Abstract
This book describes a unique class of secondary metabolites, the mono- and dimeric naphthylisoquinoline alkaloids. They occur in lianas of the paleotropical Ancistrocladaceae and Dioncophyllaceae families, exclusively. Their unprecedented structures include stereogenic centers and rotationally hindered, and thus likewise stereogenic, axes. Extended recent investigations on six Ancistrocladus species from Asia, as reported in this review, shed light on their fascinating phytochemical productivity, with over 100 such intriguing natural products. This high chemodiversity arises from a likewise unique biosynthesis from acetate-malonate units, following a novel polyketidic pathway to plant-derived isoquinoline alkaloids. Some of the compounds show most promising antiparasitic activities. Likewise presented are strategies for the regio- and stereoselective total synthesis of the alkaloids, including the directed construction of the chiral axis.
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Notes
- 1.
For naphthylisoquinoline alkaloids appearing as two rotational isomers, a numbering system is applied in which the two atropo-diastereomers are denoted as a and b, like, e.g., for ancistrocladine (1a) and hamatine (1b), see Fig. 1.
- 2.
For an easier comparison of naphthylisoquinoline alkaloids with different coupling positions, a 2-methyl-4,5-dioxy substitution pattern is throughout applied in the numbering of the naphthalene moiety, regardless of the coupling site.
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Acknowledgements
The authors would like to thank those numerous skillful and highly committed students and coworkers of our group who contributed with great enthusiasm to the manifold developments during the past decades regarding the knowledge about naphthylisoquinoline alkaloids from Asian Ancistrocladus plants. We are in particular grateful (names given in an alphabetical order) to Dr. Stefan Busemann, Dr. Michael Dreyer, Dr. Torsten Geuder, Prof. Dr. Ralf God, Dr. Klaus-Peter Gulden, Prof. Dr. Tanja Gulder, Prof. Dr. Tobias A. M. Gulder, Dr. Christian Günther, Yasmin Hemberger, Dr. Barbara Hertlein-Amslinger, Dr. Jörg Holenz, Dr. Andreas Irmer, Dr. Johannes R. Jansen, Dr. Inga Kajahn, Dr. Dagmar Koppler, Dr. Katja Maksimenka, Dr. Kim Messer, Dr. Jörg Mühlbacher, Dr. Narasimhulu Manchala, Dr. Frank Pokorny, Dr. Matthias Reichert, Dr. Helmut Reuscher, Dr. Heiko Rischer, Dr. Markus Rückert, Dr. Raina Seupel, Dr. Anu Schaumlöffel, PD Dr. Jan Schlauer, Dr. Ralf Weirich, Barbara Wiesen, Dr. Michael Wohlfarth, Dr. Kristina Wolf, Dr. Minjuan Xu, Dr. Guoliang Zhang, and, in particular, Dr. Torsten Bruhn—the names of all involved coworkers can also be seen from the literature cited. Furthermore, we are indebted to Mrs. Lioba Kinzinger, Mr. Frank Meyer, Mrs. Manuela Michel, Mrs. Stefanie Schmitt, and Mrs. Michaela Schraut for their valuable technical assistance. We are grateful to Prof. Dr. Ulrich Zimmermann (Germany) for light and fluorescence microscopy investigations on Ancistrocladus heyneanus, Prof. Dr. Wolfgang Kiefer and Prof. Dr. Jürgen Popp (Germany) for FT-Raman investigations, and Prof. Dr. Axel Haase and Prof. Dr. Peter M. Jakob (Germany) for nuclear magnetic resonance microscopy studies. Moreover, we wish to thank Prof. Dr. Reto Brun, Dr. Marcel Kaiser (Switzerland), Prof. Dr. Thomas Dandekar, Prof. Dr. Thomas Efferth, Prof. Dr. August Stich, Prof. Dr. Heidrun Moll, Prof. Dr. Joachim Morschhäuser, PD Dr. Knut Ohlsen (Germany), Prof. Dr. Alicia Ponte-Sucre (Venezuela), Dr. Łukasz Adaszek (Poland), Prof. Dr. Michael R. Boyd (USA), and Prof. Dr. Suresh Awale (Japan) for intense, stimulating, and fruitful cooperations evaluating the bioactivities of genuine naphthylisoquinoline alkaloids and related, synthetic analogues.
We would further like to express our sincere compliments to the pioneer of naphthylisoquinoline alkaloids, late Prof. Dr. Tuticorin R. Govindachari, for his brilliant early work in the field, and to all of our Asian partners who have given us all sorts of support and cooperative reliability regarding botanical and ethnobotanical work, particularly Prof. Dr. A. S. Sankara Narayanan, Prof. Dr. M. R. Almeida, Prof. Dr. N. J. De Souza (India), Prof. Dr. Hamid A. Hadi (Malaysia), Prof. Dr. Luu Hoang Ngoc (Vietnam), and Prof. Dr. Jun Wu (PR China). Our particular thank goes to Prof. Dr. Günther Heubl (Germany) and Prof. Dr. Harald Meimberg (Austria) for their long-term cooperation focusing on the molecular phylogeny, chemotaxonomy, and botanical classification of the Asian Ancistrocladus species presented in this review. Moreover, we are grateful to Prof. Dr. Markus Riederer und Dr. Gerd Vogg (Germany) for their generous hospitality and competent support permitting us to cultivate and study more closely various Ancistrocladus plants from Asia in the Botanical Garden of the University of Würzburg, with an emphasis on the Indian liana Ancistrocladus heyneanus and the newly discovered taxon Ancistrocladus benomensis from Malaysia. We gratefully acknowledge the horticultural expertise and continuous support and commitment of all involved gardeners (in particular Andreas Kreiner and Friedrich Thiele) regarding the cultivation of these fascinating lianas from seeds to adult plants.
For generous financial support of this work, the authors would like to thank the Deutsche Forschungsgemeinschaft (projects Br 699/14-1 and 14-2; “Molecular Phylogeny and Chemotaxonomy of the Ancistrocladaceae Plant Family”, Collaborative Research Center SFB 630 “Recognition, Preparation, and Functional Analysis of Agents against Infectious Diseases”, Collaborative Research Center SFB 251 “Ecology, Physiology, and Biochemistry of Plants and Animals under Stress”, Clinical Research Unit KFO 216 “Characterization of the Oncogenic Signaling Network in Multiple Myeloma: Development of Targeted Therapies”, Priority Program SPP 1152 “Evolution of Metabolic Diversity”, and Research Training Group “NMR in vivo and in vitro for Biological Basic Research”). This work was also funded by grants from the Bundesministerium für Bildung und Forschung (BMBF), project no. 0310722, the BASF AG, the Fonds der Chemischen Industrie (FCI), the Max Buchner Research Foundation, the German Academic Exchange Service (Deutscher Akademischer Austauschdienst, DAAD), and the Alexander von Humboldt Foundation.
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Feineis, D., Bringmann, G. (2023). Asian Ancistrocladus Lianas as Creative Producers of Naphthylisoquinoline Alkaloids. In: Kinghorn, A.D., Falk, H., Gibbons, S., Asakawa, Y., Liu, JK., Dirsch, V.M. (eds) Ancistrocladus Naphthylisoquinoline Alkaloids. Progress in the Chemistry of Organic Natural Products, vol 119. Springer, Cham. https://doi.org/10.1007/978-3-031-10457-2_1
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