Lotaustralin
From Wikipedia, the free encyclopedia
| Lotaustralin | |
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| 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 | [] |
| PubChem | |
| 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 | 261.24 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 |
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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.
[edit] 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 February 11, 2007.
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| Major Families of Biochemicals | ||
| Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides | ||
| Analogues of nucleic acids: | Types of Glycosides | Analogues of nucleic acids: |
| 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 | |
