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Isoquinolines form one of the largest groups of plant alkaloids and they in clude a number of valuable clinical agents such as codeine, morphine, eme tine and tubocurarine. Research into different aspects of isoquinolines con tinues in profusion, attracting the talents of botanists, chemists, bioche mists, analysts, pharmacists and pharmacologists. Many of these aspects are of an interdisciplinary nature, and in April 1984, The Phytochemical Society of Europe arranged a 3-day symposium on The Chemistry and Bi ology of Isoquinoline Alkaloids in order to provide a forum for scientists of differing disciplines who are united by a common interest in this one class of natural product. Each chapter in this volume is based on a lecture given at this symposium. Attempts have been made to make the aims and objectives, experimental findings and conclusions reached, intelligible to scientists of differing backgrounds. The introductory chapter, which is mainly based on a historical discus sion, stresses that plants containing isoquinolines have proved to be both a boon and a curse to mankind. The Opium Poppy, Papaver somniferum, produces the medicinally used alkaloids morphine, codeine, noscapine and papaverine whilst it also continues to provide drugs of abuse, particularly morphine and its readily prepared O,O-diacetyl derivative, heroin. Numer ous other alkaloids have been isolated from other members of the Papaver acea, and a knowledge of their presence and distribution within the various species has proved a useful adjunct to systematic botanical studies.
The Alkaloids: Chemistry and Pharmacology
The alkaloids were of great importance to mankind for centuries, long before they were recognized . as a chemical class. The influence they have had on literature is hinted at by some of the quotations I have used as chapter headings. Their influence on folklore and on medicine has been even greater. The scientific study of alkaloids may be said to have begun with the isolation of morphine by Sertiirner in 1804. Since that time they have remained of great interest to chemists, and now in any month there appear dozens of publications dealing with the isolation of new alkaloids or the determination of the structures of previously known ones. The area of alkaloid biochemistry, in comparison, has received little attention and today is much less developed. There is a certain amount of personal arbitrariness in defining "bio chemistry", as there is in defining "alkaloid", and this arbitrariness is doubtless compounded by the combination. Nevertheless, it seems to me that in any consideration of the biochemistry of a group of compounds three aspects are always worthy of attention-pathways of biosynthesis, function or activity, and pathways of degradation. For the alkaloids, treatment of these three aspects is necessarily lopsided. Much has been learned about routes of biosynthesis, but information on the other aspects is very scanty. It would be possible to enter into some speculation regarding the biosynthesis of all the more than 4,000 known alkaloids.
The Alkaloids: Chemistry and Physiology
Internationally acclaimed for more than forty years, this serial, founded by the late Professor R.H.F. Manske, continues to provide outstanding coverage of the rapidly expanding field of the chemotaxonomy, structureelucidation, synthesis, biosynthesis, and biology of all classes of alkaloids from higher and lower plants, marine organisms, or various terrestrial animals. Each volume provides, through its distinguished authors, up-to-date and detailed coverage of particular classes or sources of alkaloids. Over the years, this series has become the standard in natural product chemistry to which all other book series aspire. The Alkaloids: Chemistry and Pharmacology endures as an essential reference for all natural product chemists and biologists who have an interest in alkaloids, their diversity, and their unique biological profile. - Indispensible reference work written by leading experts in the field - Provides up-to-date, timely reviews on compounds and classes of great interest - Covers synthesis, biosynthesis, biology, as well as isolation and structure elucidation - An essential research tool for anyone working with alkaloids from a chemical or biological perspective
The aim of this book is to gather under one cover most of the data presently available on the carbon-13 nuclear magnetic resonance (cmr) spectra of alkaloids. The term "alkaloids" is used here in a very broad sense to include synthetic analogues of the natural products. Simple model amines are also incorporated since these often supply the basic information required in the assignment of chemical shifts for the more complex compounds. The literature on alkaloid cmr spectroscopy has been covered through 1977, but the collec tion of compounds presented here is illustrative rather than exhaustive. The papers included in the reference list afford further information not only on the cmr assignments of the particular compounds provided here, but also incorporate data on additional related structures. Only a few dimeric indole alkaloids are included since to a large extent their cmr spectra can be corre lated directly with those of their monomeric analogues. The present volume is thus a representative empirical compendium of cmr assignments focusing upon alkaloids and model amines, and is intended to aid cmr research in heterocyclic and alkaloid chemistry. The compounds and data presented in this book are classified and organized according to structural similarity. The purpose of such a presenta tion is to demonstrate the common cmr characteristics of a given structural type, while also facilitating an empirical evaluation of the cmr spectral changes specifically reSUlting from relatively minor variations in oxidation level, substitution, or stereochemistry.
Volume 11 of this series presents five timely reviews on current research on alkaloids. Chapter 1 by Paul L. Schiff, Jr. is a monumental survey of research that has been carried out over the past decade on the Thalictrum alkaloids. Forty-six new alkaloids are described from fifteen species of the genus Thalictrum, as well as 116 alkaloids of known structure from thirty-six species and subspecies of the genus. The chapter includes discussions of isolation and structure elucidation, analysis, biosynthesis, cell culture, and pharmacology. Also featured are inclusive compilations of botanical sources, alkaloids by alkaloid types, and calculated molecular weights of the Thalictrum alkaloids.Chapter 2 by Giovanni Appendino provides a fascinating treatment of Taxine, a collective name referring to a mixture of diterpenoid alkaloids from the yew tree (genus: Taxus). Taxine is responsible for the toxic properties of the yew tree that has been documented in historical and fictional literature, from Julius Caesar to Shakespeare, and from Agatha Christie to T.S. Eliot. The chapter treats the history, isolation techniques, structure elucidation, chemistry, and pharmacology of Taxine.Chapter 3 by Mary D. Menachery surveys the alkaloids of South American Menispermaceae (moonseed family). Many different structural types are included in this family. The alkaloid-bearing plants are woody-vines, shrubs, or small trees. Several of these species possess potent curare activity. The chemistry as well as pharmacology of these alkaloids is summarized.Chapter 4 by Russell J. Molyneux, Robert J. Nash, and Naoki Asano treats the chemistry and biological activity of the calystegines and related nortropane alkaloids. These polyhydroxylated bicyclic alkaloids represent another class of compounds that inhibit glycosidases, producing profound effects in biological systems by disrupting the essential cellular function of glycoprotein processing.Chapter 5, a related chapter by Robert J. Nash, Naoki Asano, and Alison A. Watson, reviews polyhydroxylated alkaloids that inhibit glycosidases. Topics covered include distribution, ecological significance and toxicity, isolation, synthesis, and biosynthesis.
Isoquinoline ring system is present in a wide variety of pharmacologically active compounds and natural products.1 Several 1-substituted 3-hydroxy isoquinolines derivatives also possess valuable biological activities.