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Chemical Compound Review

AC1LAQHR     (3S,7R,8S,9S,10R,13R,14S,17R)- 10,13...

Synonyms: CHEMBL497834, SureCN532559, CHEBI:42989, HMDB06119, LMST01010047, ...
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Disease relevance of cholest-5-ene-3beta,7beta-diol


High impact information on cholest-5-ene-3beta,7beta-diol


Chemical compound and disease context of cholest-5-ene-3beta,7beta-diol


Biological context of cholest-5-ene-3beta,7beta-diol


Anatomical context of cholest-5-ene-3beta,7beta-diol


Associations of cholest-5-ene-3beta,7beta-diol with other chemical compounds


Gene context of cholest-5-ene-3beta,7beta-diol

  • 7beta-Hydroxycholesterol inhibited secretion of soluble APP from cultured rat hippocampal H19-7/IGF-IR neuronal cells and inhibited tumor necrosis factor-alpha-converting enzyme alpha-secretase activity but had no effect on beta-site APP-cleaving enzyme 1 activity [9].
  • The mitogen-activated protein kinases (MAPKs) ERK1 and ERK2 (but not JNK) were activated within 5 min after addition of 7beta-hydroxycholesterol [19].
  • Enrichment of MPM from control mice with the major oxysterols found in E(0) MPM (7-ketocholesterol, beta-epoxycholesterol and 7beta-hydroxycholesterol) resulted in a dose-dependent increase (60-80%) in PKC activity, AA release, p47phox translocation, superoxide anion release and cell-mediated oxidation of LDL [22].
  • The 7-hydroxycholesterol in SRM 909, most of which appeared to be already present in the serum rather than formed during saponification, may account for as much as 20% of the observed difference between the methods [23].
  • Lung cancer risk adjusted for sports activity significantly increased by 26% (CI = 1.050-1.506, P = 0.01) per unit (1 nmol/mmol plasma cholesterol) of 7beta-hydroxycholesterol [3].

