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), 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.
Asibal
C F
CF
School of Chemistry, Georgia Institute of Technology, Atlanta 30332.
Glinski
J A
JA
Gelbaum
L T
LT
Zalkow
L H
LH
D002775:Cholestadienols / Q000302:isolation & purification / Q000494:pharmacology*; D005697:Galactosides / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010944:Plants / Q000032:analysis*; D011763:Pyrrolizidine Alkaloids / Q000032:analysis* / Q000096:biosynthesis / Q000494:pharmacology
D002775:Cholestadienols; D005697:Galactosides; D006027:Glycosides; D011763:Pyrrolizidine Alkaloids; C059855:eryloside A; C018336:indicine