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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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
 9.2 µM [IC50]
Inhibitor
8297
 8.83 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Iridoid glycosides from Globularia trichosantha.
2001 Jan
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
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
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
Aragoside and iridoid glucosides from Aragoa cundinamarcensis.
2003 Sep
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
[Study on optimizing the analysis condition for active compound in Eucommia olive].
2004 Dec
Patterns of iridoid glycoside production and induction in Plantago lanceolata and the importance of plant age.
2004 Sep
Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
2005 May
On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR.
2005 Nov-Dec
[Research advances in pharmacology of aucubin and aucubigenin].
2007 Dec
Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides.
2007 Jan 29
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
Chinese medicines as a resource for liver fibrosis treatment.
2009 Aug 20
The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L.
2009 Jul
Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.
2009 Nov 1
Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.
2010
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.
2010 Dec 13
[Studies on the chemical constituents of Buddleja albiflora (II)].
2010 Jun
Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.
2010 Nov-Dec
[The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach].
2010 Oct-Dec
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
Patents

Patents

20030180400
1

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:22:13 UTC 2023
Edited
by admin
on Fri Dec 15 19:22:13 UTC 2023
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 Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
NSC
407293
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
MERCK INDEX
m2138
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY Merck Index
PUBCHEM
91458
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
FDA UNII
2G52GS8UML
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
MESH
C006650
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
WIKIPEDIA
AUCUBIN
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
CAS
479-98-1
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID60963965
Created by admin on Fri Dec 15 19:22:13 UTC 2023 , Edited by admin on Fri Dec 15 19:22:13 UTC 2023
PRIMARY
Related Record Type Details
REHMANNIA GLUTINOSA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
PLANTAGO OVATA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
CHASTE TREE FRUIT
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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