Isolation and Structure of a New Metabolite of Pyridoxine in Seedlings ofPisum sativumL.

Agricultural and Biological Chemistry
1983.0

Abstract

Reports on metabolism of vitamin B6 in higher plants are scarce except for the partial purification of pyridoxine (pyridoxamine) 5'-phosphate oxidase from barley seedlings. Previously, we demonstrated that the main metabolite of pyridoxine (1) in etiolated plant seedlings is 5'-O-(β-D-glucopyranosyl)pyridoxine (2). In this study, we surveyed metabolites of 1 in seedlings of podded pea (Pisum sativum L. cv. Kinusaya) and found a small amount of a derivative (3) in addition to 2. The present paper describes the isolation and structure of 3. Seedlings of podded pea grown on a solution of 1 were extracted with hot 75% EtOH. Metabolite 3 was separated from 1 and 2 by adsorption on Dowex 1×4 (AcO⁻) and further purified by serial column chromatography on cellulose powder, Dowex 1×4 (AcO⁻), and P-cellulose (H⁺), yielding a colorless powder. The structure of 3 was elucidated using UV, IR, PMR, and ¹³C NMR spectroscopy, alkaline hydrolysis, and the Gibbs color reaction. Compound 3 showed the same UV absorption spectrum as 1 and 2 (λmax 292 nm in 0.1 N HCl) and IR bands for ester carbonyl and carboxyl groups. PMR and ¹³C NMR data indicated the presence of the 2 structure plus additional moieties. Alkaline hydrolysis of 3 produced 2 and 3-hydroxy-3-methylglutaric acid (4). The Gibbs reaction revealed unsubstituted hydroxyl groups at C-3 and C-4' of the pyridoxine moiety. ¹³C NMR chemical shift differences between 3 and 2 indicated the ester bond was at the C-12 hydroxyl of the glucose moiety of 2. Thus, the structure of 3 was determined to be 5'-O-[6-O-(3-hydroxy-3-methyl-4-carboxybutanoyl)-β-D-glucopyranosyl]pyridoxine. Compound 3 is formed from 1 in various Leguminosae seedlings and likely occurs naturally in plant tissues.

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