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Chemical Compound Review

Aucubin     (2S,3R,4S,5S,6R)-2- [[(1R,2S,6S,7S)-7...

Synonyms: rhinanthin, S2267_Selleck, CHEMBL514882, SureCN381032, CHEBI:69796, ...
 
 
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Disease relevance of C09771

 

High impact information on C09771

 

Biological context of C09771

 

Anatomical context of C09771

  • The partition coefficients of aucubin between n-octanol and buffers of pH 3.0-10.0 were low, while 18.5 +/- 1.3% of aucubin in whole blood partitioned into the blood cells [7].
  • In conclusion, these results suggest that aucubin is a specific inhibitor of NF-kappaB activation in mast cells, which might explain its beneficial effect in the treatment of chronic allergic inflammatory diseases [12].
  • The inhibition of ethoxy coumarin O-deethylase (ECOD) activity by aucubin and its aglycone was examined in a microsomal system and in freshly isolated hepatocytes [13].
  • Except for aucubin, these glucosides induced neurite outgrowth at 0.1 microgram/ml and above in medium after 3 d of treatment [14].
  • Using the human skin fibroblast HS68 cell line in the present study, we investigated the photoprotective effects of aucubin from Eucommia ulmoides [11].
 

Associations of C09771 with other chemical compounds

  • It was found that the representatives of Veroniceae, as well as Globularia, were characterized by mannitol, aucubin, catalpol and catalpol esters [15].
  • Micellar electrokinetic chromatography (MEKC) was used for the separation and determination of two iridoid glycosides, aucubin and catalpol, in several Plantago species growing in Croatia: P. altissima L., P. argentea Chaix, P. coronopus L., P. holosteum Scop [16].
  • The promoting effects of geniposidic acid and aucubin in Eucommia ulmoides Oliver leaves on collagen synthesis [17].
  • Two new iridoids, 10-O-benzoylglobularigenin (1) and dumuloside (2) were isolated from the aerial parts of Globularia dumulosa together with seven known iridoid glucosides, davisioside (3), aucubin (4), melampyroside (5), catalpol (6), 10-O-benzoylcatalpol (7), alpinoside (8) and deacetylalpinoside (9) [18].
  • In addition, GA (IC50: 4.43 x 10(-7) M), AU and GP were significantly inhibited proliferation of osteoclast [19].
 

Gene context of C09771

 

Analytical, diagnostic and therapeutic context of C09771

  • Aucubin, which was not included in the sample mixture used in method development because of overlapping with catalpol in MEKC, was also detected [20].
  • Liver-protective activities of aucubin derived from traditional oriental medicine [21].
  • The duration of hypnosis for the saline control group, the CCl4 alone treated group and the aucubin plus CCl4 treated group was 24.8 +/- 8.5, 60.5 +/- 9.5 and 28.0 +/- 3.2 min, respectively [22].

References

  1. Structural considerations on the iridoids as anti-inflammatory agents. Recio, M.C., Giner, R.M., Máñez, S., Ríos, J.L. Planta Med. (1994) [Pubmed]
  2. Mechanism of covalent adduct formation of aucubin to proteins. Kim, D.H., Kim, B.R., Kim, J.Y., Jeong, Y.C. Toxicol. Lett. (2000) [Pubmed]
  3. Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells. Park, K.S., Chang, I.M. Planta Med. (2004) [Pubmed]
  4. Effects of some iridoids from plant origin on arachidonic acid metabolism in cellular systems. Bermejo Benito, P., Díaz Lanza, A.M., Silván Sen, A.M., De Santos Galindez, J., Fernandez Matellano, L., Sanz Gómez, A., Abad Martínez, M.J. Planta Med. (2000) [Pubmed]
  5. Iridoid Glucosides from Penstemon ovatus. König, M., Seifert, K. Planta Med. (1995) [Pubmed]
  6. In vitro antispasmodic activity of peracetylated penstemonoside, aucubin and catalpol. Ortiz de Urbina, A.V., Martín, M.L., Fernández, B., San Román, L., Cubillo, L. Planta Med. (1994) [Pubmed]
  7. Pharmacokinetic study of an iridoid glucoside: aucubin. Suh, N.J., Shim, C.K., Lee, M.H., Kim, S.K., Chang, I.M. Pharm. Res. (1991) [Pubmed]
  8. Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues. Rakotondramasy, V.C., Laschiazza, R., Lecsö-Bornet, M., Koch, M., Tillequin, F., Deguin, B. J. Nat. Prod. (2007) [Pubmed]
  9. Systemic, genotype-specific induction of two herbivore-deterrent iridoid glycosides in Plantago lanceolata L. in response to fungal infection by Diaporthe adunca (Rob.) Niessel. Marak, H.B., Biere, A., Van Damme, J.M. J. Chem. Ecol. (2002) [Pubmed]
  10. Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore. Nieminen, M., Suomi, J., Van Nouhuys, S., Sauri, P., Riekkola, M.L. J. Chem. Ecol. (2003) [Pubmed]
  11. Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts. Ho, J.N., Lee, Y.H., Park, J.S., Jun, W.J., Kim, H.K., Hong, B.S., Shin, D.H., Cho, H.Y. Biol. Pharm. Bull. (2005) [Pubmed]
  12. Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells. Jeong, H.J., Koo, H.N., Na, H.J., Kim, M.S., Hong, S.H., Eom, J.W., Kim, K.S., Shin, T.Y., Kim, H.M. Cytokine (2002) [Pubmed]
  13. Inhibition of P-450 by aucubin: is the biological activity of aucubin due to its glutaraldehyde-like aglycone? Bartholomaeus, A., Ahokas, J. Toxicol. Lett. (1995) [Pubmed]
  14. Neuritogenic effect of natural iridoid compounds on PC12h cells and its possible relation to signaling protein kinases. Yamazaki, M., Chiba, K., Mohri, T. Biol. Pharm. Bull. (1996) [Pubmed]
  15. Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae. Taskova, R.M., Gotfredsen, C.H., Jensen, S.R. Phytochemistry (2006) [Pubmed]
  16. Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography. Jurisić, R., Debeljak, Z., Vladimir-Knezević, S., Vuković, J. Z. Naturforsch., C, J. Biosci. (2004) [Pubmed]
  17. The promoting effects of geniposidic acid and aucubin in Eucommia ulmoides Oliver leaves on collagen synthesis. Li, Y., Sato, T., Metori, K., Koike, K., Che, Q.M., Takahashi, S. Biol. Pharm. Bull. (1998) [Pubmed]
  18. Iridoids from Globularia dumulosa. Kirmizibekmez, H., Akbay, P., Sticher, O., Caliş, I. Z. Naturforsch., C, J. Biosci. (2003) [Pubmed]
  19. Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition. Ha, H., Ho, J., Shin, S., Kim, H., Koo, S., Kim, I.H., Kim, C. Arch. Pharm. Res. (2003) [Pubmed]
  20. Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique. Suomi, J., Wiedmer, S.K., Jussila, M., Riekkola, M.L. Electrophoresis (2001) [Pubmed]
  21. Liver-protective activities of aucubin derived from traditional oriental medicine. Chang, I.M. Res. Commun. Mol. Pathol. Pharmacol. (1998) [Pubmed]
  22. Protective activities of aucubin against carbon tetrachloride-induced liver damage in mice. Chang, I.M., Ryu, J.C., Park, Y.C., Yun, H.S., Yang, K.H. Drug and chemical toxicology. (1983) [Pubmed]
 
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