Alkaloids: Chemical and Biological Perspectives – serie

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.

Acronycine, a potent antitumor agent, was discovered in the bark of the small Australian Rutaceous tree, Acronychia baueri Schott. This new work presents a comprehensive survey of the isolation, structure determination, methods of synthesis, and the biological properties of acronycine, as well as an account of natural and synthetic analogues of acronycine, and their biological properties.Solanum alkaloids were reviewed in 1990 and this book surveys the new developments (isolation procedures, structural elucidation methods) and critically updates earlier reviews. In addition it presents the interesting chemistry and synthesis of cyclopeptide alkaloids. These cyclopeptide alkaloids have been isolated from ascidians, sea hares, and cyanobacteria. Also included are reviews of the use of the functionalized lactam, pyroglutamic acid, as a chiral template for the synthesis of alkaloids. The second review examines the on-line coupling of capillary electrophoresis (CE) and mass spectrometry (MS) for the analysis of alkaloid mixtures. Finally a review of oxygenated analogs of the alkaloid Marcfortine for their potent antiparasitic activity is included at the end of this work. Each chapter in this volume has been reviewed by at least one expert in the field. Indexes for both subjects and organisms are provided.

Volume 13 of this series presents five timely reviews of research on alkaloids such as new developments in the chemistry and biology of alkaloids from amphibian skins. It provides a synopsis and tabulation of the hundreds of alkaloids that have been detected, with an emphasis on occurrence, structure, dietary origins, and biological activity. Alkaloids containing the 1, 2, 3, 3a, 8, 8a - hexahydropyrrolo [2,3b] indole ring system and the cyclotryptamines are discussed. An exhaustive list of available structures is provided. The chemical and biological structures have been evaluated critically so as to identify existing errors and expose irregularities in appearance or biological function. In addition, attention is drawn to the possible implications of the accumulated knowledge related to the synthesis, occurrence, and biochemistry of this class of alkaloids.Recent work on alkaloids containing the comparatively non - basic pyrrole ring system is summarized. One of the chapters covers isolation, structure elucidation, biological activity, and selected chemical syntheses of certain pyrrole alkaloids.Recent developments in the chemistry of diterpenoid and norditerpenoid alkaloids occurring in Aconitum, Delphinium and Consolida genera of the Ranunculaceae family used in Chinese and Indian medicine are surveyed and the book ends with a focus on transition metal - catalyzed carbonylations as efficient and novel approaches to the construction of piperidine, izidine and quinazoline alkaloids, which occur in great numbers in nature.

Volume 14 of this series presents three interesting reviews of research on alkaloids. Chapter 1, by Paul L. Schiff, Jr., is a monumental effort, presenting a selective, comprehensive tabular review of research on the bisbenzylisoquinoline alkaloids, with an analysis of the respective alkaloid types. The chapter should serve as a very useful tool for the bench research scientist who is involved in the isolation and elucidation of structures of bisbenzylisoquinoline alkaloids. Moreover, the data in these tables provides the botanical distribution and occurrence (family, genus, species) of the various classes of these alkaloids. The alkaloids are also categorized by their molecular weights and structural types.

Chapter 2, by Toh-Seok Kam, is a review of alkaloids derived from Malaysian flora. Malaysia's position near the Equator confers on it a tropical climate characterized by high temperatures, humidity, and rainfall, conditions favorable for plant life that has resulted in a rich flora of about 15,000 species of higher plants. This review concentrates on work published during the past twenty years and where appropriate compares the occurrence of alkaloids with studies of similar plants from countries neighboring to Malaysia, especially Thailand and Indonesia.

Chapter 3, by Jie Jack Li, presents a collection of very interesting total syntheses of naturally occurring indole alkaloids where palladium chemistry plays a central role in the syntheses. Five different types of palladium-mediated reactions are treated: (1) oxidative cyclization reactions promoted by palladium (II) species; (2) transmetallation reactions with organoboranes, organostannanes, and organozinc reagents; (3) inter- and intramolecular Heck reactions; (4) reactions with &pgr;-allylpalladium as the intermediate; and (5) reactions using C-N bond formation as the key step for the synthesis.

Alkaloids: Chemical and Biological Perspectives, the 15th volume of the ACBP series, features four important reviews of research on alkaloids. Chapter 1 is the first comprehensive review of the carbon-13 and proton NMR shift assignments and physical constants of diterpene alkaloids and their derivatives. In addition to the catalogue of spectral and physical data, the chapter includes a table of the occurrences of these alkaloids in various plant species, tables containing molecular formulas versus calculated high-resolution mass values, and calculated high-resolution mass values versus the molecular formulas of diterpenoid alkaloids, as well as seven tables summarizing the carbon-13 chemical shifts of various functional groups in diterpenoid alkaloids. Chapter 2 is a fascinating review of the supercritical fluid extraction of alkaloids. This technique using basic modifiers, provides an alternative method for the extraction of alkaloids.Chapter 3 summarizes recent advances in the synthesis of Amaryllidaceae alkaloids, an important class of naturally-occurring bases and neutral compounds. The increased activity in the synthesis of these alkaloids over the last decade is undoubtedly due to the fact that certain members of this family possess interesting and useful biological properties. Elegant syntheses, chiral and otherwise, of structures incorporating many asymmetric centres are reviewed.Chapter 4 reviews radical cyclization reactions in the total synthesis of indole alkaloids. The use of free radical chemistry in the synthesis of alkaloids has grown markedly because of the mild reaction conditions, tolerance of a wide variety of functional groups, and the good stereoselectivities.Each chapter in this volume has been reviewed by at least one specialist in the field.

Volume 8 of this series presents four timely reviews on alkaloids: Chapter 1 is a magnificent and monumental review of curare, "a group of dart and/or arrow poisons varying in composition and featuring muscle relaxation as their basic pharmacological action." The fascinating history of curare is recounted, beginning with early encounters by the Spanish Conquistadores through its use as arrow poisons by the forest tribes in hunting and warfare, its chemistry, ethnography, botany and pharmacology. A terminal section of this chapter treats the development of modern muscle relaxants. This chapter thus traces how curare-initially only a crude plant extract-has given rise to the widely used and very important neuromuscular blocking agents of today. The precise role of plant secondary metabolites and their interactions with insect herbivores have been focal points for research by chemists, botanists and entomologists for many years. Alkaloids and their glycosides are frequently involved as feeding deterrents. Chapter 2 treats the relationships between the chemistry of alkaloids in host plants and the effects that these compounds may have on insect herbivores. Interestingly, an alkaloid produced by a plant may manifest different effects on different insects.