Abstract
To elucidate the biosynthetic pathways of 3-epihydroxymugineic acid and 3-hydroxymugineic acid, feeding experiments using 2H- and/or 13C-labeled compounds were conducted with barley (Hordeum vulgare L. cv Ehimehadaka) and rye (Secale cereale L. cv Elubon), respectively. Feeding of [1, 4′, 4″13C3]2′-deoxymugineic acid (25 atom% 13C) to iron-deficient barley yielded mugineic acid and 3-epihydroxymugineic acid enriched with 13C 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, 42H4] 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 positions) from the three 2H-labeled methionine molecules were lost in 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 13C-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-methionineℲ2′-deoxymugineic acid→mugineic acid→3-epihydroxymugineic acid in barley and→hydroxymugineic acid in rye.
| Original language | English |
|---|---|
| Pages (from-to) | 311-317 |
| Number of pages | 7 |
| Journal | Soil Science and Plant Nutrition |
| Volume | 40 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 1994 |
| Externally published | Yes |
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Keywords
- 3-epihydroxymugineic acid
- 3-hydroxymugineic acid
- Barley
- Biosynthesis
- Rye
ASJC Scopus subject areas
- Soil Science
- Plant Science
- Agronomy and Crop Science
Cite this
Biosynthetic pathways of 3-epihydroxymugineic acid and 3-hydroxymugineic acid in gramineous plants. / Ma, Jian Feng; Nomoto, Kyosuke.
In: Soil Science and Plant Nutrition, Vol. 40, No. 2, 1994, p. 311-317.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Biosynthetic pathways of 3-epihydroxymugineic acid and 3-hydroxymugineic acid in gramineous plants
AU - Ma, Jian Feng
AU - Nomoto, Kyosuke
PY - 1994
Y1 - 1994
N2 - To elucidate the biosynthetic pathways of 3-epihydroxymugineic acid and 3-hydroxymugineic acid, feeding experiments using 2H- and/or 13C-labeled compounds were conducted with barley (Hordeum vulgare L. cv Ehimehadaka) and rye (Secale cereale L. cv Elubon), respectively. Feeding of [1, 4′, 4″13C3]2′-deoxymugineic acid (25 atom% 13C) to iron-deficient barley yielded mugineic acid and 3-epihydroxymugineic acid enriched with 13C 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, 42H4] 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 positions) from the three 2H-labeled methionine molecules were lost in 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 13C-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-methionineℲ2′-deoxymugineic acid→mugineic acid→3-epihydroxymugineic acid in barley and→hydroxymugineic acid in rye.
AB - To elucidate the biosynthetic pathways of 3-epihydroxymugineic acid and 3-hydroxymugineic acid, feeding experiments using 2H- and/or 13C-labeled compounds were conducted with barley (Hordeum vulgare L. cv Ehimehadaka) and rye (Secale cereale L. cv Elubon), respectively. Feeding of [1, 4′, 4″13C3]2′-deoxymugineic acid (25 atom% 13C) to iron-deficient barley yielded mugineic acid and 3-epihydroxymugineic acid enriched with 13C 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, 42H4] 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 positions) from the three 2H-labeled methionine molecules were lost in 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 13C-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-methionineℲ2′-deoxymugineic acid→mugineic acid→3-epihydroxymugineic acid in barley and→hydroxymugineic acid in rye.
KW - 3-epihydroxymugineic acid
KW - 3-hydroxymugineic acid
KW - Barley
KW - Biosynthesis
KW - Rye
UR - http://www.scopus.com/inward/record.url?scp=0028133953&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0028133953&partnerID=8YFLogxK
U2 - 10.1080/00380768.1994.10413305
DO - 10.1080/00380768.1994.10413305
M3 - Article
VL - 40
SP - 311
EP - 317
JO - Soil Science and Plant Nutrition
JF - Soil Science and Plant Nutrition
SN - 0038-0768
IS - 2
ER -