AUCUBIN

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430063 | http://www.hmdb.ca/metabolites/HMDB36562
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

Targets

Primary Target	Pharmacology	Potency
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430063	Inhibitor 7728
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26618515	Inhibitor 7728
Apoptosis regulator BAX 1 Target ID: CHEMBL5318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24586300	Inhibitor 7728
Hepatitis B virus 7 Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100510	Inhibitor 7728
Leishmania donovani 13 Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15680992	Inhibitor 7728
TNF-alpha 16 Target ID: CHEMBL4984 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15326552 \| https://www.ncbi.nlm.nih.gov/pubmed/12161100 \| https://www.ncbi.nlm.nih.gov/pubmed/18955286	Inhibitor 7728	9.2 µM [IC50]
Cyclooxygenase-2 189 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25576403 \| https://www.ncbi.nlm.nih.gov/pubmed/19735174	Inhibitor 7728	8.83 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 195 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430063	Primary	Basic research	Unknown Approved Use Unknown
Fungal infection 18 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26618515	Curative	Basic research	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 27 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24586300 https://www.ncbi.nlm.nih.gov/pubmed/10100510	Primary	Basic research	Unknown Approved Use Unknown
Hepatitis B 52 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100510	Primary	Basic research	Unknown Approved Use Unknown
Osteoarthritis 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25576403	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Iridoid glucosides from Veronica hederifolia.	2002 Aug	12192146
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	12564791
Antiviral activity of Plantago major extracts and related compounds in vitro.	2002 Jul	12076751
Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells.	2002 Jun 7	12161100
Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.	2003 Jul	12898413
Iridoids from Globularia dumulosa.	2003 Mar-Apr	12710725
Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition.	2003 Nov	14661859
Earthworms and litter distribution affect plant-defensive chemistry.	2004 Apr	15260217
Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?	2004 Aug	15146326
Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography.	2004 Jan-Feb	15018047
Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.	2004 Jul	15279984
Iridoids as DNA topoisomerase I poisons.	2005 Aug	16206835
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.	2005 May	17192013
Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts.	2005 Nov	16306708
Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.	2006 Feb	16386770
Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.	2006 May 10	16644551
Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.	2007 Apr 4	17123759
[Research advances in pharmacology of aucubin and aucubigenin].	2007 Dec	18338591
Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.	2007 Mar	16972093
[Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction].	2007 Nov	18309665
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts.	2007 Winter	20368951
Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).	2008 Aug	18599096
Neuroprotection of aucubin in primary diabetic encephalopathy.	2008 Jun	18488169
Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.	2008 Mar 17	18230397
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.	2008 Sep	18430063
A new iridoid glycoside from Scrophularia ningpoensis.	2009	19731136
Iridoids from Euphrasia genargentea, a rare Sardinian endemism.	2009	19296385
Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.	2009 Jan-Feb	19382566
The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L.	2009 Jul	19568812
Aucubin prevents loss of hippocampal neurons and regulates antioxidative activity in diabetic encephalopathy rats.	2009 Jul	19140154
Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.	2009 Jun	19271240
Free Radical Scavenging Activity of Calotropis gigantea on Streptozotocin-Induced Diabetic Rats.	2009 Nov	20376213
X-ray crystal structure of iridoid glucoside aucubin and its aglycone.	2009 Nov 2	19762008
Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.	2010	21565762
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].	2010 Dec	21438408
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.	2010 Nov-Dec	21319708
[The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach].	2010 Oct-Dec	21598566
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	20885979
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011 Dec 15	21872416

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

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