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Chemical Compound Review

AC1MHYLY     (4S)-4- [(8R,9S,10S,13R,14S,17S)- 10,13...

Synonyms: 29565-36-4
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Disease relevance of Cardenolide


Psychiatry related information on Cardenolide

  • Various cardenolide genins and cardenolide glycosides were administered to light-grown and dark-grown DIGITALIS LANATA shoot cultures to investigate conversion reactions related to the formation and rearrangement of the sugar side chain of DIGITALIS glycosides [6].

High impact information on Cardenolide

  • We demonstrated previously that mutations of the hapten contact residue HTrp-100 to Arg (where H refers to the heavy chain) resulted in increased specificity for digoxin analogs substituted at the cardenolide 16 position [7].
  • However, mutagenesis of H:CDR1 did not result in such a specificity change despite the proximity of the H:CDR1 hapten contact residue Asn-35 to the cardenolide 16 position [7].
  • Cross-resistance and biochemical studies with two classes of HeLa cell mutants resistant to cardiac glycosides. The unusual behavior of cardenolide SC4453 [8].
  • This single amino acid substitution has already been shown to confer cardenolide insensitivity in the monarch butterfly [9].
  • By analyzing the DNA sequence of the putative ouabain-binding site of the alpha-subunit of the Na(+)/K(+)-ATPase gene of Chrysochus and its close relatives feeding on plants with or without cardenolides, we here trace the evolution of cardenolide insensitivity in this group of beetles [9].

Biological context of Cardenolide

  • These data suggest an important role for C16 esters and possibly the presence of a separate binding site on Na+,K+-ATPase corresponding to the cardenolide C16 position [10].
  • Identification of a novel cardenolide (2''-oxovoruscharin) from Calotropis procera and the hemisynthesis of novel derivatives displaying potent in vitro antitumor activities and high in vivo tolerance: structure-activity relationship analyses [11].
  • ISOPLEXIS CANARIENSIS plants obtained from seeds accumulated cardenolides to about 20 - 40 mumol g (-1) dw as calculated from the levels of cardenolide genins released after acidic hydrolysis of methanolic extracts [12].
  • Shoot-tips from several genotypes of the cardenolide-producing perennial shrub Digitalis obscura L. were successfully cryopreserved using the encapsulation-dehydration technique [13].
  • Especially in myocardial tissue a significantly lower DH-DGT concentration was measured, indicating the loss of affinity to cardenolide binding sites by hydrogenation [14].

Anatomical context of Cardenolide

  • Ouabain-like factor (OLF), a mammalian cardenolide, is a counterpart to plant-derived ouabain and is found in the adrenal, hypothalamus, and blood of several mammalian species [15].
  • Ouabain, a cardenolide previously shown to inhibit the export of FGF2 from transiently transfected COS-1 cells, blocked the appearance of FGF2 onto the surface of transfected CF18 cells and MAE ZIP cells but had no detectable effect on C6 and U87MG cells [16].
  • The same close correlations are found if dissociation constants of cardenolide receptor complexes and concentrations causing 86Rb-uptake inhibition in human erythrocytes are examined [17].
  • Molecular basis of B cell activiation--II. Mitogenicity of cardenolide derivatives [18].
  • Now it appears that the inhibitors are steroids released from the adrenal gland and are members of the cardenolide family, e.g., ouabain, and the bufadienolide family, e.g., marinobufagenin [19].

Associations of Cardenolide with other chemical compounds


Gene context of Cardenolide

  • Cardenolide glucohydrolase II (CGH II) is a cardenolide-specific glucohydrolase obtained from Digitalis lanata leaves [25].
  • The chemical structure of a new cardenolide, euonymusoside A (3) has been elucidated on the basis of extensive spectral analysis and enzymic hydrolysis to be acovenosigenin A (1 beta, 3 beta, 14 beta-trihydroxy-5 beta-cardenolide) 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl(1-->4)-alpha-L-rhamnopyranoside [26].
  • The combination of positive and negative ion FAB mass spectrometry of the cardenolide-type cardiac glycosides provides useful information concerning the molecular weight as well as the structures of both aglycone and sugar moieties [27].

