The Alkaloids

Chemistry and Physiology

1st Edition - May 12, 2014
Editor: R. H. F. Manske
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 2 - 2 2 0 0 - 4

The Alkaloids: Chemistry and Physiology, Volume VIII: The Indole Alkaloids focuses on the advances in the chemistry of indole alkaloids. This book discusses the tryptamine and i… Read more

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The Alkaloids: Chemistry and Physiology, Volume VIII: The Indole Alkaloids focuses on the advances in the chemistry of indole alkaloids.

This book discusses the tryptamine and its derivatives, postulated biosyntheses of the physostigmine ring system, and source of the alkaloids. The simple lysergic acid amides, mass spectra of mitraphylline and rhynchophylline, and alkaloids of gelsemium species are also elaborated. This text likewise covers the determination of the structure of the alkaloids, stereochemistry of cinchonamine, dimeric alkaloids of calabash curare, and chemistry of the reserpine group. Other topics include the biology of ergot and short history of its active principles up to the discovery of ergotamine.

This volume is recommended for chemists and researchers interested in indole alkaloids.

List of Contributors

Preface

Contents of Previous Volumes

Chapter 1. The Simple Bases

I. Introduction

II. Abrine and Hypaphorine

III. Gramine and Its Derivatives

IV. Tryptamine and Its Derivatives

V. Psilocin and Psilocybin

VI. 5-Hydroxytryptamine and Its Derivatives

VII. Cryptolepine

References

Chapter 2. Alkaloids of the Calabar Bean

I. Source of the Alkaloids

II. Alkaloids Isolated

III. Physostigmine

IV. Postulated Biosyntheses of the Physostigmine Ring System

V. Geneserine

VI. Pharmacology

References

Chapter 3. The Carboline Alkaloids

I. Introduction

II. Occurrence

III. Properties

IV. Structure

References

Chapter 4. The Quinazolinocarbolines

I. Introduction

II. Occurrence

III. Structure

References

Chapter 5. Alkaloids of Mitragyna and Ourouparia Species

I. Occurrence

II. Mitragynine

III. Mitraphylline

IV. Uncarine-A and Formosanine (Uncarine-B)

V. Rhynchophylline (Mitrinermine)

VI. Adifoline

VII. The Mass Spectra of Mitraphylline and Rhynchophylline

VIII. Rotundifoline, Isorotundifoline (Mitragynol), and Speciofoline

References

Chapter 6. Alkaloids of Gelsemium Species

I. Occurrence

II. Gelsemine

III. Sempervirine

IV. Gelsemicine

V. Gelsedine

VI. Gelseverine

References

Chapter 7. Alkaloids of Picralima Nitida

I. Occurrence

II. Akuammigine

III. Akuammicine

IV. Pseudoakuammicine

V. Akuammidine (Rhazine)

VI. Pseudoakuammigine

VII. Akuammine

VIII. Picraline

IX. Akuammiline

X. Akuammenine

References

Chapter 8. Alkaloids of Alstonia Species

I. Occurrence

II. Alstonine and Tetrahydroalstonine

III. Alstoniline

IV. Alstonidine

V. Echitamine

VI. Echitamidine

VII. Villalstonine

VIII. Macralstonine

IX. Macralstonidine

X. Alkaloid C

References

Addendum: Venenatine

Chapter 9. The Iboga and Voacanga Alkaloids

I. The Iboga Alkaloids

II. The Voacanga Alkaloids

III. Miscellaneous

References

Chapter 10. The Chemistry of the 2,2'-Indolylquinuclidine Alkaloids

I. Determination of the Structure of the Alkaloids

II. Synthesis of Cinchonamine

III. Stereochemistry of Cinchonamine

IV. Miscellaneous

References

Chapter 11. The Pentaceras and the Ebumamine (Hunteria)-Vicamine Alkaloids

I. The Pentaceras Alkaloids (Canthin-6-Ones)

II. The Ebumamine (Hunteria)-Vincamine Alkaloids

III. The Hunteria and Pleiocarpa Alkaloids

References

Chapter 12. The Vinca Alkaloids

I. The Alkaloids of Vinca rosea L

II. The Alkaloids of Vinca minor L

III. The Alkaloids of Vinca difformis Pourr. and V. major L

IV. The Alkaloids of Vinca herbacea and V. lancea

References

Chapter 13. Rauwolfia Alkaloids with Special Reference To the Chemistry of Reserpine

I. Rauwolfia Species and Their Alkaloids

II. The Chemistry of the Reserpine Group

III. Synthetic Work

References

Chapter 14. The Alkaloids of Aspidosperma, Diplorrhyncus, Kopsia, Ochrosia, Pleiocarpa, and Related Genera

I. Introduction

II. The Aspidospermine Group

III. The Aspidofractinine Group

IV. The Aspidoalbine Group

V. The Condylocarpine Group

VI. Alkaloids Related to Akuammicine

VII. The Uleine Group

VIII. Tetrahydro β-Carboline and Related Alkaloids

IX. Alkaloids of Unknown Structure

References

Chapter 15. Alkaloids of Calabash Curare and Strychnos Species

I. Introduction

II. The C20-Alkaloids

III. The Dimeric Alkaloids of Calabash Curare

References

Chapter 16. The Alkaloids of Calycanthaceae

I. Introduction

II. Occurrence

III. Calycanthine

IV. Calycanthidine

V. Folicanthine and Chimonanthine

VI. Hodgkinsine

Addendum

References

Chapter 17. Strychnos Alkaloids

I. Strychnine and Brucine: Historical Survey

II. The Reactions of Strychnine, Brucine, and Their Derivatives and Degradation Products

III. α- and β-Colubrines

IV. The Total Synthesis of Strychnine

V. Vomicine: Historical Survey

VI. The Reactions of Vomicine and Its Derivatives and Degradation Products

VII. Minor Alkaloids

References

Chapter 18. Alkaloids of Haplophy ton cimicidum

Text

Addendum

References

Chapter 19. The Alkaloids of Geissospermum Species

I. Introduction

II. Geissoschizoline (Pereirine)

III. Geissoschizine

IV. Geissospermine

V. Other Alkaloids

VI. Flavopereirine

References

Chapter 20. Alkaloids of Pseudocinchona and Yohimbe

I. Introduction

II. Yohimbane

III. Heteroyohimbane

IV. Corynane (17,18-Secoyohimbane)

V. Corynoxane

References

Chapter 21. The Ergot Alkaloids

I. The Biology of Ergot and a Short History of Its Active Principles up to the Discovery of Ergotamine

II. Structural Types with Tables of the Natural Ergot Alkaloids

III. Lysergic Acid and Isolysergic Acid

IV. Simple Lysergic Acid Amides

V. Peptide Alkaloids

VI. The Alkaloids of the Clavine Series

VII. Biogenesis of the Ergot Alkaloids

VIII. Derivatives of Ergot Alkaloids

IX. The Pharmacology and Therapeutic Use of Ergot Alkaloids and Their Derivatives

References

Chapter 22. The Ajmaline-Sarpagine Alkaloids

I. The Ajmaline Group

II. The Sarpagine Group

III. Mass Spectra of the Ajmaline-Sarpagine Alkaloids

IV. Pharmacological Notes

References

Author Index

Subject Index

Life Sciences

Physical Sciences & Engineering

Social Sciences & Humanities

Health

The Alkaloids

Chemistry and Physiology

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R. H. F. Manske