Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds

Edgar B Cahoon, Charles R. Dietrich, Knut Meyer, Howard G. Damude, John M. Dyer, Anthony J. Kinney

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

Expression of Δ12-oleic acid desaturase-related fatty acid conjugases from Calendula officinalis, Momordica charantia, and Vernicia fordii in seeds of soybean (Glycine max) or an Arabidopsis thaliana fad3/fae1 mutant was accompanied by the accumulation of the conjugated fatty acids calendic acid or α-eleostearic acid to amounts as high as 20% of the total fatty acids. Conjugated fatty acids, which are synthesized from phosphatidylcholine (PC)-linked substrates, accumulated in PC and phosphatidylethanolamine, and relative amounts of these fatty acids were higher in PC than in triacylglycerol (TAG) in the transgenic seeds. The highest relative amounts of conjugated fatty acids were detected in PC from seeds of soybean and A. thaliana that expressed the C. officinalis and M. charantia conjugases, where they accounted for nearly 25% of the fatty acids of this lipid class. In these seeds, >85% of the conjugated fatty acids in PC were detected in the sn-2 position, and these fatty acids were also enriched in the sn-2 position of TAG. In marked contrast to the transgenic seeds, conjugated fatty acids composed <1.5% of the fatty acids in PC from seeds of five unrelated species that naturally synthesize a variety of conjugated fatty acid isomers, including seeds that accumulate conjugated fatty acids to >80% of the total fatty acids. These results suggest that soybean and A. thaliana seeds are deficient in their metabolic capacity to selectively catalyze the flux of conjugated fatty acids from their site of synthesis on PC to storage in TAG.

Original languageEnglish (US)
Pages (from-to)1166-1176
Number of pages11
JournalPhytochemistry
Volume67
Issue number12
DOIs
StatePublished - Jun 1 2006

Fingerprint

Soybeans
Arabidopsis
Seed
Phospholipids
Seeds
phospholipids
Fatty Acids
soybeans
fatty acids
Phosphatidylcholines
seeds
phosphatidylcholines
Calendula
gamma-Glutamyl Hydrolase
Momordica charantia
Calendula officinalis
Triglycerides
Arabidopsis thaliana
triacylglycerols
Fatty Acid Desaturases

Keywords

  • Arabidiopsis thaliana
  • Calendic acid
  • Conjugated fatty acid
  • FAD2
  • Fatty acid conjugase
  • Glycine max
  • Leguminosae
  • Metabolic engineering
  • Oilseed engineering
  • Phosphatidylcholine
  • Soybean
  • Triacylglycerol
  • Unusual fatty acid
  • α-Eleostearic acid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds. / Cahoon, Edgar B; Dietrich, Charles R.; Meyer, Knut; Damude, Howard G.; Dyer, John M.; Kinney, Anthony J.

In: Phytochemistry, Vol. 67, No. 12, 01.06.2006, p. 1166-1176.

Research output: Contribution to journalArticle

Cahoon, Edgar B ; Dietrich, Charles R. ; Meyer, Knut ; Damude, Howard G. ; Dyer, John M. ; Kinney, Anthony J. / Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds. In: Phytochemistry. 2006 ; Vol. 67, No. 12. pp. 1166-1176.
@article{8b0adda1b4e14854b142752991777dff,
title = "Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds",
abstract = "Expression of Δ12-oleic acid desaturase-related fatty acid conjugases from Calendula officinalis, Momordica charantia, and Vernicia fordii in seeds of soybean (Glycine max) or an Arabidopsis thaliana fad3/fae1 mutant was accompanied by the accumulation of the conjugated fatty acids calendic acid or α-eleostearic acid to amounts as high as 20{\%} of the total fatty acids. Conjugated fatty acids, which are synthesized from phosphatidylcholine (PC)-linked substrates, accumulated in PC and phosphatidylethanolamine, and relative amounts of these fatty acids were higher in PC than in triacylglycerol (TAG) in the transgenic seeds. The highest relative amounts of conjugated fatty acids were detected in PC from seeds of soybean and A. thaliana that expressed the C. officinalis and M. charantia conjugases, where they accounted for nearly 25{\%} of the fatty acids of this lipid class. In these seeds, >85{\%} of the conjugated fatty acids in PC were detected in the sn-2 position, and these fatty acids were also enriched in the sn-2 position of TAG. In marked contrast to the transgenic seeds, conjugated fatty acids composed <1.5{\%} of the fatty acids in PC from seeds of five unrelated species that naturally synthesize a variety of conjugated fatty acid isomers, including seeds that accumulate conjugated fatty acids to >80{\%} of the total fatty acids. These results suggest that soybean and A. thaliana seeds are deficient in their metabolic capacity to selectively catalyze the flux of conjugated fatty acids from their site of synthesis on PC to storage in TAG.",
keywords = "Arabidiopsis thaliana, Calendic acid, Conjugated fatty acid, FAD2, Fatty acid conjugase, Glycine max, Leguminosae, Metabolic engineering, Oilseed engineering, Phosphatidylcholine, Soybean, Triacylglycerol, Unusual fatty acid, α-Eleostearic acid",
author = "Cahoon, {Edgar B} and Dietrich, {Charles R.} and Knut Meyer and Damude, {Howard G.} and Dyer, {John M.} and Kinney, {Anthony J.}",
year = "2006",
month = "6",
day = "1",
doi = "10.1016/j.phytochem.2006.04.013",
language = "English (US)",
volume = "67",
pages = "1166--1176",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds

