Biosynthetic origin of conjugated double bonds: Production of fatty acid components of high-value drying oils in transgenic soybean embryos

E. B. Cahoon, T. J. Carlson, K. G. Ripp, B. J. Schweiger, G. A. Cook, S. E. Hall, A. J. Kinney

Research output: Contribution to journalArticle

146 Citations (Scopus)

Abstract

Vegetable oils that contain fatty acids with conjugated double bonds, such as tung oil, are valuable drying agents in paints, varnishes, and inks. Although several reaction mechanisms have been proposed, little is known of the biosynthetic origin of conjugated double bonds in plant fatty acids. An expressed sequence tag (EST) approach was undertaken to characterize the enzymatic basis for the formation of the conjugated double bonds of α- eleostearic (18:3Δ(9cis, 11trans, 13 trans)) and α-parinaric (18:4Δ(9cis,11trans,13trans,15cis)) acids. Approximately 3,000 ESTs were generated from cDNA libraries prepared from developing seeds of Momordica charantia and Impatiens balsamina, tissues that accumulate large amounts of α-eleostearic and α-parinaric acids, respectively. From ESTs of both species, a class of cDNAs encoding a diverged form of the Δ12-oleic acid desaturase was identified. Expression of full-length cDNAs for the Momordica (MomoFadX) and Impatiens (ImpFadX) enzymes in somatic soybean embryos resulted in the accumulation of α-eleostearic and α-parinaric acids, neither of which is present in untransformed soybean embryos. α-Eleostearic and α-parinaric acids together accounted for as much as 17% (wt/wt) of the total fatty acids of embryos expressing MomoFadX. These results demonstrate the ability to produce fatty acid components of high-value drying oils in transgenic plants. These findings also demonstrate a previously uncharacterized activity for Δ12-oleic acid desaturase-type enzymes that we have termed 'conjugase'.

Original languageEnglish (US)
Pages (from-to)12935-12940
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume96
Issue number22
DOIs
StatePublished - Oct 26 1999

Fingerprint

Soybeans
Expressed Sequence Tags
Oils
Impatiens
Fatty Acids
Embryonic Structures
Paint
Oleic Acid
Momordica
gamma-Glutamyl Hydrolase
Complementary DNA
Hygroscopic Agents
Momordica charantia
Ink
Plant Oils
Genetically Modified Plants
Enzymes
Gene Library
Seeds
Acids

ASJC Scopus subject areas

  • General

Cite this

Biosynthetic origin of conjugated double bonds : Production of fatty acid components of high-value drying oils in transgenic soybean embryos. / Cahoon, E. B.; Carlson, T. J.; Ripp, K. G.; Schweiger, B. J.; Cook, G. A.; Hall, S. E.; Kinney, A. J.

In: Proceedings of the National Academy of Sciences of the United States of America, Vol. 96, No. 22, 26.10.1999, p. 12935-12940.

Research output: Contribution to journalArticle

@article{94ec40e3e4694ab98e14cde5e1566396,
title = "Biosynthetic origin of conjugated double bonds: Production of fatty acid components of high-value drying oils in transgenic soybean embryos",
abstract = "Vegetable oils that contain fatty acids with conjugated double bonds, such as tung oil, are valuable drying agents in paints, varnishes, and inks. Although several reaction mechanisms have been proposed, little is known of the biosynthetic origin of conjugated double bonds in plant fatty acids. An expressed sequence tag (EST) approach was undertaken to characterize the enzymatic basis for the formation of the conjugated double bonds of α- eleostearic (18:3Δ(9cis, 11trans, 13 trans)) and α-parinaric (18:4Δ(9cis,11trans,13trans,15cis)) acids. Approximately 3,000 ESTs were generated from cDNA libraries prepared from developing seeds of Momordica charantia and Impatiens balsamina, tissues that accumulate large amounts of α-eleostearic and α-parinaric acids, respectively. From ESTs of both species, a class of cDNAs encoding a diverged form of the Δ12-oleic acid desaturase was identified. Expression of full-length cDNAs for the Momordica (MomoFadX) and Impatiens (ImpFadX) enzymes in somatic soybean embryos resulted in the accumulation of α-eleostearic and α-parinaric acids, neither of which is present in untransformed soybean embryos. α-Eleostearic and α-parinaric acids together accounted for as much as 17{\%} (wt/wt) of the total fatty acids of embryos expressing MomoFadX. These results demonstrate the ability to produce fatty acid components of high-value drying oils in transgenic plants. These findings also demonstrate a previously uncharacterized activity for Δ12-oleic acid desaturase-type enzymes that we have termed 'conjugase'.",
author = "Cahoon, {E. B.} and Carlson, {T. J.} and Ripp, {K. G.} and Schweiger, {B. J.} and Cook, {G. A.} and Hall, {S. E.} and Kinney, {A. J.}",
year = "1999",
month = "10",
day = "26",
doi = "10.1073/pnas.96.22.12935",
language = "English (US)",
volume = "96",
pages = "12935--12940",
journal = "Proceedings of the National Academy of Sciences of the United States of America",
issn = "0027-8424",
number = "22",

