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Fronza, Marcio Thesis Phytochemical investigation of the roots of Peltodon longipes and in vitro cytotoxic studies of abietane diterpenes INAUGURALDISSERTATION zur Erlangung des Doktorgrades der Fakultät für Chemie, Pharmazie und Geowissenschaften der Albert-Ludwigs-Universität Freiburg im Breisgau vorgelegt von Marcio Fronza aus Tucunduva, RS (Brasilien) June 2011 Dekan: Prof. Dr. Harald Hillebrecht Leiterin der Arbeit: Prof. Dr. Irmgard Merfort Referentin: Prof. Dr. Irmgard Merfort Korreferent: Prof. Dr. Stefan Laufer Drittprüfer: Prof. Dr. Andreas Bechthold Tag der Verkündigung des Prüfungsergebnisses: 15-07-2011 Parts of this work have been published in the following conference presentations and publications: Publications Fronza M., Lamy E., Günther S., Murillo R., Heinzmann B., Laufer S., Merfort I. In vitro cytotoxic molecular mechanism studies of abietane diterpenes from Peltodon longipes . In preparation. Fronza M., Murillo R., Ślusarczyk S., Adams M., Hamburger M., Heinzmann B., Laufer S., Merfort I. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and S. sahendica . Bioorganic & Medicinal Chemistry, in press . Geller F., Schmidt C., Gottert M., Fronza M., Heinzmann B., Flores E.M., Merfort I., Laufer S. Identification of rosmarinic acid as the major active compound constituent in Cordia americana . Journal of Ethnopharmacology . v.130, p.333 - 338, 2010. Schmidt C. A., Fronza M., Gottert M., Geller F., Laufer S., Merfort I. Biological studies on Brazilian plants used in wound healing. Journal of Ethnopharmacology . v.122, p.523 - 532, 2009. Fronza M., Heinzmann B., Hamburger M., Laufer S., Merfort I. Determination of the wound healing effect of Calendula extracts using the scratch assay with 3T3 fibroblasts. Journal of Ethnopharmacology . v.126, p.463 - 467, 2009. Conferences - poster presentation Fronza M., Günther S., Murillo R., Lamy E, Heinzmann B., Laufer S., Merfort I. Antiproliferative activity of diterpenes from Peltodon longipes . In : Deutsch-Brasilianisches Jahr 2010/11- Workshop: Drugs from Natural Sources - São Paulo, SP, Brazil, 2010. Schmidt C.A., Fronza M., Murillo R., Brecht V., Heinzmann B., Laufer S.A., Merfort, I. Wound Healing Properties of Catechin Derivatives Isolated from Barks of Parapiptadenia rigida . In : Deutsch-Brasilianisches Jahr 2010/11- Workshop: Drugs from Natural Sources - São Paulo, SP, Brazil, 2010. Geller F., Schmidt C., Goettert M., Fronza M., Heinzmann B., Werz O., Merfort I., Laufer S. Rosmarinic acid as the effective compound in Cordia americana . In : Deutsch-Brasilianisches Jahr 2010/11- Workshop: Drugs from Natural Sources - São Paulo, SP, Brazil, 2010. Fronza M., Günther S., Murillo R., Lamy E, Heinzmann B., Laufer S., Merfort I. Antiproliferative activity of diterpenes from Peltodon longipes . In : XIX° Congreso Italo-Latinoamericano de Etnomedicina, Cagliari (Villasimius), Italy, 2010. Fronza M., Günther S., Murillo R., Lamy E, Heinzmann B., Laufer S., Merfort, I. Abietane diterpenoids from the roots of the Lamiaceae Peltodon longipes preferentially inhibit topoisomerase-I. In : 22 nd Irsser Naturstofftage - Aktuelle Entwicklungen in der Naturstoff-Forschung, Irsee - Germany, 2010. Gottert M., Fronza M., Schmidt C. A., Geller F., Heinzmann B., Merfort I., Laufer S. Effect of natural phenolic compounds on p38 α MAPK activity. In : IV Simpósio Brasil-Alemanha / 4. Deutsch-Brasilianisches Symposium, Curitiba-Brazil, 2009. Fronza M., Gottert M., Schmidt C. A., Heinzmann B., Jaroszewski J.W., Laufer S., Merfort I. Isolation of cytotoxic diterpenes from the lipophilic extract of Peltodon longipes. In : IV Simpósio Brasil-Alemanha / 4. Deutsch-Brasilianisches Symposium, Curitiba-Brazil, 2009. Schmidt C. A., Fronza M., Gottert M., Murillo R., Heinzmann B., Laufer S., Merfort I. New catechin derivates from Parapiptadenia rigida. In : IV Simpósio Brasil-Alemanha / 4. Deutsch-Brasilianisches Symposium, Curitiba-Brazil, 2009. Fronza M., Gottert M., Murillo R., Laufer S., Merfort I. Abietane diterpenoids from the roots of Peltodon longipes with cytotoxic activity and inhibitory activity towards p38 α MAPK. In: 6 th Status Seminar Chemical Biology - DECHEMA - Natural products and nucleic acids as chemical tools, Frankfurt - Germany, 2009. Geller F., Gottert M., Fronza M., Schmidt C.A., Heinzmann B., Merfort I., Laufer S. Phytochemical and biological investigation on the ethanolic extract of Cordia americana. In : 6 th Status Seminar Chemical Biology - DECHEMA - Natural products and nucleic acids as chemical tools, Frankfurt-Germany, 2009. Fronza M., Gottert M., Schmidt C. A., Heinzmann B., Jaroszewski J.W., Laufer S., Merfort I. Diterpenes from Peltodon longipes with caspase-3 activity. In: Drug Discovery and Delivery: Membrane