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Chemical Compound Review

Tadeodal     (1R,4aS,8aS)-5,5,8a- trimethyl-1,4,4a,6,7,8...

Synonyms: Tadeonal, Poligodial, Polygodial, Epipolygodial, CHEMBL254550, ...
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Disease relevance of QUIRAL TADEODAL

  • The mechanism by which polygodial produces antinociception seems likely to involve an interaction with the opioid system, mainly kappa and delta subtypes, depend on the activation of G(i/o) protein sensitive to pertussis toxin, alpha(1)-adrenoceptors, and the serotoninergic system [1].
  • Polygodial and (2E)-hexenal were found to possess antibacterial activity against Salmonella choleraesuis with the minimum bactericidal concentrations (MBC) of 50 microg/mL (0.17 mM) and 100 microg/mL (0.98 mM), respectively [2].
  • Finally, polygodial (4.2-42.7 micromol/kg, i.p.) produced dose-related inhibition of paw oedema induced by ovalbumin, protecting in a time-dependent manner the anaphylactic shock induced by endovenous administration of ovalbumin in animals which had been actively sensitised by this antigen [3].
  • Stereospecificity of allergic contact dermatitis (ACD) to enantiomers. Part III. experimentally induced ACD to a natural sesquiterpene dialdehyde, polygodial in guinea pigs [4].
  • OBJECTIVE: The aim of the present study was to test the hypothesis that protein-calorie malnutrition aggravates the gut translocation of Candida albicans triggered by mesenteric ischemia-reperfusion (IR) injury in an experimental model while testing a natural product containing the antifungal anethole/polygodial mixture (Kolorex) [5].

High impact information on QUIRAL TADEODAL


Chemical compound and disease context of QUIRAL TADEODAL

  • In contrast, polygodial antinociception was significantly attenuated by i.p. treatment of animals with naloxone, naltrindole, 2-(3, 4-dichlorophenyl)-n-methyl-n-[(1S)-1-(3-isothiocynatophenyl)-2-(1- pry rolidinyl)ethyl]acetamide, p-chlorophenylalanine, prazosin, or by i. c.v. treatment with pertussis toxin [1].

Biological context of QUIRAL TADEODAL

  • The effect of polygodial on the mitochondrial energy metabolism is described in this paper [8].
  • We postulate that polygodial uncouples mitochondrial ATP synthesis by affecting the electrical properties of the membrane surface and consequently collapsing the membrane potential (Deltapsi) and/or the localized transmembrane pH difference (DeltapH(S)) without affecting the DeltapH between the two bulk aqueous phases (DeltapH(B)) [8].
  • Based on killing kinetics against growing and nongrowing C. albicans, polygodial showed strong and rapid fungicidal activity [9].
  • These results demonstrate that the vasorelaxation of polygodial is partly dependent on the release of nitric oxide (NO )or an NO-derived substance from the vascular endothelium through an activation of a guanylyl cyclase-dependent mechanism [10].
  • At the median inhibitory concentration (IC50) level, polygodial was approximately 114- to 177-fold more active in inhibiting mediated contractions to senktide and phorbol ester [11].

Anatomical context of QUIRAL TADEODAL


Associations of QUIRAL TADEODAL with other chemical compounds


Gene context of QUIRAL TADEODAL

  • The polygodial-induced formation of IP1 was reduced by 71% under extracellular calcium-free conditions, which suggests feedback interactions between the IP formation and the increase in [Ca2+]i to account for a periodic activation of phospholipase C(PLC) [16].
  • In addition, these data confirm and extend our previous suggestion that polygodial preferentially antagonizes tachykinin-mediated contraction, especially the NK3-mediated responses [11].
  • When assessed in the tonic contraction induced by endothelin-1 (0.5 nM) or by phorbol (3 microM), polygodial (0.1-100 microM) produced concentration-dependent relaxation, with maximal inhibition (E(max)) of 62 +/- 2% and 100%, respectively [11].
  • The sesquiterpene, polygodial, also exhibited strong inhibitory activity against human platelet aggregation and 5-LOX [17].

