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Chemical Compound Review

Chol-sulf     (3S,8S,9S,10R,13R,14S,17R)- 10,13-dimethyl...

Synonyms: CCRIS 7559, AG-D-54171, C9523_SIGMA, CHEBI:41321, HMDB00653, ...
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Disease relevance of CHOLESTEROL-SULFATE


High impact information on CHOLESTEROL-SULFATE

  • Thus, LXR and PPAR activators regulate the expression of SULT2B1b, the key enzyme in the synthesis of CS, which is a potent regulator of epidermal differentiation and corneocyte desquamation [4].
  • Cholesterol sulfotransferase type 2B isoform 1b (SULT2B1b) is a key enzyme in the synthesis of cholesterol sulfate (CS), a critical regulator of keratinocyte differentiation and desquamation, as well as a mediator of barrier homeostasis [4].
  • The acute LD50 of amphotericin B-deoxycholate was 5.1 mg/kg versus 20 mg/kg for the amphotericin/cholesterol-sulfate complexes [2].
  • However, 3-hr incubation with HBCD plus ChS or with 1 mM ChS alone decreased the percentage of sperm undergoing the induced acrosome reaction without significantly affecting viability when compared to the control [5].
  • Biochemical characterization of cholesterol-3-sulfate as the sole effector for the phosphorylation of HMG1 by casein kinase I in vitro [6].

Biological context of CHOLESTEROL-SULFATE


Anatomical context of CHOLESTEROL-SULFATE

  • Spermatozoa were exposed to MBCD or a combination of MBCD and cholesterol-3-sulfate over a period of 3 hours while being cooled slowly from 25 degrees C to 5 degrees C, and were subsequently cryopreserved by the pellet method [10].
  • We also present evidence that the recognition of sulfatides, cholesterol-3-sulfate, or other cross-reactive sulfated macromolecules by region II may be required during sporozoite invasion of liver cells [11].
  • Thus, CS and I3SO3-GalCer in the digestive tracts of mammals were shown to function as epithelial inhibitors of pancreatic elastase [3].
  • RESULTS: Human gastric epithelium contained both sulfatide and cholesterol sulfate (CS) as sulfolipids, which were also detected in gastric fluid, showing their stable natures in the gastric fluid [12].
  • Here, we show such a novel function of the most abundant sulfated sterol in human blood, cholesterol sulfate (CS), to suppress LT production in human polymorphonuclear leukocytes (PMNL) and Mono Mac6 cells [13].


  • Although the insoluble CS sulfatase in the microsomal fraction remained at a relatively constant level, the soluble CST in the cytosol fraction showed a 6-fold increase from day 14 to day 16, and the activity decreased continuously in the following period, reaching one forty-sixth of the maximum level at 4-months-old mice [8].
  • Activation of C-kinase eta through its cholesterol-3-sulfate-dependent phosphorylation by casein kinase I in vitro [14].
  • Cholesterol increased the effect of CS on 5-LO product synthesis [13].
  • The system is based on making cells dependent on cholesterol-sulfate as the sole source of cholesterol, allowing only STS+ cells to grow [15].


  1. Recessive x-linked ichthyosis: role of cholesterol-sulfate accumulation in the barrier abnormality. Zettersten, E., Man, M.Q., Sato, J., Denda, M., Farrell, A., Ghadially, R., Williams, M.L., Feingold, K.R., Elias, P.M. J. Invest. Dermatol. (1998) [Pubmed]
  2. Treatment of experimental invasive aspergillosis with novel amphotericin B/cholesterol-sulfate complexes. Patterson, T.F., Miniter, P., Dijkstra, J., Szoka, F.C., Ryan, J.L., Andriole, V.T. J. Infect. Dis. (1989) [Pubmed]
  3. Inhibition of pancreatic elastase by sulfated lipids in the intestinal mucosa. Ito, N., Iwamori, Y., Hanaoka, K., Iwamori, M. J. Biochem. (1998) [Pubmed]
  4. LXR and PPAR activators stimulate cholesterol sulfotransferase type 2 isoform 1b in human keratinocytes. Jiang, Y.J., Kim, P., Elias, P.M., Feingold, K.R. J. Lipid Res. (2005) [Pubmed]
  5. Effects of 2-hydroxypropyl-beta-cyclodextrin and cholesterol on porcine sperm viability and capacitation status following cold shock or incubation. Galantino-Homer, H.L., Zeng, W.X., Megee, S.O., Dallmeyer, M., Voelkl, D., Dobrinski, I. Mol. Reprod. Dev. (2006) [Pubmed]
  6. Biochemical characterization of cholesterol-3-sulfate as the sole effector for the phosphorylation of HMG1 by casein kinase I in vitro. Okano, M., Kano, S., Munakata, H., Ohtsuki, K. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  7. Protection of boar spermatozoa from cold shock damage by 2-hydroxypropyl-beta-cyclodextrin. Zeng, W.X., Terada, T. Theriogenology (2001) [Pubmed]
  8. Programmed expression of cholesterol sulfotransferase and transglutaminase during epidermal differentiation of murine skin development. Kagehara, M., Tachi, M., Harii, K., Iwamori, M. Biochim. Biophys. Acta (1994) [Pubmed]
  9. The effects of cholesterol-3-sulfate (CH-3S) on the phosphorylation of human C3a (hC3a) in vitro and on the ability of hC3a to induce vascular permeability in rats. Kawakami, F., Ito, M., Matsuda, Y., Hayashi, I., Ohtsuki, K. Biol. Pharm. Bull. (2004) [Pubmed]
  10. Effects of methyl-beta-cyclodextrin on cryosurvival of boar spermatozoa. Zeng, W.X., Terada, T. J. Androl. (2001) [Pubmed]
  11. Binding of malarial circumsporozoite protein to sulfatides [Gal(3-SO4)beta 1-Cer] and cholesterol-3-sulfate and its dependence on disulfide bond formation between cysteines in region II. Cerami, C., Kwakye-Berko, F., Nussenzweig, V. Mol. Biochem. Parasitol. (1992) [Pubmed]
  12. Lipid compositions of human gastric fluid and epithelium: the role of sulfated lipids in gastric cytoprotection. Iwamori, M., Suzuki, H., Ito, N., Iwamori, Y., Hanaoka, K. J. Clin. Gastroenterol. (2005) [Pubmed]
  13. Cholesterol and its anionic derivatives inhibit 5-lipoxygenase activation in polymorphonuclear leukocytes and MonoMac6 cells. Aleksandrov, D.A., Zagryagskaya, A.N., Pushkareva, M.A., Bachschmid, M., Peters-Golden, M., Werz, O., Steinhilber, D., Sud'ina, G.F. FEBS J. (2006) [Pubmed]
  14. Activation of C-kinase eta through its cholesterol-3-sulfate-dependent phosphorylation by casein kinase I in vitro. Okano, M., Yokoyama, T., Miyanaga, T., Ohtsuki, K. Biol. Pharm. Bull. (2004) [Pubmed]
  15. Inactivation and reactivation of sex-linked steroid sulfatase gene in murine cell culture. Schorderet, D.F., Keitges, E.A., Dubois, P.M., Gartler, S.M. Somat. Cell Mol. Genet. (1988) [Pubmed]
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