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50 Years of Phytochemistry Research Volume 43 Recent Advances in Phytochemistry Editorial Board Editor-in-Chief: David R. Gang, Institute of Biological Chemistry, Washington State University, Pullman, WA, USA Associate Editors: Mark A. Bernards, Department of Biology, University of Western Ontario, London, ON, Canada Laurence B. Davin, Institute of Biological Chemistry, Washington State University, Pullman, WA, USA Steven C. Halls, Monsanto Company, St. Louis, MO, USA Reinhard Jetter, Departments of Botany and Chemistry, University of British Columbia, Vancouver, BC, Canada Susan McCormick, Bacterial Foodborne Pathogens and Mycology Research Unit, USDA-ARS-NCAUR, Peoria, IL, USA Jan Fred Stevens, Linus Pauling Institute, Oregon State University, Corvallis, OR, USA Deyu Xie, Department of Plant and Microbial Biology, North Carolina State University, Raleigh, NC, USA For further volumes: http://www.springer.com/series/6474 David R. Gang Editor 50 Years of Phytochemistry Research 1 3 Editor David R. Gang Institute of Biological Chemistry Washington State University Pullman Washington USA ISBN 978-3-319-00580-5 ISBN 978-3-319-00581-2 (eBook) DOI 10.1007/978-3-319-00581-2 Springer Cham Heidelberg New York Dordrecht London Library of Congress Control Number: 2013952723 © Springer International Publishing Switzerland 2013 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, re- citation, 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. Exempted from this legal reservation are brief excerpts in connection with reviews or scholarly analysis or material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Du- plication of this publication or parts thereof is permitted only under the provisions of the Copyright Law of the Publisher’s location, in its current version, and permission for use must always be obtained from Springer. Permissions for use may be obtained through RightsLink at the Copyright Clearance Center. Violations are liable to prosecution under the respective Copyright Law. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publica- tion 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. While the advice and information in this book are believed to be true and accurate at the date of publi- cation, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein. Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com) Preface Introduction to the 43rd Volume of the Recent Advances in Phytochemistry Series This is the third volume since the reintroduction of the Recent Advances in Phy- tochemistry ( RAP) series, an annual publication supported by the Phytochemical Society of North America. Topics appropriate for RAP include the biosynthesis of natural products and regulation of metabolism, the ecology of specialized meta- bolites and the evolution of their pathways, and the effects of natural products or plants on human health. Research appropriate for RAP involves genomics, proteo- mics, metabolomics, natural product structural determination and new technology development, medicinal chemistry and metabolic engineering, or any of the my- riad of fields that are now closely associated with what may be called “traditional phytochemistry” and plant biochemistry. The advent of postgenomics-based ways of thinking, systems biology, synthetic biology, comparative genomics/proteomics/ transcriptomics/metabolomics, and especially of the introduction and establishment of a mentality that leads to the support of large collaborative projects has opened up many new doors to scientists interested and versed in the (bio)chemistry of plants. The goal of RAP is to highlight these developments. Two main types of articles are printed in RAP: Perspectives and Communicati- ons. Perspectives in RAP are expected to synthesize results from the primary lite- rature and perhaps from new/novel results and place these in perspective relative to the broader field. These articles may be similar to review articles, but also are intended to present important ideas and hypotheses and may present proposals for interesting directions in the field. It is the hope of the Editorial Board that these articles will be of great value to a large audience. Communications are intended to present new advances in the field that will be of interest to a large audience. Articles of both types are typically solicited from the society membership based on the con- tent of the annual meeting talks, but in keeping with the title “Recent Advances in Phytochemistry” the editorial board reserves the right to solicit additional Perspec- tives and/or Communications from non-attendees as well (e.g., where an editorial board member has knowledge of an interesting recent advancement that would be of general interest to the society membership). v vi Preface All submissions to RAP go through a rigorous peer review process, overseen by the Editorial Board, which includes external review. RAP is indexed with Springer published journals. All RAP papers are available not only in the published volu- me form, but also electronically through Springer’s