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Chemical Compound Review

SureCN6229327     (2S,3R,4S,5R,6R)-2-[3- hydroxy-5-[2-(4...

Synonyms: KB-206626, MCULE-9265326904
 
 
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Disease relevance of Piceid

 

High impact information on Piceid

 

Chemical compound and disease context of Piceid

 

Biological context of Piceid

  • To investigate the possible mechanism of this action, we determined the effects of polydatin on the expression of cell adhesion molecules (CAMs) after ischemia-induced cerebral injury [1].
  • 3, 4'-Dimethoxy-5-hydroxystilbene (DMHS) is a hydroxystilbene compound obtained by methylation and acid hydrolysis of piceid (resveratrol-3-O-glucoside) from Polygonum cuspidatum [7].
  • Comparison of the IC50 values of resveratrol for protein-tyrosine kinase inhibitory activity with those of piceid (resveratrol-O3-beta-glucoside) [2] and resveratrol-O4'-beta-glucoside [3] shows the requirement of free hydroxyl groups on both phenyl rings for the protein-tyrosine kinase inhibition [8].
  • We have shown that the administration of Polydatin, a crystalline product isolated from a traditional Chinese medicine, can restore the pulse pressure with high survival rate in irreversible shock [9].
  • RESULTS: Phospholipase A(2) activity and the gene expression of secretory phospholipase A(2) type IIA increased after endotoxin injection, but polydatin could inhibit these effects of endotoxin [10].
 

Anatomical context of Piceid

  • A reversed-phase high-performance liquid chromatographic (RPHPLC) method has been developed for the determination of polydatin (PD) in rat plasma, bile, urine, feces and tissue homogenates using 2,3,5,4'-tetrahydroxychrysophenine-beta-d-glucoside as an internal standard [11].
  • After LPS stimulation, the staining for F-actin was faint or even invisible in the cortex, with the formation of stress fibers observed in the cells, which disappeared upon the 10-min polydatin treatment and the F-actin resumed normal arrangement [12].
 

Associations of Piceid with other chemical compounds

 

Analytical, diagnostic and therapeutic context of Piceid

  • Simple and rapid method for cis- and trans-resveratrol and piceid isomers determination in wine by high-performance liquid chromatography using chromolith columns [17].
  • Despite the presence of piceid, in our experimental conditions no increased resistance against the pathogen Melampsora pulcherrima, which causes rust disease, was observed when in vitro bioassays were performed [4].
  • On the basis of our experience in capillary electrophoresis for separation of polyphenolic compounds, we developed a general analytical method for piceid identification which was also applicable to complex natural mixtures such as red wine [18].
  • The study suggests that Polydatin has multiple effects on VSMC, MC, WBC and EC, which are related to the enhancement of heart function and improvement of microcirculatory perfusion in shock [19].
  • A total of 8 rats received normal saline intravenously (control group), 8 rats received 10 mg/kg of endotoxin (endotoxic shock group), 8 rats received 1 mg/kg of polydatin after endotoxin injection (polydatin treatment group), and 8 rats received 1 mg/kg of polydatin (polydatin prevention group) 30 minutes before endotoxin injection [10].

