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Plant Physiology 135:71-84 (2004)
© 2004 American Society of Plant Biologists

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BIOCHEMICAL PROCESSES AND MACROMOLECULAR STRUCTURES

Biosynthesis of the Nitrile Glucosides Rhodiocyanoside A and D and the Cyanogenic Glucosides Lotaustralin and Linamarin in Lotus japonicus1

Karin Forslund2, Marc Morant, Bodil Jørgensen, Carl Erik Olsen, Erika Asamizu, Shusei Sato, Satoshi Tabata and Søren Bak*

Plant Biochemistry Laboratory, Department of Plant Biology, and Center for Molecular Plant Physiology (PlaCe; K.F., M.M., S.B.), Biotechnology Group, Danish Institute of Agricultural Sciences (B.J.), and Department of Chemistry (C.E.O.), Royal Veterinary and Agricultural University, 40 Thorvaldsensvej, DK–1871 Frederiksberg C, Copenhagen, Denmark; Kazusa DNA Research Institute, Kisarazu, Chiba 292–0818, Japan (E.A., S.S., S.T.); and Department of Physiological Botany, Evolutionary Biology Centre, Uppsala University, Villavagen 6, SE–752 36 Uppsala, Sweden (K.F.)

Lotus japonicus was shown to contain the two nitrile glucosides rhodiocyanoside A and rhodiocyanoside D as well as the cyanogenic glucosides linamarin and lotaustralin. The content of cyanogenic and nitrile glucosides in L. japonicus depends on plant developmental stage and tissue. The cyanide potential is highest in young seedlings and in apical leaves of mature plants. Roots and seeds are acyanogenic. Biosynthetic studies using radioisotopes demonstrated that lotaustralin, rhodiocyanoside A, and rhodiocyanoside D are derived from the amino acid L-Ile, whereas linamarin is derived from Val. In silico homology searches identified two cytochromes P450 designated CYP79D3 and CYP79D4 in L. japonicus. The two cytochromes P450 are 94% identical at the amino acid level and both catalyze the conversion of Val and Ile to the corresponding aldoximes in biosynthesis of cyanogenic glucosides and nitrile glucosides in L. japonicus. CYP79D3 and CYP79D4 are differentially expressed. CYP79D3 is exclusively expressed in aerial parts and CYP79D4 in roots. Recombinantly expressed CYP79D3 and CYP79D4 in yeast cells showed higher catalytic efficiency with L-Ile as substrate than with L-Val, in agreement with lotaustralin and rhodiocyanoside A and D being the major cyanogenic and nitrile glucosides in L. japonicus. Ectopic expression of CYP79D2 from cassava (Manihot esculenta Crantz.) in L. japonicus resulted in a 5- to 20-fold increase of linamarin content, whereas the relative amounts of lotaustralin and rhodiocyanoside A/D were unaltered.

1 This work was supported by the Danish National Research Foundation by a grant to the Center for Molecular Plant Physiology (PlaCe), by the Danish Agricultural and Veterinary Research Council (grant no. 23–02–0095), and by the Swedish Research Council for Environment, Agricultural Sciences and Spatial Planning (FORMAS; grant no. 672.0825/0096 to K.F.).

2 Present address: Department of Physiological Botany, EBC, Uppsala University, Villavagen 6, SE–752 36 Uppsala, Sweden.

Article, publication date, and citation information can be found at www.plantphysiol.org/cgi/doi/10.1104/pp.103.038059.

* Corresponding author; e-mail bak{at}kvl.dk; fax 45–35283333.

Received December 19, 2003; returned for revision February 20, 2004; accepted February 20, 2004.




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