CRC handbook of terpenoids / Triterpenoids. Volume II: Pentacyclic and Hexacyclic Triterpenoids

633 Pages·1989·343.112 MB·English

by  Sukh Dev

CRC Handbook
of
Terpenoids
Triterpenoids
Volume II: Pentacyclic and Hexacyclic
Triterpenoids
Editor
Sukh Dev
Authors
Sukh Dev
Malti-Chem Research Centre
Nandesari, Vadodara
India
Amrit Sagar Gupta
Retired
National Chemical Laboratory
Pune
India
Sarita A. Patwardhan
National Chemical Laboratory
Pune
India
Boca Raton London New York
CRC Press is an imprint of the
Taylor & Francis Group, an informa business
First published 1989 by CRC Press
Taylor & Francis Group
6000 Broken Sound Parkway NW, Suite 300
Boca Raton, FL 33487-2742
Reissued 2018 by CRC Press
© 1989 by CRC Press, Inc.
CRC Press is an imprint of Taylor & Francis Group, an Informa business
No claim to original U.S. Government works
This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish
reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the
consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this
publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has
not been acknowledged please write and let us know so we may rectify in any future reprint.
Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form
by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording,
or in any information storage or retrieval system, without written permission from the publishers.
For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.
com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-
for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy
license by the CCC, a separate system of payment has been arranged.
Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and
explanation without intent to infringe.
Library of Congress Cataloging-in-Publication Data
Dev, Sukh, 1925-
CRC handbook of terpenoids--Triterpenoids.
Includes bibliographies and indexes.
Vol. 2 has authors, Sukh Dev, Amrit Sagar Gupta,
Sarita A. Patwardhan.
Contents: v. 1. Acyclic, monocyclic, bicyclic,
tricyclic, and tetraycyclic terpenoids -- v. 2. Penta-
cyclic and hexacyclic triterpenoids.
1. Terpenes. I. Nagasampagi, Bhimsen A. II. Gupta,
Amrit Sagar. III. Patwardhan, Sarita A. IV. Title:
Handbook of terpenoids.
QD416.D49 1989 547.7’1 89.9956
ISBN 0-8493-3611-2 (v. 1)
ISBN 0-8493-3612-0 (v. 2)
A Library of Congress record exists under LC control number: 89009956
Publisher’s Note
The publisher has gone to great lengths to ensure the quality of this reprint but points out that some imperfections in the original copies
may be apparent.
Disclaimer
The publisher has made every effort to trace copyright holders and welcomes correspondence from those they have been unable to
contact.
ISBN 13: 978-1-315-89366-2 (hbk)
ISBN 13: 978-1-351-07276-2 (ebk)
Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the
CRC Press Web site at http://www.crcpress.com
PREFACE
Around 1950, a new era in natural products chemistry can be considered to have begun.
Aided by more and more effective techniques of separation, and increasingly useful spec-
troscopic methods, structures of natural products have been accumulating at an overwhelming
rate. This is certainly true of terpenoids, one of the most widely distributed and important
class of the so-called secondary metabolites. Terpenoids have singularly enriched organic
chemistry by its variety of structural types, by its wealth of 'unexpected' reactions, rear-
rangements and spectral features, and by offering exciting targets for synthesis. Much
imaginative experimental work has been invested in exploring their natural pathways. Recent
years have revealed an increasingly important biological and ecological role for several of
its members.
In view of these advances workers in this area have often felt a need for a sort of Handbook,
pinpointing salient features of known information, in a format which is at once accessible
and readable. The present work is in continuation of the effort in that direction.
A total of four sections covering the following categories are planned:
• Monoterpenoids
• Sesquiterpenoids
• Diterpenoids
• Triterpenoids
Steroids, carotenoids and certain classes of meroterpenoids (for example, indole alkaloids)
have been kept outside the purview of the present work. Each section will consist of two
or more volumes. Two volumes covering Monoterpenoids appeared in mid-1982. Four
volumes embracing Diterpenoids were published in 1985 to 1986.
The present work covers Triterpenoids in two volumes:
• Volume I: Acyclic, Monocyclic, Bicyclic, Tricyclic, and Tetracyclic
• Volume II: Pentacyclic, and Hexacyclic
Every effort has been made to cover naturally occurring compounds which have appeared
in accessible literature until the end of 1982. However, it will be unrealistic not to expect