online literature services. This marks a significant change from past volumes of RAP and it is the hope of the Editorial Board that this will lead to broader dissemination of the contents of and greater interest in RAP. This 43rd volume of RAP includes a total of seven articles based on talks presen- ted at the 50th Anniversary meeting of the PSNA, which was held at the Fairmont Orchid in Waikaloa, Hawai’i, USA. These seven Perspectives give a very good picture of the breadth of plant (bio)chemistry research in North America, which is also indicative of the state of the field worldwide. Each of these articles describes the integration of several different approaches to ask and then answer fascinating questions regarding the function of interesting plant metabolites, either in the plant itself or in interactions with the environment (natural setting or human health ap- plication). Two perspectives outline very clearly the power of approaching biological ques- tions from a modern “omics” or systems biology approach. Beale and Ward outline how metabolomics approaches can be brought to bear on plant biosynthetic ques- tions and quickly lead to important advances in our understanding or how plants produce important metabolites. Zandkarimi et al. outline the integration of ion mo- bility spectrometry into mass spectrometry-based metabolomics investigations and show clearly how powerful those two spectrometric technologies can be when used together. Plant biotechnology and its application to plant protection, pathogen/pest deter- rence and drug production is discussed in three perspectives. Asano et al. describe the development of plant cell cultures and tissue culture techniques that lead to pro- duction of important indole alkaloid compound production, particularly of camp- tothecin production in cultures from Ophiorrhiza species. Mitchell Wise outlines how cereal crops can be protected from disease by application of plant defense ac- tivators, bioactive compounds that are typically derived from specific plants. Duke et al. provide an extensive review of the history and future prospects of prospecting within the plant kingdom for compounds that protect both crops and humans from insect pests. The last two perspectives emphasize the role of plant-derived compounds in hu- man health. Zhang et al. review the role of sulfhydryl-reactive compounds, such as the sulforaphanes from broccoli and related plants and several phenolics, including curcumin, in modulating two important pathways that are involved in protecting mammalian cells from oxidative and inflammation-induced damage, such as that which occurs in a number of degenerative diseases and cancer. Eggler and Savinov focus on phytochemicals that are involved in activating the Nrf2 pathway, and the- reby help prevent disease. As always, we hope that you will find these Perspectives to be interesting, in- formative, and timely. It is our goal that RAP will act not only as the voice of the Preface vii PSNA, but that it will serve as an authoritative, up-to-date resource that helps to set the gold standard for thought and research in fields related to plant biochemistry. We welcome suggestions for future articles and comments on the new format. The RAP Editorial Board David R. Gang Laurence B. Davin Steven C. Halls Reinhard Jetter Susan McCormick J. Fred Stevens Deyu Xie Contents 1 Metabolomics Reveals Hemiterpenoids as New Players in the Carbon–Nitrogen Economy ................................. 1 Michael H. Beale and Jane L. Ward 2 Electrospray Ionization Traveling Wave Ion Mobility Spectrometry Mass Spectrometry for the Analysis of Plant Phenolics: An Approach for Separation of Regioisomers ....................... 21 Fereshteh Zandkarimi, Samanthi Wickramasekara, Jeff Morre, Jan F. Stevens and Claudia S. Maier 3 Camptothecin Production and Biosynthesis in Plant Cell Cultures ................................................................................ 43 Takashi Asano, Kazuki Saito and Mami Yamazaki 4 Plant Defense Activators: Application and Prospects in Cereal Crops ........................................................................................... 55 Mitchell L. Wise 5 Phytochemicals for Pest Management: Current Advances and Future Opportunities ......................................... 71 Stephen O. Duke, Scott R. Baerson, Charles L. Cantrell, David E. Wedge, Kumudini M. Meepagala, Zhiqiang Pan, Agnes M. Rimando, Kevin K. Schrader, Nurhayat Tabanca, Daniel K. Owens and Franck E. Dayan 6 Sulfhydryl-Reactive Phytochemicals as Dual Activators of Transcription Factors NRF2 and HSF1 ............................ 95 Ying Zhang, Sharadha Dayalan Naidu, Rumen V. Kostov, Ashley Pheely, Vittorio Calabrese and Albena T. Dinkova-Kostova ix x Contents 7 Chemical and Biological Mechanisms of Phytochemical Activation of NRF2 and Importance in Disease Prevention ................ 121 Aimee L. Eggler and Sergey N. Savinov Index ................................................................................................................ 157

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