cholestanes

Summary

Summary: Derivatives of the saturated steroid cholestane with methyl groups at C-18 and C-19 and an iso-octyl side chain at C-17.

Top Publications

  1. Ditscheid B, Keller S, Jahreis G. Faecal steroid excretion in humans is affected by calcium supplementation and shows gender-specific differences. Eur J Nutr. 2009;48:22-30 pubmed publisher
    ..Dietary calcium supplementation diversely affects BA and NSt in faeces and in faecal water but does not influence the genotoxicity of faecal water in healthy adults. ..
  2. Boonananwong S, Kongkathip B, Kongkathip N. First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa. Steroids. 2008;73:1123-7 pubmed publisher
    ..65-47.22 microM. Compound 2 showed moderate activity against NCI (IC(50) 42.68 microM) but was inactive against MCF7 and KB whereas compound 1 showed no activity against all tested cells. ..
  3. Lantz K, Hart S, Planey S, Roitman M, Ruiz White I, Wolfe H, et al. Inhibition of PTP1B by trodusquemine (MSI-1436) causes fat-specific weight loss in diet-induced obese mice. Obesity (Silver Spring). 2010;18:1516-23 pubmed publisher
    ..These data establish trodusquemine as an effective central and peripheral PTP1B inhibitor with the potential to elicit noncachectic fat-specific weight loss and improve insulin and leptin levels...
  4. Love G, Grosjean E, Stalvies C, Fike D, Grotzinger J, Bradley A, et al. Fossil steroids record the appearance of Demospongiae during the Cryogenian period. Nature. 2009;457:718-21 pubmed publisher
    ..Biomarker analysis has yet to reveal any convincing evidence for ancient sponges pre-dating the first globally extensive Neoproterozoic glacial episode (the Sturtian, approximately 713 Myr ago in Oman). ..
  5. D Yakonov V, Tuktarova R, Islamov I, Khalilov L, Dzhemilev U. Catalytic cyclometallation in steroid chemistry IV: Efficient method for the synthesis of tetrahydrothiophene, tetrahydroselenophen and cyclopentanone derivatives of (5α)-cholestane. Steroids. 2016;108:77-84 pubmed publisher
  6. Tagiri Endo M, Nakagawa K, Sugawara T, Ono K, Miyazawa T. Ozonation of cholesterol in the presence of ethanol: identification of a cytotoxic ethoxyhydroperoxide molecule. Lipids. 2004;39:259-64 pubmed
    ..Hence, 7alpha-ethoxy-5-OOH is a toxic molecule of primary importance, arising during cholesterol ozonation in the presence of ethanol. ..
  7. Abdel Hameed E, El Nahas H, El Wakil E, Ahmed W. Cytotoxic cholestane and pregnane glycosides from Tribulus macropterus. Z Naturforsch C. 2007;62:319-25 pubmed
    ..The three steroidal compounds 1, 2 and 5 were also tested against the same cell line HepG2 and their IC50 values were 2.4, 2.2 and 1.1 microg/ml, respectively. ..
  8. Jeanneau L, Jardé E, Gruau G. Influence of salinity and natural organic matter on the solid phase extraction of sterols and stanols: application to the determination of the human sterol fingerprint in aqueous matrices. J Chromatogr A. 2011;1218:2513-20 pubmed publisher
    ..We conclude that this analytical method is fully applicable to the determination of sterol fingerprints in the dissolved phase (<0.7 ?m) of natural aqueous samples. ..
  9. Kuroda M, Mimaki Y, Yokosuka A, Hasegawa F, Sashida Y. Cholestane glycosides from the bulbs of Ornithogalum thyrsoides and their cytotoxic activity against HL-60 leukemia cells. J Nat Prod. 2002;65:1417-23 pubmed
    ..30 microg/mL), used as a positive control. These cholestanes were concluded to contribute to the potent cytotoxicity of the crude O. thyrsoides bulb extract.

