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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 of AUCUBIN

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

Molecular Formula C15H22O9
Molecular Weight 346.3304
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 glucosides from Veronica hederifolia.
2002 Aug
Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells.
2002 Jun 7
Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.
2003 Apr
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
Iridoids from Globularia dumulosa.
2003 Mar-Apr
Earthworms and litter distribution affect plant-defensive chemistry.
2004 Apr
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
Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography.
2004 Jan-Feb
Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.
2004 Jul
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
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
2005 May
[Study on the chemical constituents of Buddleja purdomii].
2005 Nov
A validation protocol for the HPTLC standardization of herbal products: application to the determination of acteoside in leaves of Plantago palmata Hook. f.s.
2006 Apr 15
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
Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.
2007 Apr 4
Overexpression of selenoprotein H reduces Ht22 neuronal cell death after UVB irradiation by preventing superoxide formation.
2007 Feb 11
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
Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds.
2007 Jun
Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.
2007 Mar
Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.
2007 May
[Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction].
2007 Nov
Effects of aucubin on the healing of oral wounds.
2007 Nov-Dec
The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.
2008 Jan 22
Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.
2008 Mar 17
Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.
2008 Sep
Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.
2009
Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.
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
The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells.
2009 May
X-ray crystal structure of iridoid glucoside aucubin and its aglycone.
2009 Nov 2
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
2010 Dec
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
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 Jun 26 04:07:56 UTC 2021
Edited
by admin
on Sat Jun 26 04:07:56 UTC 2021
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 Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
MERCK INDEX
M2138
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
FDA UNII
2G52GS8UML
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
MESH
C006650
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
WIKIPEDIA
AUCUBIN
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
CAS
479-98-1
Created by admin on Sat Jun 26 04:07:57 UTC 2021 , Edited by admin on Sat Jun 26 04:07:57 UTC 2021
PRIMARY
Related Record Type Details
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