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INFORMATION to USERS the Most Advanced Technology Has Been Used to Photo­ Graph and Reproduce This Manuscript from the Microfilm Master INFORMATION TO USERS The most advanced technology has been used to photo­ graph and reproduce this manuscript from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. 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University Microfilms International A Bell & Howell Information Company 300 North Zeeb Road, Ann Arbor, Ml 48106-1346 USA 313/761-4700 800/521-0600 Order Number 8913687 Flavonoid chemistry and evolution of Dendroseris and Gunnera in the Juan Fernandez Islands (Chile) Pacheco-Jara, Patricia, Ph.D. The Ohio State University, 1989 UMI 300 N. Zeeb Rd. Ann Arbor, MI 48106 FLAVONOID CHEMISTRY AND EVOLUTION OF DENDROSERT.q AND GUNNERA IN THE JUAN FERNANDEZ ISLANDS (CHILE) DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in the Graduate School of The Ohio State University By Patricia Pacheco Jara ***** The Ohio State University 1989 Dissertation Comnittee: Approved By: Dr. Michael L. Evans Dr. Daniel J. Crawford Dr. Tod F. Stuessy Department of Botany Dedicated to Hugo Marcela Cristina Javier ACKNOWLEDGMENTS I wish to thank all the people who have helped me during the completion of this study. First, I thank Dr. Tod F. Stuessy and Dr. Daniel J. Crawford for all the teaching, help, opportunities and encouragement given throughout the course of this work. I am also grateful to Dr. Michael L. Evans for his comments and criticisms on this dissertation. This study was supported by grants from Sigma Xi, NSF doctoral dissertation improvement grant INT-8317088, OEA PRA Fellowship, Tinker Foundation Travel Grant and an Graduate Student Alumnii Research Award. I am especially grateful to Dr. Jim Solomon for his invaluable help during field work in Bolivia. I also wish to thank Dr. Stephan Beck (LPB), Dr. R. Rodriguez, Dr. R. Peralta, Ms. N. Salinas, V. Campos and many others who made the field work possible. Especial thanks to Rich Whitkus, Paul Lewis, and John Frederick for their help during the complextion of part of this work. Thanks also go to the curators of F, MO, NY, and UC for the loan of specimens. A very special thanks go to Hugo, my husband, for his encouragement and faith, without which this work would have been impossible. Thanks to Marcela, Christina and Javier (my children) for their understanding and help. iii VITA 1962-1967 ................ Licenciado en Biologla, Universidad de Concepcion, Concepcion, CHILE. 1968-1971 ................ Researcher, Universidad de Concepcion, Concepcion, CHILE 1972-1973 ................ Associate Professor, Universidad de Santiago, Santiago, CHILE. 197^—1975 ................ Associate Professor, Universidad de Chile, Santiago, CHILE. 1976-1981 ................ Researcher, Universidad de Concepcion, Concepcion, CHILE. 1982-1988 ................ Graduate Teaching Associate and Graduate Research Associate, Botany Department, The Ohio State University, Columbus, Ohio. PUBLICATIONS Journal Articles Pacheco, P., M.Silva, P.G. Sammes and T.W. Tyler. 1973. Triterpenoids of Colletia spinosissima. Phytochemistry, 12:893-897. Pacheco, P., S.M.H. Albonico, and M. Silva. 1973. Alkaloids, triterpenes and other constituents of Discaria crenata. Phytochemistry, 12: 954-955. Gopalakrishna, E.M., W.H. Watson, P. Pacheco and M. Silva. 1976. Lycorine. C^gH^NOij. Cryst. Struct. Comm. 5: 795-799. Watson, W.H., Z. Taira, M. Silva and P. Pacheco. 1977. 1,2,3>4,4a,6 hexahydro-10 hydroxy-3, 8,9-trimethoxy-H, 10b ethanophenanthridinium picrate. (C^gH2 c0 4 NH)+ ^C6h12n3°7^~* Cryst* Struct. Comm., 0 : 797- 801. iv 1 Gopalakrishna, E.M., W.H. Watson, M. Silva, and P. Pacheco. 1978. 17-Epihomolycorine, C^gHg^NO^. Cryst. Struct. Comm., 7 • ^1. Pacheco, P., M.Silva, W. Steglich and W.H. Watson. 1978. Hippeastidine and Epihomolycorine, two novel alkaloids. Rev. Latinoamer. Quim., 9: 28-32. Zabel, V., W.H. Watson, P. Pacheco and M. Silva. 1979. Maritidine. ^17^21^®3* Cryst. Struct. Comm., 8: 371. Kimura, M . , W.H. Watson, P. Pacheco and M. Silva. 1979. Rel-(2S, 3S)- 3- hydroxy- 7- methoxy-31, 4' methylenedioxyflavan. Acta Cryst. B 35: 3124-3126. Kimura, M . , W.H. Watson, P. Pacheco and M. Silva. 