Abstract
Methanolic extracts of
fresh Arnsinckia menziesii (Lehm.) Nels, and Macbr. (Boraginaceae) yielded
three known pyrrolizidine alkaloids, intermedinet (I), lycopsaminet (2) and
7-acetyllycopsaminet (3). In addition, two new alkaloids were isolated and
shown to be 9-[(2'S,3'S)-3'-acetoxy-2'-hydroxy-
2'-isopropylbutanoyl]retronecine,t (3'-acetyllycopsamine) (4) and
7-acetoxy-9-[(2'S,3'S)-3'-acetoxy- 2'-hydroxy-2'-isopropylbutanoyl]retronecine,
(3',7-diacetyllycopsamine) (5). Structures of all of the alkaloids were
determined by means of mass spectrometry and 13C and 1H n.m.r. spectroscopy.
The structures of the new alkaloids were confirmed by acetylation of
lycopsamine (2) to give 3'-acetyl- lycopsamine (4) and 3',7-diacetyllycopsamine
(5).
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