+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus



Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus



Plant Physiology 135(1): 71-84



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.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 004058324

Download citation: RISBibTeXText

PMID: 15122013

DOI: 10.1104/pp.103.038059


Related references

Biosynthesis of the Nitrile Glucosides Rhodiocyanoside a and D and the Cyanogenic Glucosides Lotaustralin and Linamarin in Lotus japonicus. Plant Physiology 135(1): 71-84, 2004

Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. J Biol Chem 239(6): 1674-1679, 1964

Biosynthesis of the Cyanogenic Glucosides Linamarin and Lotaustralin. I. Labeling Studies in Vivo with Linum Usitatissimum. Journal of Biological Chemistry 239: 1674-1679, 1964

Occurrence variation and biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in species of the heliconiini insecta lepidoptera. Comparative Biochemistry & Physiology B 75(1): 65-74, 1983

Biosynthesis and quantitative relationships of the cyanogenic glucosides linamarin and lotaustralin in genera of the heliconiini insecta lepidoptera. Comparative Biochemistry & Physiology B 82(4): 745-749, 1985

Biosynthesis of cyanogenic glucosides in the Lepidoptera. Incorporation of -2-methylpropanealdoxime, 2S--methylbutanealdoxime and D,L--N-hydroxyisoleucine into linamarin and lotaustralin by the larvae of Zygaena trifolii. Insect Biochemistry and Molecular Biology 24(2): 161-165, 1994

Biosynthesis of cyanogenic glucosides in the Lepidoptera Incorporation of U-14C-2-methylpropanealdoxime, 2S-U-14C-methylbutanealdoxime and D,L-U-14C-N-hydroxyisoleucine into linamarin and; lotaustralin by the larvae of Zygaena trifolii. Insect Biochemistry and Molecular Biology 24.2: 161-165, 1994

Biosynthesis of cyanogenic glucosides in the lepidoptera. Incorporation of [U-14C]-2-methylpropanealdoxime, 2S-[U-14C]-nethylbutanealdoxime and d,l-[U-14C]-N-hydroxyisoleucine into linamarin and lotaustralin by the larvae of Zygaena trifolli. Insect Biochemistry and Molecular Biology 24(2): 161-165, 1994

Biosynthesis of cyanogenic glucosides in butterflies and moths effective incorporation of 2 methylpropanenitrile and 2 methylbutanenitrile into linamarin and lotaustralin by zygaena and heliconius species lepidoptera. Insect Biochemistry 17(5): 689-694, 1987

Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme. Plant Physiology 155(1): 282-292, 2011

Biosynthesis of the Cyanogenic Glucosides Linamarin and Lotaustralin in Cassava: Isolation, Biochemical Characterization, and Expression Pattern of Cyp71E7, the Oxime-Metabolizing Cytochrome P450 Enzyme. Plant Physiology 155(1): 282-292, 2011

The origin of the glucosidic linkage oxygen of the cyanogenic glucosides, linamarin and lotaustralin. Journal of Biological Chemistry 247(8): 2384-2386, 1972

Occurrence and variation of the cyanogenic glucosides linamarin and lotaustralin in species of the zygaenidae insecta lepidoptera. Comparative Biochemistry & Physiology B 71(2): 329-332, 1982

Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. Cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes. Journal of Biological Chemistry 275(3): 1966-1975, 2000

Evidence that linamarin and lotaustralin the 2 cyanogenic glucosides of trifolium repens are synthesized by a single set of microsomal enzymes controlled by the ac ac locus. Plant Science Letters 34(1-2): 119-126, 1984