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Natural Aphrodisiacs. Studies of Commercially-Available Herbal Recipes, and Phytochemical Investigation of Erythroxylum Vacciniifolium Mart

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Natural Aphrodisiacs. Studies of Commercially-Available Herbal Recipes, and Phytochemical Investigation of Erythroxylum Vacciniifolium Mart FACULTE DES SCIENCES Institut de Pharmacognosie et Phytochimie Natural aphrodisiacs. Studies of commercially-available herbal recipes, and phytochemical investigation of Erythroxylum vacciniifolium Mart. (Erythroxylaceae) from Brazil Thèse de doctorat présentée à la Faculté des Sciences de l’Université de Lausanne par Boris Zanolari Pharmacien diplômé de la Confédération Helvétique Jury Prof. Jean Hernandez, Président Prof. Kurt Hostettmann, Directeur de thèse Prof. Manfred Hesse, Expert Dr. David Guilet, Expert Dr. Andrew Marston, Expert LAUSANNE 2003 A mes parents et ma sœur A Laura Remerciements Ce travail de thèse a été réalisé d’octobre 1999 à juin 2003 à l’Institut de Pharmacognosie et Phytochimie de l’Université de Lausanne sous la direction du Prof. Kurt Hostettmann. J’aimerais tout d’abord exprimer ma profonde gratitude au Prof. Kurt Hostettmann pour m’avoir accueilli dans son institut et donné la possibilité de faire une thèse sur un sujet très intéressant. Je le remercie également pour m’avoir permis de participer à l’organisation du congrès international de phytochimie à Lausanne et de participer aussi à des congrès à Bamako (Mali) et à Barcelone (Espagne). J’adresse également mes remerciements au prof. Manfred Hesse (Université de Zurich) qui a accepté de venir de Zurich, pour faire partie de mon jury de thèse et pour l’intérêt qu’il a porté à mon travail. Je remercie aussi le Prof. Jean Hernandez pour avoir présidé le jury de séance d’examen. Mes sincères remerciements vont à mon “technical advisor”, le Dr. Andrew Marston, pour sa gentillesse, son encadrement, ses précieux conseils et sa disponibilité. Je voudrais aussi remercier le Prof. Jean-Luc Wolfender pour son aide et ses nombreux conseils scientifiques concernant la LC-MS et la LC-RMN. Je tiens aussi à remercier les Dr. Karine Ndjoko et Jean-Robert Ioset pour leur amitié et pour les discussions enrichissantes à propos de l’analyse quantitative. Merci au Dr. David Guilet pour nos intéressantes discussions scientifiques, pour avoir partagé le bureau et enfin pour son amitié. J’aimerais encore exprimer ma gratitude au Dr. Emerson Ferreira Queiroz pour avoir apporté la plante Catuaba du Brésil mais surtout pour son amitié pendant ces quatre ans de thèse. Je remercie mes collègues pour tous les moments, professionnels ou non, que nous avons partagés, aussi que les anciens collègues et copains de thèse Alain, Julien et Anne Laure. Un grand remerciement va, enfin, à toute ma famille, à Laura ainsi qu’au personnel de l’hôpital Nestlé qui m’ont toujours soutenu et m’ont permis de finir ma thèse. Scientific communications The present work was carried out from October 1999 to June 2003 at the Institute of Phytochemistry and Pharmacognosy of the University of Lausanne, under the guidance of Prof. Dr. Kurt Hostettmann. Some aspects of the present research have been published and presented at international scientific congresses as poster presentations. Publications Zanolari, B., Guilet, D., Marston, A., Queiroz, E. F., de Q. Paulo, M. and Hostettmann, K. (2003a). Tropane alkaloids from the bark of Erythroxylum vacciniifolium. J. Nat. Prod. 66, 497-502. Zanolari, B., Ndjoko, K., Ioset, J.-R., Marston, A. and Hostettmann, K. (2003b). Qualitative and quantitative determination of yohimbine in authentic yohimbe bark and in commercial aphrodisiacs by LC-UV-API/MS methods. Phytochem. Anal. 14, 193-201. Zanolari, B., Wolfender, J.-L., Guilet, D., Marston, A., Queiroz, E. F., de Q. Paulo, M. and Hostettmann, K. (2003c). On-line identification of tropane alkaloids from Erythroxylum vacciniifolium by LC-UV-MSn and LC-NMR. J. Chromatogr. A.1020, 75-89. Zanolari, B., Guilet, D., Marston, A., Queiroz, E. F., de Q. Paulo, M. and Hostettmann, K. (2003d). Methylpyrrolic tropane alkaloids from the bark of Erythroxylum vacciniifolium. J. Nat. Prod. Submitted Posters Zanolari, B., Ndjoko, K., Ioset, J.-R., Marston, A. and Hostettmann, K. (2001). Qualitative and quantitative determination of yohimbine in authentic yohimbe bark and in commercial aphrodisiacs by LC/UV/API-MS methods. 9th NAPRECA (Natural Products Research Network for Eastern and Central Africa) Symposium, Nairobi, Kenia, August 27-31. Zanolari, B., Marston, A., Queiroz, E. F. and Hostettmann, K. (2001). Tropane alkaloids from the bark of Erythroxylum catuaba Part 1. Phytochemical Society of Europe, Annual Symposium 2001, Lead Compounds from Higher Plants, Lausanne, Switzerland, September 12-14. Zanolari, B., Ndjoko, K., Ioset, J.