Pyrrolizidine Alkaloids from Cynoglossum creticum. Synthesis of the Pyrrolizidine Alkaloids Echinatine, Rinderine, and Analogues

Reinvestigation of Cynoglossum creticum led to the isolation of the previously reported echinatine [1] and heliosupine [2] as well as rinderine [3], 7-angelylheliotridine [4] and a new alkaloid, cynoglossamine [5]. The structures have been determined by spectral means (ir, ms, 1H-13C HETCOR nmr), co...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1989-01, Vol.52 (1), p.109-118
Main Authors: Asibal, Clarita F, Glinski, Jan A, Gelbaum, Leslie T, Zalkow, Leon H
Format: Article
Language:English
Subjects:
ALCALOIDE
ALCALOIDES
ALKALOIDS
BORAGINACEAE
CHEMICOPHYSICAL PROPERTIES
Chemistry
Cholestadienols - isolation & purification
Cholestadienols - pharmacology
Exact sciences and technology
Galactosides - isolation & purification
Galactosides - pharmacology
Glycosides - pharmacology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Plants - analysis
Preparations and properties
PROPIEDADES FISICO-QUIMICAS
PROPRIETE PHYSICO-CHIMIQUE
Pyrrolizidine Alkaloids - analysis
Pyrrolizidine Alkaloids - biosynthesis
Pyrrolizidine Alkaloids - pharmacology
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Description
Summary:Reinvestigation of Cynoglossum creticum led to the isolation of the previously reported echinatine [1] and heliosupine [2] as well as rinderine [3], 7-angelylheliotridine [4] and a new alkaloid, cynoglossamine [5]. The structures have been determined by spectral means (ir, ms, 1H-13C HETCOR nmr), comparison with literature data and authentic samples, and/or syntheses. In addition, 1 and all three of its isomers 3, 6, and 7 and other semisynthetic analogues (8-13) were prepared and characterized.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50061a014