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7-Demethylsuberosin and osthenol as intermediates in furanocoumarin biosynthesis

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1016/0031-9422(73)80558-8
AuthorSearch for: ; Search for: 1
Affiliation
  1. National Research Council of Canada. Prairie Regional Laboratory
FormatText, Article
SubjectConium maculatum; Heracleum lanatum; Ruta graveolens; Coronilla glauca; coumarins; furanocoumarins; biosynthesis; 7-demethylsuberosin; osthenol
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.
Publication date
PublisherElsevier
Pergamon Press
In
  • Phytochemistry 12, no. 6 (June 1973): 1315–1324.
LanguageEnglish
Peer reviewedYes
Identifier0031942273805588
NRCC-13735
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Record identifier3388a276-fe6a-4bd4-bfc0-7345206b60e2
Record created2023-10-11
Record modified2023-10-11
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