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Lotaustralin

Lotaustralin


IUPAC name	(2S)-2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5- trihydroxy-6-(hydroxymethyl)tetrahydro-2H- pyran-2-yl]oxy}butanenitrile
Identifiers
CAS number	534-67-8
PubChem	441467
SMILES	CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H] ([C@H](O1)CO)O)O)O
Properties
Molecular formula	C₁₁H₁₉NO₆
Molar mass	261.27 g mol^-1
Density	1.36 g·cm^-3
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Lotaustralin is a cyanogenic glucoside found in small amounts in cassava (Manihot esculenta), lima bean (Phaseolus lunatus),^[1] roseroot (Rhodiola rosea)^[2] and white clover (Trifolium repens),^[3] among other plants. Lotaustralin is structurally related to linamarin, another glucoside found in these plants, and differs from it only by the presence of an extra methyl group. Both lotaustralin and linamarin may be hydrolysed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.

Additional recommended knowledge

References

^ Frehner M, Scalet M, Conn EE (1990). "Pattern of the Cyanide-Potential in Developing Fruits : Implications for Plants Accumulating Cyanogenic Monoglucosides (Phaseolus lunatus) or Cyanogenic Diglucosides in Their Seeds (Linum usitatissimum, Prunus amygdalus)". Plant Physiol 94 (1): 28–34. PMID 16667698. Full text at PMC: 1077184
^ Akgul Y, Ferreira D, Abourashed E, Khan I (2004). "Lotaustralin from Rhodiola rosea roots". Fitoterapia 75 (6): 612–4. PMID 15351122.
^ Notes on poisoning: Trifolium repens. Canadian Poisonous Plants Information System (May 30, 2006). Retrieved on 2007-02-11.

Bond:	O-glycosidic bond \| S-glycosidic bond \| N-glycosidic bond
Geometry:	α-Glycoside \| β-Glycoside \| 1,4-Glycoside \| 1,6-Glycoside
Glycone:	Glucoside \| Fructoside \| Glucuronide
Aglycone:	Alcoholic glycoside \| Anthraquinone glycoside \| Coumarin glycoside \| Cyanogenic glycoside \| Flavonoid glycoside \| Phenolic glycoside \| Saponin \| Cardiac glycoside \| Steviol glycoside \| Thioglycoside \| Glycosylamine \| Bufanolide \| Cardenolide