U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H22O9
Molecular Weight 346.3298
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AUCUBIN

SMILES

[H][C@@]12C=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1([H])C(CO)=C[C@H]2O

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
Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique.
2001 Aug
Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.
2003 Jul
Iridoid and bisiridoid glycosides from Globularia cordifolia.
2003 May-Jun
Earthworms and litter distribution affect plant-defensive chemistry.
2004 Apr
Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.
2005 Jul
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
2005 May
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
Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.
2007 May
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.
2008 Jan 22
A new iridoid glycoside from Scrophularia ningpoensis.
2009
Iridoids from Euphrasia genargentea, a rare Sardinian endemism.
2009
[Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides].
2009 Aug
Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds.
2009 Aug
Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.
2009 Jan-Feb
Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour.
2009 Jan-Feb
Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.
2009 Jun
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.
2009 Nov 1
X-ray crystal structure of iridoid glucoside aucubin and its aglycone.
2009 Nov 2
Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.
2010
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.
2010 Dec 13
[The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach].
2010 Oct-Dec
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 Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
NSC
407293
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
MERCK INDEX
M2138
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
FDA UNII
2G52GS8UML
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
MESH
C006650
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
WIKIPEDIA
AUCUBIN
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
CAS
479-98-1
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
EPA CompTox
DTXSID60963965
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY