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A coumarin‐specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley
Author(s) -
Karamat Fazeelat,
Olry Alexandre,
Munakata Ryosuke,
Koeduka Takao,
Sugiyama Akifumi,
Paris Cedric,
Hehn Alain,
Bourgaud Frédéric,
Yazaki Kazufumi
Publication year - 2014
Publication title -
the plant journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 3.058
H-Index - 269
eISSN - 1365-313X
pISSN - 0960-7412
DOI - 10.1111/tpj.12409
Subject(s) - furanocoumarin , umbelliferone , prenyltransferase , prenylation , psoralen , coumarin , chemistry , stereochemistry , biochemistry , enzyme , organic chemistry , dna
Summary Furanocoumarins constitute a sub‐family of coumarin compounds with important defense properties against pathogens and insects, as well as allelopathic functions in plants. Furanocoumarins are divided into two sub‐groups according to the alignment of the furan ring with the lactone structure: linear psoralen and angular angelicin derivatives. Determination of furanocoumarin type is based on the prenylation position of the common precursor of all furanocoumarins, umbelliferone, at C6 or C8, which gives rise to the psoralen or angelicin derivatives, respectively. Here, we identified a membrane‐bound prenyltransferase Pc PT from parsley ( Petroselinum crispum ), and characterized the properties of the gene product. Pc PT expression in various parsley tissues is increased by UV irradiation, with a concomitant increase in furanocoumarin production. This enzyme has strict substrate specificity towards umbelliferone and dimethylallyl diphosphate, and a strong preference for the C6 position of the prenylated product (demethylsuberosin), leading to linear furanocoumarins. The C8‐prenylated derivative (osthenol) is also formed, but to a much lesser extent. The Pc PT protein is targeted to the plastids in planta . Introduction of this Pc PT into the coumarin‐producing plant Ruta graveolens showed increased consumption of endogenous umbelliferone. Expression of Pc PT and a 4–coumaroyl CoA 2'–hydroxylase gene in Nicotiana benthamiana , which does not produce furanocoumarins, resulted in formation of demethylsuberosin, indicating that furanocoumarin production may be reconstructed by a metabolic engineering approach. The results demonstrate that a single prenyltransferase, such as Pc PT , opens the pathway to linear furanocoumarins in parsley, but may also catalyze the synthesis of osthenol, the first intermediate committed to the angular furanocoumarin pathway, in other plants.