The Last Step in Cocaine Biosynthesis Is Catalyzed by a BAHD Acyltransferase

The esterification of methylecgonine (2-carbomethoxy-3β-tropine) with benzoic acid is the final step in the biosynthetic pathway leading to the production of cocaine inErythoxylum coca.Here we report the identification of a member of the BAHD family of plant acyltransferases as cocaine synthase. The...

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Published in:Plant physiology (Bethesda) 2015-01, Vol.167 (1), p.89-101
Main Authors: Schmidt, Gregor Wolfgang, Jirschitzka, Jan, Porta, Tiffany, Reichelt, Michael, Luck, Katrin, Torre, José Carlos Pardo, Dolke, Franziska, Varesio, Emmanuel, Hopfgartner, Gérard, Gershenzon, Jonathan, D'Auria, John Charles
Format: Article
Language:English
Subjects:
Acyltransferases - metabolism
Alkaloids
Antibodies
BIOCHEMISTRY AND METABOLISM
Biosynthesis
Catalysis
Cocaine
Cocaine - analogs & derivatives
Cocaine - analysis
Cocaine - biosynthesis
Enzymes
Erythroxylaceae - enzymology
Erythroxylaceae - metabolism
Imaging
Leaves
Mass spectroscopy
Mesophyll Cells - enzymology
Mesophyll Cells - metabolism
Plant Leaves - enzymology
Plant Leaves - metabolism
Plant Proteins - chemistry
Plant Proteins - metabolism
Plants
Tropanes
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Summary:The esterification of methylecgonine (2-carbomethoxy-3β-tropine) with benzoic acid is the final step in the biosynthetic pathway leading to the production of cocaine inErythoxylum coca.Here we report the identification of a member of the BAHD family of plant acyltransferases as cocaine synthase. The enzyme is capable of producing both cocaine and cinnamoylcocaine via the activated benzoyl- or cinnamoyl-Coenzyme A thioesters, respectively. Cocaine synthase activity is highest in young developing leaves, especially in the palisade parenchyma and spongy mesophyll. These data correlate well with the tissue distribution pattern of cocaine as visualized with antibodies. Matrix-assisted laser-desorption ionization mass spectral imaging revealed that cocaine and cinnamoylcocaine are differently distributed on the upper versus lower leaf surfaces. Our findings provide further evidence that tropane alkaloid biosynthesis in the Erythroxylaceae occurs in the above-ground portions of the plant in contrast with the Solanaceae, in which tropane alkaloid biosynthesis occurs in the roots.
ISSN:0032-0889
1532-2548
DOI:10.1104/pp.114.248187