Abstract
The biosynthesis of the mustard oil glucoside, benzylglucosinolate, was studied in Tropaeolum majus L. A number of labeled compounds were administered to plant shoots and the incorporation of tracer into benzylglucosinolate, isolated as the crystalline tetramethyl-ammonium salt, was measured. In order of decreasing efficiency of conversion into benzyl-glucosinolate the compounds fed were S-(β-d-glucopyranosyl)phenylacetothiohydroximic acid (desulfobenzylglucosinolate), sodium phenylacetothiohydroximate, dl-phenylalanine, d-glucose, and sodium-d-1-glucopyranosyl mercaptide (1-thioglucose). The results are consistent with the hypothesis that the thioglucosyl group of benzylglucosinolate is derived by glucosylation of phenylacetothiohydroximate and not from 1-thioglucose. The results also suggest that benzylglucosinolate is formed by sulfation of desulfobenzylglucosinolate as the final step in its biosynthesis.
A method for the isolation of a number of glucosinolates (mustard oil glucosides) is described which utilizes anion exchange chromatography on diethylaminoethyl (DEAE) cellulose. Potassium allylglucosinolate, tetramethylammonium benzylglucosinolate, potassium 2-hydroxy-2-phenylethylglucosinolate and potassium 2-phenylethylglucosinolate were obtained on recrystallization of the glucosinolate fraction eluted from the column.
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- DAVIS B. D. Intermediates in amino acid biosynthesis. Adv Enzymol Relat Subj Biochem. 1955;16:247–312. doi: 10.1002/9780470122617.ch5. [DOI] [PubMed] [Google Scholar]
- Gessner T., Acara M. Metabolism of thiols. S-Glucosylation. J Biol Chem. 1968 Jun 10;243(11):3142–3147. [PubMed] [Google Scholar]
- Matsuo M. Biosynthesis of sinigrin. V. On the origin of thioglucoside moiety of sinigrin. Chem Pharm Bull (Tokyo) 1968 Jun;16(6):1128–1129. doi: 10.1248/cpb.16.1128. [DOI] [PubMed] [Google Scholar]
- Meakin D. The biosynthesis of the thioglucoside moiety of benzyl glucosinolate. Experientia. 1967 Mar 15;23(3):174–175. doi: 10.1007/BF02136266. [DOI] [PubMed] [Google Scholar]
- UNDERHILL E. W., CHISHOLM M. D., WETTER L. R. Biosynthesis of mustard oil glucosides. I. Administration of C14-labelled compounds to horseradish, nasturtium, and watercress. Can J Biochem Physiol. 1962 Nov;40:1505–1514. [PubMed] [Google Scholar]
- Underhill E. W. Biosynthesis of mustard oil glucosides: conversion of phenylacetaldehyde oxime and 3-phenylpropionaldehyde oxime to glucotropaeolin and gluconasturtiin. Eur J Biochem. 1967 Jul;2(1):61–63. doi: 10.1111/j.1432-1033.1967.tb00106.x. [DOI] [PubMed] [Google Scholar]
- Wetter L. R., Chisholm M. D. Sources of sulfur in the thioglucosides of various higher plants. Can J Biochem. 1968 Aug;46(8):931–935. doi: 10.1139/o68-139. [DOI] [PubMed] [Google Scholar]