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 2596

PubMed

Title	Date	PubMed
Tri-trophic level impact of host plant linamarin and lotaustralin on Tetranychus urticae and its predator Phytoseiulus persimilis.	2010-12	20953678
Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism.	2010-05	20453117
Biosynthesis of 2-hydroxyisobutyric acid (2-HIBA) from renewable carbon.	2010-02-25	20184738
454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides.	2009-12-02	19954531
Cyanogenesis of wild lima bean (Phaseolus lunatus L.) is an efficient direct defence in nature.	2009	19424497
The beta-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus.	2008-07	18467457
Leaching of cyanogenic glucosides and cyanide from white clover green manure.	2008-06	18472138
Sequencing analysis of 20,000 full-length cDNA clones from cassava reveals lineage specific expansions in gene families related to stress response.	2007-12-20	18096061
Intimate roles for cyanogenic glucosides in the life cycle of Zygaena filipendulae (Lepidoptera, Zygaenidae).	2007-11	17916505
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.	2007-01	17175442
Comparative phytochemical characterization of three Rhodiola species.	2006-11	16956631
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.	2005-09	16126856
Lotaustralin from Rhodiola rosea roots.	2004-09	15351122
Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus.	2004-05	15122013
Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide.	2004-02	15000716
Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis.	2001-04	11310664
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).	1990-09	16667698

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 `Mon Mar 31 18:53:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:53:35 GMT 2025`
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)-

Preferred Name

English

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

Systematic Name

English

Code System Code Type Description

FDA UNII

P588137A94