterdam, The Netherlands Received 15 February 2006; accepted 4 March 2006 Available online 10 March 2006 Edited by Sandro Sonnino the peroxisomal acyl-CoA oxidases anymore. For further Abstract Phytol is a naturally occurring precursor of phytanic acid. The last step in the conversion of phytol to phytanoyl-CoA breakdown, the chain-shortened product is transported to is the reduction of phytenoyl-CoA mediated by an, as yet, the mitochondrion [3], where it is totally degraded to acetyl- unidentified enzyme. A candidate for this reaction is a previously CoA and propionyl-CoA units [4]. Besides breakdown of described peroxisomal trans-2-enoyl-CoA reductase (TER). To pristanic acid, peroxisomal b-oxidation is also involved in investigate this, human TER was expressed in E. coli as an the degradation of very long-chain fatty acids, long-chain MBP-fusion protein. The purified recombinant protein was dicarboxylic acids and bile acid intermediates [4]. shown to have high reductase activity towards trans-phytenoyl- Another metabolic process that recently has been shown to CoA, but not towards the peroxisomal b-oxidation intermediates occur, at least partly, in the peroxisome is the degradation of C24:1-CoA and pristenoyl-CoA.