Accession Number:

AD0614512

Title:

BIOSYNTHESIS OF MUSTARD OIL GLUCOSIDES. VI. BIOSYNTHESIS OF GLUCOBARBARIN IN RESEDA LUTEOLA L,

Descriptive Note:

Corporate Author:

NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB

Personal Author(s):

Report Date:

1964-08-12

Pagination or Media Count:

10.0

Abstract:

A number of C14-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 C14. 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 C14 in the aglycone resulted from feeding DL-gamma-phenylbutyrine-2- and -3-C14, DL-phenylalanine-2- and -3-C14, and acetate-2-C14. The conversion of C14 from 10 additional compounds into the aglycone was less than that from D-glucose-G-C14. 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-C14N15 and of DL-gamma-phenylbutyrine-2-C14-N15 were not incorporated as a unit into the aglycone of glucobarbarin. Author

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Distribution Statement:

APPROVED FOR PUBLIC RELEASE