Biosynthetic Pathways of 3-Epihydroxymugineic Acid and 3-Hydroxymugineic Acid in Gramineous Plants
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概要
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To elucidate the biosynthetic pathways of 3-epihydroxymugineic acid and 3-hydroxymugineic acid, feeding experiments using ^2H- and/or ^<13>C-labeled compounds were conducted with barley (Hordeum vulgare L. cv Ehimehadaka) and rye (Secale cereale L. cv Elubon), respectively. Feeding of [1,4', 4"-^<13>C_3] 2'-deoxymugineic acid (25 atom% ^<13>C) to iron-deficient barley yielded mugineic acid and 3-epihydroxymugineic acid enriched with ^<13>C at their corresponding positions. These results enabled us to demonstrate that 2'-deoxymugineic acid acts as a precursor for mugineic acid and 3-epihydroxymugineic acid. The ^2H-labeled 3-hydroxymugineic acid was obtained by feeding D,L-[3,3,4,4-^2H_4] methionine (98.6 atom% ^2H) to iron-deficient rye plants. The ^2H-NMR study revealed that two deuterium atoms (one each at the C-2' and C-3 hydroxymugineic acid, whereas the other 10 deuterium atoms were incorporated in a manner similar to that of 2'-deoxymugineic acid and mugineic acid. These findings suggested that 3-hydroxymugineic acid, instead of being biosynthesized from 3-epihydroxymugineic acid by epimerization, was in fact derived from mugineic acid by hydroxylation at the C-3 position. This assumption was further confirmed by the results of the incorporation of ^<13>C-labeled 2'-deoxymugineic acid into 3-hydroxymugineic acid. These results revealed that the biosynthetic pathways of both 3-epihydroxymugineic acid and 3-hydroxymugineic acid are as follows : L-methionine 2'-deoxymugineic acid mugineic acid 3-epihydroxymugineic acid in barley and hydroxymugineic acid in rye.
- 社団法人日本土壌肥料学会の論文
著者
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NOMOTO Kyosuke
Suntory Institute for Bioorganic Research
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Nomoto Kyosuke
Suntory Institute For Bioorganic Reseach
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Ma Jian
Suntory Institute for Bioorganic Research
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