More Information

Publications62

  1. Alarif W, Al Lihaibi S, Abdel Lateff A, Ayyad S. New antifungal cholestane and aldehyde derivatives from the red alga Laurencia papillosa. Nat Prod Commun. 2011;6:1821-4 pubmed
    ..All compounds, except 2, were tested for their antifungal activity. Significant activities were associated with 1 and 3 against Candida albicans, Aspergillus fumigatus, and A. flavus. ..
  2. Baldessari A, Iglesias L. Lipases in green chemistry: acylation and alcoholysis on steroids and nucleosides. Methods Mol Biol. 2012;861:457-69 pubmed publisher
    ..In the field of steroids, a variety of acetyl and fatty acid derivatives of androstanes, pregnanes, and cholestanes have been prepared through lipase-catalyzed acylation and alcoholysis reactions taking advantage of the high ..
  3. Hoye T, Dvornikovs V, Fine J, Anderson K, Jeffrey C, Muddiman D, et al. Details of the structure determination of the sulfated steroids PSDS and PADS: new components of the sea lamprey (petromyzon marinus) migratory pheromone. J Org Chem. 2007;72:7544-50 pubmed
    ..The logic underlying the iterative analyses used is presented...
  4. Brocks J, Logan G, Buick R, Summons R. Archean molecular fossils and the early rise of eukaryotes. Science. 1999;285:1033-6 pubmed
  5. Lau W, Das N. In vitro modulation of rat adipocyte ghost membrane fluidity by cholesterol oxysterols. Experientia. 1995;51:731-7 pubmed
    ..This differential interaction may cause selective changes in membrane fluidity at different depths of the bilayer and thus may modulate the activities of membrane-bound proteins such as enzymes and receptors. ..
  6. Thompson D, Morrice N, Grant L, Le Sommer S, Lees E, Mody N, et al. Pharmacological inhibition of protein tyrosine phosphatase 1B protects against atherosclerotic plaque formation in the LDLR-/- mouse model of atherosclerosis. Clin Sci (Lond). 2017;131:2489-2501 pubmed publisher
    ..Our findings are the first to demonstrate that PTP1B inhibitors could be used in prevention and reversal of atherosclerosis development and reduction in CVD risk. ..
  7. Shamsuzzaman -, Khan M, Alam M, Tabassum Z, Ahmad A, Khan A. Synthesis, antibacterial and antifungal activities of 6,5 fused steroidal oxazoles in cholestane series. Eur J Med Chem. 2010;45:1094-7 pubmed publisher
    ..Chloramphenicol (30 microg) was used as standard drug in case of bacteria and nystatin was used as a standard drug in case of fungi. ..
  8. Fine J, Sorensen P. Production and fate of the sea lamprey migratory pheromone. Fish Physiol Biochem. 2010;36:1013-20 pubmed publisher
    ..In conclusion, it appears highly likely that a mixture of PADS, PSDS and PS is present at biologically relevant concentrations and ratios in many Great Lakes streams where it functions as a pheromonal attractant. ..
  9. McCance R. Osteomalacia with Looser's nodes (Milkman's syndrome) due to a raised resistance to vitamin D acquired about the age of 15 years. Q J Med. 1947;16:33-46 pubmed
  10. Rajnikant -, Dinesh -, Bhavnaish C. Comparative crystallographic and hydrogen-bonding analysis of cholestane derivatives. Acta Crystallogr A. 2006;62:136-45 pubmed
    ..Distance-angle scatter plots for both kinds of interactions are presented for better understanding of packing interactions existing in cholestane molecules. ..
  11. Wachtel E, Bach D, Epand R, Tishbee A, Epand R. A product of ozonolysis of cholesterol alters the biophysical properties of phosphatidylethanolamine membranes. Biochemistry. 2006;45:1345-51 pubmed
    ..The chemical and physical interactions of 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al with phosphatidylethanolamines may contribute to damaging effects of this lipid on cell membranes, resulting in pathology. ..
