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 9 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430063	Inhibitor 3315
Candida albicans 6 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26618515	Inhibitor 3315
Apoptosis regulator BAX 1 Target ID: CHEMBL5318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24586300	Inhibitor 3315
Hepatitis B virus 3 Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100510	Inhibitor 3315
Leishmania donovani 4 Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15680992	Inhibitor 3315
TNF-alpha 9 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 3315	9.2 µM [IC50]
Cyclooxygenase-2 86 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25576403 \| https://www.ncbi.nlm.nih.gov/pubmed/19735174	Inhibitor 3315	8.83 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 79 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430063	Primary	Basic research	Unknown Approved Use Unknown
Fungal infection 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26618515	Curative	Basic research	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 13 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 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100510	Primary	Basic research	Unknown Approved Use Unknown
Osteoarthritis 77 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25576403	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Iridoid glycosides from Globularia trichosantha.	2001 Jan	11170667
Changes in the concentrations of bioactive compounds in plantain leaves.	2002 Apr 24	11958614
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
Antileukemic activity of selected natural products in Taiwan.	2003	12723753
Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.	2003 Apr	12775146
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	12811452
Iridoid glucosides from Veronica pectinata var. glandulosa.	2003 Jul-Aug	12939031
Iridoids from Globularia dumulosa.	2003 Mar-Apr	12710725
Iridoid and bisiridoid glycosides from Globularia cordifolia.	2003 May-Jun	12872925
Aragoside and iridoid glucosides from Aragoa cundinamarcensis.	2003 Sep	12943770
Earthworms and litter distribution affect plant-defensive chemistry.	2004 Apr	15260217
Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells.	2004 Aug	15326552
Chemotaxonomic markers in Digitalideae (Plantaginaceae).	2005 Jun	15907957
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.	2005 May	17192013
[Study on the chemical constituents of Buddleja purdomii].	2005 Nov	16514886
Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.	2006 May 10	16644551
Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.	2007 Jan	17253843
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.	2007 Jan 29	17261169
Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds.	2007 Jun	17298877
Effects of aucubin on the healing of oral wounds.	2007 Nov-Dec	18210752
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts.	2007 Winter	20368951
Cytotoxic activities of Stachys species.	2008 Dec	18672034
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.	2008 Jan 22	17988817
A potential agent for treating non-small cell lung cancer.	2008 Sep	18782201
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.	2008 Sep	18430063
Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.	2009	19418360
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
Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory.	2009 Jul	19408016
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
The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells.	2009 May	19442820
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.	2009 Nov 1	19744895
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].	2010 Dec	21438408
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.	2010 Dec 13	21144003
Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.	2010 Feb	20127151
A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.	2010 Jun	20227146
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.	2010 Nov-Dec	21319708
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