}

TY - JOUR

T1 - Biosynthetic origin of conjugated double bonds

T2 - Production of fatty acid components of high-value drying oils in transgenic soybean embryos

AU - Cahoon, E. B.

AU - Carlson, T. J.

AU - Ripp, K. G.

AU - Schweiger, B. J.

AU - Cook, G. A.

AU - Hall, S. E.

AU - Kinney, A. J.

PY - 1999/10/26

Y1 - 1999/10/26

N2 - Vegetable oils that contain fatty acids with conjugated double bonds, such as tung oil, are valuable drying agents in paints, varnishes, and inks. Although several reaction mechanisms have been proposed, little is known of the biosynthetic origin of conjugated double bonds in plant fatty acids. An expressed sequence tag (EST) approach was undertaken to characterize the enzymatic basis for the formation of the conjugated double bonds of α- eleostearic (18:3Δ(9cis, 11trans, 13 trans)) and α-parinaric (18:4Δ(9cis,11trans,13trans,15cis)) acids. Approximately 3,000 ESTs were generated from cDNA libraries prepared from developing seeds of Momordica charantia and Impatiens balsamina, tissues that accumulate large amounts of α-eleostearic and α-parinaric acids, respectively. From ESTs of both species, a class of cDNAs encoding a diverged form of the Δ12-oleic acid desaturase was identified. Expression of full-length cDNAs for the Momordica (MomoFadX) and Impatiens (ImpFadX) enzymes in somatic soybean embryos resulted in the accumulation of α-eleostearic and α-parinaric acids, neither of which is present in untransformed soybean embryos. α-Eleostearic and α-parinaric acids together accounted for as much as 17% (wt/wt) of the total fatty acids of embryos expressing MomoFadX. These results demonstrate the ability to produce fatty acid components of high-value drying oils in transgenic plants. These findings also demonstrate a previously uncharacterized activity for Δ12-oleic acid desaturase-type enzymes that we have termed 'conjugase'.

AB - Vegetable oils that contain fatty acids with conjugated double bonds, such as tung oil, are valuable drying agents in paints, varnishes, and inks. Although several reaction mechanisms have been proposed, little is known of the biosynthetic origin of conjugated double bonds in plant fatty acids. An expressed sequence tag (EST) approach was undertaken to characterize the enzymatic basis for the formation of the conjugated double bonds of α- eleostearic (18:3Δ(9cis, 11trans, 13 trans)) and α-parinaric (18:4Δ(9cis,11trans,13trans,15cis)) acids. Approximately 3,000 ESTs were generated from cDNA libraries prepared from developing seeds of Momordica charantia and Impatiens balsamina, tissues that accumulate large amounts of α-eleostearic and α-parinaric acids, respectively. From ESTs of both species, a class of cDNAs encoding a diverged form of the Δ12-oleic acid desaturase was identified. Expression of full-length cDNAs for the Momordica (MomoFadX) and Impatiens (ImpFadX) enzymes in somatic soybean embryos resulted in the accumulation of α-eleostearic and α-parinaric acids, neither of which is present in untransformed soybean embryos. α-Eleostearic and α-parinaric acids together accounted for as much as 17% (wt/wt) of the total fatty acids of embryos expressing MomoFadX. These results demonstrate the ability to produce fatty acid components of high-value drying oils in transgenic plants. These findings also demonstrate a previously uncharacterized activity for Δ12-oleic acid desaturase-type enzymes that we have termed 'conjugase'.

UR - http://www.scopus.com/inward/record.url?scp=0033607294&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033607294&partnerID=8YFLogxK

U2 - 10.1073/pnas.96.22.12935

DO - 10.1073/pnas.96.22.12935

M3 - Article

C2 - 10536026

AN - SCOPUS:0033607294

VL - 96

SP - 12935

EP - 12940

JO - Proceedings of the National Academy of Sciences of the United States of America

JF - Proceedings of the National Academy of Sciences of the United States of America

SN - 0027-8424

IS - 22

ER -