  12. Choi H, Kim Y. [Oxysterol (3,5-cholestadien-7-one, 5 beta-cholestan-3-one, 5,24-cholestadien-3 beta-OL) induced cytotoxicity and apoptosis in gallbladder epithelial cells]. Korean J Gastroenterol. 2004;44:328-36 pubmed
  13. Antonchick A, Schneider B, Zhabinskii V, Khripach V. Synthesis of [26,27-2H6]brassinosteroids from 23,24-bisnorcholenic acid methyl ester. Steroids. 2004;69:617-28 pubmed
    ..The key step in the synthesis of the side chain involved addition of (2S)-[3,4-(2)H(6)]2,3-dimethylbutylphenyl sulfone to the corresponding C-22 aldehydes. ..
  14. Dongowski G, Lorenz A. Intestinal steroids in rats are influenced by the structural parameters of pectin. J Nutr Biochem. 2004;15:196-205 pubmed
    ..Besides the degree of methylation, the molecular weight of pectin used in the diets influenced concentration and composition of intestinal and fecal steroids in rats. ..
  15. Pérez Díaz J, Rárová L, Muñoz Ocampo J, Magaña Vergara N, Farfán N, Strnad M, et al. Synthesis and biological activity of 23-ethylidene-26-hydroxy-22-oxocholestane derivatives from spirostanic sapogenins. Eur J Med Chem. 2012;51:67-78 pubmed publisher
    ..These modified derivatives exhibit cytotoxic activity against CEM and MCF7 cells and are able to induce apoptosis in them. Its effect on the cell cycle was determined. ..
  16. Jing X, Vogel H, Grebenok R, Zhu Salzman K, Behmer S. Dietary sterols/steroids and the generalist caterpillar Helicoverpa zea: physiology, biochemistry and midgut gene expression. Insect Biochem Mol Biol. 2012;42:835-45 pubmed publisher
    ..Second, they provide unique mechanistic insights into how variation in dietary sterol/steroid structure can affect insect herbivores. ..
  17. Wang H, Guo Y, Guan Y, Zhou L, Lei P. The synthesis of cholestane and furostan saponin analogues and the determination of sapogenin's absolute configuration at C-22. Steroids. 2011;76:18-27 pubmed publisher
    ..The cytotoxicities of the synthetic analogues toward four types of tumor cells were shown also. ..
  18. Nakagawa K, Anzai K. Stratum corneum lipid structure investigated by EPR spin-probe method: application of terpenes. Lipids. 2010;45:1081-7 pubmed publisher
    ..The results imply that CHL permeates into SC lipid differently from 5-DSA. The enhancement of the 5-DSA is more significant than that of CHL. Therefore, the present results can be useful for various drug administrations via the skin. ..
  19. Sharma K, Mishra S, Mishra A. Experimental and theoretical assessment of the mechanism involved in the reaction of steroidal ketone semicarbazone with hydrogen peroxide. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:1493-8 pubmed publisher
    ..Frontier molecular orbital, spin electronic density, electrostatic potential and atomic charges were discussed. ..
  20. Li K, Wang H, Brant C, Ahn S, Li W. Multiplex quantification of lamprey specific bile acid derivatives in environmental water using UHPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2011;879:3879-86 pubmed publisher
    ..4) and water conditioned with male sea lampreys (SD<4.8). Utilizing this method provides a routine analysis of lamprey bile acid derivatives and may prove useful for sea lamprey population estimates in future studies and applications. ..
  21. Pandey N, Zhou X, Qin Z, Zaman T, Gomez Smith M, Keyhanian K, et al. The LIM domain only 4 protein is a metabolic responsive inhibitor of protein tyrosine phosphatase 1B that controls hypothalamic leptin signaling. J Neurosci. 2013;33:12647-55 pubmed publisher
    ..Thus, unleashed PTP1B activity attributable to loss of LMO4 palmitoylation may account for rapid loss of central leptin signaling after acute exposure to saturated fat. ..