-R., Marston, A. and Hostettmann, K. (2001). Qualitative and quantitative determination of yohimbine in authentic yohimbe bark and in commercial aphrodisiacs by LC/UV/API-MS methods. Swiss Chemical Society (Analytical Chemistry Division), Fall Meeting 2001, Zürich, Switzerland, October 12. Zanolari, B., Guilet, D., Marston, A., Queiroz, E. F., de Q. Paulo, M. and Hostettmann (2002). Tropane alkaloids from the bark of Erythroxylum catuaba (Erythroxylaceae) Part 2. Society for Medicinal Plant Research (GA), 50th Annual Congress 2002, Barcelona, Spain, September 8-12. Zanolari, B., Wolfender, J.-L., Guilet, D., Marston, A., Queiroz, E. F., de Q. Paulo, M. and Hostettmann, K. (2002). On-line identification of tropane alkaloids from Erythroxylum catuaba by LC-UV-MSn and LC-NMR. International Association of Environmental Analytical Chemistry, 19th LC/MS Symposium, Montreux, Switzerland, November 6-8. i Abbreviations [α]D specific rotation at the wavelength D of sodium Abs. absorbance ACh acetylcholine AChE acetylcholinesterase ACTH adrenocorticotrophic hormone APCI atmospheric pressure chemical ionization (MS) APG Angiosperm Phylogeny Group API atmospheric pressure ionization br s broad singulet cAMP cyclic adenosine monophosphate CC column chromatography CD circular dichroism cGMP cyclic guanosine monophosphate CI confidence interval CNS central nervous system Col2 colon cell lines d doublet (NMR) D/CI desorption/chemical ionization (MS) Da Dalton DCM dichloromethane δ chemical shift (ppm) (NMR) dd double doublet (NMR) DEPT distortionless enhancement by polarisation transfer (NMR) DHEA dehydroepiandrosterone DMSO dimethylsulfoxide EI electron impact (MS) ESI electrospray ionization (MS) Et3N triethylamine EtOH ethanol FIA flow injection analysis GABA γ-aminobutyric acid gDQF-COSY gradient double quantum filtered correlation spectroscopy (NMR) gHMBC gradient heteronuclear multiple bond correlation (NMR) gHSQC gradient heteronuclear single quantum coherence (NMR) Hdmb 4-hydroxy-3,5-dimethoxybenzoic acid HPLC high performance liquid chromatography HR high resolution (MS) HRESMS high-resolution electrospray ion cyclotron resonance mass spectrometry hTERT-RPE1 human telomerase reverse transcriptase-retinal pigment epithelial cells iii HUVEC human umbilical vein endothelial cells Hz Herz i.d. internal diameter IR infrared spectrum J coupling constant (NMR) KB oral epidermoid cell lines LC-DAD-UV high performance liquid chromatography coupled with ultraviolet photodiode array detector LC-MS high performance liquid chromatography coupled with mass spectrometry LC-NMR high performance liquid chromatography coupled with nuclear magnetic resonance spectroscopy LNCaP hormone-dependant prostate cell lines Lu1 human lung cancer cell lines m multiplet (NMR) MAO monoamine oxidase [M+H]+ protonated molecule + [MD+D] deutered molecule m/z mass per electronic charge MDR multidrug-resistance MeCN acetonitrile MeNE methylnorepinephrine MeOH methanol Mpc 1-methyl-1H-pyrrole-2-carboxylic acid MPLC medium pressure liquid chromatography MS mass spectrometry MSn multiple stage tandem MS MW molecular weight NE norepinephrine NMR nuclear magnetic resonance NO nitric oxide NOE nuclear overhauser effect (NMR) NOESY nuclear overhauser effect spectroscopy (NMR) NOS nitric oxide synthase PDE phosphodiesterase ppm parts per million (NMR unity) Pc 1H-pyrrole-2-carboxylic acid RSD relative standard deviation RT retention time R.T. room temperature s singlet (NMR) SD standard deviation sp. unspecified species (one) iv SP-HPLC semi-preparative high performance liquid chromatography spp. species (several) ssp. subspecies t triplet (NMR) TLC thin-layer chromatography TMS tetramethylsilane TOCSY total correlation spectroscopy (NMR) TOF time of flight (MS) UV ultraviolet spectrum VLB vinblastine WET fast solvent suppression (LC-NMR) yohimbine-d3 deuterium-labeled yohimbine v vi Table of contents Scientific communications ..................................................................................................i Abbreviations.....................................................................................................................iii Table of contents ...............................................................................................................iii I. Aim of the work.......................................................................................................1 II. Introduction ............................................................................................................5 1. Aphrodisiacs: the eternal dream............................................................................7 2. Definition.................................................................................................................9 3. Aphrodisiacs in history: the ancient traditions...................................................11 4. Assessing the effects of potential aphrodisiacs.................................................16 5. Aphrodisiacs that increase potency (allow or sustain erection) ........................17
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