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
SMILES
OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O)C=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Iridoid glucosides from Veronica hederifolia. | 2002 Aug |
|
| Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002 Jul |
|
| Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. | 2003 Jul |
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| 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 |
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| Earthworms and litter distribution affect plant-defensive chemistry. | 2004 Apr |
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| Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs? | 2004 Aug |
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| [Study on optimizing the analysis condition for active compound in Eucommia olive]. | 2004 Dec |
|
| Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica. | 2004 Jul |
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| Iridoids as DNA topoisomerase I poisons. | 2005 Aug |
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| Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts. | 2005 Jul |
|
| [Study on the chemical constituents of Buddleja purdomii]. | 2005 Nov |
|
| Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts. | 2005 Nov |
|
| [Research advances in pharmacology of aucubin and aucubigenin]. | 2007 Dec |
|
| Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides. | 2007 Jan 29 |
|
| Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana. | 2007 May |
|
| [Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction]. | 2007 Nov |
|
| Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt. | 2008 Apr 15 |
|
| 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 |
|
| A potential agent for treating non-small cell lung cancer. | 2008 Sep |
|
| Oviposition cues for a specialist butterfly--plant chemistry and size. | 2008 Sep |
|
| Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells. | 2008 Sep |
|
| Iridoids from Euphrasia genargentea, a rare Sardinian endemism. | 2009 |
|
| The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L. | 2009 Jul |
|
| Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory. | 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 |
|
| Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants. | 2010 Feb |
|
| A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships. | 2010 Jun |
|
| Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites. | 2010 Nov-Dec |
|
| Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
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
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207-540-8
Created by
admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
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M2138
Created by
admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
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PRIMARY | Merck Index | ||
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91458
Created by
admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
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C006650
Created by
admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
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AUCUBIN
Created by
admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
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479-98-1
Created by
admin on Tue Oct 22 08:37:05 UTC 2019 , Edited by admin on Tue Oct 22 08:37:05 UTC 2019
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PRIMARY |
SUBSTANCE RECORD
