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Chemical Compound Review

Glyciram     (2S,4aS,6aR,6aS,6bR,8aR,10S,12 aS,14bR)-10...

Synonyms: Biosone, Enoloxone, enoxolone, Arthrodont, Jintan, ...
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Disease relevance of enoxolone


High impact information on enoxolone

  • In the presence of GA, there was a shift of the ACTH concentration-response curves in the two culture conditions [3].
  • Gap junction blockade with 18 alpha-glycyrrhetinic acid resulted in a loss of coordination between connected cells [4].
  • Total inhibition of fluorescent dye transfer between normal and transformed cells by the 3 beta-O-hemisuccinate of 18 alpha-glycyrrhetinic acid (18 alpha-carbenoxolone), an inhibitor of gap-junctional communication in human fibroblasts, did not prevent growth inhibition of transformed cells in the cocultivation assay [5].
  • A blockade of junctional communication by 18-beta-glycyrrhetinic acid (betaGA) reduced, in a concentration-dependent manner, the viability of undifferentiated neural progenitor cells [6].
  • In parallel experiments, AGA decreased the immunodetection of phosphorylated Cx43 as analyzed by Western blot and inhibited fluorescent dye transfer [7].

Biological context of enoxolone

  • The 9L cells exhibited a very good bystander effect, which was completely blocked by a long-term inhibitor of GJIC, 18 alpha-glycyrrhetinic acid [8].
  • When the inhibitory activities were examined with intact transfected cells, 11 alpha OH-P was more potent than GA (IC50 = 5 and 150 nM, respectively) [9].
  • These data implicate a gap junctional-mediated pathway insensitive to 18-beta-glycyrrhetinic acid in dilating the two arterioles upstream of the capillary module during "remote" muscle contraction [10].
  • Last, our data indicate that the closure of gap junctions by the decoupling agent alpha-glycyrrhetinic acid increases cell apoptosis and inhibits hESC colony growth [11].
  • An unexpected observation was the apparent lack of any effect of inhibiting GJIC by exposure to AGA on blastocyst formation and cell number allocation in the two principal stem cell lineages of the preimplantation mammalian embryo, trophectoderm and inner cell mass [12].

Anatomical context of enoxolone


Associations of enoxolone with other chemical compounds


Gene context of enoxolone

  • Moreover, AGA-exposed cells showed a dose-dependent decrease in AP activity and a delay in the appearance of BN [21].
  • Treatment with AGA, but not with an inactive analog, reversed the PTH-induced ECM mineralization [22].
  • In contrast, 18-beta-glycyrrhetinic acid and competitive 5-lipoxygenase inhibitors (e.g., ZM-230,487 and L-739,010) did not affect labeling [23].
  • Blockage of the RA + Tx-induced GJIC with 18-beta-glycyrrhetinic acid (beta-Gly) prevented in 34% the inhibition of MCF-7 proliferation and the E-cadherin increment in 30% at 96 h of culture [24].
  • Since these substances mimic two known inhibitory activities of GA, they have been named 'Glycyrrhetic Acid-Like Factors', abbreviated as 'GALFs' or, more specifically 11 beta-GALF for substance(s) active against 11 beta-OHSD, and 5 beta-GALF for those inhibitory to 5 beta-SR [25].

