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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22O9
Molecular Weight 346.3304
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AUCUBIN

SMILES

C1=CO[C@]([H])([C@]2([H])C(=C[C@]([H])([C@]12[H])O)CO)O[C@@]3([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O3)O)O)O

InChI

InChIKey=RJWJHRPNHPHBRN-FKVJWERZSA-N
InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25576403

Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Aucubin has been shown to exhibit anti-proliferative and apoptotic functions. Aucubin has shown effectiveness as antifungal and suggests its promising potential use as solution for C. albicans biofilm-related infections. Aucubin has a range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities.

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Iridoid glycosides from Globularia trichosantha.
2001 Jan
Changes in the concentrations of bioactive compounds in plantain leaves.
2002 Apr 24
Systemic, genotype-specific induction of two herbivore-deterrent iridoid glycosides in Plantago lanceolata L. in response to fungal infection by Diaporthe adunca (Rob.) Niessel.
2002 Dec
Antileukemic activity of selected natural products in Taiwan.
2003
Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.
2003 Apr
Determination of iridoid glycosides in larvae and adults of butterfly Melitaea cinxia by partial filling micellar electrokinetic capillary chromatography-electrospray ionisation mass spectrometry.
2003 Jul
Iridoid glucosides from Veronica pectinata var. glandulosa.
2003 Jul-Aug
Iridoids from Globularia dumulosa.
2003 Mar-Apr
Iridoid and bisiridoid glycosides from Globularia cordifolia.
2003 May-Jun
Aragoside and iridoid glucosides from Aragoa cundinamarcensis.
2003 Sep
Earthworms and litter distribution affect plant-defensive chemistry.
2004 Apr
Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells.
2004 Aug
Chemotaxonomic markers in Digitalideae (Plantaginaceae).
2005 Jun
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
2005 May
[Study on the chemical constituents of Buddleja purdomii].
2005 Nov
Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.
2006 May 10
Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.
2007 Jan
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.
2007 Jan 29
Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds.
2007 Jun
Effects of aucubin on the healing of oral wounds.
2007 Nov-Dec
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts.
2007 Winter
Cytotoxic activities of Stachys species.
2008 Dec
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.
2008 Jan 22
A potential agent for treating non-small cell lung cancer.
2008 Sep
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.
2008 Sep
Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.
2009
Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.
2009 Jan-Feb
The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L.
2009 Jul
Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory.
2009 Jul
Aucubin prevents loss of hippocampal neurons and regulates antioxidative activity in diabetic encephalopathy rats.
2009 Jul
Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.
2009 Jun
The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells.
2009 May
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.
2009 Nov 1
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
2010 Dec
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.
2010 Dec 13
Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.
2010 Feb
A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.
2010 Jun
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.
2010 Nov-Dec
Curcumin protects intestinal mucosal barrier function of rat enteritis via activation of MKP-1 and attenuation of p38 and NF-κB activation.
2010 Sep 24
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
Patents

Patents

Sample Use Guides

Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.
Route of Administration: Intraperitoneal
Aucubin (244 ug/ml) exhibited a strong fungicidal activity at its highest concentration against C. albicans growth.
Name Type Language
AUCUBIN
MI  
Common Name English
AUCUBOSIDE
Common Name English
AUCUBIN [MI]
Common Name English
AUCUBIN (CONSTITUENT OF CHASTE TREE) [DSC]
Common Name English
RHINANTHIN
Common Name English
NSC-407293
Code English
(1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA(C)PYRAN-1-YL-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
207-540-8
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
MERCK INDEX
M2138
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
FDA UNII
2G52GS8UML
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
MESH
C006650
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
WIKIPEDIA
AUCUBIN
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
CAS
479-98-1
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY