Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H19NO6 |
Molecular Weight | 261.2717 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@@](C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C#N
InChI
InChIKey=WEWBWVMTOYUPHH-QHAQEBJBSA-N
InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1
Molecular Formula | C11H19NO6 |
Molecular Weight | 261.2717 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16667698Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/21045121|https://www.ncbi.nlm.nih.gov/pubmed/15351122|http://dx.doi.org/10.1590/S0104-79301996000100002|https://www.ncbi.nlm.nih.gov/pubmed/5651322|https://www.ncbi.nlm.nih.gov/pubmed/9332002
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16667698
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/21045121|https://www.ncbi.nlm.nih.gov/pubmed/15351122|http://dx.doi.org/10.1590/S0104-79301996000100002|https://www.ncbi.nlm.nih.gov/pubmed/5651322|https://www.ncbi.nlm.nih.gov/pubmed/9332002
Lotaustralin is a cyanogenic glucoside found in small amounts in tropical root crop cassava (Manihot esculenta), lima bean (Phaseolus lunatus), roseroot (Rhodiola rosea) and other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and a precursor to the toxic compound hydrogen cyanide. Extracted from Rhodiola sacra lotaustralin potently inhibited the histamine release from rat peritoneal exudate cells induced by an antigen-antibody reaction exhibiting antiallergic activity.
Approval Year
PubMed
Title | Date | PubMed |
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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). | 1990 Sep |
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Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis. | 2001 Apr |
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Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide. | 2004 Feb |
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Sequencing analysis of 20,000 full-length cDNA clones from cassava reveals lineage specific expansions in gene families related to stress response. | 2007 Dec 20 |
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The beta-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus. | 2008 Jul |
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Leaching of cyanogenic glucosides and cyanide from white clover green manure. | 2008 Jun |
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Cyanogenesis of wild lima bean (Phaseolus lunatus L.) is an efficient direct defence in nature. | 2009 |
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454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides. | 2009 Dec 2 |
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Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis. | 2010 Dec |
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Biosynthesis of 2-hydroxyisobutyric acid (2-HIBA) from renewable carbon. | 2010 Feb 25 |
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Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism. | 2010 May |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9332002
Extracted from Rhodiola sacra lotaustralin inhibited the histamine release from rat peritoneal exudate cells induced by an antigen-antibody reaction at 760 uM - 6.6 mM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:48:58 UTC 2023
by
admin
on
Fri Dec 15 17:48:58 UTC 2023
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Record UNII |
P588137A94
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Record Status |
Validated (UNII)
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Record Version |
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P588137A94
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LOTAUSTRALIN
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DTXSID30897501
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441467
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534-67-8
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