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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

Molecular Formula C15H22O9
Molecular Weight 346.3298
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique.
2001 Aug
Studies on the possible mechanisms of protective activity against alpha-amanitin poisoning by aucubin.
2001 Feb
Iridoid glycosides from Globularia trichosantha.
2001 Jan
Changes in the concentrations of bioactive compounds in plantain leaves.
2002 Apr 24
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
Iridoid patterns of genus Plantago L. and their systematic significance.
2002 Jan-Feb
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Phenylethanoid and iridoid glycosides from Veronica persica.
2002 Jun
Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells.
2002 Jun 7
Antileukemic activity of selected natural products in Taiwan.
2003
Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.
2003 Apr
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
Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.
2004 Jul
Patterns of iridoid glycoside production and induction in Plantago lanceolata and the importance of plant age.
2004 Sep
Iridoids as DNA topoisomerase I poisons.
2005 Aug
Antioxidant activity of Plantago bellardii All.
2005 Dec
Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.
2005 Feb
Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.
2005 Jul
Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts.
2005 Nov
On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR.
2005 Nov-Dec
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
Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.
2007 Jan
Effects of aucubin on the healing of oral wounds.
2007 Nov-Dec
Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).
2008 Aug
Cytotoxic activities of Stachys species.
2008 Dec
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.
2008 Jan 22
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
A potential agent for treating non-small cell lung cancer.
2008 Sep
Oviposition cues for a specialist butterfly--plant chemistry and size.
2008 Sep
A new iridoid glycoside from Scrophularia ningpoensis.
2009
Iridoids from Euphrasia genargentea, a rare Sardinian endemism.
2009
Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds.
2009 Aug
Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour.
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
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.
2009 Nov 1
Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro.
2010 Mar
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.
Substance Class Chemical
Created
by admin
on Sat Dec 17 02:39:15 UTC 2022
Edited
by admin
on Sat Dec 17 02:39:15 UTC 2022
Record UNII
2G52GS8UML
Record Status Validated (UNII)
Record Version
  • Download
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 Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
NSC
407293
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
MERCK INDEX
M2138
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
FDA UNII
2G52GS8UML
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
MESH
C006650
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
WIKIPEDIA
AUCUBIN
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
CAS
479-98-1
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
EPA CompTox
DTXSID60963965
Created by admin on Sat Dec 17 02:39:15 UTC 2022 , Edited by admin on Sat Dec 17 02:39:15 UTC 2022
PRIMARY
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