Methods in Molecular Biology 1694 Rubén Alcázar Antonio F. Tiburcio Editors Polyamines Methods and Protocols M ETHODS IN M OLECULAR B IOLOGY Series Editor John M. Walker School of Life and Medical Sciences University of Hertfordshire Hatfield, Hertfordshire, AL10 9AB, UK For further volumes: http://www.springer.com/series/7651 Polyamines Methods and Protocols Edited by Rubén Alcázar and Antonio F. Tiburcio Department of Biology, Healthcare and Environment, Faculty of Pharmacy and Food Sciences, Section of Plant Physiology, University of Barcelona, Spain Editors Rube´n Alca´zar Antonio F. Tiburcio Department of Biology, Department of Biology, Healthcare and Environment, Healthcare and Environment, Faculty of Pharmacy and Food Sciences, Faculty of Pharmacy and Food Sciences, Section of Plant Physiology Section of Plant Physiology University of Barcelona University of Barcelona Spain Spain ISSN 1064-3745 ISSN 1940-6029 (electronic) Methods in Molecular Biology ISBN 978-1-4939-7397-2 ISBN 978-1-4939-7398-9 (eBook) DOI 10.1007/978-1-4939-7398-9 Library of Congress Control Number: 2017956111 © Springer Science+Business Media LLC 2018 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. The publisher remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. Printed on acid-free paper This Humana Press imprint is published by Springer Nature The registered company is Springer Science+Business Media LLC The registered company address is: 233 Spring Street, New York, NY 10013, U.S.A. Preface The history of polyamine (PA) research starts more than 300 years ago. In 1678, Antoni van Leeuwenhoek noted the deposition of stellate crystals in aging human semen. More than 200 years later, the basic constituent of such crystals was named spermine, but it was not until the mid-1920s that its correct chemical composition and structure was determined. Spermidine was also discovered and named at this time. In 1971, Seymor Cohen [1] addressed the biological relevance of these compounds and stimulated PA research in many areas, including plant physiology. Among the provocative generalizations in his book [1] was the observation that modern biochemistry was concerned mainly with anions and generally tended to neglect cations, of which PAs are one of the cell’s major organic representatives. Since then, pioneering works in the PA field started in a limited number of research laboratories studying plant physiology and biochemistry, microbiology, cancer research and chemistry, among others. Research on this topic expanded during the last decades and nowadays, polyamines are recognized to participate in relevant biological functions in plants, microorganisms, and animals. Protocols for PA research are continuously evolving, and we attempted to provide a comprehensive collection of updated protocols by key researchers in different fields. In addition, we provide the reader with a selection of excellent reviews introducing the different topics of polyamine research covered by the protocols (Chapters 1–4, 36–37, and 40). The book covers the quantification of different polyamines and conjugates (Chapters 5–10), polyamine and related enzymatic activities (Chapters 11–18), subcellular localization studies (Chapters 19–20), transport (Chapters 21–23), DNA methylation (Chapter 24), ODC regulation (Chapters 25–26), modulation of protein synthesis and post-translational modifications (Chapters 27–28), genetic and phenotyping analyses (Chapters 29–33), determination of ROS (Chapter 34), genome-wide association mapping (Chapter 35), and polyamine applications and cancer (Chapters 36–40). We believe that this book contains most of the essential protocols for polyamine research and will be a helpful manual in research laboratories. The editors would like to express their gratitude to all authors who have greatly contributed to this book, which we hope will stimulate research on the fascinating topic of polyamines. Barcelona, Spain Rube´n Alca´zar Antonio F. Tiburcio Reference 1. Cohen SS (1971) Introduction to the Polyamines. Prentice-Hall, Englewood Cliffs, NJ. v Contents Preface . ................................................................... v Contributors................................................................. xi 1 Polyamines in the Context of Metabolic Networks . ....................... 