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The Calabar Bean and its Alkaloids:From Magic, via Miracle, to Memory '17

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発行年月	2023年03月
出版社／提供元	Springer Netherlands
出版国	オランダ
言語	英語
媒体	冊子
装丁	hardcover
ページ数／巻数	XXVI, 267 p. 240 illus.
ジャンル	洋書／生命科学・医学／薬学／生薬学・本草学
ISBN	9789402411904
商品コード	1025098883
本の性格	学術書
新刊案内掲載月	2018年01月
商品URL	https://kw.maruzen.co.jp/ims/itemDetail.html?itmCd=1025098883

内容

Investigations into Calabar beans (the dried ripe seeds of Physostigma venenosum) and their alkaloidal components compose a classical scientific journey throughout some one-and-a-half centuries and not only represent a fascinating aspect of the history of medicine but which is, moreover, still ongoing at the forefront of chemical and medical discovery. Those in particular involving its major such component, l-physostigmine, have led to an understanding of some of the fundamental mechanisms occurring in physiology, pharmacology and biochemistry and, either actually or potentially (by providing a template and thereby acting as a “lead compound”) have provided a useful treatment for a variety of neurological disorders associated with irregularities in cholinergic transmission in which augmentation of cholinergic activity has proved to be beneficial.
Physostigma venenosum is distributed throughout equatorial West Africa and having a colourful history - by virtue of their former use as an ordeal poison in trials for witchcraft in the Efik society of Old Calabar - are its dried ripe seeds (Calabar beans). The major toxic compound isolated from these, l-physostigmine, which is also known as eserine and is the only alkaloid as yet also to be isolated from a microbial source (along with l-N(8)-norphysostigmine) and is the first alkaloid found to contain a 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole ring system, and the first natural product found to contain a carbamyl group. It also became one of the first examples whereby the mechanism of action of a drug could be defined at the molecular level relatively simply, played a crucial role in the Nobel Prize - winning discovery of the mechanism of neurohumoral transmission, and has led to products for the treatment of a wide range of disorders associated with deficiencies in cholinergic transmission. Several other alkaloids have also been isolated from the Calabar bean. For some of these, structures have been established, syntheses effected and pharmacology investigated.

Chronology.- Abbreviations.- Preface and acknowledgements.- 1. Introduction.- 2. l-Physostigmine (eserine).- 2.1. Natural occurrence.- 2.2. Structure elucidation.- 2.3. Synthesis of:- 2.3.1. by early approaches, including the first to be successful.- 2.3.2. l-physostigmine and the 3a-alkyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole ring system.- 2.3.3. d-physostigmine.- 2.4. Absolute configuration, together with that of the other structurally-established alkaloids of the Calabar bean.- 2.5. Biogenesis.- 2.6. Ultraviolet absorption spectrum and reaction in an acidic medium.- 2.7. Mass spectrum.- 2.8. Detection, assay and instability.- 2.8.1. Qualitative and quantitative analysis.- 2.8.2. Rubreserine.- 2.8.3. Eserine blue.- 2.8.4. Eserine brown.- 3. l-Physovenine.- 3.1. Isolation and structure elucidation.- 3.2. Synthesis of the:- 3.2.1. racemate.- 3.2.2. l<- and d-enantiomers.- 3.2.3. 3a-alkyl-3,3a,8,8a-tetrahydro-2H<-furo[2,3-b]indole ring system.- 3.3. Biogenesis.- 4. l-Eseramine.- 4.1. Isolation and structure elucidation.- 4.2. Synthesis of the:- 4.2.1. racemate.- 4.2.2. l-enantiomer.- 5. l-N(8)-Norphysostigmine.- 5.1. Isolation and structure elucidation.- 5.2. Synthesis of the l-enantiomer.- 6. l-Geneserine.- 6.1. Isolation and structure elucidation.- 6.2. Synthesis of the l-enantiomer and the racemate.- 7. 1H-, 13C- and 15N-Nuclear magnetic resonance spectra of the alkaloids of the Calabar bean.- 8. Other alkaloids of, as yet, unknown structures that have been isolated, or allegedly so, from the Calabar bean.- 8.1. Calabarine.- 8.2. Eseridine.- 8.3. Isophysostigmine.- 8.4. Calabatine and calabacine.- 8.5. Investigations still to be effected.- 9. Non-alkaloidal components of the Calabar bean.- 10. Biological activities of the alkaloids of the Calabar bean.- 10.1. AntiAchE activity.- 10.1.1. AchE – its function in neurohumoral transmission, structure and inhibition.- 10.2. Pharmacology of l-physostigmine.- 10.3. Role of l-physostigmine in the discovery of the mechanism of neurohumoral transmission.- 10.4. AntiAchE activities of the minor alkaloids of the Calabar bean – the l-physostigmine pharmacophore.- 10.5. Clinical use of l-physostigmine in ophthalmology – miotic activity and the reduction of intraocular pressure in glaucoma.- 10.6. Clinical use of l-physostigmine in the treatment of:- 10.6.1. Myasthenia gravis.- 10.6.2. Paraplegic anejaculation.- 10.7. Use of l-physostigmine in the:- 10.7.1. Prophylactic protection against intoxication by organophosphates (including “nerve gases”).- 10.7.2. Enhancement of cognition and memory (including antiamnesic activity in dementia of the Alzheimer’s type – Alzheimer’s disease).- 10.8. Bactericidal and insecticidal activities of l-physostigmine.- 10.9. Prophylactic protection with d-physostigmine against intoxication by organophosphates (including “nerve gases”).- 10.10. Other clinical uses of l-physostigmine.- 10.11. Antinociceptive activity of l-eseroline and its synthetic analogues.- 10.12. Cytotoxicities of rubreserine and another structurally-related degradation product of l-physostigmine.- 10.13. Poisonings (either accidental or malicious) with the Calabar bean.- 11. Notes.- 12. References.- 13. Index.

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