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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The pyrrolizidine alkaloids of Amsinckia menziesii

JN Roitman

Australian Journal of Chemistry 36(4) 769 - 778
Published: 1983

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).

https://doi.org/10.1071/CH9830769

© CSIRO 1983

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