7-Demethylsuberosin and osthenol as intermediates in furanocoumarin biosynthesis |
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Authors: | Stewart A Brown Warren Steck |
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Institution: | Department of Chemistry, Trent University, Peterborough, Ontario, Canada K9J 7B8 |
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Abstract: | 14C-Labelled 7-demethylsuberosin (DMS) was a precursor of linear furanocoumarins in Conium maculatum and Heracleum lanatum (Umbelliferae), and in Ruta graveolens (Rutaceae), but not in Coronilla glauca (Leguminosae). Trapping experiments with 14C-umbelliferone over 3- to 24-hr periods revealed that DMS is rapidly metabolized, and that in short experiments its specific activity relative to the linear furano- coumarins′ is that of an intermediate. The specific activity of umbelliferone exhibited anomalies attributed to pool compartmentation. Analogous but less extensive experiments established that osthenol is an intermediate in angular furanocoumarin biosynthesis, but is much less rapidly metabolized than DMS. No significant incorporation into furanocoumarins of 14C from labelled l-valine, l-leucine, acetate, 2,3-di-hydroxyisovaleric acid, senecioic acid, isopentenylpyrophosphate, or mevalonate could be demonstrated. A synthesis of 1-14C]2,3-dihydroxyisovaleric acid is described. |
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Keywords: | coumarins furanocoumarins biosynthesis 7-demethylsuberosin osthenol |
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