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Stress metabolites ofSolanummelongena: biosynthetic studies and isolation of auberganol and α- and β-eudesmol

 

作者: Albert Stoessl,   J.B. Stothers,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1986)
卷期: Volume 64, issue 1  

页码: 1-4

 

ISSN:0008-4042

 

年代: 1986

 

DOI:10.1139/v86-001

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

Attempts to clarify the biosynthetic origin of the eggplant stress metabolite aubergenone (1) by incorporation of label from sodium [2-2H3,1-13C]acetate were frustrated by low yields and enrichment levels. However, the presence of deuterium in the biosynthetically significant 5-position was demonstrated by2Hmr for the closely related auberganol (5) and α-and β-eudesmol (10and11), suggesting that these compounds, and hence also1, are normal eudesmanes and not the products of a possible double rearrangement. Deuterium was also incorporated into the expected positions of 9-oxonerolidol (12), 9-oxynerolidol (13), and lubimin (4). Incorporation of label from [1,2-13C2]acetate could be determined satisfactorily only for13and its allylic isomer14, corresponding with expectations. This is the first report of5as a natural product and of10,11, and the 10-epimer of4as eggplant stress metabolites.

 

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