Proteins and Natural Product Research, Freiburg - Germany, 2009. Gottert M., Fronza M., Schmidt C. A., Geller F., Merfort I., Laufer S. Natural phenolic compounds as inhibitors of P38 α MAPK. In : Drug Discovery and Delivery: Membrane Proteins and Natural Product Research, Freiburg-Germany, 2009. Schmidt C.A., Fronza M., Gottert M., Murillo R., Heinzmann B., Laufer S., Merfort I. Two new catechin derivatives from Parapiptadenia rigida . In : Drug Discovery and Delivery: Membrane Proteins and Natural Product Research, Freiburg-Germany, 2009. Schmidt C.A., Fronza M., Gottert M., Murillo R., Heinzmann B., Laufer S., Merfort I. Phytochemical and biological studies of the bark from Parapiptadenia rigida. In: 2 nd BCNP - Brazilian Conference on Natural Products, São Pedro - Brazil, 2009. Gottert M., Luik S., Fronza M., Geller F., Schmidt C.A., Merfort I., Laufer S. Biological testing of bioactive compounds that inhibit p38 MAPK. In : 5 th Status Seminar Chemical Biology - DECHEMA - Chemical Biology in Europe: Research across disciplines and countries, Frankfurt-Germany, 2008. Fronza M., Geller F., Bittencourt C., Flores E.M.M., Heinzmann B., Laufer S., Merfort I. The scratch assay: a suitable in vitro tool for studying wound healing effects. In : 7 th Joint Meeting of the Association Francophone pour l'Enseignement et la Recherche en Pharmacognosie (AFERP), American Society of Pharmacognosy (ASP), Society for Medicinal Plant Research (GA), Phytochemical Society of Europe (PSE), and Societ Italiana di Fitochimica (SIF), Athens - Greece, 2008. Conferences - short talks Fronza M., Merfort I. Antiproliferative activity of diterpenes from Peltodon longipes . In : XIX° Congreso Italo-Latinoamericano de Etnomedicina, Cagliari (Villasimius), Italy, 2010. Fronza M., Günther S., Murillo R., Lamy E, Heinzmann B., Laufer S., Merfort I. Cytotoxic abietane diterpenes from Peltodon longipes and their mode of action. In : 58 th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research and 7th Tannin Conference, Berlin - Germany, 2010. Fronza M., Günther S., Murillo R., Lamy E, Heinzmann B., Laufer S., Merfort I. Abietane diterpenoids from the roots of the Lamiaceae Peltodon longipes preferentially inhibit topoisomerase-I. In : 22 nd Irsser Naturstofftage - Aktuelle Entwicklungen in der Naturstoff-Forschung, Irsee - Germany, 2010. Fronza M., Günther S., Murillo R., Lamy E, Heinzmann B., Laufer S., Merfort I. Diterpenoids from a Brazilian medicinal plant preferentially inhibit topoisomerase-I. In : 7 th Immunology meeting, Freiburg - Germany, 2010. Fronza M., Heinzmann B., Geller F., Laufer S., Merfort I. An improved scratch assay for studying the wound healing effects of medicinal plants. In : IV Simpósio Brasil-Alemanha / 4. Deutsch-Brasilianisches Symposium, Curitiba-Brazil, 2009. Index I 1. Introduction........................................................................................................... 1 1.1. Natural products as leads for the development of potential drugs......................... 1 1.2. Peltodon longipes A.St.-Hil. ex Benth..................................................................... 6 1.3. Diterpenes ................................................................................................................. 8 1.3.1. Abietane diterpenes......................................................................................... 11 1.4. Aim of the thesis ..................................................................................................... 24 2. Results .................................................................................................................. 25 2.1. Scratch assay .......................................................................................................... 25 2.2. Studies of Brazilian medicinal plants on HNE..................................................... 32 2.3. Peltodon longipes ................................................................................................... 34 2.3.1. Isolation procedure.......................................................................................... 34 2.3.2. Structure elucidation of the isolated abietane diterpenes................................ 35 2.3.2.1 7 α-acetoxyroyleanone (syn. 7-O-acetylhorminone)(1)............................. 35 2.3.2.2 7 α-hydroxyroyleanone (syn horminone) (2)............................................. 45 2.3.2.3 Royleanone (3)........................................................................................... 53 2.3.2.4 7-ketoroyleanone (syn 7-oxoroyleanon) (4)............................................... 61 2.3.2.5 7 α-ethoxyroyleanone (5)..........................................................................
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