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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:: 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
Changes in the concentrations of bioactive compounds in plantain leaves.
2002 Apr 24
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.
2003 Apr
Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells.
2004 Aug
Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?
2004 Aug
Patterns of iridoid glycoside production and induction in Plantago lanceolata and the importance of plant age.
2004 Sep
Iridoids as DNA topoisomerase I poisons.
2005 Aug
Antioxidant activity of Plantago bellardii All.
2005 Dec
Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.
2005 Feb
Chemotaxonomic markers in Digitalideae (Plantaginaceae).
2005 Jun
Overexpression of selenoprotein H reduces Ht22 neuronal cell death after UVB irradiation by preventing superoxide formation.
2007 Feb 11
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.
2007 Jan 29
Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.
2008 Apr 15
Cytotoxic activities of Stachys species.
2008 Dec
A potential agent for treating non-small cell lung cancer.
2008 Sep
Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.
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
Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour.
2009 Jan-Feb
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.
2009 Nov 1
Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.
2010 Feb
Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro.
2010 Mar
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