1 Wegi Wuddineh, Rakesh Minocha, and Subhash C. Minocha 2 Molecules for Sensing Polyamines and Transducing Their Action in Plants..... 25 Tomonobu Kusano, G.H.M Sagor, and Thomas Berberich 3 Polyamine Metabolism Responses to Biotic and Abiotic Stress. ............... 37 Fernando M. Romero, Santiago J. Maiale, Franco R. Rossi, Maria Marina, Oscar A. Ruı´z, and Andre´s Ga´rriz 4 Thermospermine: An Evolutionarily Ancient but Functionally New Compound in Plants . ............................................. 51 Taku Takahashi 5 Determination of Polyamines by Capillary Electrophoresis Using Salicylaldehyde-5-Sulfonate as a Derivatizing Reagent . ............... 61 Takashi Kaneta 6 Detection of Thermospermine and Spermine by HPLC in Plants ............. 69 Taku Takahashi, Ayaka Takano, and Jun-Ichi Kakehi 7 Development of Amine-Oxidase-Based Biosensors for Spermine and Spermidine Analysis ................................................. 75 Cristina Tortolini, Gabriele Favero, and Franco Mazzei 8 Identification of Branched-Chain Polyamines in Hyperthermophiles . ........ 81 Ryota Hidese, Wakao Fukuda, Masaru Niitsu, and Shinsuke Fujiwara 9 Analysis of Polyamines Conjugated with Hydroxycinnamoyl Acids by High-Performance Liquid Chromatography Coupled to Electrospray Ionization Tandem Mass Spectrometry ...................... 95 Laura Torras-Claveria, Jaume Bastida, Francesc Viladomat, and Antonio F. Tiburcio 10 Analysis of Glutathione in Biological Samples by HPLC Involving Pre-Column Derivatization with o-Phthalaldehyde . ............... 105 Yongqing Hou, Xilong Li, Zhaolai Dai, Zhenlong Wu, Fuller W. Bazer, and Guoyao Wu 11 Determination of Arginine and Ornithine Decarboxylase Activities in Plants . ............................................................ 117 Rube´n Alca´zar and Antonio F. Tiburcio 12 Determination of S-Adenosylmethionine Decarboxylase Activity in Plants . ............................................................ 123 Antonio F. Tiburcio and Rube´n Alca´zar 13 Determination of Copper Amine Oxidase Activity in Plant Tissues............ 129 Riccardo Angelini, Alessandra Cona, and Paraskevi Tavladoraki vii viii Contents 14 Determination of diÀ/Polyamine Oxidase Activity in Plants by an In-Gel Spermidine Oxidation Assay .................................. 141 Panagiotis N. Moschou 15 Pentamine as a Substrate for Measuring Spermine Oxidase Activity . ........ 149 Koichi Takao and Yoshiaki Sugita 16 Spectrophotometric Quantification of Reactive Oxygen, Nitrogen and Sulfur Species in Plant Samples .............................. 155 Chrystalla Antoniou, Andreas Savvides, Egli C. Georgiadou, and Vasileios Fotopoulos 17 Novel Route for Agmatine Catabolism in Aspergillus niger: 4-Guanidinobutyrase Assay . ............................................. 163 Tejaswani Saragadam and Narayan S. Punekar 18 Determination of Transglutaminase Activity in Plants ....................... 173 S. Del Duca, P.L.R. Bonner, I. Aloisi, D. Serafini-Fracassini, and G. Cai 19 Procedures for ADC Immunoblotting and Immunolocalization for Transmission Electron Microscopy During Organogenic Nodule Formation in Hop . ............................................. 201 Ana Margarida Fortes and Jose M. Seguı´-Simarro 20 Analysis of the Intracellular Localization of Transiently Expressed and Fluorescently Labeled Copper-Containing Amine Oxidases, Diamine Oxidase and N-Methylputrescine Oxidase in Tobacco, Using an Agrobacterium Infiltration Protocol .............................. 215 Tsubasa Shoji 21 Techniques Used for Functional Characterization of Polyamine Transporters ........................................................... 225 Claudio A. Pereira, Melisa Saye´, Chantal Reigada, and Mariana R. Miranda 22 Quantitative Trait Loci for Root Growth Response to Cadaverine in Arabidopsis ............................................. 233 Nicole M. Gibbs, Laura Vaughn Rouhana, and Patrick H. Masson 23 Methods Related to Polyamine Control of Cation Transport Across Plant Membranes................................................. 257 Isaac Zepeda-Jazo and Igor Pottosin 24 Analysis of DNA Methylation Content and Patterns in