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Chemical Compound Review

Squamocin     (5S)-3-[(13R)-13-[(2R,5R)-5- [(2R,5R)-5...

Synonyms: Squamocin A, Annonin I, CHEMBL41177, SureCN2702440, CHEBI:162208, ...
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Disease relevance of C08545


High impact information on C08545


Biological context of C08545


Anatomical context of C08545


Associations of C08545 with other chemical compounds

  • A novel acetogenin, joolanin ( 1), along with eight known acetogenins, squamocin ( 2), desacetyluvaricin ( 3), chamuvarinin ( 4), tripoxyrollin ( 5), diepoxyrollin ( 6), dieporeticanin-1 ( 7), dieporeticanin-2 ( 8) and dieporeticenin ( 9) were isolated from the seeds of UVARIA CHAMAE (Annonaceae) [8].
  • Bioactivity-directed fractionation of the MeOH extract of the stem barks of Rollinia emarginata resulted in the isolation of six compounds, four acetogenins, rolliniastatin-1, sylvaticin, squamocin, and rollidecin B, one lignan, lirioresinol B, and an oxoaporphine, liriodenin [9].
  • Cytotoxic activity of adriamycin was not restored in MCF7-R Pgp expressing cells by squamocin addition [2].

Gene context of C08545

  • These results suggest that squamocin inhibits the proliferation of K562 cells via G2/M arrest in association with the induction of p21, p27 and the reduction of Cdk1 and Cdc25C kinase activities [3].
  • Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways [10].
  • These results suggest that apoptosis of HL-60 cells induced by squamocin requires caspase-3 activation and is related to SAPK activation [5].

Analytical, diagnostic and therapeutic context of C08545


  1. Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy. Queiroz, E.F., Roblot, F., Duret, P., Figadère, B., Gouyette, A., Laprévote, O., Serani, L., Hocquemiller, R. J. Med. Chem. (2000) [Pubmed]
  2. Antitumoral effects of squamocin on parental and multidrug resistant MCF7 (human breast adenocarcinoma) cell lines. Raynaud, S., Némati, F., Miccoli, L., Michel, P., Poupon, M.F., Fourneau, C., Laurens, A., Hocquemiller, R. Life Sci. (1999) [Pubmed]
  3. Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells. Lu, M.C., Yang, S.H., Hwang, S.L., Lu, Y.J., Lin, Y.H., Wang, S.R., Wu, Y.C., Lin, S.R. Life Sci. (2006) [Pubmed]
  4. Stimulatory effects of squamocin, an Annonaceous acetogenin, on Ca(2+)-activated K+ current in cultured smooth muscle cells of human coronary artery. Wu, S.N., Chiang, H.T., Chang, F.R., Liaw, C.C., Wu, Y.C. Chem. Res. Toxicol. (2003) [Pubmed]
  5. Involvement of caspase-3 activation in squamocin-induced apoptosis in leukemia cell line HL-60. Zhu, X.F., Liu, Z.C., Xie, B.F., Li, Z.M., Feng, G.K., Xie, H.H., Wu, S.J., Yang, R.Z., Wei, X.Y., Zeng, Y.X. Life Sci. (2002) [Pubmed]
  6. Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction. Duval, R., Lewin, G., Hocquemiller, R. Bioorg. Med. Chem. (2003) [Pubmed]
  7. Annonaceous acetogenins: the hydroxyl groups and THF rings are crucial structural elements for targeting the mitochondria, demonstration with the synthesis of fluorescent squamocin analogues. Derbré, S., Roué, G., Poupon, E., Susin, S.A., Hocquemiller, R. Chembiochem (2005) [Pubmed]
  8. A New Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenin from the Seeds of Uvaria chamae. Fall, D., Pimentel, L., Champy, P., Gleye, C., Laurens, A., Hocquemiller, R. Planta Med. (2006) [Pubmed]
  9. Acetogenins and other compounds from Rollinia emarginata and their antiprotozoal activities. Février, A., Ferreira, M.E., Fournet, A., Yaluff, G., Inchausti, A., Rojas de Arias, A., Hocquemiller, R., Waechter, A.I. Planta Med. (1999) [Pubmed]
  10. Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways. Yuan, S.S., Chang, H.L., Chen, H.W., Kuo, F.C., Liaw, C.C., Su, J.H., Wu, Y.C. Life Sci. (2006) [Pubmed]
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