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Thesis Phytochemical investigation of two Crassulaceae species: Rhodiola rosea L., the New "Herbal Stress Buster", and Sedum dasyphyllum L. VAN DIERMEN, Daphné Abstract Rhodiola rosea L. (Crassulaceae), the most investigated species of the genus Rhodiola, grows at elevated altitudes in the Arctic and in mountainous regions throughout Europe and Asia, where it is also knows as "Golden root" or "Arctic root". The roots have been used for centuries in traditional medicine to enhance physical and mental performance, improve resistance to high altitude sickness and to treat fatigue, psychological stress and depression. The present work aims at clarifying the pharmacological effects of R. rosea and identifying the active metabolites. The plant was tested on three targets : monoamine oxidase, acetylcholinesterase and oxidative stress. As the roots of R. rosea exhibited interesting activities against the three targets, a phytochemical investigation was undertaken on the plant. An agronomical study was also realised on R. rosea. Another part of this work consisted in studying different Crassulaceae species in order to discover new potential herbal stress buster. Six new flavonols were isolated from Sedum dasyphyllum L. Reference VAN DIERMEN, Daphné. Phytochemical investigation of two Crassulaceae species: Rhodiola rosea L., the New "Herbal Stress Buster", and Sedum dasyphyllum L.. Thèse de doctorat : Univ. Genève, 2009, no. Sc. 4122 URN : urn:nbn:ch:unige-46200 DOI : 10.13097/archive-ouverte/unige:4620 Available at: http://archive-ouverte.unige.ch/unige:4620 Disclaimer: layout of this document may differ from the published version. 1 / 1 UNIVERSITE DE GENEVE FACULTE DES SCIENCES Section des Sciences Pharmaceutiques Laboratoire de Pharmacognosie et de Phytochimie Prof. Kurt Hostettmann Phytochemical Investigation of two Crassulaceae Species: Rhodiola rosea L., the New "Herbal Stress Buster", and Sedum dasyphyllum L. THESE Présentée à la Faculté des Sciences de l’Université de Genève Pour obtenir le grade de Docteur ès Sciences, mention Sciences Pharmaceutiques par Daphné van Diermen de Blonay (VD) Thèse N o 4122 Atelier d’impression ReproMail - Uni Mail Genève 2009 REMERCIEMENTS En premier lieu, je tiens à exprimer toute ma gratitude à mon directeur de thèse, Monsieur le Professeur Kurt Hostettmann, pour m’avoir accueilli au sein de son laboratoire de renommée internationale et permis d’effectuer mon travail de thèse dans d’excellentes conditions. Je remercie également le Professeur pour m’avoir donné l’occasion de présenter une partie de mes résultats de recherche lors de congrès nationaux et internationaux, notamment en Indonésie et en Grèce. Je tiens également à lui exprimer ma reconnaissance pour la confiance qu’il m’a accordée en m’incluant dans un projet de développement de médicaments traditionnels améliorés à Haïti. Je remercie chaleureusement mon responsable technique, Monsieur le Docteur Andrew Marston pour ses précieux conseils et son soutien. Mes sincères remerciements vont également aux membres de mon jury de thèse : Monsieur le Professeur Pascal Richome du Laboratoire : Substances d’Origine Naturelles et Analogues Structuraux de l’Université d’Angers, Monsieur le Docteur Bruno David des Laboratoires Pierre Fabre de Ramonville, et Madame le Docteur Pia Malnoe de l’Agroscope Changins-Wädenswill de Conthey, pour leur lecture approfondie de mon manuscrit et leur remarques pertinentes et pour avoir fait le déplacement lors de la soutenance de thèse. Je remercie tout particulièrement le membre interne du jury, Madame le Docteur Karine Ndjoko Ioset du Laboratoire de Pharmacognosie et Phytochimie de l’Université de Genève qui m’a guidée tout au long de ce travail. Merci également à Monsieur le Professeur Pierre-Alain Carrupt pour avoir accepté de présider ce jury. Ce travail de thèse a également pu être réalisé grâce à différentes collaborations : Le Laboratoire de Chimie Thérapeutique, groupe de Pharmacochimie de l’Université de Genève, en particulier Monsieur le Docteur Juan Bravo qui a testé mes extraits et produits purs sur la monoamine oxydase. L’Agroscope de Changins-Wäadenswill, plus spécialement Madame le Docteur Pia Malnoe qui nous a fourni une partie du matériel végétal nécessaire pour ce projet. Je tiens également à remercier Monsieur Egidio Anchisi pour avoir récolté les différentes plantes nécessaires à mes recherches. I Mes sincères remerciements vont également à tous mes collègues de laboratoire : A Jean-Luc, Karine et Emerson pour leur