Analytical, diagnostic and therapeutic context of QUIRAL TADEODAL


  1. Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial. Mendes, G.L., Santos, A.R., Malheiros, A., Filho, V.C., Yunes, R.A., Calixto, J.B. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  2. Naturally occurring anti-Salmonella agents. Kubo, I., Fujita, K. J. Agric. Food Chem. (2001) [Pubmed]
  3. Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial. da Cunha, F.M., Fröde, T.S., Mendes, G.L., Malheiros, A., Cechinel Filho, V., Yunes, R.A., Calixto, J.B. Life Sci. (2001) [Pubmed]
  4. Stereospecificity of allergic contact dermatitis (ACD) to enantiomers. Part III. experimentally induced ACD to a natural sesquiterpene dialdehyde, polygodial in guinea pigs. Stampf, J.L., Benezra, C., Asakawa, Y. Arch. Dermatol. Res. (1982) [Pubmed]
  5. Preventive strategy for Candida gut translocation during ischemia-reperfusion injury supervening on protein-calorie malnutrition. Marotta, F., Barreto, R., Kawakita, S., Minelli, E., Pavasuthipaisit, K., Lorenzetti, A., Nishiwaki, M., Gelosa, F., Fesce, E., Okura, R. Chinese journal of digestive diseases. (2006) [Pubmed]
  6. Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. Lunde, C.S., Kubo, I. Antimicrob. Agents Chemother. (2000) [Pubmed]
  7. Pharmacological characterisation of the plant sesquiterpenes polygodial and drimanial as vanilloid receptor agonists. André, E., Campi, B., Trevisani, M., Ferreira, J., Malheiros, A., Yunes, R.A., Calixto, J.B., Geppetti, P. Biochem. Pharmacol. (2006) [Pubmed]
  8. Inhibition of the mitochondrial ATP synthesis by polygodial, a naturally occurring dialdehyde unsaturated sesquiterpene. Castelli, M.V., Lodeyro, A.F., Malheiros, A., Zacchino, S.A., Roveri, O.A. Biochem. Pharmacol. (2005) [Pubmed]
  9. In vitro antifungal susceptibilities of Candida albicans and other fungal pathogens to polygodial, a sesquiterpene dialdehyde. Lee, S.H., Lee, J.R., Lunde, C.S., Kubo, I. Planta Med. (1999) [Pubmed]
  10. Mechanisms underlying the relaxation caused by the sesquiterpene polygodial in vessels from rabbit and guinea-pig. André, E., Malheiros, A., Cechinel-Filho, V., Yunes, R.A., Calixto, J.B. Eur. J. Pharmacol. (1999) [Pubmed]
  11. Action of polygodial on agonist-induced contractions of the rat portal vein in vitro. El Sayah, M., Filho, V.C., Yunes, R.A., Malheiros, A., Calixto, J.B. J. Cardiovasc. Pharmacol. (2000) [Pubmed]
  12. Action of polygodial, a sesquiterpene isolated from Drymis winteri, in the guinea-pig ileum and trachea 'in vitro'. El Sayah, M., Cechinel Filho, V., Yunes, R.A., Pinheiro, T.R., Calixto, J.B. Eur. J. Pharmacol. (1998) [Pubmed]
  13. Effect of EDTA alone and in combination with polygodial on the growth of Saccharomyces cerevisiae. Kubo, I., Lee, S.H., Ha, T.J. J. Agric. Food Chem. (2005) [Pubmed]
  14. Multifunctional action of antifungal polygodial against Saccharomyces cerevisiae: involvement of pyrrole formation on cell surface in antifungal action. Fujita, K., Kubo, I. Bioorg. Med. Chem. (2005) [Pubmed]
  15. Synergism of polygodial and trans-cinnamic acid on inhibition of root elongation in lettuce seedling growth bioassays. Fujita, K., Kubo, I. J. Chem. Ecol. (2003) [Pubmed]
  16. Polygodial induces inositol phosphate turnover in human neuroblastoma SH-SY5Y cells. Forsby, A., Walum, E. Neurosci. Lett. (1996) [Pubmed]
  17. A Novel Labdane-Type Trialdehyde from Myoga (Zingiber mioga Roscoe) That Potently Inhibits Human Platelet Aggregation and Human 5-Lipoxygenase. Abe, M., Ozawa, Y., Uda, Y., Morimitsu, Y., Nakamura, Y., Osawa, T. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
  18. Subchronic toxicity study of water pepper extract in F344 rats. Kuroiwa, K., Shibutani, M., Inoue, K., Lee, K.Y., Woo, G.H., Hirose, M. Food Chem. Toxicol. (2006) [Pubmed]
  19. Polygodial, the fungitoxic component from the Brazilian medicinal plant Polygonum punctatum. de Almeida Alves, T.M., Ribeiro, F.L., Kloos, H., Zani, C.L. Mem. Inst. Oswaldo Cruz (2001) [Pubmed]
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