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Plant Physiol, November 2002, Vol. 130, pp. 1536-1544
Differential Production of meta Hydroxylated
Phenylpropanoids in Sweet Basil Peltate Glandular Trichomes and Leaves
Is Controlled by the Activities of Specific Acyltransferases and
Hydroxylases1
David R.
Gang,2*
Till
Beuerle,
Pascaline
Ullmann,
Daniéle
Werck-Reichhart, and
Eran
Pichersky
Department of Molecular, Cellular, and Developmental Biology,
University of Michigan, Ann Arbor, Michigan 48109-1048 (D.R.G., T.B.,
E. P.); and Department of Plant Stress Response, Institute of
Plant Molecular Biology, Centre National de la Recherche Scientifique
Unité Propre de Recherche 2357, Université Louis
Pasteur, 28 Rue Goethe, F-67083 Strasbourg Cedex, France (P.U.,
D.W.-R.)
Sweet basil (Ocimum basilicum)
peltate glandular trichomes produce a variety of small molecular weight
phenylpropanoids, such as eugenol, caffeic acid, and rosmarinic acid,
that result from meta hydroxylation reactions.
Some basil lines do not synthesize eugenol but instead synthesize
chavicol, a phenylpropanoid that does not contain a meta
hydroxyl group. Two distinct acyltransferases, p-coumaroyl-coenzyme A:shikimic acid
p-coumaroyl transferase and p-coumaroyl-coenzyme A:4-hydroxyphenyllactic acid
p-coumaroyl transferase, responsible for the production
of p-coumaroyl shikimate and of
p-coumaroyl 4-hydroxyphenyllactate, respectively, were partially purified and shown to be specific for their substrates. p-Coumaroyl-coenzyme A:shikimic acid
p-coumaroyl transferase is expressed in basil peltate
glands that are actively producing eugenol and is not active in glands
of noneugenol-producing basil plants, suggesting that the levels of
this activity determine the levels of synthesis of some
meta-hydroxylated phenylpropanoids in these glands such as eugenol. Two
basil cDNAs encoding isozymes of cytochrome P450 CYP98A13, which
meta hydroxylates p-coumaroyl shikimate,
were isolated and found to be highly similar (90% identity) to the
Arabidopsis homolog, CYP98A3. Like the Arabidopsis enzyme, the basil
enzymes were found to be very specific for p-coumaroyl shikimate. Finally, additional hydroxylase activities were identified in basil peltate glands that convert p-coumaroyl
4-hydroxyphenyllactic acid to its caffeoyl derivative and
p-coumaric acid to caffeic acid.
1
This work was supported by the U.S. Department
of Agriculture National Research Initiative (competitive grant no.
0003497), by a Margaret and Herman Sokal Fellowship in the Sciences (to D.R.G.), and by the Deutscher Akademischer Austauschdienst
(Gemeinsames Hochschulsonderprogramm III von Bund und Ländern,
Germany; fellowship to T.B.).
2
Present address: Department of Plant Sciences,
University of Arizona, Tucson, AZ 85721-0036.
*
Corresponding author; e-mail gang{at}ag.arizona.edu; fax
520-621-7186.
© 2002 American Society of Plant Biologists
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