aide et leurs conseils expérimentés en RMN et en spectrométrie de masse. Et à Philipe Christen pour, entre autres, ses conseils en extraction. A Anne-Emmanuelle Hay pour ses conseils, son soutien et plus particulièrement pour son amitié. A Monica, ma diplômante, pour son excellent travail qui a contribué à cette étude. A Sandra et Fred pour nos nombreuses et précieuses discussions scientifiques ou non ainsi que pour les bons moments partagés à Bangkok et à Bali. A Martine, Peihong, Trixie, Claudia, Gaëtan, Sylvian, Raimana, Caro et Anne-Laure avec qui j’ai travaillé pendant trois ans. Merci pour leur aide, leur motivation, leur encouragement et les bons moments sérieux et un peu moins sérieux partagés durant les congrès et les différentes sorties du Laboratoire. Je souhaite encore remercier tout particulièrement mes parents pour leurs encouragements et pour leur soutien tout au long de mes études et également pour les corrections de l’anglais du présent manuscrit. Finalement, je remercie du fond du cœur Cédric pour sa patience, sa compréhension et son précieux soutien. II SCIENTIFIC COMMUNICATIONS The present work was carried out at the Laboratory of Pharmacognosy and Phytochemistry, School of Pharmaceutical Sciences, University of Geneva, University of Lausanne from January 2006 to Mai 2009, under the guidance of Prof. Dr. Kurt Hostettmann. Some aspects of the present research have been published and presented at scientific congresses as poster presentations. Publications Van Diermen D., Marston A., Bravo J., Reist M., Carrupt, J.-C. and Hostettmann K. Monoamine oxidase inhibition by Rhodiola rosea L. roots (2009). Journal of Ethnopharmacology 122 : 397-401. Van Diermen D., Ndjoko Ioset K., Marston A., Malnoe P. and Hostettmann, K. Chemical profile dynamics in a wild population of Rhodiola rosea L. plants from the Swiss Alps. (Submitted to Journal of Agricultural Sciences ). Van Diermen D., Pierreclos M., and Hostettmann, K. Antioxidant phenolic compounds from Sedum dasyphyllum L. (Submitted to Journal of Natural Products ). Ndjoko Ioset K., Nyberg N. T., van Diermen D., Malnoe P. and Hostettmann K. Metabolic profiling of Rhodiola rosea by 1H NMR spectroscopy. (Submitted to Metabolomics ). Hostettmann K. and van Diermen D. La plante du jour: Rhodiola rosea (2007). Phytotherapie Européenne 37 : 14-17. Posters Van Diermen D., Marston A., Bravo J., Reist M., Carrupt, P.-A. and Hostettmann K. Inhibition of monoamine oxidase and acetylcholinesterase by Rhodiola rosea L. root extract. 7th Joint Meeting of AFERP, ASP, GA, PSE & SIF, Athens, Greece, August 2008. Van Diermen, D., Marston A., Ndjoko Ioset K. and K. Hostettmann. Analyses and bioactivities of wild populations of Rhodiola rosea L. (Crassulaceae) from Switzerland. Swiss Chemical Society, Lausanne 2007. Van Diermen D., Ndjoko Ioset K., Marston A. and Hostettmann, K. Qualitative and quantitative analyses of wild populations of Rhodiola rosea L. (Crassulaceae) from Switzerland. International Symposium by IOCD, “Biology, Chemistry, Pharmacology and Clinical studies of Asian plants”, Surabaya, Indonesia. April 2007. III ABBREVIATIONS AND SYMBOLS The units used in the present work are in agreement with the International System of Units (SI). 2D Bidimensional 4CL Hydroxycinnamate-CoA ligase 5-HT Serotonin δ Chemical shift (NMR) λmax Wavelength of the absorption maxima [α]D Specific rotation at the wavelength D of sodium Abs Absorbance ACh Acetylcholine AChE Acetylcholinesterase AD Alzheimer’s disease ALDH Aldehyde dehydrogenase ATP Adenosine triphosphate br s Broad singlet (NMR) BuOH Butanol CAD Cinnamyl alcohol dehydrogenase CAM Crassulaceae acid metabolism CCR Cinnamyl-CoA reductase CD 3OD Deuterated methanol CG Cyanogenic glycosides CoA Coenzyme A CNS Central nervous system COMT Catechol-O-methyltransferase COSY Correlation spectroscopy (NMR) CPC Centrifugal partition chromatography d Doublet (NMR) DA Dopamine DAD Diode array detector (UV) DCM Dichloromethane dd Double doublet (NMR) DMSO Dimethylsulfoxide DMSO-d6 Deuterated dimethylsulfoxide DNA Deoxyribonucleic acid DPPH 1,1-diphenyl-2-picrylhydrazyl EC 50 Effective concentration of a compound required for 50% scavenging activity V EI Electron impact (MS) ESI Electrospray ionization (MS interface) EtOAc Ethyl acetate EtOH Ethanol FA Formic acid GSH Glutathione HMBC Heteronuclear multiple bond correlation (NMR) HPLC High performance liquid chromatography HPLC-UV/DAD HPLC coupled with ultraviolet photodiode array detector HPLC-MS HPLC coupled with mass spectrometry HR-ESI/TOF/MS High resolution ESI TOF MS HSQC Heteronuclear single quantum coherence (NMR) Hz Herz Inhibitory concentration of ligand to equal 50% of the effect produced by a IC 50 standard OCD Obsessive-compulsive disorder i.d. Internal diameter IT Ion trap (MS detector) J Coupling constant (NMR) LC Liquid chromatography LDL Low density lipoprotein LLE Liquid-liquid extraction LPP Laboratory of Pharmacognosy and Phytochemistry LPLC Low pressure liquid chromatography m Multiplet (NMR) m/z Mass per electronic charge
