Disease relevance of Lotaustralin

• The toxicity of cassava has been attributed to its two cyanogenic glycosides, linamarin and lotaustralin [1].

High impact information on Lotaustralin

• 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 [2].
• These data demonstrate that it is possible to drastically reduce the linamarin and lotaustralin content in cassava tubers by blockage of cyanogenic glucoside synthesis in leaves and petioles [3].
• Transgenic cassava (Manihot esculenta Crantz, cv MCol22) plants with a 92% reduction in cyanogenic glucoside content in tubers and acyanogenic (<1% of wild type) leaves were obtained by RNA interference to block expression of CYP79D1 and CYP79D2, the two paralogous genes encoding the first committed enzymes in linamarin and lotaustralin synthesis [3].
• 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 [4].
• These include amygdalin (occurring widely in the Rosaceae), the aliphatic cyanogens linamarin and lotaustralin (widely occurring, especially in the Leguminosae), and dhurrin together with its epimer taxiphyllin (occurring in the genus SORGHUM) [5].

Associations of Lotaustralin with other chemical compounds

• Passiflora morifolia, which under natural conditions contains cyanohydrin glucosides linamarin, lotaustralin and epilotaustralin, converted cyclopentanecarbonitrile, 2-cyclopentenecarbonitrile and 3-methylbutanenitrile into the corresponding cyanohydrin glucosides [6].

Gene context of Lotaustralin

• Analysis of the levels of cyanoglucoside in Acac progeny shows that the level of cyanoglucoside (linamarin and lotaustralin) is inherited and that part of the inherited variation in cyanoglucoside levels is attributable to the existence of different Ac alleles in the parent plant [7].
• The structure of lotaustralin was established by 1D and 2D-NMR spectroscopy, including 1H-1H COSY, NOESY, HMQC, and HMBC, and FAB and HR MS [8].

References