AUCUBIN

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 Search

SMILES

[H][C@@]12C=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1([H])C(CO)=C[C@H]2O

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 8297
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26618515	Inhibitor 8297
Apoptosis regulator BAX 2 Target ID: CHEMBL5318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24586300	Inhibitor 8297
Hepatitis B virus 8 Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100510	Inhibitor 8297
Leishmania donovani 13 Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15680992	Inhibitor 8297
TNF-alpha 18 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 8297	9.2 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25576403 \| https://www.ncbi.nlm.nih.gov/pubmed/19735174	Inhibitor 8297	8.83 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18430063	Primary	Basic research	Unknown Approved Use Unknown
Fungal infection 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26618515	Curative	Basic research	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 30 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 57 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100510	Primary	Basic research	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25576403	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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
Iridoids from Globularia dumulosa.	2003 Mar-Apr	12710725
Iridoid and bisiridoid glycosides from Globularia cordifolia.	2003 May-Jun	12872925
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
Chemotaxonomic markers in Digitalideae (Plantaginaceae).	2005 Jun	15907957
Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.	2007 Apr 4	17123759
Overexpression of selenoprotein H reduces Ht22 neuronal cell death after UVB irradiation by preventing superoxide formation.	2007 Feb 11	17389926
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
Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.	2007 Mar	16972093
Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.	2007 May	17399747
Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts.	2007 Winter	20368951
Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.	2008 Apr 15	18415863
Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).	2008 Aug	18599096
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.	2008 Jan 22	17988817
Neuroprotection of aucubin in primary diabetic encephalopathy.	2008 Jun	18488169
A potential agent for treating non-small cell lung cancer.	2008 Sep	18782201
Oviposition cues for a specialist butterfly--plant chemistry and size.	2008 Sep	18612691
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
[Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides].	2009 Aug	19894530
Chinese medicines as a resource for liver fibrosis treatment.	2009 Aug 20	19695098
The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L.	2009 Jul	19568812
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
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.	2009 Nov 1	19744895
X-ray crystal structure of iridoid glucoside aucubin and its aglycone.	2009 Nov 2	19762008
[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
[Studies on the chemical constituents of Buddleja albiflora (II)].	2010 Jun	21049618
A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.	2010 Jun	20227146
Chungsim-Yeunja-Tang decreases the inflammatory response in peripheral blood mononuclear cells from patients with cerebral infarction through an NF-κB dependent mechanism.	2010 Nov 25	21108840
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