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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 glucosides from Veronica hederifolia.
2002 Aug
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
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells.
2002 Jun 7
Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.
2003 Jul
Iridoids from Globularia dumulosa.
2003 Mar-Apr
Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition.
2003 Nov
Earthworms and litter distribution affect plant-defensive chemistry.
2004 Apr
Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?
2004 Aug
Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography.
2004 Jan-Feb
Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.
2004 Jul
Iridoids as DNA topoisomerase I poisons.
2005 Aug
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
2005 May
Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts.
2005 Nov
Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.
2006 Feb
Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.
2006 May 10
Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.
2007 Apr 4
[Research advances in pharmacology of aucubin and aucubigenin].
2007 Dec
Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.
2007 Mar
[Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction].
2007 Nov
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts.
2007 Winter
Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).
2008 Aug
Neuroprotection of aucubin in primary diabetic encephalopathy.
2008 Jun
Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.
2008 Mar 17
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
Iridoids from Euphrasia genargentea, a rare Sardinian endemism.
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
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
Free Radical Scavenging Activity of Calotropis gigantea on Streptozotocin-Induced Diabetic Rats.
2009 Nov
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
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
2010 Dec
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.
2010 Nov-Dec
[The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach].
2010 Oct-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