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Screening of Panamanian Plant Extracts for Agricultural and Cosmetic Activities, and Metabolomic Study of Isatis Tinctoria Accessions

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Screening of Panamanian Plant Extracts for Agricultural and Cosmetic Activities, and Metabolomic Study of Isatis Tinctoria Accessions Screening of Panamanian plant extracts for agricultural and cosmetic activities, and metabolomic study of Isatis tinctoria accessions Inauguraldissertation zur Erlangung der Würde eines Doktors der Philosophie vorgelegt der Philosophisch-Naturwissenschaftlichen Fakultät der Universität Basel von Niels Henrik Guldbrandsen aus Zürich ZH Basel, 2015 Originaldokument gespeichert auf dem Dokumentenserver der Universität Basel edoc.unibas.ch Dieses Werk ist unter dem Vertrag „Creative Commons Namensnennung‐Keine kommerzielle Nutzung‐Keine Bearbeitung 3.0 Schweiz“ (CC BY‐NC‐ND 3.0 CH) lizenziert. Die vollständige Lizenz kann unter creativecommons.org/licenses/by‐nc‐nd/3.0/ch/ eingesehen werden. Genehmigt von der Philosophisch-Naturwissenschaftlichen Fakultät auf Antrag von: Prof. Dr. Matthias Hamburger Prof. Dr. Jean-Luc Wolfender Basel, den 09.12.2014 Prof. Dr. Jörg Schibler Dekan Namensnennung-Keine kommerzielle Nutzung-Keine Bearbeitung 3.0 Schweiz (CC BY-NC-ND 3.0 CH) Sie dürfen: Teilen — den Inhalt kopieren, verbreiten und zugänglich machen Unter den folgenden Bedingungen: Namensnennung — Sie müssen den Namen des Autors/Rechteinhabers in der von ihm festgelegten Weise nennen. Keine kommerzielle Nutzung — Sie dürfen diesen Inhalt nicht für kommerzielle Zwecke nutzen. Keine Bearbeitung erlaubt — Sie dürfen diesen Inhalt nicht bearbeiten, abwandeln oder in anderer Weise verändern. Wobei gilt: Verzichtserklärung — Jede der vorgenannten Bedingungen kann aufgehoben werden, sofern Sie die ausdrückliche Einwilligung des Rechteinhabers dazu erhalten. Public Domain (gemeinfreie oder nicht-schützbare Inhalte) — Soweit das Werk, der Inhalt oder irgendein Teil davon zur Public Domain der jeweiligen Rechtsordnung gehört, wird dieser Status von der Lizenz in keiner Weise berührt. Sonstige Rechte — Die Lizenz hat keinerlei Einfluss auf die folgenden Rechte: o Die Rechte, die jedermann wegen der Schranken des Urheberrechts oder aufgrund gesetzlicher Erlaubnisse zustehen (in einigen Ländern als grundsätzliche Doktrin des fair use bekannt); o Die Persönlichkeitsrechte des Urhebers; o Rechte anderer Personen, entweder am Lizenzgegenstand selber oder bezüglich seiner Verwendung, zum Beispiel für Werbung oder Privatsphärenschutz. Hinweis — Bei jeder Nutzung oder Verbreitung müssen Sie anderen alle Lizenzbedingungen mitteilen, die für diesen Inhalt gelten. Am einfachsten ist es, an entsprechender Stelle einen Link auf diese Seite einzubinden. Quelle: http://creativecommons.org/licenses/by-nc-nd/3.0/ch/ Datum: 12.11.2013 Für meine Eltern 1 2 Table of Contents List of abbreviations ................................................................................................................. 4 Summary ................................................................................................................................... 5 Zusammenfassung .................................................................................................................... 7 1. Aim of the work .................................................................................................................... 9 2. Introduction ........................................................................................................................ 12 2.1 Discovery of natural products as lead compounds .................................................... 13 Screening and activity profiling of plant extracts ............................................................. 13 Isolation and structure elucidation of natural products ..................................................... 13 2.2 Screening of compounds for agricultural chemistry ................................................. 15 Natural products as leads for agricultural chemistry ........................................................ 15 Methods for agrochemical screening of compounds ........................................................ 17 2.3 Screening of compounds for cosmetics ....................................................................... 18 2.4 Metabolomics and multivariate statistics ................................................................... 19 Multivariate statistics: A mathematical tool for extracting essential information ............ 19 Application of NMR and multivariate statistics to pharmacognosy ................................. 22 STOCSY as a tool for structure elucidation of compounds in complex mixtures ............ 26 3. Results and discussion ........................................................................................................ 