Über ein neues Guanidinderivat aus der Geissraute, Galega officinalis L

Abstract

Aus Samen der Geißraute wurde außer Galegin [3‐Methyl‐buten‐(2)‐yl‐guanidin (I)] ein noch unbekanntes Guanidinderivat C6H13N3O isoliert. Die einfach ungesättigte Verbindung ergab bei der katalytischen Hydrierung 4‐Hydroxy‐3‐methyl‐butyl‐guanidin (V). Das neue Guanidinderivat, 4‐Hydroxy‐galegin [4‐Hydroxy‐3‐methyl‐buten‐(2)‐yl‐guanidin (II)], ließ sich papierchromatographisch neben I in allen untersuchten Organen der Pflanze nachweisen.

Some Aspects of Guanidine Secondary Metabolites

“…The chemistry of galegine was reviewed by BRAUN (719). (571) has also been isolated from Galega officinalis (720)(721)(722) and identified by chemical degradation (catalytic reduction, acetylation and permanganate oxidation) and spectroscopic analysis (IR). The structure was also confirmed by synthesis (723).…”

Isolation and Characterization of Two Guanidines from Galega orientalis Lam. Cv. Gale (Fodder Galega)

“…The agronomic potential of the plant has been assessed for cooltemperate regions (Varis, 1986), and a proposal has been made by the Estonian Research Institute of Agriculture and Land Improvement to the International Seed Testing Association to have the species included in their list of field and forage crops under the name "fodder galega" (Raig, 1994). That common name was chosen to minimize confusion of G. orientalis with the other goat's rue, G. officinalis, which contains the guanidino-alkaloids galegine (1; Tanret, 1914;Spa ¨th and Prokopp, 1924) and 4-hydroxygalegine (2; Pufahl and Schreiber, 1961;Schreiber et al, 1964), and the pyrroloquinazoline vasicine (peganine, Schreiber et al, 1962). Of these components, galegine has been established as toxic to sheep (Gresham and Booth, 1991;Keeler et al, 1992Keeler et al, , 1986Huxtable et al, 1993).…”