Phenol oxidation and biosynthesis. Part XXII. The alkaloids of erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma; the structure of erythratidine

Derek H R Barton, Leslie Gunatilaka, Roy M. Letcher, Awa M F T Lobo, David A. Widdowson

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41 Citations (Scopus)

Abstract

Erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma have been examined for alkaloids of biogenetic interest. In addition to the known Erythrina alkaloids, α- and β-erythroidine, eryosdine, erythraline, erythratine, and erysotrine, new alkaloids erythristemine, erythratidinone, and 3-demethoxyerythratidinone were isolated and characterised. The aporphine alkaloid isoboldine, and the benzyltetrahydroisoquinoline alkaloids (-)-orientaline and (+)-N-nororientaline were also isolated. A partial synthesis of erythratidine indicated a 2S configuration. A plausible biogenetic scheme for the new alkaloids is discussed.

Original languageEnglish (US)
Pages (from-to)874-880
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1973
Externally publishedYes

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Biosynthesis
Phenol
Alkaloids
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma have been examined for alkaloids of biogenetic interest. In addition to the known Erythrina alkaloids, α- and β-erythroidine, eryosdine, erythraline, erythratine, and erysotrine, new alkaloids erythristemine, erythratidinone, and 3-demethoxyerythratidinone were isolated and characterised. The aporphine alkaloid isoboldine, and the benzyltetrahydroisoquinoline alkaloids (-)-orientaline and (+)-N-nororientaline were also isolated. A partial synthesis of erythratidine indicated a 2S configuration. A plausible biogenetic scheme for the new alkaloids is discussed.",
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journal = "Journal of the Chemical Society, Perkin Transactions 1",
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T1 - Phenol oxidation and biosynthesis. Part XXII. The alkaloids of erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma; the structure of erythratidine

AU - Barton, Derek H R

AU - Gunatilaka, Leslie

AU - Letcher, Roy M.

AU - Lobo, Awa M F T

AU - Widdowson, David A.

PY - 1973

Y1 - 1973

N2 - Erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma have been examined for alkaloids of biogenetic interest. In addition to the known Erythrina alkaloids, α- and β-erythroidine, eryosdine, erythraline, erythratine, and erysotrine, new alkaloids erythristemine, erythratidinone, and 3-demethoxyerythratidinone were isolated and characterised. The aporphine alkaloid isoboldine, and the benzyltetrahydroisoquinoline alkaloids (-)-orientaline and (+)-N-nororientaline were also isolated. A partial synthesis of erythratidine indicated a 2S configuration. A plausible biogenetic scheme for the new alkaloids is discussed.

AB - Erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma have been examined for alkaloids of biogenetic interest. In addition to the known Erythrina alkaloids, α- and β-erythroidine, eryosdine, erythraline, erythratine, and erysotrine, new alkaloids erythristemine, erythratidinone, and 3-demethoxyerythratidinone were isolated and characterised. The aporphine alkaloid isoboldine, and the benzyltetrahydroisoquinoline alkaloids (-)-orientaline and (+)-N-nororientaline were also isolated. A partial synthesis of erythratidine indicated a 2S configuration. A plausible biogenetic scheme for the new alkaloids is discussed.

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