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Pharmaceutical Chemistry
of
Natural Products ·
Pharmaceutical Chemistry
of
Natura I Products
V agaamy
MPharm, PhD, FIC, DOMH
CBS
CBS Publishers & Distributors Pvt Ltd
Disaimer
Branches
th
nd
st
Representatives
Pharmaceutical chemistry of natural products has evolved from Pharmacognosy, and it
is a versatile area encompassing the chemical, phytochemical, biochemical, biological
(pharmacological) and pharmaceutical aspects of medicinally useful natural products. Due
to the developments in chemical techniques and pharmacological screening programme,
the active ingredients are extracted and isolated from the natural products, their chemical
structures are characterized by the spectral and analytical data, their analogues are synthesized
(synthetically or semisynthetically), and by adopting the pharmacological screening programme
these natural products fi nd their way into medicine.
Chemistry of natural products has always been a challenging subject to learn and
teach, especially for those who have not been thorough with basic organic chemistry, and
I have attempted to equip the new-generation learner and teacher with a book that is easy
to understand and provides all the essential structural elucidation and pharmacological
applications of natural products.
Methodical description of each chapter, rich chemical and pharmaceutical background
of the medicinally important compounds, and systematic structural elucidation in easy-
to-understand style are some of the unique features of this book. The pharmaceutical and
chemical aspects of the medicinally useful natural products fi nd the fi rst-of-its-kind coverage
in this book.
In preparing this textbook, I have tried to comprehensively enrich the natural products’
information with pharmaceutical application so that the anticipated audience of this book can
feel the importance of natural products. The Pharmacy and Science students of our country
are faced with the scarcity of good books to fulfi l their needs. Some authors have described
the structural elucidation but have left the pharmacological aspects of natural products
untouched, while some others have failed to provide the essential chemical structures for all
reactions, leaving the students unable to understand the reactions clearly. In this book I have
made a humble attempt to cater to the needs of all academicians belonging to the different
Indian universities, by incorporating the chemical structures of all reactions and enriching the
pharmacological information about the medicinally useful natural products.
The book is divided into 12 chapters. Each chapter comprises an overview or introduction,
classifi cation and qualitative chemical tests, and general physical and chemical properties of
natural products. Followed by this general discussion, pharmaceutically important natural
Preface
vi
Preface
products of each chapter are discussed in detail with the source, pharmacological properties
and uses along with their general properties. In this section the structure of the natural
product elucidation is presented in a systematic way, which is easy to understood and able
to reproduce well in examinations. Structure–Activity Relationship (SAR) of some important
groups of natural products like oestrogens, progesterones, penicillins, etc., has also been
included, which is the fi rst-of-its-kind coverage.
I hope that this special volume will be a good source of information and reference for
not only graduate and postgraduate students but also basic and applied researchers in the
fi eld. Moreover, it will also be of interest to a wide range of scientists who are involved in the
natural products research. I welcome suggestions and constructive criticism from all corners
of scientifi c community.
—V. Alagarsamy
E-mail: samy_veera@yahoo.com
A warm response to my earlier book on the Textbook of Medicinal Chemistry (published by
Elsevier), prompted me to write this book on Pharmaceutical Chemistry of Natural Products,
covering all the topics suggested by the PCI, AICTE and the various universities in India
for graduate and postgraduate students. I dedicate this book to the hundreds of pharmacy
students whom I have taught over the years and my teachers who have encouraged me to
convert my class notes into the textbook.
It is my pleasure to put on record my heartfelt thanks to all those who have made this
book possible, especially my beloved teacher Dr U.S. Pathak, who made me to learn the
reactions and mechanisms of the structural elucidation, while many students feel diffi culty in
reading the reactions of structural elucidation itself.
I am immensely grateful to Dr B. Suresh, Prof. K. Chinnaswamy. Dr C.J. Shishoo,
Dr R.K. Goyal, Dr Rajani Giridhar and Dr M.R. Yadav for inspiring and initiating me to author
this book.
I gratefully acknowledge the constant and continuous encouragement and moral support
extended by Shri M.N. Raju, Chairman, and Mr Ravi Varma, Director, MNR Educational
Trust, Hyderabad, for my entire academic and research pursuit. It has been a great motivation
for me to take up this new challenge.
I express my sincere appreciation to my students, research scholars and friends, especially
Dr V. Raja Solomon (Postdoctoral Research Associate, Nagoya City University, Japan), Mr
P. Parthiban, Mr J.C. Hanish Singh, Mr G. Saravanan, Mr D. Shankar, Mr B. Narendhar and
Dr S. Murugesan for their untiring support in making this book.
The friendly interaction I experienced with the Elsevier team, Ms Ritu Sharma,
Mr Subodh Kumar, Mr Nitin Valecha, and Kryon Project Manager Ms Usha K. Nair, offered
a caffeine-like stimulation to eliminate the fatigue during the preparation of this book. As I
mentioned in my earlier book, Textbook of Medicinal Chemistry (published by Elsevier), if the
author gets such a cooperative and energetic publication team, publishing any number of
books will not be a diffi cult task. I thank them wholeheartedly for helping me reach this
target and am requesting them to continue their service to the author community in the
same intensity.
Acknowledgements
viii
Acknowledgements
In all my academic efforts the motivation I gain from my father, mother, sister, brothers
and wife to reach this goal is the same as the nature continues to yield novel, diverse chemical
entities for healthy maintenance of the mankind, and the patience and cooperation extended
by my children, Aish and Abhi, made me think of the goal without any diversion. To express
my thankfulness, I pray the Almighty to bless my children with teachers like those I got in my
life, so that they too are inspired by their teachers and dedicate to the fi eld of Pharmacy and,
in turn, serve the mankind.
—V. Alagarsamy
Preface v
Acknowledgements vii
Chapter 1 Introduction to Pharmaceutical Chemistry of Natural Products 1
Introduction 1
Drug Discovery from Natural Products 2
Nomenclature 3
Classifi cation of Natural Products 3
Identifi cation of Natural Products 6
Techniques Involved in Natural Product Lead Discovery 6
Natural Products as Pharmacological Tools 8
Chapter 2 Carbohydrates 11
Introduction 11
Classifi cation of Carbohydrates 12
Qualitative Chemical Tests for Carbohydrates 14
Monosaccharides 16
Confi guration of Monosaccharides 16
Ascending and Descending in Monosaccharides 18
Chemical Reactions of Monosaccharides 20
Ring Size of Monosaccharides 27
Ring structure of aldoses (glucose) 28
Ring structure of ketoses (fructose) 39
Conformations of Monosaccharides 42
Monosaccharides of Pharmaceutical Importance 42
Glucose 42
Fructose 44
Disaccharides 47
Biological Importance of Disaccharides 47
Classifi cation and Nomenclature of Disaccharides 47
Determination of the Structure of Disaccharides 49
Contents