Analytical, diagnostic and therapeutic context of enoxolone


  1. Adenoviral delivery of human connexin37 induces endothelial cell death through apoptosis. Seul, K.H., Kang, K.Y., Lee, K.S., Kim, S.H., Beyer, E.C. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  2. Re-evaluation of tacrine hepatotoxicity using gel entrapped hepatocytes. Meng, Q., Ru, J., Zhang, G., Shen, C., Schmitmeier, S., Bader, A. Toxicol. Lett. (2007) [Pubmed]
  3. Gap junction-mediated cell-to-cell communication in bovine and human adrenal cells. A process whereby cells increase their responsiveness to physiological corticotropin concentrations. Munari-Silem, Y., Lebrethon, M.C., Morand, I., Rousset, B., Saez, J.M. J. Clin. Invest. (1995) [Pubmed]
  4. Coordinated intercellular calcium waves induced by noradrenaline in rat hepatocytes: dual control by gap junction permeability and agonist. Tordjmann, T., Berthon, B., Claret, M., Combettes, L. EMBO J. (1997) [Pubmed]
  5. Growth inhibition of oncogene-transformed rat fibroblasts by cocultured normal cells: relevance of metabolic cooperation mediated by gap junctions. Martin, W., Zempel, G., Hülser, D., Willecke, K. Cancer Res. (1991) [Pubmed]
  6. Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells. Duval, N., Gomès, D., Calaora, V., Calabrese, A., Meda, P., Bruzzone, R. J. Cell. Sci. (2002) [Pubmed]
  7. Gap junction-mediated bystander effect in primary cultures of human malignant gliomas with recombinant expression of the HSVtk gene. Asklund, T., Appelskog, I.B., Ammerpohl, O., Langmoen, I.A., Dilber, M.S., Aints, A., Ekström, T.J., Almqvist, P.M. Exp. Cell Res. (2003) [Pubmed]
  8. A cell type-specific and gap junction-independent mechanism for the herpes simplex virus-1 thymidine kinase gene/ganciclovir-mediated bystander effect. Princen, F., Robe, P., Lechanteur, C., Mesnil, M., Rigo, J.M., Gielen, J., Merville, M.P., Bours, V. Clin. Cancer Res. (1999) [Pubmed]
  9. 11 beta-Hydroxysteroid dehydrogenase type 2 complementary deoxyribonucleic acid stably transfected into Chinese hamster ovary cells: specific inhibition by 11 alpha-hydroxyprogesterone. Morita, H., Zhou, M., Foecking, M.F., Gomez-Sanchez, E.P., Cozza, E.N., Gomez-Sanchez, C.E. Endocrinology (1996) [Pubmed]
  10. Remote arteriolar dilations in response to muscle contraction under capillaries. Cohen, K.D., Berg, B.R., Sarelius, I.H. Am. J. Physiol. Heart Circ. Physiol. (2000) [Pubmed]
  11. Gap junctions modulate apoptosis and colony growth of human embryonic stem cells maintained in a serum-free system. Wong, R.C., Dottori, M., Koh, K.L., Nguyen, L.T., Pera, M.F., Pébay, A. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  12. Gap junction intercellular communication mediates the competitive cell proliferation disadvantage of irradiated mouse preimplantation embryos in aggregation chimeras. Vance, M.M., Wiley, L.M. Radiat. Res. (1999) [Pubmed]
  13. The enhancement of glucose uptake caused by the collapse of gap junction communication is due to an increase in astrocyte proliferation. Tabernero, A., Jiménez, C., Velasco, A., Giaume, C., Medina, J.M. J. Neurochem. (2001) [Pubmed]
  14. Intercellular communication in the immune system: differential expression of connexin40 and 43, and perturbation of gap junction channel functions in peripheral blood and tonsil human lymphocyte subpopulations. Oviedo-Orta, E., Hoy, T., Evans, W.H. Immunology (2000) [Pubmed]
  15. Gap junctional communication and connexin43 expression in relation to apoptotic cell death and survival of granulosa cells. Krysko, D.V., Mussche, S., Leybaert, L., D'Herde, K. J. Histochem. Cytochem. (2004) [Pubmed]
  16. Cardiac mitochondrial connexin 43 regulates apoptosis. Goubaeva, F., Mikami, M., Giardina, S., Ding, B., Abe, J., Yang, J. Biochem. Biophys. Res. Commun. (2007) [Pubmed]
  17. 18-beta-Glycyrrhetinic acid (BGA) as an electrical uncoupler for intracellular recordings in confluent monolayer cultures. Böhmer, C., Kirschner, U., Wehner, F. Pflugers Arch. (2001) [Pubmed]
  18. Gap junctions and inhibitory synapses modulate inspiratory motoneuron synchronization. Bou-Flores, C., Berger, A.J. J. Neurophysiol. (2001) [Pubmed]
  19. Gap junction channels reconstituted in two closely apposed lipid bilayers. Ramundo-Orlando, A., Serafino, A., Villalobo, A. Arch. Biochem. Biophys. (2005) [Pubmed]
  20. Role of gap junctions in acetylcholine-induced vasodilation of proximal and distal arteries of the rat mesentery. Hill, C.E., Hickey, H., Sandow, S.L. J. Auton. Nerv. Syst. (2000) [Pubmed]
  21. Gap-junctional communication is required for the maturation process of osteoblastic cells in culture. Schiller, P.C., D'Ippolito, G., Balkan, W., Roos, B.A., Howard, G.A. Bone (2001) [Pubmed]
  22. Gap-junctional communication mediates parathyroid hormone stimulation of mineralization in osteoblastic cultures. Schiller, P.C., D'Ippolito, G., Balkan, W., Roos, B.A., Howard, G.A. Bone (2001) [Pubmed]
  23. Characterization of an acetyl-11-keto-beta-boswellic acid and arachidonate-binding regulatory site of 5-lipoxygenase using photoaffinity labeling. Sailer, E.R., Schweizer, S., Boden, S.E., Ammon, H.P., Safayhi, H. Eur. J. Biochem. (1998) [Pubmed]
  24. Increased gap junctional intercellular communication is directly related to the anti-tumor effect of all-trans-retinoic acid plus tamoxifen in a human mammary cancer cell line. Sáez, C.G., Velásquez, L., Montoya, M., Eugenín, E., Alvarez, M.G. J. Cell. Biochem. (2003) [Pubmed]
  25. Inhibitors of 11 beta-hydroxysteroid dehydrogenase and 5 beta-steroid reductase in urine from patients with congestive heart failure. Semafuko, W.E., Sheff, M.F., Grimes, C.A., Latif, S.A., Sadaniantz, A., Levinson, P., Morris, D.J. Ann. Clin. Lab. Sci. (1993) [Pubmed]
  26. Determination of 18 beta-glycyrrhetic acid in human plasma by high-performance liquid chromatography. Abe, K., Suzuki, A., Katayama, H., Tatsumi, Y., Yumioka, E. J. Chromatogr. B, Biomed. Appl. (1994) [Pubmed]
  27. Simultaneous HPLC analysis, with isocratic elution, of glycyrrhizin and glycyrrhetic acid in liquorice roots and confectionery products. Sabbioni, C., Ferranti, A., Bugamelli, F., Forti, G.C., Raggi, M.A. Phytochemical analysis : PCA. (2006) [Pubmed]
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