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(L.) Moench (Asteraceae) with a Different Type

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(L.) Moench (Asteraceae) with a Different Type Université d'Ottawa University of Ottawa THE TAXONOMY, PHYTOCHEMISTRY AND BIOLOGICAL ACTMTY OF THE GENUS ECHINACEA (ASTERACEAE) O SHANNON E. BINNS Thesis submitted to the Faculty of Graduate and Postdoctoral Studies University of Ottawa In partial fulfillrnent of the requirements for the Ph.D. degree in the Ottawa-Carleton Institute of Biology Faculty of Science Department of Biology University of Ottawa Ottawa, Ontario Canada National Library Bibliothèque nationale 1+1 ,,"da du Canada Acquisitions and Acquisitions et Bibliographie Services sewices bibliographiques 395 WeUingtori Çtreet 395, rue Weliïmgton 01ÉiwaON K1AONs OthwaON K1AW canada Canada The author has granteci a non- L'auteur a accordé une licence non exclusive licence allowhg the exclusive permettant a la National Libmy of Canada to Bibliothèque nationale du Canada de reproduce, loan, distriïuîe or seil reproduire, prêter, distribuer ou copies of this thesis in microfonn, vendre des copies de cette thèse sous paper or electronic formats. la forme de microfiche/^ de reproduction sur papier ou sur format electronique. The author retains ownership of the L'auteur conserve la propriété du copyright in this thesis. Neither the droit d'auteur qui protège cette thèse. thesis nor substantial extracts fi-om it Ni la îhèse ni des extraits substantiels may be printed or othenvise de celle-ci ne doivent être imprimés reproduced without the author's ou autrement reproduits sans son permission. autorisation. We are deeply indebted " to those predecessors of ours on the North American continent who,. .. studied the flora of a new world, learned its secrets, and encouraged the next generations to study closer and to lem more. Theù diligence and energy, their insight and creativity, these are the marks of true scientists, dedicated to gahing meaninghil and usefùl knowledge nom a complex and confiising world." D. E. Moerman Native American Ethnobotanv Timber Press, 1998. ABSTRACT Echinacea Moench (Asteraceae) is a native North American plant genus with a long history of use as phytomedicine in both the Indigenous and European traditions (Shemluck 1982; Bauer 1998). A taxonomic revision of the genus Echinacea was conducted for the first time using morphometric analysis of natural populations sampled throughout the entire genus range. Individual plants were grouped without a priori taxonomic labeling, by morphological similarity using non-hierarchical and hierarchical, agglomerative clustering strategies. Canonical discriminant analysis (CDA) supported the distinction of two new subgenera, four species and eight varieties in the genus according to overall morphological similarity. When the sarne dataset was labeled a prion' according to McGregor's taxonomy (1968), his taxa were supported (with the exception of one variety) at the variety level. The new morpho-taxa were sufficiently distinguished by CDA of phytochemical variation (except for two varieties). Also, a class of outliers (including artificial hybrids) was not supported in either dataset as a taxon, and was therefore classified as 'hybrids/intro~essants'.In the most parsirnonious cladistic solution, one new subgenus was basally divergent to a clade of al1 others (70% bootstrap value) and al1 four species were distinguishable by at least one synapomorphy. Phytochemical profiles and average content of each known compound were reported here for the fmt thefrom al1 taxa of Echinacea, and revealed that five diene alkamides, one polyyne and two phenolic compounds (cichonc acid and echinacoside) were al1 chemotaxonomic markers within the genus Echinacea. Some of the same chemotaxonomic markers contributed heavily to the quantitative multivariate analysis of 26 phytochemicals, which identified five chernotypes among nine wild populations of the revised E. pallida var. angustfoiïa in a controlled greenhouse study. The alkamides and polyynes were also induced to higher concentrations in young roots of E. pallida (Nutt.) Nutt., that were sprayed with methyl jasmonate. Furthemore, plant extracts of the Echinacea taxa were variably phototoxic to clinically relevant pathogenic fûngi, such as Candida spp. The different phototoxic activities be~eenEchinacea taxa reflected the observed phytochemical variation, especially in the polyynes. Antiviral activity to Herpes simplex was linked to the presence of polyynes and cichoric acid in fiactionated Echinacea root and inflorescence extracts. Echinacea Moench (Asteraceae) est un genre de plantes indigènes en l'Amérique du Nord qui a été une source de phytomédicamments dans les systèmes de medicine traditionelle chez les autochtones et aussi en Europe (Shernluck 1982; Bauer 1998). Une revision systématique