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Plant Physiol, February 2002, Vol. 128, pp. 615-624
Transgenic Production of Epoxy Fatty Acids by Expression of a
Cytochrome P450 Enzyme from Euphorbia lagascae
Seed
Edgar B.
Cahoon,*
Kevin G.
Ripp,
Sarah E.
Hall, and
Brian
McGonigle
DuPont Crop Genetics, Experimental Station, Wilmington, Delaware
19880-0402
Seed oils of a number of Asteraceae and Euphorbiaceae species are
enriched in 12-epoxyoctadeca-cis-9-enoic acid (vernolic acid), an
unusual 18-carbon  12-epoxy fatty acid with potential
industrial value. It has been previously demonstrated that the epoxy
group of vernolic acid is synthesized by the activity of a
12-oleic acid desaturase-like enzyme in seeds of the
Asteraceae Crepis palaestina and Vernonia
galamensis. In contrast, results from metabolic studies have
suggested the involvement of a cytochrome P450 enzyme in vernolic acid
synthesis in seeds of the Euphorbiaceae species Euphorbia
lagascae. To clarify the biosynthetic origin of vernolic acid
in E. lagascae seed, an expressed sequence tag analysis
was conducted. Among 1,006 randomly sequenced cDNAs from developing
E. lagascae seeds, two identical expressed sequence tags
were identified that encode a cytochrome P450 enzyme classified as
CYP726A1. Consistent with the seed-specific occurrence of vernolic acid
in E. lagascae, mRNA corresponding to the
CYP726A1 gene was abundant in developing seeds, but was
not detected in leaves. In addition, expression of the E.
lagascae CYP726A1 cDNA in Saccharomyces cerevisiae was accompanied by production of vernolic acid in
cultures supplied with linoleic acid and an epoxy fatty acid
tentatively identified as 12-epoxyoctadeca-9,15-dienoic acid
(12-epoxy-18:29,15) in cultures supplied with
 -linolenic acid. Consistent with this, expression of CYP726A1 in
transgenic tobacco (Nicotiana tabacum) callus or somatic
soybean (Glycine max) embryos resulted in the
accumulation of vernolic acid and 12-epoxy-18:29,15.
Overall, these results conclusively demonstrate that Asteraceae species
and the Euphorbiaceae E. lagascae have evolved
structurally unrelated enzymes to generate the 12-epoxy
group of vernolic acid.
*
Corresponding author; e-mail
Edgar.B.Cahoon{at}usa.dupont.com; fax 302-695-8480.
© 2002 American Society of Plant Physiologists
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