Progress in the Chemistry of Organic Natural Products
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Progress in the Chemistry of Organic Natural Products A. Douglas Kinghorn · Heinz Falk Simon Gibbons · Jun’ichi Kobayashi Yoshinori Asakawa · Ji-Kai Liu Editors Progress in the Chemistry of Organic Natural Products Progress in the Chemistry of Organic Natural Products Series Editors A. Douglas Kinghorn, Columbus, OH, USA Heinz Falk, Linz, Austria Simon Gibbons, London, UK Jun’ichi Kobayashi, Sapporo, Japan Yoshinori Asakawa, Tokushima, Japan Ji-Kai Liu, Wuhan, China Advisory Editors Giovanni Appendino, Novara, Italy Roberto G. S. Berlinck, São Carlos, Brazil Verena Dirsch, Wien, Austria Agnieszka Ludwiczuk, Lublin, Poland Rachel Mata, Mexico, Mexico Nicholas H. Oberlies, Greensboro, USA Deniz Tasdemir, Kiel, Germany Dirk Trauner, New York, USA Alvaro Viljoen, Pretoria, South Africa Yang Ye, Shanghai, China The volumes of this classic series, now referred to simply as “Zechmeister” after its founder, Laszlo Zechmeister, have appeared under the Springer Imprint ever since the series’ inauguration in 1938. It is therefore not really surprising to find out that the list of contributing authors, who were awarded a Nobel Prize, is quite long: Kurt Alder, Derek H.R. Barton, George Wells Beadle, Dorothy Crowfoot-Hodgkin, Otto Diels, Hans von Euler-Chelpin, Paul Karrer, Luis Federico Leloir, Linus Pauling, Vladimir Prelog, with Walter Norman Haworth and Adolf F.J. Butenandt serving as members of the editorial board. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in the field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline. Listed in Medline. All contributions are listed in PubMed. More information about this series at http://www.springer.com/series/10169 A. Douglas Kinghorn • Heinz Falk • Simon Gibbons • Jun’ichi Kobayashi • Yoshinori Asakawa • Ji-Kai Liu Editors Progress in the Chemistry of Organic Natural Products Volume 109 With contributions by E. Gössinger H. Shigemori N. Blicharska Á V. Seidel Editors A. Douglas Kinghorn Heinz Falk College of Pharmacy Institute of Organic Chemistry The Ohio State University Johannes Kepler University Columbus, OH, USA Linz, Austria Simon Gibbons Jun’ichi Kobayashi UCL School of Pharmacy Graduate School of Pharmaceutical Science University College London, Research Hokkaido University London, UK Fukuoka, Japan Yoshinori Asakawa Ji-Kai Liu Faculty of Pharmaceutical Sciences School of Pharmaceutical Sciences Tokushima Bunri University South-Central University for Nationalities Tokushima, Japan Wuhan, China ISSN 2191-7043 ISSN 2192-4309 (electronic) Progress in the Chemistry of Organic Natural Products ISBN 978-3-030-12857-9 ISBN 978-3-030-12858-6 (eBook) https://doi.org/10.1007/978-3-030-12858-6 © Springer Nature Switzerland AG 2019 This work is subject to copyright. 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The registered company address is: Gewerbestrasse 11, 6330 Cham, Switzerland Contents Chemistry of the Secondary Metabolites of Termites ............... 1 Edda Gössinger Bioactive Compounds Involved in the Life Cycle of Higher Plants ..... 385 Hideyuki Shigemori Chemical Diversity and Biological Activity of African Propolis ....... 415 Natalia Blicharska and Veronique Seidel v Chemistry of the Secondary Metabolites of Termites Edda Gössinger Contents 1 Introduction .................................................................................. 5 2 Pheromones .................................................................................. 11 2.1 Releaser Pheromones .................................................................. 13 2.1.1 Trail-Following Pheromones ................................................ 13 2.1.2 Sex-Pairing Pheromones ..................................................... 23 2.1.3 Syntheses of Trail-Following and Sex-Pairing Pheromones ................ 34 2.1.4 Home-Marking Pheromones? ................................................ 