69369-89-7Relevant academic research and scientific papers
Stress metabolites of Solanum melongena: biosynthetic studies and isolation of auberganol and α- and β-eudesmol
Stoessl, Albert,Stothers, J. B.
, p. 1 - 4 (2007/10/02)
Attempts to clarify the biosynthetic origin of the eggplant stress metabolite aubergenone (1) by incorporation of label from sodium acetate were frustrated by low yields and enrichment levels.However, the presence of deuterium in the biosynthetically significant 5-position was demonstrated by 2Hmr for the closely related auberganol (5) and α- and β-eudesmol (10 and 11), suggesting that these compounds, and hence also 1, 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).Inco rporation of label from acetate could be determined satisfactorily only for 13 and its allylic isomer 14, corresponding with expectations.This is the first report of 5 as a natural product and of 10, 11, and the 10-epimer of 4 as eggplant stress metabolites.
