Five-membered Monoheterocyclic Compounds Alkaloids (continued): Amaryllidaceae Alkaloids

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

The Amaryllidaceae alkaloids comprise some one hundred structures isolated from the bulbs of plants from almost all genera of the subfamily Amaryllidoidae. A number of different types of alkaloids are recognized, all of which contain a basic skeleton of fifteen carbon atoms subdivided into a phenylmethyl (C6–C1) unit and a cyclohexylethyl or cyclohexenylethyl (C6-C2) unit, and the majority contain a simple or fused pyrrolidine ring. The best known alkaloid of the Amaryllidaceae is lycorine, the carbon skeleton of which forms the basic framework for a series of natural products. The biosynthetic derivation of the various Amaryllidaceae alkaloids from belladine type precursors suggests that lycorine, crinane and alanthamine alkaloids are derived by the oxidative cyclization of norbelladine derivatives and this hypothesis has been substantiated subsequently by radio-tracer experiments utilizing doubly and triply labeled norbelladines. In this chapter individual alkaloids have been cited as examples. These include pyrrolo[1,2,3-d,e]phenanthridine alkaloids, 2-benzopyrano[3,4-g]indole alkaloids, galanthamine-type alkaloids, [5,10b]-ethanophenanthridine alkaloids, pretazettine-type alkaloids, montanine, coccinine and manthine, and many other miscellaneous alkaloids. Narciprimine and narciclasine, both present in the extracts of the plant Narcissus incomparabilis Mill., are unusual in that their basic skeleton contains only thirteen carbon atoms instead of the usual fifteen.

LanguageEnglish
Title of host publicationRodd's Chemistry of Carbon Compounds
Subtitle of host publicationA Modern Comprehensive Treatise
PublisherElsevier
Pages165-200
Number of pages36
Volume4
Edition2nd
ISBN (Print)9780444533456
DOIs
StatusPublished - 1964

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Amaryllidaceae Alkaloids
Alkaloids
Carbon
Phenanthridines
Galantamine
Indole Alkaloids
Atoms
Cyclization
Plant Extracts
Biological Products

Cite this

Sainsbury, M. (1964). Five-membered Monoheterocyclic Compounds Alkaloids (continued): Amaryllidaceae Alkaloids. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise (2nd ed., Vol. 4, pp. 165-200). Elsevier. https://doi.org/10.1016/B978-044453345-6.50702-1

Five-membered Monoheterocyclic Compounds Alkaloids (continued) : Amaryllidaceae Alkaloids. / Sainsbury, M.

Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. Elsevier, 1964. p. 165-200.

Research output: Chapter in Book/Report/Conference proceedingChapter

Sainsbury, M 1964, Five-membered Monoheterocyclic Compounds Alkaloids (continued): Amaryllidaceae Alkaloids. in Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd edn, vol. 4, Elsevier, pp. 165-200. https://doi.org/10.1016/B978-044453345-6.50702-1
Sainsbury M. Five-membered Monoheterocyclic Compounds Alkaloids (continued): Amaryllidaceae Alkaloids. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd ed. Vol. 4. Elsevier. 1964. p. 165-200 https://doi.org/10.1016/B978-044453345-6.50702-1
Sainsbury, M. / Five-membered Monoheterocyclic Compounds Alkaloids (continued) : Amaryllidaceae Alkaloids. Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. Elsevier, 1964. pp. 165-200
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