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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 of AUCUBIN

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
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
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
Iridoid glucosides from Veronica pectinata var. glandulosa.
2003 Jul-Aug
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
Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.
2006 May 10
Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.
2007 Jan
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
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.
2008 Jan 22
Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.
2009 Jan-Feb
Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory.
2009 Jul
A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.
2010 Jun
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
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 Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
PRIMARY
NSC
407293
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
PRIMARY
MERCK INDEX
M2138
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
PRIMARY
FDA UNII
2G52GS8UML
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
PRIMARY
MESH
C006650
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
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WIKIPEDIA
AUCUBIN
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
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CAS
479-98-1
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID60963965
Created by admin on Thu Jul 06 02:28:39 UTC 2023 , Edited by admin on Thu Jul 06 02:28:39 UTC 2023
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