Analytical, diagnostic and therapeutic context of Cardenolide


  1. Circulating bufodienolide and cardenolide sodium pump inhibitors in preeclampsia. Lopatin, D.A., Ailamazian, E.K., Dmitrieva, R.I., Shpen, V.M., Fedorova, O.V., Doris, P.A., Bagrov, A.Y. J. Hypertens. (1999) [Pubmed]
  2. Cloning and functional expression in Escherichia coli of a cDNA encoding cardenolide 16'-O-glucohydrolase from Digitalis lanata Ehrh. Framm, J.J., Peterson, A., Thoeringer, C., Pangert, A., Hornung, E., Feussner, I., Luckner, M., Lindemann, P. Plant Cell Physiol. (2000) [Pubmed]
  3. Agrobacterium tumefaciens-mediated genetic transformation of the cardenolide-producing plant Digitalis minor L. Sales, E., Segura, J., Arrillaga, I. Planta Med. (2003) [Pubmed]
  4. An antitumor cardenolide with inhibitory activity against pseudomonas pseudomallei. Ali, S.N., Kazmi, S.U., Akhtar, N., Malik, A. Pakistan journal of pharmaceutical sciences. (1993) [Pubmed]
  5. Pharmacological investigations on asclepin--a new cardenolide from Asclepius curassavica. Part I: Cardiotonic activity and acute toxicity. Patnaik, G.K., Dhawan, B.N. Arzneimittel-Forschung. (1978) [Pubmed]
  6. Effects of Digitoxigenin, Digoxigenin, and Various Cardiac Glycosides on Cardenolide Accumulation in Shoot Cultures of Digitalis lanata. Theurer, C., Kreis, W., Reinhard, E. Planta Med. (1998) [Pubmed]
  7. Complementary combining site contact residue mutations of the anti-digoxin Fab 26-10 permit high affinity wild-type binding. Short, M.K., Krykbaev, R.A., Jeffrey, P.D., Margolies, M.N. J. Biol. Chem. (2002) [Pubmed]
  8. Cross-resistance and biochemical studies with two classes of HeLa cell mutants resistant to cardiac glycosides. The unusual behavior of cardenolide SC4453. Gupta, R.S., Chopra, A. J. Biol. Chem. (1985) [Pubmed]
  9. Molecular adaptation of Chrysochus leaf beetles to toxic compounds in their food plants. Labeyrie, E., Dobler, S. Mol. Biol. Evol. (2004) [Pubmed]
  10. Cardiac glycosides. 6. Gitoxigenin C16 acetates, formates, methoxycarbonates, and digitoxosides. Synthesis and Na+,K+-ATPase inhibitory activities. Hashimoto, T., Rathore, H., Satoh, D., Hong, G., Griffin, J.F., From, A.H., Ahmed, K., Fullerton, D.S. J. Med. Chem. (1986) [Pubmed]
  11. Identification of a novel cardenolide (2''-oxovoruscharin) from Calotropis procera and the hemisynthesis of novel derivatives displaying potent in vitro antitumor activities and high in vivo tolerance: structure-activity relationship analyses. Van Quaquebeke, E., Simon, G., André, A., Dewelle, J., Yazidi, M.E., Bruyneel, F., Tuti, J., Nacoulma, O., Guissou, P., Decaestecker, C., Braekman, J.C., Kiss, R., Darro, F. J. Med. Chem. (2005) [Pubmed]
  12. Cardenolide genin pattern in isoplexis plants and shoot cultures. Schaller, F., Kreis, W. Planta Med. (2006) [Pubmed]
  13. Cryopreservation of Digitalis obscura selected genotypes by encapsulation-dehydration. Sales, E., Nebauer, S.G., Arrillaga, I., Segura, J. Planta Med. (2001) [Pubmed]
  14. Pharmacokinetics of dihydrodigitoxin in the cat. A comparison with digitoxin. Flasch, H., Heniz, N. Naunyn Schmiedebergs Arch. Pharmacol. (1979) [Pubmed]
  15. Secretion of a lactone-hydrogenated ouabain-like effector of sodium, potassium-adenosine triphosphatase activity by adrenal cells. Qazzaz, H.M., El-Masri, M.A., Valdes, R. Endocrinology (2000) [Pubmed]
