Plant Physiology Preview
Published on July 30, 2004; 10.1104/pp.104.045468
Received April 28, 2004
Returned for revision June 23, 2004
Accepted June 24, 2004
Understanding in Vivo Benzenoid Metabolism in Petunia Petal Tissue
Jennifer Boatright , Florence Negre , Xinlu Chen , Christine M. Kish , Barbara Wood , Greg Peel , Irina Orlova , David Gang , David Rhodes , and Natalia Dudareva *
Department of Horticulture and Landscape Architecture, Purdue University, West Lafayette, Indiana 47907 (J.B., F.N., X.C., C.M.K., B.W., G.P., I.O., D.R., N.D.); and Department of Plant Sciences and Institute for Biomedical Science and Biotechnology, University of Arizona, Tucson, Arizona 85721 (D.G.)
* Corresponding author; email: dudareva{at}hort.purdue.edu.
In vivo stable isotope labeling and computer-assisted metabolic flux analysis were used to investigate the metabolic pathways in petunia (Petunia hybrida) cv Mitchell leading from Phe to benzenoid compounds, a process that requires the shortening of the side chain by a C2 unit. Deuterium-labeled Phe (2H5-Phe) was supplied to excised petunia petals. The intracellular pools of benzenoid/phenylpropanoid-related compounds (intermediates and end products) as well as volatile end products within the floral bouquet were analyzed for pool sizes and labeling kinetics by gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. Modeling of the benzenoid network revealed that both the CoA-dependent,  -oxidative and CoA-independent, non--oxidative pathways contribute to the formation of benzenoid compounds in petunia flowers. The flux through the CoA-independent, non--oxidative pathway with benzaldehyde as a key intermediate was estimated to be about 2 times higher than the flux through the CoA-dependent, -oxidative pathway. Modeling of 2H5-Phe labeling data predicted that in addition to benzaldehyde, benzylbenzoate is an intermediate between L-Phe and benzoic acid. Benzylbenzoate is the result of benzoylation of benzyl alcohol, for which activity was detected in petunia petals. A cDNA encoding a benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase was isolated from petunia cv Mitchell using a functional genomic approach. Biochemical characterization of a purified recombinant benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase protein showed that it can produce benzylbenzoate and phenylethyl benzoate, both present in petunia corollas, with similar catalytic efficiencies.
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