ArticlePlant physiology2004
Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus.
Article in Plant physiology, 2004. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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35 citing papers in PubMed, 109 citations in OpenAlex.
- Plant cyanogenic glycosides: from structure to properties and potential applications.Frontiers in plant science · 2025Review
- Chemical Analysis and Biological Activities of Extracts Isolated from SymbioticLife (Basel, Switzerland) · 2024Article
- Biochemical Screening, Fabrication of Green Nanoparticles and Its Antimicrobial, and Antioxidant Studies of Endophytic FungusIndian journal of microbiology · 2023Article
- Plant Allelochemicals as Sources of Insecticides.Insects · 2021Review
- Engineering Plant Synthetic Pathways for the Biosynthesis of Novel Antifungals.ACS central science · 2020Article
- Biosynthesis of cyanogenic glucosides inPlant direct · 2020Article
- Characterization of Arabidopsis CYP79C1 and CYP79C2 by Glucosinolate Pathway Engineering inFrontiers in plant science · 2020Article
- Molecular identification and functional characterization of a cyanogenic glucosyltransferase from flax (Linum unsitatissimum).PloS one · 2020Article
- Production of the cyanogenic glycoside dhurrin in yeast.Metabolic engineering communications · 2019Article
- New paths of cyanogenesis from enzymatic-promoted cleavage of β-cyanoglucosides are suggested by a mixed DFT/QTAIM approach.Journal of molecular modeling · 2019Article
- Sequestration and biosynthesis of cyanogenic glucosides in passion vine butterflies and consequences for the diversification of their host plants.Ecology and evolution · 2019Article
- Reconfigured Cyanogenic Glucoside Biosynthesis inPlant physiology · 2018Article
- Elucidation of the Amygdalin Pathway Reveals the Metabolic Basis of Bitter and Sweet Almonds (Plant physiology · 2018Article
- Review
- The Rhizobia-Frontiers in microbiology · 2018Review
- Mass Spectrometry Based Imaging of Labile Glucosides in Plants.Frontiers in plant science · 2018Article
- Components of the SNARE-containing regulon are co-regulated in root cells undergoing defense.Plant signaling & behavior · 2017Article
- Cyanogenic Glucosides and Derivatives in Almond and Sweet Cherry Flower Buds from Dormancy to Flowering.Frontiers in plant science · 2017Article
- Article
- CYP79D enzymes contribute to jasmonic acid-induced formation of aldoximes and other nitrogenous volatiles in two Erythroxylum species.BMC plant biology · 2016Article
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8 authors.
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Abstract
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.
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