Analytical, diagnostic and therapeutic context of cholest-5-ene-3beta,7beta-diol


  1. Different apoptotic mechanisms are involved in the antiproliferative effects of 7beta-hydroxysitosterol and 7beta-hydroxycholesterol in human colon cancer cells. Roussi, S., Winter, A., Gosse, F., Werner, D., Zhang, X., Marchioni, E., Geoffroy, P., Miesch, M., Raul, F. Cell Death Differ. (2005) [Pubmed]
  2. Foam cell death induced by 7beta-hydroxycholesterol is mediated by labile iron-driven oxidative injury: mechanisms underlying induction of ferritin in human atheroma. Li, W., Hellsten, A., Xu, L.H., Zhuang, D.M., Jansson, K., Brunk, U.T., Yuan, X.M. Free Radic. Biol. Med. (2005) [Pubmed]
  3. Plasma 7beta-hydroxycholesterol as a possible predictor of lung cancer risk. Linseisen, J., Wolfram, G., Miller, A.B. Cancer Epidemiol. Biomarkers Prev. (2002) [Pubmed]
  4. 7beta-hydroxycholesterol reduces the extent of reactive gliosis caused by iron deposition in the hippocampus but does not attenuate the iron-induced seizures in rats. Yao, Y., Sun, S., Kong, Q., Tong, E. Neuroscience (2006) [Pubmed]
  5. High preoperative recipient plasma 7beta-hydroxycholesterol is associated with initial poor graft function after liver transplantation. Corradini, S.G., Micheletta, F., Natoli, S., Iappelli, M., Di Angelantonio, E., De Marco, R., Elisei, W., Siciliano, M., Rossi, M., Berloco, P., Attili, A.F., Diczfalusy, U., Iuliano, L. Liver Transpl. (2005) [Pubmed]
  6. Ceramide generation occurring during 7beta-hydroxycholesterol- and 7-ketocholesterol-induced apoptosis is caspase independent and is not required to trigger cell death. Miguet, C., Monier, S., Bettaieb, A., Athias, A., Besséde, G., Laubriet, A., Lemaire, S., Néel, D., Gambert, P., Lizard, G. Cell Death Differ. (2001) [Pubmed]
  7. Human vascular smooth muscle cells from diabetic patients are resistant to induced apoptosis due to high bcl-2 expression. Ruiz, E., Gordillo-Moscoso, A., Padilla, E., Redondo, S., Rodriguez, E., Reguillo, F., Briones, A.M., van Breemen, C., Okon, E., Tejerina, T. Diabetes (2006) [Pubmed]
  8. Induction of adaptive response and enhancement of PC12 cell tolerance by 7-hydroxycholesterol and 15-deoxy-delta(12,14)-prostaglandin J2 through up-regulation of cellular glutathione via different mechanisms. Chen, Z.H., Yoshida, Y., Saito, Y., Sekine, A., Noguchi, N., Niki, E. J. Biol. Chem. (2006) [Pubmed]
  9. Oxidation of cholesterol by amyloid precursor protein and beta-amyloid peptide. Nelson, T.J., Alkon, D.L. J. Biol. Chem. (2005) [Pubmed]
  10. Oxysterol mixtures, in atheroma-relevant proportions, display synergistic and proapoptotic effects. Larsson, D.A., Baird, S., Nyhalah, J.D., Yuan, X.M., Li, W. Free Radic. Biol. Med. (2006) [Pubmed]
  11. Inhibition of p42/p44 mitogen-activated protein kinase by oxysterols in rat astrocyte primary cultures and C6 glioma cell lines. Adamczyk, M., Scherrer, E., Kupferberg, A., Malviya, A.N., Mersel, M. J. Neurosci. Res. (1998) [Pubmed]
  12. Cytotoxicity of myeloperoxidase/nitrite-oxidized low-density lipoprotein toward endothelial cells is due to a high 7beta-hydroxycholesterol to 7-ketocholesterol ratio. Steffen, Y., Wiswedel, I., Peter, D., Schewe, T., Sies, H. Free Radic. Biol. Med. (2006) [Pubmed]
  13. Characterization and comparison of the mode of cell death, apoptosis versus necrosis, induced by 7beta-hydroxycholesterol and 7-ketocholesterol in the cells of the vascular wall. Lizard, G., Monier, S., Cordelet, C., Gesquière, L., Deckert, V., Gueldry, S., Lagrost, L., Gambert, P. Arterioscler. Thromb. Vasc. Biol. (1999) [Pubmed]
  14. Analysis of oxidative processes and of myelin figures formation before and after the loss of mitochondrial transmembrane potential during 7beta-hydroxycholesterol and 7-ketocholesterol-induced apoptosis: comparison with various pro-apoptotic chemicals. Miguet-Alfonsi, C., Prunet, C., Monier, S., Bessède, G., Lemaire-Ewing, S., Berthier, A., Ménétrier, F., Néel, D., Gambert, P., Lizard, G. Biochem. Pharmacol. (2002) [Pubmed]
  15. Detection of lipid peroxidation in vivo: total hydroxyoctadecadienoic acid and 7-hydroxycholesterol as oxidative stress marker. Yoshida, Y., Niki, E. Free Radic. Res. (2004) [Pubmed]
  16. A new LC/APCI-MS method for the determination of cholesterol oxidation products in food. Raith, K., Brenner, C., Farwanah, H., Müller, G., Eder, K., Neubert, R.H. Journal of chromatography. A. (2005) [Pubmed]
  17. Kaempferol inhibits apoptosis in vascular smooth muscle induced by a component of oxidized LDL. Ruiz, E., Padilla, E., Redondo, S., Gordillo-Moscoso, A., Tejerina, T. Eur. J. Pharmacol. (2006) [Pubmed]
  18. Effects of oxidatively modified LDL on cholesterol esterification in cultured macrophages. Zhang, H.F., Basra, H.J., Steinbrecher, U.P. J. Lipid Res. (1990) [Pubmed]
  19. 7beta-hydroxycholesterol induces Ca(2+) oscillations, MAP kinase activation and apoptosis in human aortic smooth muscle cells. Ares, M.P., Pörn-Ares, M.I., Moses, S., Thyberg, J., Juntti-Berggren, L., Berggren, P., Hultgårdh-Nilsson, A., Kallin, B., Nilsson, J. Atherosclerosis (2000) [Pubmed]
  20. Reduction of oxysterol levels up-regulates HMG-CoA reductase activity in rat liver. Tamasawa, N., Hayakari, M., Murakami, H., Matsui, J., Suda, T. Atherosclerosis (1997) [Pubmed]
  21. Photosensitized lipid peroxidation and enzyme inactivation by membrane-bound merocyanine 540: reaction mechanisms in the absence and presence of ascorbate. Bachowski, G.J., Pintar, T.J., Girotti, A.W. Photochem. Photobiol. (1991) [Pubmed]
  22. Oxysterol-induced activation of macrophage NADPH-oxidase enhances cell-mediated oxidation of LDL in the atherosclerotic apolipoprotein E deficient mouse: inhibitory role for vitamin E. Rosenblat, M., Aviram, M. Atherosclerosis (2002) [Pubmed]
  23. Factors influencing the accuracy of the national reference system total cholesterol reference method. Bernert, J.T., Akins, J.R., Cooper, G.R., Poulose, A.K., Myers, G.L., Sampson, E.J. Clin. Chem. (1991) [Pubmed]
  24. Rapid hepatic metabolism of 7-ketocholesterol by 11beta-hydroxysteroid dehydrogenase type 1: species-specific differences between the rat, human, and hamster enzyme. Schweizer, R.A., Zürcher, M., Balazs, Z., Dick, B., Odermatt, A. J. Biol. Chem. (2004) [Pubmed]
  25. Limitations of the single-cell gel electrophoresis assay to monitor apoptosis in U937 and HepG2 cells exposed to 7beta-hydroxycholesterol. O'Callaghan, Y.C., Woods, J.A., O'Brien, N.M. Biochem. Pharmacol. (2001) [Pubmed]
  26. A comparative study of the conversion of 7-hydroxycholesterol in rabbit, guinea pig, rat, hamster, and chicken. Maeda, Y., Nagatomo, H., Uchiyama, F., Nagatomo, J., Yamada, M., Shiotsuki, H., Ohta, Y., Sato, S., Kai, M.H., Kondo, K.H., Higashi, S., Setoguchi, T. Steroids (2002) [Pubmed]
  27. The use of lipid-coated microbubbles as a delivery agent of 7beta-hydroxycholesterol in a radiofrequency lesion in the rat brain. Wakefield, A.E., Ho, S.Y., Li, X.G., D'Arrigo, J.S., Simon, R.H. Neurosurgery (1998) [Pubmed]
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