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Chemical Compound Review

Beauvericin     (3S,6R,9S,12R,15S,18R)- 3,9,15-tribenzyl-4...

Synonyms: AC1MHNCT, SureCN29355, CHEBI:3000, FT-0602893, 26048-05-5, ...
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Disease relevance of AIDS208082


High impact information on AIDS208082

  • Beauvericin induced apoptosis of nonmalignant cholangiocytes in a concentration- (0 to 25 micromol/L) and time- (0 to 6 hours) dependent manner [6].
  • An 18 mer bcl-2 antisense oligonucleotide reduced expression of Bcl-2 protein by 50% and increased the rate of beauvericin-induced apoptosis more than threefold in the malignant cells [6].
  • We now report that cells infected with T. gondii are resistant to multiple inducers of apoptosis, including Fas-dependent and Fas-independent CTL-mediated cytotoxicity, IL-2 deprivation, gamma irradiation, UV irradiation, and the calcium ionophore beauvericin [7].
  • It was inhibited by forming purple membrane films on glass and by using the synergistic ionophores beauvericin and valinomycin, in an equimolar ratio with bR, at 7 degrees C. These systems afforded enrichment in the M intermediate and a rate of decay that could be conveniently studied [8].
  • We endeavored to elucidate the mechanism of beauvericin-induced [Ca(2+)](i) increase by studying the effects of beauvericin in Xenopus oocytes [9].

Chemical compound and disease context of AIDS208082

  • Assays of Fusarium culture extracts using Artemia salina larvae, showed F. subglutinans as one of the most toxigenic species, and its toxicity was mostly correlated to the capability to produce beauvericin (BEA) [10].

Biological context of AIDS208082


Anatomical context of AIDS208082


Associations of AIDS208082 with other chemical compounds


Gene context of AIDS208082

  • Our data suggest that beauvericin-induced apoptosis occurs by a Ca(2+)-dependent CPP-32 protease-sensitive pathway despite cholangiocyte expression of Bcl-2 [20].
  • These data indicate that beauvericin is one of the most potent and specific ACAT inhibitors of microbial origin [21].
  • A large number of proapoptotic agents were ineffective in inducing apoptosis in rat or human cholangiocytes in culture; in contrast, beauvericin, a K+ ionophore, caused apoptosis in both cell lines, despite their expression of Bcl-2 [20].
  • All 15 isolates produced FB1, FB2, MON and BEA in culture on rice [22].