du genre Echinacea Moench (Asteraceae) a été menée pour la première fois avec l'analyse morphométrique des populations naturelles représentant la variation géographique totale du genre. L'étude de ce genre est significative pour la compréhension et la protection de ses populations naturelles en face de son importance économique et pharmacologiqw. L'analyse 'Canonical Discriminant Analysis" (CDA) a vérifié les groupes de plantes classifiés selon des méthodes agglomératives, hiérarchiques ' et non-hiérarchiques, sans identification a prion'. Deux sous-genres, quatre espèces et huit variétés ont été délimités par les calculs de similarité morphologique, et vérifiés en utilisant CDA. Une analyse préliminaire avec les données de cette étude a été menée selon la taxonomie de McGregor (1968), le seul à étudier le genre complet; elle a résulté à la prise en compte des taxa de McGregor comme variétés (sauf une de ses variétés). De plus, les taxa morphologiques ont été aussi déterminés sur des variations phytochimiques par CDA (sauf deux variétés). Mais, les spécimens qui restaient hors de la classification morphométrique n'étaient pas soutenus par le test CDA pour former un nouveau taxon, ils ont donc été classés comme hybrides ou introgressants (ce qui inclut les hybrides artificiels). Une analyse cladistique des quatres espèces de la taxonomie présente a démontré qu'elles se distinguaient par au moins une apomorphie (souvent plus) et les deux sous-genres divergaient plus fortement (70% "bootstrap"). La composition chimique a été identifiée pour la première fois pour tous les taxa du genre Echinacea : 26 composés dans lesquels se sont révélés comme marqueurs chimiotaxonomiques, cinq alkamides, une polype et deux composés phénoliques (l'acide cichorique et I'échinacoside). Parmi ceux- ci, quelques-uns ont contribué le plus à l'ordination par CDA de la variation quantitative dans une expérience en serre identifiant cinq chimiotypes parmi neuf populations sauvages de la variété E. paliida (Nutt.) Nutt. var. angtl~tr~liaDC. Cronq. (nom révisé). La concentration de certains composés aikamides et polyynes augmente dans les jeunes racines d'E. pallida (Nutt.) Nutt. var. pallida par traitement avec l'hormone méthyle jasmonate. Enfin, une activité phototoxique contre des souches pathogènes fongiques comme le Candida spp., et contre le virus Herpes simplex, a été démontrée dans les extraits d'Echinacea. Grâce aux différences dans la composition chimique des extraits, surtout des alkamides et polypes, les taxa ici-révisés possédent chacun des activités antimicrobie~esuniques. 1 would like to dedicate this work with enthusiasm to the growing medicinai plant community, and to al1 our ancestors who fostered the wisdom of ecological awareness and relationships. 1 offer heartfelt thanks to my parents, my brother, my farnily, my niends and al1 my grandmothers for their spirit, creativity and encouragement. For unconditional love and understanding, 1 am grateful to Mark Macfarlane DC. This study was conducted in collaboration with Trout Lake Farm LLC, Mediplant hc.,and Agriculture and Agri-Food Canada. 1 would like to thank them al1 for generous funding contributions through a Matching Investrnent Initiative Program. My research was also funded in part by Ontario Graduate Scholarships and a Natural Sciences and Enginee~gResearch Council Scholarship, for which 1 am grateful. For the skillful and timely completion of this work, both of my CO-supe~sors,Dr. J.T. Amason and Dr. B.R. Baum provided essential teachings, wisdom and compassion from their wealth of experience, which will remain an inspiration to me. 1 would like to acknowledge the following individuals for their invaluable contributions to the germplasm collections for this work: Echinacea growers and landowners, especially Trout Lake Fm LLC, T. Pitts and 1. Grossari; botanists and graduate students, especially L. St. Laurent, V. Assinewe, B. Purgina, B. Campbell, Dr. D. Price-Hurlburi, K. McKeown, Dr. M. Widrelechner (NCRPIS, USDA), Dr. R Marles and C. Ludwig (VA), A. Shea (TN) and C. Nordstrom (TN) fkom State Departrnents of Natural Heritage. I am also gratefid for the collaboration of S. Foster (Steven Foster Group, Inc.) and Dr. K. Kindscher (University of Kansas) in field research and the use of photographs. Permission to collect two federally protected species was granted fiom the US. Fish and Wildife Senrice. 1 appreciate the constructive suggestions of my cornmittee members, as well as al1 those colleagues at the University of Ottawa and ECORC (Agriculture Canada) who assisted with the experiments and reviewed the manuscripts in preparation. 1 would also like to acknowledge the fkiendly staff of the following Herbaria: BM, DAO, HUH, KANU, MO, N'Y, PH, and US for locating and loaning voucher specimens. For technical assistance and moral support, 1
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