The Quinoline Alkaloids

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

The quinoline alkaloids from higher plants are best classified according to their biogenetic derivation from either anthranilic acid or tryptophan. A number of simple quinolines, including the parent structure have been isolated from rutaceous plants. Most of these alkaloids are substituted at position 2 of the heterocycle. In addition to the quinolines, angostura bark also contains 1-methyl-2-quinolone. The co-occurrence of 2- and 4-quinolones is a common feature in many plants of the Rutaceae; fortunately spectroscopy allows an easy distinction to be made between these two types of alkaloids. Some thirty alkaloids derived from 9-acridone have been isolated from rutaceous plants; the main structural diversity stems from the substitution of O-methyl, methylenedioxy or O-prenyl functions at the 1-, 2-, 3- or 4-positions. The seeds of several Echinops species (Compositae) contain the alkaloid echinorine. The cinchona alkaloids occur in the bark of Cinchona and Remijia species (Family Rubiaceae), which are indigenous to the eastern tropical slopes of the Andes. Until quite recent times cinchona preparations have been the sole treatment for malaria, for example, Quinine. Pumiliotoxin-C1 is one of the toxic principals of the skin of the highly colored Panamanian frog Dendrobates pumilio.

LanguageEnglish
Title of host publicationRodd's Chemistry of Carbon Compounds
Subtitle of host publicationA Modern Comprehensive Treatise
Pages171-255
Number of pages85
Volume4
Edition2nd
DOIs
StatusPublished - 1964

Fingerprint

quinoline alkaloids
Cinchona
alkaloids
quinolines
quinolones
bark
Echinops
anthranilic acid
quinine
Rutaceae
Rubiaceae
skin (animal)
tryptophan
malaria
Asteraceae
frogs
spectroscopy
stems
seeds

Cite this

Sainsbury, M. (1964). The Quinoline Alkaloids. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise (2nd ed., Vol. 4, pp. 171-255) https://doi.org/10.1016/B978-044453345-6.50764-1

The Quinoline Alkaloids. / Sainsbury, M.

Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. 1964. p. 171-255.

Research output: Chapter in Book/Report/Conference proceedingChapter

Sainsbury, M 1964, The Quinoline Alkaloids. in Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd edn, vol. 4, pp. 171-255. https://doi.org/10.1016/B978-044453345-6.50764-1
Sainsbury M. The Quinoline Alkaloids. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd ed. Vol. 4. 1964. p. 171-255 https://doi.org/10.1016/B978-044453345-6.50764-1
Sainsbury, M. / The Quinoline Alkaloids. Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. 1964. pp. 171-255
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