References

  1. Involvement of cell adhesion molecules in polydatin protection of brain tissues from ischemia-reperfusion injury. Cheng, Y., Zhang, H.T., Sun, L., Guo, S., Ouyang, S., Zhang, Y., Xu, J. Brain Res. (2006) [Pubmed]
  2. Resveratrol glucoside (Piceid) synthesis in seeds of transgenic oilseed rape (Brassica napus L.). Hüsken, A., Baumert, A., Milkowski, C., Becker, H.C., Strack, D., Möllers, C. Theor. Appl. Genet. (2005) [Pubmed]
  3. Influence of lipophilicity on the interactions of hydroxy stilbenes with cytochrome P450 3A4. Regev-Shoshani, G., Shoseyov, O., Kerem, Z. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  4. Expression of the stilbene synthase (StSy) gene from grapevine in transgenic white poplar results in high accumulation of the antioxidant resveratrol glucosides. Giorcelli, A., Sparvoli, F., Mattivi, F., Tava, A., Balestrazzi, A., Vrhovsek, U., Calligari, P., Bollini, R., Confalonieri, M. Transgenic Res. (2004) [Pubmed]
  5. Biotransformation of resveratrol to piceid by Bacillus cereus. Cichewicz, R.H., Kouzi, S.A. J. Nat. Prod. (1998) [Pubmed]
  6. Effects of naturally occurring stilbene glucosides from medicinal plants and wine, on tumour growth and lung metastasis in Lewis lung carcinoma-bearing mice. Kimura, Y., Okuda, H. J. Pharm. Pharmacol. (2000) [Pubmed]
  7. Induction of apoptosis by 3,4'-dimethoxy-5-hydroxystilbene in human promyeloid leukemic HL-60 cells. Lee, S.H., Ryu, S.Y., Kim, H.B., Kim, M.Y., Chun, Y.J. Planta Med. (2002) [Pubmed]
  8. Kinase inhibitors from Polygonum cuspidatum. Jayatilake, G.S., Jayasuriya, H., Lee, E.S., Koonchanok, N.M., Geahlen, R.L., Ashendel, C.L., McLaughlin, J.L., Chang, C.J. J. Nat. Prod. (1993) [Pubmed]
  9. Hemorheologic events in severe shock. Zhao, K.S. Biorheology. (2005) [Pubmed]
  10. Effect of polydatin on phospholipase A2 in lung tissues in rats with endotoxic shock. Shu, S.Y., Wang, X.Y., Ling, Z.Y., Lu, Z.Y. Chinese journal of traumatology = Zhonghua chuang shang za zhi / Chinese Medical Association. (2004) [Pubmed]
  11. HPLC determination of polydatin in rat biological matrices: application to pharmacokinetic studies. Gao, S., Fan, G., Hong, Z., Yin, X., Yang, S., Wu, Y. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  12. Protective effect of polydatin against lipopolysaccharide-induced myocardial injury. Zhao, Q., Huang, H.X., Jin, C.H. Di Yi Jun Yi Da Xue Xue Bao (2003) [Pubmed]
  13. Determination of piceid and resveratrol in Spanish wines deriving from Monastrell (Vitis vinifera L.) grape variety. Moreno-Labanda, J.F., Mallavia, R., Pérez-Fons, L., Lizama, V., Saura, D., Micol, V. J. Agric. Food Chem. (2004) [Pubmed]
  14. Antioxidant activity and inhibition of alpha-glucosidase by trans-resveratrol, piceid, and a novel trans-stilbene from the roots of Israeli Rumex bucephalophorus L. Kerem, Z., Bilkis, I., Flaishman, M.A., Sivan, L. J. Agric. Food Chem. (2006) [Pubmed]
  15. Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation. Adrian, M., Jeandet, P., Douillet-Breuil, A.C., Tesson, L., Bessis, R. J. Agric. Food Chem. (2000) [Pubmed]
  16. Anticomplementary activity of stilbenes from medicinal plants. Oh, S.R., Ryu, S.Y., Park, S.H., Jung, K.Y., Lee, I.S., An, K.S., Lee, J.J., Lee, H.K. Arch. Pharm. Res. (1998) [Pubmed]
  17. Simple and rapid method for cis- and trans-resveratrol and piceid isomers determination in wine by high-performance liquid chromatography using chromolith columns. Vian, M.A., Tomao, V., Gallet, S., Coulomb, P.O., Lacombe, J.M. Journal of chromatography. A. (2005) [Pubmed]
  18. Capillary electrophoresis determination, synthesis, and stability of resveratrol and related 3-O-beta-D-glucopyranosides. Brandolini, V., Maietti, A., Tedeschi, P., Durini, E., Vertuani, S., Manfredini, S. J. Agric. Food Chem. (2002) [Pubmed]
  19. The mechanism of Polydatin in shock treatment. Zhao, K.S., Jin, C., Huang, X., Liu, J., Yan, W.S., Huang, Q., Kan, W. Clin. Hemorheol. Microcirc. (2003) [Pubmed]
 
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