(2RS)-Lotaustralin - CAS 1973415-50-7
Catalog number: B0005-053966
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Molecular Formula:
C11H19NO6
Molecular Weight:
261.27
COA:
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Chemical Family:
Other Natural Compounds
Description:
(2RS)-Lotaustralin is found in the roots of Rhodiola rosea L.
Ordering Information
Catalog Number Size Price Stock Quantity
B0005-053966 5 mg $499 In stock
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Purity:
>98%
Solubility:
Soluble in DMSO
MSDS:
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1.Neurotoxic effect of linamarin in rats associated with cassava (Manihot esculenta Crantz) consumption.
Rivadeneyra-Domínguez E;Vázquez-Luna A;Rodríguez-Landa JF;Díaz-Sobac R Food Chem Toxicol. 2013 Sep;59:230-5. doi: 10.1016/j.fct.2013.06.004. Epub 2013 Jun 15.
Cassava (Manihot esculenta Crantz) is a plant widely used for food consumption in different processed products in rural areas of Africa, Asia, and Latin America. Cassava is a good source of carbohydrates and micronutrients. However, if it is not adequately processed or the consumer has nutritional deficiencies, then its cyanogenic glycoside (i.e., linamarin and lotaustralin) content makes it potentially neurotoxic. In the present study, the neurotoxic effects of different concentrations of linamarin (0.075, 0.15, 0.22, and 0.30 mg/kg) contained in cassava juice were evaluated in the open field and swim tests to identify locomotor alterations in adult male Wistar rats. The linamarin concentration in cassava juice was determined by high-performance liquid chromatography, and the juice was administered intraesophageally for 28 days. The results suggested that the consumption of linamarin in cassava juice increased the number of crossings and rearings in the open field test and caused behavioral deficiency, reflected by lateral swimming, in the swim test on days 21 and 28 of treatment.
2.The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous β-glucosidases resulting from a crucial amino acid substitution.
Lai D;Abou Hachem M;Robson F;Olsen CE;Wang TL;Møller BL;Takos AM;Rook F Plant J. 2014 Jul;79(2):299-311. doi: 10.1111/tpj.12561. Epub 2014 Jun 23.
Lotus japonicus, like several other legumes, biosynthesizes the cyanogenic α-hydroxynitrile glucosides lotaustralin and linamarin. Upon tissue disruption these compounds are hydrolysed by a specific β-glucosidase, resulting in the release of hydrogen cyanide. Lotus japonicus also produces the non-cyanogenic γ- and β-hydroxynitrile glucosides rhodiocyanoside A and D using a biosynthetic pathway that branches off from lotaustralin biosynthesis. We previously established that BGD2 is the only β-glucosidase responsible for cyanogenesis in leaves. Here we show that the paralogous BGD4 has the dominant physiological role in rhodiocyanoside degradation. Structural modelling, site-directed mutagenesis and activity assays establish that a glycine residue (G211) in the aglycone binding site of BGD2 is essential for its ability to hydrolyse the endogenous cyanogenic glucosides. The corresponding valine (V211) in BGD4 narrows the active site pocket, resulting in the exclusion of non-flat substrates such as lotaustralin and linamarin, but not of the more planar rhodiocyanosides.
3.Variation in cyanogenic glycosides across populations of wild lima beans (Phaseolus lunatus) has no apparent effect on bruchid beetle performance.
Shlichta JG;Glauser G;Benrey B J Chem Ecol. 2014 May;40(5):468-75. doi: 10.1007/s10886-014-0434-0. Epub 2014 May 27.
Cyanogenic glycosides (CNGs) act as feeding or oviposition deterrents and are toxic after enzymatic hydrolysis, thus negatively affecting herbivore performance. While most studies on CNGs focus on leaf herbivores, here we examined seeds from natural populations of Phaseolus lunatus in Mexico. The predominant CNGs, linamarin and lotaustralin, were quantified for each population by using ultra-high pressure liquid chromatography-mass spectrometry. We also examined whether there was a correlation between the concentration of CNGs and the performance of the Mexican bean beetle, Zabrotes subfasciatus, on seeds from each population(.) The concentrations of CNGs in the seeds were relatively high compared to the leaves and were significantly variable among populations. Surprisingly, this had little effect on the performance of the bruchid beetles. Zabrotes subfasciatus can tolerate high concentrations of CNGs, most likely because of the limited β-glucosidase activity in the seeds.
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CAS 1973415-50-7 (2RS)-Lotaustralin

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