1980. 7-hydroxy-6-methoxycoumarin. Cryst. Stryct. Comm., 9 - 257. Watson, W.H., M. Kimura, P. Pacheco and M. Silva. 1981. Proanthocyanidins of Hippeastrum ananuca I. Rev. Latinoamer. Quim., 12: 30-32. Sepulveda, B.A., P. Pacheco, M. Silva and R. Zemelman. 1982. Alkaloids of the Chilean Amaryllidaceae III. Chemical study and biological activity in Hippeastrum bioolor (R. et P.) Baker. Bol. Soc. Chil. Quim., 27(2): 178-180. Pacheco, P., M. Silva, P.G. Sammes and W.H. Watson. 1982. New alkaloids from Hippeastrum ananuca Phil. Bol. Soc. Chil. Quim., 27: 289-290. Schmeda, G., P. Pacheco and M. Silva. 1983. Flavonoids of Eupatorlum laeve DC. Rev. Latinoamer. Quim., 14: 36-37. Pacheco, P., D.J. Crawford, T.F. Stuessy and M. Silva. 1985. Flavonoid evolution in Robinsonia (Compositae) of the Juan Fernandez Islands. Amer. J. Bot., 72: 989-998. Bittner, M., M. Silva, Z. Rozas, P. Pacheco, T. Stuessy, F. Bohlmann and J. Jakupovic. 1988. New kaurane derivatives from Robinsonia evenia. Phytochemistry 27: 487-488. Abstracts Pacheco, P. and M. Silva 0. 1972. Alkaloids, triterpenes and other constituents of Discaria crenata (Clos) Regel. XI Latinoamerican Congress of Chemistry. Santiago, Chile (Abstract). v 'I Pacheco, P. and M. Silva 0. 1975. Chemotaxonomic studies in Solanaceae based on steroidal' lactones. VII Annual meeting of the Chilean Chemical Society,. Valparaiso, Chile. (Abstract). Pacheco, P. and M. Silva 0. 1976. Alkaloids of Hippeastrum ananuca. VIII Annual meeting of the Chilean Chemical Society. Santiago, Chile (Abstract). Pacheco, P. and M. Silva 0. 1977. Hippeastidine and Epi-homolycorine, two new alkaloids from Hippeastrum ananuca. IX Annual meeting of the Chilean Chemical Society. Jahuel, Chile (Abstract) Silva, M . , P. Pacheco, M.T. Chiang and C. Marticorena. 1977. Quimica de plantas chilenas usadas en medicina popular. Simposio Internazionale Sulla Medicina Indigena e Popolare Dell'America Latina. Instituto Italo Latinoamericano IILA. Roma, Italia. (Abstract) Pacheco, P. and M. Silva. 1978. Proanthocyanidins and alkaloids of Hippeastrum ananuca. XIII Latinoamerican Congress of Chemistry. Lima, Peru (Abstract). Pacheco, P. 1978. Proanthocyanidins of Hippeastrum ananuca. X Annual meeting of the Chilean Chemical Society. Valdivia, Chile (Abstract). Gonzalez, F. and P. Pacheco. 1981. Secondary metabolites of Antholoba achates Coutony, 1846. Meeting of Sciences of the Sea. Institute of Oceanology. Valparaiso, Chile (Abstract). Pacheco, P. and M. Silva. 1979. New proanthocyanidins from Hippeastrum ananuca. XI Annual meeting of the Chilean Chemical Society. Concepcion, Chile (Abstract). Pacheco, P. and M. Silva 0. 1980. Chemical studies in Chilean Amaryllldaceae. Ill National meeting of Botany. Chilean Society of Biology., Concepcion, Chile (Abstract)., Pacheco, P., D.J. Crawford, M. Silva, and T.F. Stuessy. 1983- Flavonoid evolution in Robinsonia (Compositae) of the Juan Fernandez Islands. Amer. J. Bot. (Abstr.) 70: 124. Pacheco, P., D.J. Crawford, M. Silva, and T.F. Stuessy. 1983. Flavonoid evolution in Robinsonia (Compositae) of the Juan Fernandez Islands. Ohio J. Sci. (Abstr.) 83: 14. Pacheco, P., D.J. Crawford, M. Silva, and T.F. Stuessy. 1984. Evolution in Gunnera (Gunneraceae) of the Juan Fernandez Islands. Ohio J. Sci. (Abstr.) 84: 5. Pacheco, P., D.J. Crawford, M. Silva, and T.F. Stuessy. 1985. Natural hybridization in Gunnera (Gunneraceae) of the Juan Fernandez Islands. Ohio J. Sci. (Abstr.) 85: 17- Pacheco, P., D.J. Crawford, M. Silva, and T.F. Stuessy. 1985. Flavonoid chemistry and evolution of Dendroseris (Compositae, Lactuceae) in the Juan Fernandez Islands. Amer. J. Bot. (Abstr.) 72: 965. Pacheco, P., D.J. Crawford, and TiF. Stuessy. 1987* Flavonoid evolution in Gunnera (Gunneraceae) of the Juan Fernandez Islands, Chile. Ohio J. Sci. (Abstr.) 87: 7- Pacheco, P., D.J. Crawford, M. Silva, and T.F. Stuessy. 1987. Natural hybridization in Gunnera (Gunneraceae) of the Juan Fernandez Islands, Chile. Amer. J. Bot. (Abstr.) 74: 748. Book Pacheco, P., M.T. Chiang, C. Marticorena, y M. Silva 0. 1977- Quimica de plantas Chilenas usadas en
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