Biflavonoids: Occurrence, Structural Features and Bioactivity

251 Pages·2012·4.25 MB·English

by  Andrew G. Mercader, Alicia B. Pomilio

CHEMISTRY RESEARCH AND APPLICATIONS

B : O ,
IFLAVONOIDS CCURRENCE
S F
TRUCTURAL EATURES
AND BIOACTIVITY

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C R
HEMISTRY ESEARCH AND
A
PPLICATIONS

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CHEMISTRY RESEARCH AND APPLICATIONS

B : O ,
IFLAVONOIDS CCURRENCE
S F
TRUCTURAL EATURES
AND BIOACTIVITY

ANDREW G. MERCADER
AND
ALICIA B. POMILIO
EDITORS

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LIBRARY OF CONGRESS CATALOGING-IN-PUBLICATION DATA

Biflavonoids : occurence, structural features, and bioactivity / editors, Andrew G. Mercader and
Alicia B. Pomilio.
p. cm.
Includes bibliographical references and index.
ISBN: (cid:28)(cid:26)(cid:27)(cid:16)(cid:20)(cid:16)(cid:25)(cid:21)(cid:20)(cid:19)(cid:19)(cid:16)(cid:23)(cid:27)(cid:21)(cid:16)(cid:19) (eBook))
1. Bioflavonoids. I. Mercader, Andrew G. II. Pomilio, Alicia B.
QP772.B5B54 2011
588--dc23
2011033988

Published by Nova Science Publishers, Inc. † New York
CONTENTS

Preface vii
Chapter 1 Introduction 1
Chapter 2 Nomenclature of the Biflavonoids 3
Chapter 3 Biflavonoid Structures 5
Chapter 4 Distribution 97
Chapter 5 Biological Activity 173
Chapter 6 Conclusion 189
Acknowledgements 191
References 193
Index 235

PREFACE

Biflavonoids comprise a group of the flavonoid family that possesses a
variety of structures, and biological activities of high relevance, such as
anticancer, antibacterial, antifungal, antiviral, anti-inflammatory,
antinociceptive, antioxidant, vasodilator, anticlotting, among others, regardless
of the bioactivity of each monomer unit. The chemistry of biflavonoids is very
important in many fields of research, especially because these compounds are
structurally different bioactive molecules with potential for biomedical
application.
This book aims to highlight the structural biflavonoid variability,
rearrangements, and different stereochemistry through about 470 structures
distributed in some species of Angiosperms (monocots and dicots),
Gymnosperms, ferns (Pteridophyta), and mosses (Bryophyta). Their
distribution is shown to provide the latest picture of their natural sources,
biological activities, and traditional uses. Chemical structures include simple
dimers, complex biflavonoids, rearranged biflavonoids, natural Diels-Alder
type adducts, and spirobiflavonoids.
The most important general characteristics, structures and nomenclature of
the biflavonoids have been covered, and biological activities are carefully
displayed. The structural aspects of the biflavonoids are shown in a detailed
list of figures, thus providing an overview of their structural features. The
current status and future prospects of the structure-activity studies of these
compounds are also discussed.

Chapter 1

INTRODUCTION

Biflavonoids are flavonoid-flavonoid dimers linked by a C-C or C-O-C
bond, with a variety of chemical structures. Many different combinations of
the flavonoid dimers are possible. For example, flavanone-flavone, flavone-
flavone, flavone-flavonol are some of the possible structures. Moreover, the
connecting linkage may have different positions. In natural biflavonoids, many
hydroxy and/or methoxy groups are the substituents at different positions.
Therefore, in theory an incredibly high number of biflavonoids may exist.
However, plants that contain biflavonoids as main constituents are not widely
distributed. Nevertheless, biflavonoids occur in many fruits, vegetables, and
plants; and since Furukawa extracted the leaves of maidenhair tree, Ginkgo
biloba L., to obtain a yellow pigment, which later turned out to be a
biflavonoid (II-4′,I-5,II-5,II-7-tetrahydroxy-I-4′,I-7-dimethoxy[I-3′,II-8]-
biflavone), the so-called ginkgetin (7),[1] the number of isolated and identified
biflavonoids in nature keeps growing.[2]
The biological/pharmacological activities of biflavonoids are diverse,
including anticancer, antibacterial, antifungal, antiviral, anti-inflammatory,
analgesic, antioxidant, vasorelaxant, anticlotting, among others.[3] Brief
examples of the most relevant activities are shown in the following sections.
The main purpose of this book is to highlight the structural variability,
different rearrangements and stereochemistry of biflavonoids through 466
structures that are distributed in some species of Angiosperms (monocots and
dicots), Gymnosperms, ferns (Pteridophyta), and mosses (Bryophyta). Their
distribution accompanied with the corresponding biological activities and
traditional uses is thoroughly shown, intending to offer the latest picture of
their natural sources. The most important general characteristics, structures