The Formation, Structure and Activity of Phytochemicals

221 Pages·2015·6.26 MB·English

by  Reinhard Jetter (eds.)

Recent Advances in Phytochemistry 45
Reinhard Jetter Editor
The Formation,
Structure, and
Activity of
Phytochemicals
The Formation, Structure, and Activity
of Phytochemicals
Recent Advances in Phytochemistry
Editorial Board
Editor-in-Chief:
Reinhard Jetter, Departments of Botany and Chemistry, University of British Columbia,
Vancouver, BC, Canada
Associate Editors:
John T. Arnason, Centre for Advanced Research in Environmental Genomics, University
of Ottawa, Ottawa, ON, Canada; Canadian Institutes of Health Research Team in
Aboriginal Antidiabetic Medicines, Montréal, QC, Canada; Montreal Diabetes Research
Centre, Université de Montréal, Montréal, QC, Canada
Argelia Lorence, Arkansas Biosciences Institute, Arkansas State University, AR, USA
Jan Fred Stevens, Linus Pauling Institute, Oregon State University, Corvallis, OR, USA
M. Soledade C. Pedras, Department of Chemistry, University of Saskatchewan, Saskatoon,
SK, Canada
More information about this series at h ttp://www.springer.com/series/6474
Reinhard Jetter
Editor
The Formation, Structure,
and Activity of
Phytochemicals
Volume 45
Editor
Reinhard Jetter
Departments of Botany and Chemistry
University of British Columbia
Vancouver , BC , Canada
Recent Advances in Phytochemistry
ISBN 978-3-319-20396-6 ISBN 978-3-319-20397-3 (eBook)
DOI 10.1007/978-3-319-20397-3
Library of Congress Control Number: 2015952208
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Preface to the 45th Volume of the Rec ent
Advances in Phytochemistry Series
Welcome to the fi fth volume since the reintroduction of the R ecent Advances in
Phytochemistry ( RAP ) series, an annual journal of the Phytochemical Society of
North America. R AP is dedicated to publishing both review and primary research
articles for a broad audience of biologists, chemists, biochemists, pharmacologists,
clinicians, and nutrition experts, especially those interested in the biosynthesis,
structure, function, and/or bioactivity of plant natural products. Recurring themes
include the evolution and ecology of specialized metabolites, the genetic and enzy-
matic mechanisms for their formation and metabolism, the systems biology study of
their cell/tissue/organ context, the engineering of plant natural products, as well as
various aspects of their application for human health. In addition, also new develop-
ments in the techniques used to study plant natural products are presented and dis-
cussed, for example, for structure elucidation and quantifi cation, for “omic”
(genomic/proteomic/transcriptomic/metabolomics) profi ling, or for microscopic
localization. In short, this series combines chapters from researchers that explain
and discuss current topics in the most exciting new research in phytochemistry.
Two main types of articles are published in R AP : Perspectives and Communications.
The RAP Perspectives aim to give a general introduction to a fi eld and an overview
of the pertinent literature, as a background for understanding new results from the
primary literature and (in many cases) previously unpublished results. These articles
may be similar to review articles, but also are intended to present important ideas and
hypotheses, and may put forward proposals for interesting new research directions
in the fi eld. It is the hope of the Editorial Board that these articles will be of great
value to a large audience. The RAP Communications focus more on primary data
and synthesize only a small number of papers, to showcase particular new advances
in a fi eld that will be of interest to a large audience. Articles of both types are typi-
cally solicited from prominent members of the Phytochemical Society of North
America, based on the content of presentations at the annual meeting. However, the
Editorial Board also invites additional Perspectives and/or Communications from
selected authors beyond the society’s meeting to give a rounded picture of all “Recent
Advances in Phytochemistry.”
v
vi Preface to the 45th Volume of the RecentAdvances in Phytochemistry Series
All submissions to R AP go through a rigorous, external peer review process,
overseen by the Editorial Board. R AP is indexed together with all other journals
published by S pringer. All R AP papers are available not only in the published
volume form, but also electronically through S pringer ’s online literature services.
This marks a signifi cant change from past volumes of R AP, and it is the hope of the
Editorial Board that this will lead to broader dissemination and greater interest in
RAP .
T his 45th volume of R AP includes a total of eight chapters, many, but not all,
based on talks presented at the 52nd annual meeting of the Phytochemical Society
of North America. As was seen in R AP volumes 41–44, these papers span the
breadth of plant (bio)chemistry research in North America, which is also indicative
of the state of the fi eld worldwide. The fi rst article presented here reviews the
50-year history of the Phytochemical Society of North America, thereby highlight-
ing research milestones of the past decades. The other seven chapters describe the
integration of several different approaches to ask and then answer key questions
regarding the function of interesting plant metabolites, either in the plant itself or in
chemical ecology or human health application.
Two perspectives focus on chemical structure elucidation: Nikolić et al. summa-
rize new fi ndings on the nitrogen-containing compounds found in Black Cohosh
(A ctaea racemosa syn. C imicifuga racemosa) , while Ling et al. give an overview of
natural products in various J atropha species along with other Euphorbs.
Two other chapters give updates on the biosynthesis of selected plant natural
products. In one of them, Umezawa et al. summarize recent progress on
O- methyltransferases involved in the formation of lignans. Next, Kumar et al.
review the biosynthesis and functions of the plant hormone salicylic acid and its
derivatives.
T wo more perspectives focus on phytochemicals involved in interactions between
plants and pathogens or insects. In particular, Chezem and Clay review recent litera-
ture on the regulation of enzymes involved in formation of phenylpropanoids and
aromatic alkaloids, whereas Jeschke et al. summarize the current understanding of
phytochemical metabolism in insect herbivores.
F inally, a communication by Sumarah et al. provides primary data on the isola-
tion of novel fungal endophytes from Eastern white pine (P inus strobus ), and on
their secondary metabolites enhancing pathogen tolerance of the host tree.
Overall, we are excited to present this broad set of review papers on various
aspects of modern Phytochemistry. We hope you will fi nd them to be interesting,
informative, and timely. It is our goal that R AP will act not only as the voice of the
Phytochemical Society of North America, but that it will serve as an authoritative,
up-to-date resource that helps to set the standard for thought and research in plant
natural products. Enjoy the read!
Preface to the 45th Volume of the RecentAdvances in Phytochemistry Series vii
The RAP Editorial Board
Vancouver, BC Reinhard Jetter
Ottawa, ON John T. Arnason
Jonesboro, AR Argelia Lorence
Saskatoon, SK M. Soledade C. Pedras
Corvallis, OR J. Fred Stevens