  16. Translocation of FGF2 to the cell surface without release into conditioned media. Trudel, C., Faure-Desire, V., Florkiewicz, R.Z., Baird, A. J. Cell. Physiol. (2000) [Pubmed]
  17. Correlation between inhibition of (Na+, K+)-membrane-ATPase and positive inotropic activity of cardenolides in isolated papillary muscles of guinea pig. Flasch, H., Heinz, N. Naunyn Schmiedebergs Arch. Pharmacol. (1978) [Pubmed]
  18. Molecular basis of B cell activiation--II. Mitogenicity of cardenolide derivatives. Hammarström, L., Smith, C.I. Mol. Immunol. (1980) [Pubmed]
  19. Role of dietary salt in hypertension. Haddy, F.J. Life Sci. (2006) [Pubmed]
  20. Euonymoside A: a new cytotoxic cardenolide glycoside from the bark of Euonymus sieboldianus. Baek, N.I., Lee, Y.H., Park, J.D., Kim, S.I., Ahn, B.Z. Planta Med. (1994) [Pubmed]
  21. Synthesis and structure-activity relationships of 14 beta-hydroxy-5 alpha-pregnanes: pregnanes that bind to the cardiac glycoside receptor. Templeton, J.F., Ling, Y., Kumar, V.P., LaBella, F.S. Steroids (1993) [Pubmed]
  22. Convallasaponin A, a New 5beta-Spirostanol Triglycoside from the Rhizomes of Convallaria majalis. Higano, T., Kuroda, M., Sakagami, H., Mimaki, Y. Chem. Pharm. Bull. (2007) [Pubmed]
  23. Glycosides of 19-formylthevetiogenin and 5 alpha-thevetiogenin from Thevetia neriifolia. Abe, F., Yamauchi, T., Yahara, S., Nohara, T. Phytochemistry (1994) [Pubmed]
  24. An androstane bioside and 3'-thiazolidinone derivatives of doubly-linked cardenolide glycosides from the roots of Asclepias tuberosa. Abe, F., Yamauchi, T. Chem. Pharm. Bull. (2000) [Pubmed]
  25. Structure-specificity relationship of cardiac glycosides as a substrate for glucohydrolase II. Terada, Y., Misoi, R., Watanabe, N., Hornberger, M., Kreis, W. Chem. Pharm. Bull. (2000) [Pubmed]
  26. Cytotoxic cardenolides from woods of Euonymus alata. Kitanaka, S., Takido, M., Mizoue, K., Nakaike, S. Chem. Pharm. Bull. (1996) [Pubmed]
  27. Evaluation of positive and negative ion fast atom bombardment mass spectrometry for structural investigations on cardenolide-type cardiac glycosides. Isobe, R., Komori, T., Abe, F., Yamauchi, T. Biomed. Environ. Mass Spectrom. (1986) [Pubmed]
  28. Development of an immunoassay for endogenous digitalislike factor. Harris, D.W., Clark, M.A., Fisher, J.F., Hamlyn, J.M., Kolbasa, K.P., Ludens, J.H., DuCharme, D.W. Hypertension (1991) [Pubmed]
  29. High-performance liquid chromatographic determination of cardenolides in Digitalis leaves after solid-phase extraction. Wiegrebe, H., Wichtl, M. J. Chromatogr. (1993) [Pubmed]
  30. Effects of Various Pregnanes and Two 23-Nor-5-cholenic Acids on Cardenolide Accumulation in Cell and Organ Cultures of Digitalis lanata. Haussmann, W., Kreis, W., Stuhlemmer, U., Reinhard, E. Planta Med. (1997) [Pubmed]
  31. Characterization of digoxin and related cardiac glycosides by fast atom bombardment mass spectrometry. Paré, J.R., Lafontaine, P., Bélanger, J., Sy, W.W., Jordan, N., Loo, J.C. Journal of pharmaceutical and biomedical analysis. (1987) [Pubmed]
  32. Systemic induction of the biosynthesis of terpenic compounds in Digitalis lanata. Gutierrez Mañero, F.J., Ramos, B., Lucas García, J.A., Probanza, A., Barrientos Casero, M.L. J. Plant Physiol. (2003) [Pubmed]
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