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    UNIVERZITET U NIŠU PRIRODNO-MATEMATIĈKI FAKULTET DEPARTMAN ZA BIOLOGIJU I EKOLOGIJU MAJA D. JOVANOVIĆ Morfološka varijabilnost vrste Sedum album L. (Crassulaceae) na Balkanskom poluostrvu MASTER RAD Niš, 2017. UNIVERZITET U NIŠU PRIRODNO-MATEMATIĈKI FAKULTET DEPARTMAN ZA BIOLOGIJU I EKOLOGIJU Morfološka varijabilnost vrste Sedum album L. (Crassulaceae) na Balkanskom poluostrvu MASTER RAD Kandidat: Mentor: Maja D. Jovanović 206 Dr Bojan Zlatković Niš, 2017. UNIVERSITY OF NIŠ FACULTY OF SCIENCE AND MATHEMATICS DEPARTMENT OF BIOLOGY AND ECOLOGY Morphological variability of species Sedum album L. (Crassulaceae) on the Balkan Peninsula MASTER THESIS Candidate: Mentor: Maja D. Jovanović 206 Dr Bojan Zlatković Niš, 2017. BIOGRAFIJA KANDIDATA Maja D. Jovanović roĊena je u Nišu 27.03.1992. godine. Osnovnu školu ,,Stojan Ţivković Stole“ završava u Trnjanu (Aleksinac) nakon ĉega upisuje Srednju medicinsku školu ,,Milenko Hadţić“ (opšti smer) u Nišu. Prirodno-matematiĉki fakultet, Univerziteta u Nišu, upisuje 2011. godine, gde završava osnovne a potom i master studije, studijski program Ekologija i zaštita prirode, na Departmanu za biologiju i ekologiju. Tokom master studija uĉestvuje u promotivnim aktivnostima na projektima ,,Uspostavljanje konzervacionog menadţmenta slatina u Srbiji na osnovu monitoringa zajednice makroinvertebrata“ i ,,Uticaj lokalnog folklora i kulturnog nasleĊa na odnos ĉoveka prema šumskoj kornjaĉi (Testudo hermanii) u Srbiji“, finansiranih od strane Rufford Fondation kao i projektu ,,Divlji Viki Parkovi“ podrţanog od strane organizacije Vikimedija Srbije. Zahvalnica Neizmernu zahvalnost dugujem svom mentoru, Dr Bojanu Zlatkoviću, na ukazanom znanju, strpljenju, izvanrednoj saradnji i stručnom usmeravanju tokom godina studija i izrade ovog rada. Takođe, veoma sam zahvalna svim istraživačima koji su pomogli u sakupljanju biljnog materijala iz različitih delova Balkanskog poluostrva, i time doprineli da ovaj rad bude sveobuhvatniji.
  • Final Project Report (To Be Submitted by 30Th September 2016)

    Final Project Report (To Be Submitted by 30Th September 2016)

    Final Project Report (to be submitted by 30th September 2016) Instructions: Document length: maximum 10 pages, excluding this cover page and the last page on project tags. Start with an abstract (max 1 page). Final report text: Do not forget to mention your methodology; the people involved (who, how many, what organization they are from – if applicable); and the expected added value for biodiversity, society and the company. Finally, state whether the results of your project can be implemented at a later stage, and please mention the ideal timing and estimated costs of implementation. Annexes are allowed but will not be taken into account by the jury and must be sent separately. Word/PDF Final Report files must be less than 10 MB. If you choose to submit your final report in your local language, you are required to also upload your final report in English if you wish to take part in the international competition. To be validated, your file must be uploaded to the Quarry Life Award website before 30th September 2016 (midnight, Central European Time). To do so, please log in, click on ‘My account’/ ‘My Final report’. In case of questions, please liaise with your national coordinator. 1. Contestant profile . Contestant name: Moldovan Ștefan . Contestant occupation: Ornithologist . University / Organisation Romanian Ornithological Society . E-mail: . Phone (incl. country code): . Number of people in your team: 7 2. Project overview Title: Search for the critically endangered Apollo Butterfly at Bicaz Chei Quarry Contest: Quarry Life Award Quarry name: Bicaz Chei Quarry Prize category: ☐ Education and Raising Awareness (select all appropriate) X Habitat and Species Research ☐ Biodiversity Management ☐ Student Project ☐ Beyond Quarry Borders 1/3 Abstract The Apollo butterfly (Parnassius apollo Linnaues 1758) is a post-glacial relict, considered extinct from the Romanian fauna by most lepideptorologists.