84 2.1.5 Phagostimulating and Food-Marking Pheromones ......................... 86 2.1.6 Aggregation Pheromones .................................................... 86 2.1.7 Alarm Pheromones ........................................................... 87 2.1.8 Worker-Arresting Pheromone ............................................... 93 2.1.9 Egg-Recognition Pheromones ............................................... 93 2.1.10 Building Pheromones? ....................................................... 93 2.1.11 Necromones .................................................................. 93 2.1.12 Cuticular Hydrocarbons ...................................................... 94 2.2 Primer Pheromones .................................................................... 102 2.2.1 Caste Differentiation .......................................................... 103 2.2.2 Queen (King) Pheromones (Reproductive-Specific Pheromones) . 104 2.2.3 Syntheses of (Presumed) Primer Pheromones ................................ 107 3 Chemical Defense ........................................................................... 109 3.1 Acetogenins ............................................................................ 117 3.1.1 The Long-Chain Contact Poisons of the Rhinotermitidae . 117 3.1.2 Macrolactones (Macrolides) .................................................. 121 3.2 Compounds of Mixed Biosynthesis Pathways . .. ... ... ... .. ... ... ... ... .. ... ... ... .. 131 3.2.1 Novel Free Ceramides ......................................................... 131 3.2.2 Aliphatic Nitro Compounds as Defense in Termites ......................... 134 E. Gössinger (*) Institute of Chemistry, University of Vienna, Vienna, Austria Mistelbach, Austria e-mail: [email protected] © Springer Nature Switzerland AG 2019 1 A. D. Kinghorn, H. Falk, S. Gibbons, J. Kobayashi, Y. Asakawa, J.-K. Liu (eds.), Progress in the Chemistry of Organic Natural Products, Vol. 109, https://doi.org/10.1007/978-3-030-12858-6_1 2 E. Gössinger 3.3 Isoprenoids ............................................................................. 136 3.3.1 Monoterpenes ................................................................. 136 3.3.2 Sesquiterpenes ................................................................. 142 3.3.3 Diterpenes ..................................................................... 197 4 Biosynthesis of Secondary Metabolites of Termites ........................................ 327 4.1 Biosynthesis of Pheromones .......................................................... 327 4.1.1 Acetogenins ................................................................... 327 4.1.2 Biosynthesis of Isoprenoids ................................................... 330 4.2 Biosynthesis of Components of the Frontal Gland Secretion ... ..................... 332 4.2.1 Isoprenoids .................................................................... 332 4.2.2 Acetogenins ................................................................... 339 4.2.3 Defensive Compounds with a Mixed Biosynthesis Origin .................. 340 5 Families and Subfamilies of the Termites .................................................. 344 References ....................................................................................... 345 Abbreviations % ee Enantiomeric excess [α]D Optical rotation at λ ¼ 589 nm 0 Minutes 00 Seconds 18-crown-6 1,4,7,10,13,16-Hexaoxacyclooctadecane 2D-NMR Two-dimensional nuclear magnetic resonance 8H-BINAP 2,20-Bis(diphenylphosphino)-5,50,6,60,7,70,8,80-octahydro- 1,10-binaphthalene 9-BBN 9-Borabicyclo[3.3.1]nonane abs Absolute Ac Acetyl acac Acetylacetonate AIBN Azobisisobutyronitrile aq Aqueous ATP Adenosine-50-triphosphate ATPB Acetonyltriphenylphosphonium bromide BHT 2,6-Di-t-butyl-4-methylphenol Bn Benzyl brsm Based on recovered starting material Bu n-Butyl Bz Benzoyl CAN Cerium ammonium nitrate cat. Catalytic CD Circular dichroism CHC Cuticular hydrocarbon