Contents
1 A Half-Century of the Phytochemical Society
of North America: 1961–2011 .................................................................. 1
Stewart A. Brown , Constance Nozzolillo , and Tom J. Mabry
2 Nitrogen-Containing Constituents of Black Cohosh:
Chemistry, Structure Elucidation, and Biological Activities ................ 31
Dejan Nikolić , David C. Lankin , Tamara Cisowska ,
Shao-Nong Chen , Guido F. Pauli , and Richard B. van Breemen
3 Jatropha Natural Products as Potential Therapeutic Leads ................. 77
Taotao Ling , Victor Hadi , Armand Guiguemde ,
Scott M. Landfear , and Fatima Rivas
4 O-Methyltransferases Involved in Lignan Biosynthesis ........................ 99
Toshiaki Umezawa , Safendrri Komara Ragamustari ,
Eiichiro Ono , and Masaomi Yamamura
5 Hormone Signaling: Current Perspectives on the Roles
of Salicylic Acid and Its Derivatives in Plants ........................................ 115
Dhirendra Kumar , Imdadul Haq , Danda Chapagai ,
Diwaker Tripathi , David Donald , Mir Hossain ,
and Shivakumar Devaiah
6 Regulators and Pathway Enzymes That Contribute
to Chemical Diversity in Phenylpropanoid and Aromatic
Alkaloid Metabolism in Plant Immunity ................................................ 137
William R. Chezem and Nicole K. Clay
7 Metabolism of Glucosinolates and Their Hydrolysis
Products in Insect Herbivores .................................................................. 163
Verena Jeschke , Jonathan Gershenzon ,
and Daniel Giddings Vassão
ix