BIOSYNTHESIS OF THE COUMARINS. TRACER STUDIES ON COUMARIN FORMATION IN HIEROCHLOË ODORATA AND MELILOTUS OFFICINALIS
- 1 January 1960
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Biochemistry and Physiology
- Vol. 38 (1), 143-156
- https://doi.org/10.1139/y60-016
Abstract
Coumarin formation has been studied with C14 in the perennial grass, Hierochloë odorata, and in yellow sweet clover, Melilotus officinalis. In general the latter species yielded inconsistent data. In Hierochloë, o-coumaric, cinnamic, and shikimic acids and L-phenylalanine were the best of 10 compounds tested as coumarin precursors, the first two at least being incorporated with little randomization of C14. Acetate was more poorly utilized. It was concluded that the aromatic ring of coumarin arises via the shikimic acid pathway in preference to acetate condensation. When the time of metabolism was varied, o-coumaryl glucoside and free o-coumaric acid rapidly acquired high specific activities from cinnamic acid-C14, but coumarin and melilotic acid became active much more slowly. A lag in the acquisition of C14 by coumarin for the first 6 to 8 hours was followed by a rectilinear increase until at least 24 hours. Much the greatest accumulation of C14 was found in o-coumaryl glucoside during this entire period. Furthermore, this compound when fed to Hierochloë is comparable to cinnamic acid as a coumarin precursor. These findings suggest a possible function for o-coumaryl glucoside or a derivative in coumarin biosynthesis.Keywords
This publication has 9 references indexed in Scilit:
- The Metabolism of Aromatic Compounds in Higher PlantsJournal of Biological Chemistry, 1959
- Über den Metabolismus14C-markierter Ferulasäure im PflanzenversuchThe Science of Nature, 1957
- Shikimic Acid as a Precursor in Lignin BiosynthesisNature, 1955
- Die Wurzel als Bildungsstätte für CumarineThe Science of Nature, 1955
- The identification of coumarins and related compounds by filter-paper chromatographyBiochemical Journal, 1953
- Preparation and Reactions of o-Hydroxycinnamic Acids and EstersJournal of the American Chemical Society, 1952
- A Method for Simultaneous Determination of Carbon-14 and Total CarbonJournal of the American Chemical Society, 1952
- Pyridinium Analogs of the Pressor Amines. II. The Guaiacol Series1Journal of the American Chemical Society, 1946
- Geometrical inversion in the acids derived from the coumarinsProceedings of the Indian Academy of Sciences - Section A, 1936