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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

OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O)C=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

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

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

PubMed

PubMed

TitleDatePubMed
Iridoid glucosides from Veronica hederifolia.
2002 Aug
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
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
Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.
2005 Feb
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
2005 May
[Study on the chemical constituents of Buddleja purdomii].
2005 Nov
On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR.
2005 Nov-Dec
Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.
2006 Feb
Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.
2007 Apr 4
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.
2007 Jan 29
Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.
2007 May
Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).
2008 Aug
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.
2008 Sep
A new iridoid glycoside from Scrophularia ningpoensis.
2009
Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.
2009
Iridoids from Euphrasia genargentea, a rare Sardinian endemism.
2009
Chinese medicines as a resource for liver fibrosis treatment.
2009 Aug 20
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
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
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
Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.
2010 Feb
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.
2010 Nov-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

In Vivo Use Guide
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
In Vitro Use Guide
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 Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
PRIMARY
MERCK INDEX
M2138
Created by admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
PRIMARY
MESH
C006650
Created by admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
PRIMARY
WIKIPEDIA
AUCUBIN
Created by admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
PRIMARY
CAS
479-98-1
Created by admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
PRIMARY