LOTAUSTRALIN

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

Structure Search

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

HIDE SMILES / InChI

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

Description
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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
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	16667698
Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis.	2001 Apr	11310664
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	15000716
Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus.	2004 May	15122013
Lotaustralin from Rhodiola rosea roots.	2004 Sep	15351122
Cassava plants with a depleted cyanogenic glucoside content in leaves and tubers. Distribution of cyanogenic glucosides, their site of synthesis and transport, and blockage of the biosynthesis by RNA interference technology.	2005 Sep	16126856
Comparative phytochemical characterization of three Rhodiola species.	2006 Nov	16956631
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	18096061
The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles.	2007 Jan	17175442
Intimate roles for cyanogenic glucosides in the life cycle of Zygaena filipendulae (Lepidoptera, Zygaenidae).	2007 Nov	17916505
The beta-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus.	2008 Jul	18467457
Leaching of cyanogenic glucosides and cyanide from white clover green manure.	2008 Jun	18472138
Cyanogenesis of wild lima bean (Phaseolus lunatus L.) is an efficient direct defence in nature.	2009	19424497
454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides.	2009 Dec 2	19954531
Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis.	2010 Dec	20953678
Biosynthesis of 2-hydroxyisobutyric acid (2-HIBA) from renewable carbon.	2010 Feb 25	20184738
Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism.	2010 May	20453117

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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 `Fri Dec 15 17:48:58 GMT 2023` Edited by `admin` on `Fri Dec 15 17:48:58 GMT 2023`
Record UNII	P588137A94
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOTAUSTRALIN

Common Name

English

BUTANENITRILE, 2-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-METHYL-, (2R)-

Common Name

English

.BETA.-D-GLUCOPYRANOSYLOXY-2-METHYLBUTYRONITRILE (R)

Systematic Name

English

Code System Code Type Description

FDA UNII

P588137A94