BIOSYNTHESIS OF MUSTARD OIL GLUCOSIDES. VI. BIOSYNTHESIS OF GLUCOBARBARIN IN RESEDA LUTEOLA L,
Abstract
A number of C(14)-labelled compounds were fed to Reseda luteola L.; after a 24-hour period of metabolism, the thioglucoside aglycone (5-phenyl-2-oxazolidinethione) was isolated and its specific activity determined. In some instances the aglycone was degraded to determine the distribution of C(14). DL-gammaPhenylbutyrine (2-amino-4-phenylbutyric acid) was the most efficient precursor of the aglycone, followed by phenylalanine and acetate; the carboxyl carbon of these compounds was not incorporated into the thioglucoside aglycone. Little or no randomization of C(14) in the aglycone resulted from feeding DL-gamma-phenylbutyrine-2- and -3-C(14), DL-phenylalanine-2- and -3-C(14), and acetate-2-C(14). The conversion of C(14) from 10 additional compounds into the aglycone was less than that from D-glucose-G-C(14). Isotope competition experiments suggest that beta-benzylmalic acid also may be a precursor. It appears that the C6-C3 aglycone is formed from phenylalanine and acetate via C6-C5 and C6-C4 intermediates (including gamma-phenylbutyrine or its keto acid analogue) in a manner analogous to the formation of gluconasturtiin in watercress. The carbon-14 and nitrogen-15 of L-phenylalanine-G-C(14)N(15) and of DL-gamma-phenylbutyrine-2-C(14)-N(15) were not incorporated as a unit into the aglycone of glucobarbarin. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Aug 12, 1964
- Accession Number
- AD0614512
Entities
People
- E. W. Underhill
Organizations
- National Research Council Canada