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Chemical Compound Review

Cholestane     10,13-dimethyl-17-(6- methylheptan-2-yl)-2...

Synonyms: Coprostane, ACMC-20am6p, C2005_SIGMA, NSC-140722, NSC-224313, ...
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Disease relevance of NSC 224419


High impact information on NSC 224419

  • OSW-1 is a new member of cholestane saponin family, which is cytotoxic against several types of malignant cells [3].
  • We report the protective effects of two novel antioxidant compounds, 3 beta-doxyl-5 alpha cholestane and 2,2,6,6-tetramethyl-piperdinoxyl, in HL-60 and U937 leukemic cells subjected to a number of cytotoxic insults [4].
  • Four chain spin labels and a spin-labeled cholestane were used to study the dynamic structure of plasma membrane vesicles (PMV) prepared from RBL-2H3 mast cells at temperatures ranging from 22 degrees C to 45 degrees C. Analysis shows that the spectra from most labels consist of two components [5].
  • In the Lo phase, acyl chains undergo a faster rotational diffusion and higher ordering than in the Lc phase, whereas spin-labeled cholestane exhibits slower rotational diffusion and higher ordering [6].
  • Behavior of cholesterol and spin-labeled cholestane in model bile systems studied by electron spin resonance and synchrotron x-ray [7].

Biological context of NSC 224419

  • The most abundant bile acid of this type was (25 epsilon)-3 alpha, 7 alpha, 12 alpha, 25-tetrahydroxy-5 beta-cholestan-26-oic acid, which suggested that C-25 hydroxylation may be an important step in the shortening of the C8 side chain of the cholestane triol to the C5 side chain of cholic acid in the neonatal period [8].
  • It was demonstrated that the incorporated fatty acids and monoglycerides interacted with the polar region of the membranes by ESR study with cholestane label and 1H-NMR study [9].
  • Potent growth inhibitory activity of a novel Ornithogalum cholestane glycoside on human cells: induction of apoptosis in promyelocytic leukemia HL-60 cells [10].

Anatomical context of NSC 224419


Associations of NSC 224419 with other chemical compounds


Gene context of NSC 224419

  • These studies were performed over a range of blends of POPC and POPS and temperatures, utilizing the spin-labeled lipids 16-phosphatidylcholine and 5-phosphatidylcholine as well as cholestane (CSL) [21].
  • The lipid preparations were dibromide-purified cholesterol, air-oxidized cholesterol, 25-hydroxycholesterol, cholesterol-5alpha, 6 beta-epoxide and cholestane 3 beta, 5 alpha, 6 beta-triol [22].
  • The ESR spectra of lipoproteins labeled with Cholestane showed even higher sensitivity to the mobility constraints [23].
  • (3) FB1 also restricts the mobility of the (rigid) cholestane spin label [24].