30 3.1 Screening of Panamanian plant extracts for pesticidal properties, and HPLC- based identification of active compounds ......................................................................... 31 3.2 Screening of Panamanian plants for cosmetic properties, and HPLC-based identification of constituents with antioxidant and UV-B protecting activities ............ 64 3.3 Metabolomic studies on Isatis tinctoria – Comparison of different accessions, harvesting dates, and the effect of repeated harvesting .................................................. 87 4. Conclusions and outlook .................................................................................................. 128 Acknowledgements ............................................................................................................... 133 Curriculum vitae .................................................................................................................. 135 3 List of abbreviations ABTS 2,2‘-Azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) AGROCOS Agricultural chemistry and cosmetics (FP7 project) BASF Badische Anilin- & Soda-Fabrik (German chemical company) Calcein-AM Calcein acetomethoxy CA Canonical analysis COSY Correlation spectroscopy (NMR technique) DAD Diode array detector DNA Deoxyribonucleic acid DPPH 2,2-Diphenyl-1-pikrylhydrazyl ECD Electronic circular dichroism FP7 Framework Program 7 GABA gamma-aminobutyric acid HMBC Heteronuclear multiple bond correlation (NMR technique) HPLC High performance liquid chromatography HSQC Heteronuclear single quantum correlation (NMR technique) HTS High throughput screening IL Interleukin k-NN k-nearest neighbor concept MANOVA Multivariate analysis of variance MS Mass spectrometry MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide nAChR Nicotinic acetylcholine receptor NMR Nuclear magnetic resonance OPLS Orthogonal partial least squares regression OPLS-DA Orthogonal partial least squares discriminant analysis PCA Principal component analysis PCA/CA/k-NN Combination of PCA, CA, and k-NN PLE Pressurized liquid extraction PLS Partial least squares regression PLS-DA Partial least squares discriminant analysis STOCSY Statistical total correlation spectroscopy (statistical method) TLC Thin layer chromatography TOCSY Total correlation spectroscopy (NMR technique) TOF Time of flight TXI Triple resonance inverse (NMR probe) UV Ultraviolet light 4 Summary The FP7 project AGROCOS aimed at the discovery of new natural product scaffolds for possible uses in agrochemistry and as cosmetic ingredients. In addition, novel tools for metabolomics and multivariate statistics were applied to Isatis tinctoria as a model plant. Nature provides compounds that are not only important for pharmaceutical industry, but also for agrochemistry and cosmetics. Extracts and pure natural compounds are widely used in cosmetics. For agrochemistry, natural products rather play a role for lead discovery, i.e. the discovery of a model compound that is further developed to a synthetic agrochemical. In the first part of the project, a library of 600 Panamanian plant extracts was screened for agrochemical and cosmetic properties. Selected extracts were submitted to HPLC-based activity profiling whereby five extracts showed activity in the agrochemistry screens, and two extracts in the cosmetic screens. For the agrochemical part of the project, extracts and microfractions were screened for fungicidal, insecticidal, and herbicidal properties. Compounds from Bocconia frutescens, Miconia affinis, Myrcia splendens, Combretum affinis laxum, and Erythroxylum macrophyllum were isolated, identified, and submitted to screening for the corresponding indication. Benzophenanthridine alkaloids and arjunolic acid from B. frutescens and M. affinis, respectively, showed moderate to good fungicidal activity. Myricetin-3-O-(6''-O- galloyl)-β-galactopyranoside from M. splendens showed moderate insecticidal activity. From the two plants selected for herbicidal activity of their extracts, no herbicidal compounds could be identified. For the cosmetic part, phenolic compounds and flavonoids were isolated from methanolic extracts of leaves from Mosquitoxylum jamaicense and Combretum cacoucia. All isolated compounds showed either activity in the DPPH assay, in the UV-B protection assay, or in both. Gallic acid derivatives were the most active in the DPPH assay (IC50 < 10 μg/mL), while protocatechuic acid and isoquercitrin showed the best activity in the UV-B protection assay (< 10% UV-B-induced cell death). Metabolomics of plant extracts combined with multivariate statistics is increasingly used for the differentiation of plant samples and assessment of quality traits. Metabolomics provides a metabolic fingerprint, in contrast to the classical quantitative analysis of single compounds, or a single class of compounds. The second part of the AGROCOS project comprised a metabolomic study on Isatis tinctoria of five different accessions,
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