Aucubin

Names

[ CAS No. ]:
479-98-1

[ Name ]:
Aucubin

[Synonym ]:
Rhimanthin
EINECS 207-540-8
Aucubin
Rhinanthin
(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Rhimantin
(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl β-D-glucopyranoside
β-D-Glucopyranoside, (1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl
AUCUBOSIDE
[1S-(1a,4aa,5a,7a)]-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-b-D-glucopyranoside
MFCD00136026
(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxyméthyl)-1,4a,5,7a-tétrahydrocyclopenta[c]pyran-1-yl]oxy}-6-(hydroxyméthyl)tétrahydro-2H-pyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyr-1-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyr-1-yl-β-D-glucopyranoside

Biological Activity

[Description]:

Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities.IC50 value:Target:In vitro: Aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus [1]. Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1β challenge in rat chondrocytes [2]. In vivo:

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Sheng-nan Wang, et al. Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-κB signaling pathway in rat articular chondrocytes. International Immunopharmacology, Volume 24, Issue 2, February 2015

[2]. Xue B, et al. Pharmacokinetics and tissue distribution of Aucubin, Ajugol and Catalpol in rats using a validated simultaneous LC-ESI-MS/MS assay. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:245-53.

[3]. Shirley KP, et al. In Vitro Effects of Plantago Major Extract, Aucubin, and Baicalein on Candida Albicans Biofilm Formation, Metabolic Activity, and Cell Surface Hydrophobicity. J Prosthodont. 2015 Nov 30.

[4]. Yong Min Kim, et al. Aucubin Promotes Neurite Outgrowth in Neural Stem Cells and Axonal Regeneration in Sciatic Nerves. Exp Neurobiol. 2014 Sep; 23(3): 238–245.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
669.0±55.0 °C at 760 mmHg

[ Melting Point ]:
180 - 184ºC

[ Molecular Formula ]:
C₁₅H₂₂O₉

[ Molecular Weight ]:
346.330

[ Flash Point ]:
358.4±31.5 °C

[ Exact Mass ]:
346.126373

[ PSA ]:
149.07000

[ LogP ]:
-3.17

[ Vapour Pressure ]:
0.0±4.6 mmHg at 25°C

[ Index of Refraction ]:
1.660

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Binding properties of antimicrobial agents to lipid membranes using surface plasmon resonance.

Biol. Pharm. Bull. 37(8) , 1383-9, (2014)

In the present study, we examined the interaction of antimicrobial agents with four model lipid membranes that mimicked mammalian cell membranes and Gram-positive and -negative bacterial membranes and...

Positive cooperativity between acceptor and donor sites of the peptidoglycan glycosyltransferase.

Biochem. Pharmacol. 93(2) , 141-50, (2015)

The glycosyltransferases of family 51 (GT51) catalyze the polymerization of lipid II to form linear glycan chains, which, after cross linking by the transpeptidases, form the net-like peptidoglycan ma...

Investigation of the interactions between the EphB2 receptor and SNEW peptide variants.

Growth Factors 32(6) , 236-46, (2014)

EphB2 interacts with cell surface-bound ephrin ligands to relay bidirectional signals. Overexpression of the EphB2 receptor protein has been linked to different types of cancer. The SNEW (SNEWIQPRLPQH...

Related Compounds

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