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Chemical Compound Review

gingerol     5-hydroxy-1-(4-hydroxy-3- methoxy...

Synonyms: CHEMBL1950582, SureCN2121898, AIDS-228299, CHEBI:10136, HMDB05783, ...
 
 
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Disease relevance of gingerol

  • Ginger extract and its constituents gingerol, shogaol and zingerone were tested in Salmonella typhimurium strains TA 100, TA 98, TA 1535 and TA 1538 in the presence and in absence of S9 mix [1].
  • The concentrations of gingerols, the major constituents of fresh ginger, were reduced slightly in dry ginger, while the concentrations of shogaols, the major gingerol dehydration products, increased [2].
 

High impact information on gingerol

  • The gingerol structure may be used as a template for the development of drugs acting as moderately potent activators of the VR1 receptor [3].
  • Gingerol, a plant derivative, is known to produce similar effects when tested in isolated cardiac muscle [4].
  • The purpose of the present study was to compare the effects of gingerol and another plant derivative, ellagic acid, on the kinetics of the SR Ca2+ pump with those of PKA-catalyzed phospholamban phosphorylation to elucidate their mechanisms of Ca2+ pump regulation [4].
  • The stimulation of Ca2+ uptake attributable to gingerol in unphosphorylated microsomes at saturating Ca2+ was 30% to 40% when assayed at 0.05 to 2 mM MgATP and only about 12% in phosphorylated microsomes as well as in rabbit fast skeletal muscle light SR [4].
  • The measurement of extravesicular Ca++ concentration using a Ca++ electrode indicated that gingerol (3 X 10(-6) to 3 X 10(-5) M) accelerated the Ca++ uptake of fragmented sarcoplasmic reticulum (SR) prepared from canine cardiac muscle in a concentration-dependent manner.(ABSTRACT TRUNCATED AT 250 WORDS)[5]
 

Biological context of gingerol

  • In guinea pig left atria, gingerol (1 X 10(-6) to 3 X 10(-5) M) gave little influence on the action potential, although it increased the contractile force of the atria [5].
  • Gingerol metabolite and a synthetic analogue Capsarol inhibit macrophage NF-kappaB-mediated iNOS gene expression and enzyme activity [6].
  • In contrast to previous findings, this study did not find significant differences in gingerol concentrations between the tetraploid clones and their parent diploid cultivar [7].
  • In this study, structure-activity relationship of gingerol related compounds was evaluated [8].
  • These results provide a basis for the design of more potent synthetic gingerol analogues, with similar potencies to aspirin, as platelet activation inhibitors with potential value in cardiovascular disease [9].
 

Anatomical context of gingerol

 

Gene context of gingerol

  • This occurred at the transcriptional level, since the gingerol compounds decreased LPS-induced IkappaB-alpha degradation, prevented nuclear translocation of NF-kappaB p65 and reduced NF-kappaB activity in a concentration-dependent manner [6].
  • However, a subset of agonists (tinyatoxin, gingerol, and zingerone) was approximately 10-fold more potent for rVR1 compared to hVR1 [11].
  • Antioxidant properties of gingerol related compounds from ginger [8].
  • The COX-1 inhibitory activity of [8]-paradol (IC(50)=4+/-1 microM) was more potent than the gingerol analogues (1 and 5) (IC(50) approximately 20 microM) [12].
 

Analytical, diagnostic and therapeutic context of gingerol

References

  1. Mutagenicity of gingerol and shogaol and antimutagenicity of zingerone in Salmonella/microsome assay. Nagabhushan, M., Amonkar, A.J., Bhide, S.V. Cancer Lett. (1987) [Pubmed]
  2. Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production. Jolad, S.D., Lantz, R.C., Chen, G.J., Bates, R.B., Timmermann, B.N. Phytochemistry (2005) [Pubmed]
  3. Gingerols: a novel class of vanilloid receptor (VR1) agonists. Dedov, V.N., Tran, V.H., Duke, C.C., Connor, M., Christie, M.J., Mandadi, S., Roufogalis, B.D. Br. J. Pharmacol. (2002) [Pubmed]
  4. Interactions of 6-gingerol and ellagic acid with the cardiac sarcoplasmic reticulum Ca2+-ATPase. Antipenko, A.Y., Spielman, A.I., Kirchberger, M.A. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  5. Cardiotonic action of [8]-gingerol, an activator of the Ca++-pumping adenosine triphosphatase of sarcoplasmic reticulum, in guinea pig atrial muscle. Kobayashi, M., Ishida, Y., Shoji, N., Ohizumi, Y. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  6. Gingerol metabolite and a synthetic analogue Capsarol inhibit macrophage NF-kappaB-mediated iNOS gene expression and enzyme activity. Aktan, F., Henness, S., Tran, V.H., Duke, C.C., Roufogalis, B.D., Ammit, A.J. Planta Med. (2006) [Pubmed]
  7. Gingerol content of diploid and tetraploid clones of ginger (Zingiber officinale Roscoe). Wohlmuth, H., Leach, D.N., Smith, M.K., Myers, S.P. J. Agric. Food Chem. (2005) [Pubmed]
  8. Antioxidant properties of gingerol related compounds from ginger. Masuda, Y., Kikuzaki, H., Hisamoto, M., Nakatani, N. Biofactors (2004) [Pubmed]
  9. Gingerols and related analogues inhibit arachidonic acid-induced human platelet serotonin release and aggregation. Koo, K.L., Ammit, A.J., Tran, V.H., Duke, C.C., Roufogalis, B.D. Thromb. Res. (2001) [Pubmed]
  10. Chemical structural requirement in gingerol derivatives for potentiation of prostaglandin F2 alpha-induced contraction in isolated mesenteric veins of mice. Kimura, I., Pancho, L.R., Koizumi, T., Kimura, M. J. Pharmacobio-dyn. (1989) [Pubmed]
  11. Use of a fluorescent imaging plate reader--based calcium assay to assess pharmacological differences between the human and rat vanilloid receptor. Witte, D.G., Cassar, S.C., Masters, J.N., Esbenshade, T., Hancock, A.A. Journal of biomolecular screening : the official journal of the Society for Biomolecular Screening. (2002) [Pubmed]
  12. Effective anti-platelet and COX-1 enzyme inhibitors from pungent constituents of ginger. Nurtjahja-Tjendraputra, E., Ammit, A.J., Roufogalis, B.D., Tran, V.H., Duke, C.C. Thromb. Res. (2003) [Pubmed]
  13. Characterization of gingerol-related compounds in ginger rhizome (Zingiber officinale Rosc.) by high-performance liquid chromatography/electrospray ionization mass spectrometry. Jiang, H., Sólyom, A.M., Timmermann, B.N., Gang, D.R. Rapid Commun. Mass Spectrom. (2005) [Pubmed]
 
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