Biosynthesis of avenic acid A, a ferric chelating substance secreted from Avena sativa L.

Jian Feng Ma, K. Nomoto

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The biosynthesis of avenic acid A was studied by feeding L-methionine-1-13C or D,L-methionine-3,3,4,4-d4 to iron-deficient oat roots (Avena sativa L. cv Amuri II). Both avenic acid A and 2'-deoxymugineic acid labeled with 13C or 2H were isolated from root-washings of the same plants. The 13C-NMR elucidated that three molecules of L-methionine were incorporated into avenic acid A in the same way as 2'-deoxymugineic acid. The 2H-NMR spectra indicated that all deuteriums from the methionine were incorporated into 2'-deoxymugineic acid, but one of the deuteriums at C-4 was lost in avenic acid A. A possible biosynthetic pathway is L-methionine → →2'-deoxymugineic acid → avenic acid A.

Original languageEnglish
Pages (from-to)2888-2890
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume40
Issue number10
Publication statusPublished - 1992
Externally publishedYes

Fingerprint

Biosynthesis
Chelation
Methionine
Acids
Nuclear magnetic resonance
Biosynthetic Pathways
Washing
Iron
Avena
Molecules
2'-deoxymugineic acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Biosynthesis of avenic acid A, a ferric chelating substance secreted from Avena sativa L. / Ma, Jian Feng; Nomoto, K.

In: Chemical and Pharmaceutical Bulletin, Vol. 40, No. 10, 1992, p. 2888-2890.

Research output: Contribution to journalArticle

@article{20702a0881824a7589c620bd3c86946d,
title = "Biosynthesis of avenic acid A, a ferric chelating substance secreted from Avena sativa L.",
abstract = "The biosynthesis of avenic acid A was studied by feeding L-methionine-1-13C or D,L-methionine-3,3,4,4-d4 to iron-deficient oat roots (Avena sativa L. cv Amuri II). Both avenic acid A and 2'-deoxymugineic acid labeled with 13C or 2H were isolated from root-washings of the same plants. The 13C-NMR elucidated that three molecules of L-methionine were incorporated into avenic acid A in the same way as 2'-deoxymugineic acid. The 2H-NMR spectra indicated that all deuteriums from the methionine were incorporated into 2'-deoxymugineic acid, but one of the deuteriums at C-4 was lost in avenic acid A. A possible biosynthetic pathway is L-methionine → →2'-deoxymugineic acid → avenic acid A.",
author = "Ma, {Jian Feng} and K. Nomoto",
year = "1992",
language = "English",
volume = "40",
pages = "2888--2890",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "10",

}

TY - JOUR

T1 - Biosynthesis of avenic acid A, a ferric chelating substance secreted from Avena sativa L.

AU - Ma, Jian Feng

AU - Nomoto, K.

PY - 1992

Y1 - 1992

N2 - The biosynthesis of avenic acid A was studied by feeding L-methionine-1-13C or D,L-methionine-3,3,4,4-d4 to iron-deficient oat roots (Avena sativa L. cv Amuri II). Both avenic acid A and 2'-deoxymugineic acid labeled with 13C or 2H were isolated from root-washings of the same plants. The 13C-NMR elucidated that three molecules of L-methionine were incorporated into avenic acid A in the same way as 2'-deoxymugineic acid. The 2H-NMR spectra indicated that all deuteriums from the methionine were incorporated into 2'-deoxymugineic acid, but one of the deuteriums at C-4 was lost in avenic acid A. A possible biosynthetic pathway is L-methionine → →2'-deoxymugineic acid → avenic acid A.

AB - The biosynthesis of avenic acid A was studied by feeding L-methionine-1-13C or D,L-methionine-3,3,4,4-d4 to iron-deficient oat roots (Avena sativa L. cv Amuri II). Both avenic acid A and 2'-deoxymugineic acid labeled with 13C or 2H were isolated from root-washings of the same plants. The 13C-NMR elucidated that three molecules of L-methionine were incorporated into avenic acid A in the same way as 2'-deoxymugineic acid. The 2H-NMR spectra indicated that all deuteriums from the methionine were incorporated into 2'-deoxymugineic acid, but one of the deuteriums at C-4 was lost in avenic acid A. A possible biosynthetic pathway is L-methionine → →2'-deoxymugineic acid → avenic acid A.

UR - http://www.scopus.com/inward/record.url?scp=0026489171&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026489171&partnerID=8YFLogxK

M3 - Article

VL - 40

SP - 2888

EP - 2890

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 10

ER -