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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
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.
2003 Jul
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
Earthworms and litter distribution affect plant-defensive chemistry.
2004 Apr
Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?
2004 Aug
[Study on optimizing the analysis condition for active compound in Eucommia olive].
2004 Dec
Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.
2004 Jul
Iridoids as DNA topoisomerase I poisons.
2005 Aug
Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.
2005 Jul
[Study on the chemical constituents of Buddleja purdomii].
2005 Nov
Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts.
2005 Nov
[Research advances in pharmacology of aucubin and aucubigenin].
2007 Dec
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.
2007 Jan 29
Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.
2007 May
[Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction].
2007 Nov
Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.
2008 Apr 15
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
Oviposition cues for a specialist butterfly--plant chemistry and size.
2008 Sep
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.
2008 Sep
Iridoids from Euphrasia genargentea, a rare Sardinian endemism.
2009
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
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
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