AU - Cahoon, Edgar B

AU - Dietrich, Charles R.

AU - Meyer, Knut

AU - Damude, Howard G.

AU - Dyer, John M.

AU - Kinney, Anthony J.

PY - 2006/6/1

Y1 - 2006/6/1

N2 - Expression of Δ12-oleic acid desaturase-related fatty acid conjugases from Calendula officinalis, Momordica charantia, and Vernicia fordii in seeds of soybean (Glycine max) or an Arabidopsis thaliana fad3/fae1 mutant was accompanied by the accumulation of the conjugated fatty acids calendic acid or α-eleostearic acid to amounts as high as 20% of the total fatty acids. Conjugated fatty acids, which are synthesized from phosphatidylcholine (PC)-linked substrates, accumulated in PC and phosphatidylethanolamine, and relative amounts of these fatty acids were higher in PC than in triacylglycerol (TAG) in the transgenic seeds. The highest relative amounts of conjugated fatty acids were detected in PC from seeds of soybean and A. thaliana that expressed the C. officinalis and M. charantia conjugases, where they accounted for nearly 25% of the fatty acids of this lipid class. In these seeds, >85% of the conjugated fatty acids in PC were detected in the sn-2 position, and these fatty acids were also enriched in the sn-2 position of TAG. In marked contrast to the transgenic seeds, conjugated fatty acids composed <1.5% of the fatty acids in PC from seeds of five unrelated species that naturally synthesize a variety of conjugated fatty acid isomers, including seeds that accumulate conjugated fatty acids to >80% of the total fatty acids. These results suggest that soybean and A. thaliana seeds are deficient in their metabolic capacity to selectively catalyze the flux of conjugated fatty acids from their site of synthesis on PC to storage in TAG.

AB - Expression of Δ12-oleic acid desaturase-related fatty acid conjugases from Calendula officinalis, Momordica charantia, and Vernicia fordii in seeds of soybean (Glycine max) or an Arabidopsis thaliana fad3/fae1 mutant was accompanied by the accumulation of the conjugated fatty acids calendic acid or α-eleostearic acid to amounts as high as 20% of the total fatty acids. Conjugated fatty acids, which are synthesized from phosphatidylcholine (PC)-linked substrates, accumulated in PC and phosphatidylethanolamine, and relative amounts of these fatty acids were higher in PC than in triacylglycerol (TAG) in the transgenic seeds. The highest relative amounts of conjugated fatty acids were detected in PC from seeds of soybean and A. thaliana that expressed the C. officinalis and M. charantia conjugases, where they accounted for nearly 25% of the fatty acids of this lipid class. In these seeds, >85% of the conjugated fatty acids in PC were detected in the sn-2 position, and these fatty acids were also enriched in the sn-2 position of TAG. In marked contrast to the transgenic seeds, conjugated fatty acids composed <1.5% of the fatty acids in PC from seeds of five unrelated species that naturally synthesize a variety of conjugated fatty acid isomers, including seeds that accumulate conjugated fatty acids to >80% of the total fatty acids. These results suggest that soybean and A. thaliana seeds are deficient in their metabolic capacity to selectively catalyze the flux of conjugated fatty acids from their site of synthesis on PC to storage in TAG.

KW - Arabidiopsis thaliana

KW - Calendic acid

KW - Conjugated fatty acid

KW - FAD2

KW - Fatty acid conjugase

KW - Glycine max

KW - Leguminosae

KW - Metabolic engineering

KW - Oilseed engineering

KW - Phosphatidylcholine

KW - Soybean

KW - Triacylglycerol

KW - Unusual fatty acid

KW - α-Eleostearic acid

UR - http://www.scopus.com/inward/record.url?scp=33745487692&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745487692&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2006.04.013

DO - 10.1016/j.phytochem.2006.04.013

M3 - Article

VL - 67

SP - 1166

EP - 1176

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 12

ER -