Analytical, diagnostic and therapeutic context of NSC 224419


  1. Sterol requirement of Mycoplasma capricolum. Odriozola, J.M., Waitzkin, E., Smith, T.L., Bloch, K. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  2. Identification of (23S)-5 alpha-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol in urine of patients with cerebrotendinous xanthomatosis. Kihira, K., Fukuda, K., Kuramoto, T., Kuriyama, M., Fujiyama, J., Osame, M., Hoshita, T. Steroids (1991) [Pubmed]
  3. Apoptosis induced by a new member of saponin family is mediated through caspase-8-dependent cleavage of Bcl-2. Zhu, J., Xiong, L., Yu, B., Wu, J. Mol. Pharmacol. (2005) [Pubmed]
  4. The production of a reactive oxygen intermediate during the induction of apoptosis by cytotoxic insult. McGowan, A.J., Bowie, A.G., O'Neill, L.A., Cotter, T.G. Exp. Cell Res. (1998) [Pubmed]
  5. Ordered and disordered phases coexist in plasma membrane vesicles of RBL-2H3 mast cells. An ESR study. Ge, M., Gidwani, A., Brown, H.A., Holowka, D., Baird, B., Freed, J.H. Biophys. J. (2003) [Pubmed]
  6. A 2D-ELDOR study of the liquid ordered phase in multilamellar vesicle membranes. Costa-Filho, A.J., Shimoyama, Y., Freed, J.H. Biophys. J. (2003) [Pubmed]
  7. Behavior of cholesterol and spin-labeled cholestane in model bile systems studied by electron spin resonance and synchrotron x-ray. Sömjen, G.J., Lipka, G., Schulthess, G., Koch, M.H., Wachtel, E., Gilat, T., Hauser, H. Biophys. J. (1995) [Pubmed]
  8. The bile acid composition of gastric contents from neonates with high intestinal obstruction. Clayton, P.T., Muller, D.P., Lawson, A.M. Biochem. J. (1982) [Pubmed]
  9. Effect of fatty acids and monoglycerides on permeability of lipid bilayer. Muranushi, N., Takagi, N., Muranishi, S., Sezaki, H. Chem. Phys. Lipids (1981) [Pubmed]
  10. Potent growth inhibitory activity of a novel Ornithogalum cholestane glycoside on human cells: induction of apoptosis in promyelocytic leukemia HL-60 cells. Hirano, T., Oka, K., Mimaki, Y., Kuroda, M., Sashida, Y. Life Sci. (1996) [Pubmed]
  11. Isoprenoid-mediated changes in the glycerophospholipid molecular species of the sterol auxotrophic fungus Lagenidium giganteum. Kerwin, J.L., Tuininga, A.R., Wiens, A.M., Wang, J.C., Torvik, J.J., Conrath, M.L., MacKichan, J.K. Microbiology (Reading, Engl.) (1995) [Pubmed]
  12. Cholestane spin label study of filipin action on lipid planar multibilayers. Flick, C., Gelerinter, E. Chem. Phys. Lipids (1977) [Pubmed]
  13. An electron spin resonance spin-label study of lipophilin in oriented phospholipid bilayers. Post, J.F., Dijkema, C. Arch. Biochem. Biophys. (1983) [Pubmed]
  14. Properties of liver microsomal cholesterol 5,6-oxide hydrolase. Nashed, N.T., Michaud, D.P., Levin, W., Jerina, D.M. Arch. Biochem. Biophys. (1985) [Pubmed]
  15. Saundersiosides C-H, rearranged cholestane glycosides from the bulbs of Ornithogalum saundersiae and their cytostatic activity on HL-60 cells. Kuroda, M., Mimaki, Y., Sashida, Y. Phytochemistry (1999) [Pubmed]
  16. New azasterols against Trypanosoma brucei: role of 24-sterol methyltransferase in inhibitor action. Gros, L., Castillo-Acosta, V.M., Jiménez Jiménez, C., Sealey-Cardona, M., Vargas, S., Manuel Estévez, A., Yardley, V., Rattray, L., Croft, S.L., Ruiz-Perez, L.M., Urbina, J.A., Gilbert, I.H., González-Pacanowska, D. Antimicrob. Agents Chemother. (2006) [Pubmed]
  17. Models for slow anisotropic rotational diffusion in saturation transfer electron paramagnetic resonance at 9 and 35 GHz. Johnson, M.E., Lee, L., Fung, L.W. Biochemistry (1982) [Pubmed]
  18. Hydrophobic barriers of lipid bilayer membranes formed by reduction of water penetration by alkyl chain unsaturation and cholesterol. Subczynski, W.K., Wisniewska, A., Yin, J.J., Hyde, J.S., Kusumi, A. Biochemistry (1994) [Pubmed]
  19. Chromatographic separation of cholesterol in foods. Fenton, M. J. Chromatogr. (1992) [Pubmed]
  20. Cholestane as a digestibility marker in the absorption of polyunsaturated fatty acid ethyl esters in Atlantic salmon. Sigurgisladottir, S., Lall, S.P., Parrish, C.C., Ackman, R.G. Lipids (1992) [Pubmed]
  21. An electron spin resonance study of interactions between phosphatidylcholine and phosphatidylserine in oriented membranes. Ge, M., Budil, D.E., Freed, J.H. Biophys. J. (1994) [Pubmed]
  22. Connective tissue responses to oxysterols. Baranowski, A., Adams, C.W., High, O.B., Bowyer, D.B. Atherosclerosis (1982) [Pubmed]
  23. The ESR characterization of molecular mobility in the lipid surface layer of human serum lipoproteins. Kveder, M., Pifat, G., Pecar, S., Schara, M. Chem. Phys. Lipids (1994) [Pubmed]
  24. Effects of fumonisin B1 and (hydrolyzed) fumonisin backbone AP1 on membranes: a spin-label study. Yin, J.J., Smith, M.J., Eppley, R.M., Troy, A.L., Page, S.W., Sphon, J.A. Arch. Biochem. Biophys. (1996) [Pubmed]
  25. Squalamine: an aminosterol antibiotic from the shark. Moore, K.S., Wehrli, S., Roder, H., Rogers, M., Forrest, J.N., McCrimmon, D., Zasloff, M. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  26. Quantitative GLC analysis of sterols in biological samples. Hooper, S.N., Chandler, R.F. Journal of pharmaceutical sciences. (1978) [Pubmed]
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