errors and omissions in a work of this magnitude and the authors will be grateful to the
discerning readers for drawing their attention to these. Besides the Catalog Section which
forms the bulk of this work, a chapter entitled "General Introduction", which surveys the
development of triterpenoid chemistry, has been included. A selected list of references to
books, reviews, and key papers dealing with various aspects of triterpenoid chemistry has
also been added and should prove useful.
The authors would like to express their thanks to Shri. Arun P. Dindorkar for drawing
structures, to Shri. R. Kuttappan for typing almost all the manuscript, and to Shri. J. R.
Patel for checking the same. Finally, once again, I would like to thank Shashi Prabha, my
wife, for all the understanding and moral support which made the undertaking of this work
possible.
Sukh Dev
Nandesari, Vadodara
November 1986
THE EDITOR
Sukh Dev was born in Chakwal, now in Pakistan, in 1923. He studied at Dayanand Anglo
Vedic College, Lahore (B.Sc. Hons., M.Sc.), and later at the Indian Institute of Science,
Bangalore (Ph.D., D.Sc.). He served as a Research Associate and Lecturer at the Indian
Institute of Science, and for one year (1957) as a Research Associate at the University of
Illinois, Urbana, before taking over as Head of the Division of Organic Chemistry (Natural
Products) at the National Chemical Laboratory, Poona, in 1960. In 1974, he moved to the
newly created Malti-Chem Research Centre as its Research Director. In 1989 he moved to
the Indian Institute of Technology, Delhi, as an INSA Research Professor.
Sukh Dev has been a Visiting Professor at the Stevens Institute of Technology, Hoboken
in 1968, at the University of Georgia, Athens in 1969, and at the University of Oklahoma,
Norman in 1970 to 1971. He has been an invited speaker at several International Symposia
and Seminars at many Universities/Research Institutes in several countries of the world. He
is the recipient of many National awards and in 1980 received the Ernest Guenther Award
of the American Chemical Society. He was elected President of the Indian Chemical Society
for the term 1978 to 1979. In 1987 he was elected President of the Organic Chemistry
Division Committee of the International Union of Pure & Applied Chemistry for the term
1987 to 1989.
His research interests include natural products chemistry, especially terpenoids and
Ayurvedic medicinal plants, azulenes and other nonbenzenoid aromatic systems, organic
synthesis, and new technology development. He has contributed over 270 research papers
and articles, and holds 48 patents. He is author of several books and book chapters.
THE AUTHORS
Amrit Sagar Gupta, born on November 1, 1925, had his early education at Lahore
(B.Sc., Hons, Panjab University, 1946) and received his M.Sc. (Hons) and Ph.D degrees
from Panjab University, Chandigarh.
Gupta joined the Natural Chemical Laboratory in October 1948 in the Division of Organic
Chemistry where he worked in various fields until the date of his retirement in October
1985. He has published more than 45 papers in national and international journals.
For 2 years (1966 to 1968), Gupta was Research Associate at the University of Illinois
Urbana, in the Laboratory of Professor N. J. Leonard. In 1982, he spent 6 weeks at the
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Science, Prague
under a bilateral exchange program.
His particular field of interest has been the chemistry of natural products.
Mrs. Sarita A. Patwardhan received her B.Sc. (Hons.) (1958), M.Sc. (1960) and Ph.D.
(1966) from Bombay University. She worked for her Ph.D at the National Chemical Lab-
oratory, Pune, India. Mrs. Patwardhan, at present, is working as a Senior Scientist in the
Division of Organic Chemistry in National Chemical Laboratory, Pune. She has published
over 30 research papers, review articles, and chapters. Her current research interests are
isolation of bio-active compounds from renewable resources, as well as their synthesis.
To Our Parents
TABLE OF CONTENTS
Volume I
GENERAL INFORMATION AND SKELETAL-TYPE INDEX
General Remarks on the Use of the Book 3
General Introduction 7
Skeletal-Type Index 63
ACYCLIC TRITERPENOIDS 73
MONOCYCLIC TRITERPENOIDS 83
BICYCLIC TRITERPENOIDS 87
TRICYCLIC TRITERPENOIDS 91
TETRACYCLIC TRITERPENOIDS 113
GENERAL BIBLIOGRAPHY 541
INDEXES
Compound Index 553
Species Index 569
Volume II
GENERAL INFORMATION AND SKELETAL-TYPE INDEX
General Remarks on the Use of the Book 3
General Introduction 7
Skeletal-Type Index 63
PENTACYCLIC TRITERPENOIDS 73
HEXACYCLIC TRITERPENOIDS 585
GENERAL BIBLIOGRAPHY 589
INDEXES
Compound Index 601
Species Index 619

General Information and Skeletal-Type Index