Analytical, diagnostic and therapeutic context of AIDS208082


  1. Induction of calcium influx from extracellular fluid by beauvericin in human leukemia cells. Chen, B.F., Tsai, M.C., Jow, G.M. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  2. Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum. Ivanova, L., Skjerve, E., Eriksen, G.S., Uhlig, S. Toxicon (2006) [Pubmed]
  3. Beauvericin induces cytotoxic effects in human acute lymphoblastic leukemia cells through cytochrome c release, caspase 3 activation: the causative role of calcium. Jow, G.M., Chou, C.J., Chen, B.F., Tsai, J.H. Cancer Lett. (2004) [Pubmed]
  4. Involvement of Bcl-2 family, cytochrome c and caspase 3 in induction of apoptosis by beauvericin in human non-small cell lung cancer cells. Lin, H.I., Lee, Y.J., Chen, B.F., Tsai, M.C., Lu, J.L., Chou, C.J., Jow, G.M. Cancer Lett. (2005) [Pubmed]
  5. Ultrastructural effects of macrotetrolides of Streptomyces griseus LKS-1 in tissues of Culex pipiens larvae. Zizka, Z., Weiser, J., Blumauerova, M., Jizba, J. Cytobios (1989) [Pubmed]
  6. Bcl-2 is overexpressed and alters the threshold for apoptosis in a cholangiocarcinoma cell line. Harnois, D.M., Que, F.G., Celli, A., LaRusso, N.F., Gores, G.J. Hepatology (1997) [Pubmed]
  7. Toxoplasma gondii-infected cells are resistant to multiple inducers of apoptosis. Nash, P.B., Purner, M.B., Leon, R.P., Clarke, P., Duke, R.C., Curiel, T.J. J. Immunol. (1998) [Pubmed]
  8. Photoisomerization of the chromophore in bacteriorhodopsin during the proton pumping photocycle. Mowery, P.C., Stoeckenius, W. Biochemistry (1981) [Pubmed]
  9. Beauvericin activates Ca2+-activated Cl- currents and induces cell deaths in Xenopus oocytes via influx of extracellular Ca2+. Tang, C.Y., Chen, Y.W., Jow, G.M., Chou, C.J., Jeng, C.J. Chem. Res. Toxicol. (2005) [Pubmed]
  10. Occurrence and toxicity of Fusarium subglutinans from Peruvian maize. Logrieco, A., Moretti, A., Altomare, C., Bottalico, A., Carbonell Torres, E. Mycopathologia (1993) [Pubmed]
  11. Block of L-type Ca2+ current by beauvericin, a toxic cyclopeptide, in the NG108-15 neuronal cell line. Wu, S.N., Chen, H., Liu, Y.C., Chiang, H.T. Chem. Res. Toxicol. (2002) [Pubmed]
  12. Effects of beauvericin on the metabolic state and ionic homeostasis of ventricular myocytes of the guinea pig. Kouri, K., Duchen, M.R., Lemmens-Gruber, R. Chem. Res. Toxicol. (2005) [Pubmed]
  13. Observation of non-covalent interactions between beauvericin and oligonucleotides using electrospray ionization mass spectrometry. Pócsfalvi, G., Di Landa, G., Ferranti, P., Ritieni, A., Randazzo, G., Malorni, A. Rapid Commun. Mass Spectrom. (1997) [Pubmed]
  14. Noninvolvement of beauvericin in the entomopathogenicity of Beauveria bassiana. Champlin, F.R., Grula, E.A. Appl. Environ. Microbiol. (1979) [Pubmed]
  15. Occurrence of fusaproliferin and beauvericin in Fusarium-contaminated livestock feed in Iowa. Munkvold, G., Stahr, H.M., Logrieco, A., Moretti, A., Ritieni, A. Appl. Environ. Microbiol. (1998) [Pubmed]
  16. Mycotoxin-induced elevation of free sphingoid bases in precision-cut rat liver slices: specificity of the response and structure-activity relationships. Norred, W.P., Plattner, R.D., Dombrink-Kurtzman, M.A., Meredith, F.I., Riley, R.T. Toxicol. Appl. Pharmacol. (1997) [Pubmed]
  17. Mycotoxin production by Fusarium avenaceum strains isolated from Norwegian grain and the cytotoxicity of rice culture extracts to porcine kidney epithelial cells. Morrison, E., Kosiak, B., Ritieni, A., Aastveit, A.H., Uhlig, S., Bernhoft, A. J. Agric. Food Chem. (2002) [Pubmed]
  18. Inhibitory effect of beauvericin on a high K+-induced tonic contraction in guinea-pig taenia coli. Nakajyo, S., Matsuoka, K., Kitayama, T., Yamamura, Y., Shimizu, K., Kimura, M., Urakawa, N. Jpn. J. Pharmacol. (1987) [Pubmed]
  19. Effects of moniliformin in presence of cyclohexadepsipeptides on isolated mammalian tissue and cells. Kamyar, M.R., Kouri, K., Rawnduzi, P., Studenik, C., Lemmens-Gruber, R. Toxicology in vitro : an international journal published in association with BIBRA. (2006) [Pubmed]
  20. Development and initial application of an in vitro model of apoptosis in rodent cholangiocytes. Que, F.G., Gores, G.J., LaRusso, N.F. Am. J. Physiol. (1997) [Pubmed]
  21. Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. Tomoda, H., Huang, X.H., Cao, J., Nishida, H., Nagao, R., Okuda, S., Tanaka, H., Omura, S., Arai, H., Inoue, K. J. Antibiot. (1992) [Pubmed]
  22. Mycotoxin production by Fusarium proliferatum isolates from rice with Fusarium sheath rot disease. Abbas, H.K., Cartwright, R.D., Xie, W., Mirocha, C.J., Richard, J.L., Dvorak, T.J., Sciumbato, G.L., Shier, W.T. Mycopathologia (1999) [Pubmed]
  23. Determination of the Fusarium mycotoxin beauvericin at micrograms/kg levels in corn by high-performance liquid chromatography with diode-array detection. Krska, R., Schuhmacher, R., Grasserbauer, M., Scott, P.M. Journal of chromatography. A. (1996) [Pubmed]
  24. New beauvericins, potentiators of antifungal miconazole activity, Produced by Beauveria sp. FKI-1366. I. Taxonomy, fermentation, isolation and biological properties. Fukuda, T., Arai, M., Yamaguchi, Y., Masuma, R., Tomoda, H., Omura, S. J. Antibiot. (2004) [Pubmed]
  25. Beauvericin cytotoxicity to the invertebrate cell line SF-9. Calo', L., Fornelli, F., Nenna, S., Tursi, A., Caiaffa, M.F., Macchia, L. J. Appl. Genet. (2003) [Pubmed]
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