Lotaustralin

• (2R )-2- methyl-2- {[( 2S, 3R, 4S, 5S, 6R) -3,4,5 - trihydroxy -6-( hydroxymethyl) tetrahydro- 2H- pyran-2- yl] oxy} butanenitril

Colorless needles

Fixed

139 ° C

Soluble in ethyl acetate

Template: Infobox chemical / molecular formula search available

Lotaustralin is a cyanogenic glycoside, which is found in small quantities in the eponymous legume Lotus australis, in cassava (Manihot esculenta ) in Lima bean ( Phaseolus lunatus ), the golden root ( Rhodiola rosea), white clover ( Trifolium repens ) and other plants been.

The epimer ( S)- Epilotaustralin is found mainly in passion flower and the farro Triticum dicoccum.

Lotaustralin has as aglycone, the cyanohydrin of butanone, as a sugar unit, the β -D -glucose and is thus structurally related to Lina Marin. The two glycosides differ only by the respective aglycone, which differs from propanone ( linamarin ) and the butanone ( lotaustralin ) is derived. In many plants, both homologues and the epimers Epilotaustralin be found because the enzymes in the biosynthesis of the three substances are the same. This can translate to linamarin both isoleucine to lotaustralin or Epilotaustralin, and valine.

The enzyme linamarase can both cleave glycosides, the highly toxic hydrocyanic acid is formed; therefore lotaustralin one of the cyanogenic glycosides. The toxicity of linamarin, lotaustralin and Epilotaustralin are at a similar level.