  22. Cui Y, Koirala D, Kang H, Dhakal S, Yangyuoru P, Hurley L, et al. Molecular population dynamics of DNA structures in a bcl-2 promoter sequence is regulated by small molecules and the transcription factor hnRNP LL. Nucleic Acids Res. 2014;42:5755-64 pubmed publisher
    ..The excellent agreement with biochemical results firmly validates the MPD analyses, which, we expect, can be widely applicable to investigate complex equilibrium of biomacromolecules. ..
  23. Epand R, Cheetham J, Raymer K. Acid-induced fusion of liposomes: studies with 2,3-seco-5 alpha-cholestan-2,3-dioic acid. Biochim Biophys Acta. 1988;940:85-92 pubmed
    ..5 to 5.5. Several of the properties of 2,3-seco-5 alpha-cholestan-2,3-dioic acid indicate that this compound may be useful in sensitizing vesicles to acid-induced fusion for the purpose of endocytic drug delivery. ..
  24. Giner J, Faraldos J. A biomimetic approach to the synthesis of an antiviral marine steroidal orthoester. J Org Chem. 2002;67:2717-20 pubmed
    ..Steroidal model compounds incorporating 16-butyroxy and 20,22-epoxy groups were synthesized from tigogenin and were shown to rearrange to orthoesters under mild acidic catalysis. ..
  25. Elmegeed G, Wardakhan W, Younis M, Louca N. Synthesis and antimicrobial evaluation of some novel cholestane heterocyclic derivatives. Arch Pharm (Weinheim). 2004;337:140-7 pubmed
    ..The structures of the compounds were established based on the analytical and spectral data. The in vitro antimicrobial activity of some newly synthesized compounds against bacteria and fungi was studied. ..
  26. Salmi C, Loncle C, Vidal N, Letourneux Y, Brunel J. New stereoselective titanium reductive amination synthesis of 3-amino and polyaminosterol derivatives possessing antimicrobial activities. Eur J Med Chem. 2008;43:540-7 pubmed
    ..25-12.5 microg/mL. ..
  27. Kim E, Jeon S, Choi M. Effects of gamma-irradiated fats on plasma lipid concentrations and hepatic cholesterol metabolism in rats. Ann Nutr Metab. 2001;45:152-8 pubmed
    ..These results indicate that although slight changes in the lipid metabolism were observed as a result of 5-kGy-gamma-irradiated fat feeding, they were relative to the fat type and had no harmful consequences. ..
  28. Gagni S, Cam D. Stigmastane and hopanes as conserved biomarkers for estimating oil biodegradation in a former refinery plant-contaminated soil. Chemosphere. 2007;67:1975-81 pubmed
    ..These are very useful tools to assess alterations in less stable classes of saturated compounds contained in petroleum. Marked degradation of perhydro, tetrahydro, dihydro-PAH derivatives in the laboratory treatment has been evidenced. ..
  29. Okamura W, Zhu G, Hill D, Thomas R, Ringe K, Borchardt D, et al. Synthesis and NMR studies of (13)C-labeled vitamin D metabolites. J Org Chem. 2002;67:1637-50 pubmed
  30. Pandey R, Verma R, Singh S, Gupta M. 4alpha-methyl-24beta-ethyl-5alpha-cholesta-14,25-dien-3beta-ol and 24beta-ethylcholesta-5, 9(11), 22E-trien-3beta-ol, sterols from Clerodendrum inerme. Phytochemistry. 2003;63:415-20 pubmed
    ..The structure elucidations were based on analyses of physical and spectroscopic data...
  31. Mimaki Y, Kuroda M, Yokosuka A, Sashida Y. Five new polyoxygenated cholestane bisdesmosides from the bulbs of Galtonia candicans. J Nat Prod. 2001;64:1069-72 pubmed
    ..The structures of the new compounds were determined by spectroscopic analysis and chemical transformations. ..
  32. Karantonis H, Pitsinos E, Antonopoulou S, Couladouros E, Demopoulos C. Synthesis and biological evaluation of novel steroid-modified ether phospholipids. Chem Phys Lipids. 2005;138:12-9 pubmed
    ..These two novel compounds exhibit marked chemical and biological similarities to their endogenous prototype and they antagonize it being less active in inducing washed platelet aggregation through PAF receptors. ..
  33. Brooks R, Fuhler G, Iyer S, Smith M, Park M, Paraiso K, et al. SHIP1 inhibition increases immunoregulatory capacity and triggers apoptosis of hematopoietic cancer cells. J Immunol. 2010;184:3582-9 pubmed publisher
    ..Thus, SHIP1 inhibitors represent a novel class of small molecules that have the potential to enhance allogeneic transplantation, boost blood cell production, and improve the treatment of hematologic malignancies. ..
  34. Kurosawa T, Fujiwara M, Nakano H, Sato M, Yoshimura T, Murai T. Synthesis of coenzyme A esters of 3alpha,7alpha,12alpha-trihydroxy- and 3alpha,7alpha-dihydroxy-24-oxo-5beta-cholestan-26-oic acids for the study of beta-oxidation in bile acid biosynthesis. Steroids. 2001;66:499-504 pubmed
    ..The chromatographic behaviors of these CoA esters were also investigated. ..
  35. Endo Y, Hashimoto Y, Fukasawa H, Shudo K. Oxygenated cholesterols as ligands for cytosolic-nuclear tumor promoter binding protein: yakkasteroids. Biochem Biophys Res Commun. 1993;194:1529-35 pubmed
    ..Investigation of the structure-activity relationships of yakkasteroids revealed that the structure of the side chain at the 20-position is important for the binding activity to CN-TPBP. ..
  36. Lau W, Khoo H, Das N. Potentiation of beta-adrenoceptor agonist mediated-lipolysis by cholesterol-derived oxysterols. Biochem Mol Biol Int. 1995;35:1349-58 pubmed
    ..The results suggest that cholestanone exerts its potentiation effect by facilitating the binding of beta-adrenergic agonist to its receptor. ..
  37. Wei X, Rodriguez A, Wang Y, Franzblau S. Synthesis and in vitro biological evaluation of ring B abeo-sterols as novel inhibitors of Mycobacterium tuberculosis. Bioorg Med Chem Lett. 2008;18:5448-50 pubmed publisher
    ..Therefore, the 5(6-->7)abeo-sterol nucleus present in compounds 3, 5, 7, 9, and 11 represents a novel scaffold for the development of new antitubercular agents. ..
  38. Hamed A, Janda B, Mahalel U, Stochmal A, Oleszek W. Profiles of steroidal saponins from the aerial parts of Tribulus pentandrus, T. megistopterus subsp. pterocarpus and T. parvispinus by LC-ESI-MS/MS. Phytochem Anal. 2012;23:613-21 pubmed publisher
    ..It has been found that the genus Tribulus is rich in biologically active furostane-, cholestane- and spirostane-type steroidal saponins...
  39. Zhang H, Ruehl C, Chan A, Nah T, Worton D, Isaacman G, et al. OH-initiated heterogeneous oxidation of cholestane: a model system for understanding the photochemical aging of cyclic alkane aerosols. J Phys Chem A. 2013;117:12449-58 pubmed publisher
    ..These results provide new insights into the oxidation mechanism of cyclic alkanes. ..
  40. Shu Y, Jones S, Kinney W, Selinsky B. The synthesis of spermine analogs of the shark aminosterol squalamine. Steroids. 2002;67:291-304 pubmed
    ..All of the analogs possess significant antimicrobial activity, suggesting that substitution at C7 and C24 of the aminosterols plays a minor role in their antimicrobial potency. ..
  41. Fuhler G, Brooks R, Toms B, Iyer S, Gengo E, Park M, et al. Therapeutic potential of SH2 domain-containing inositol-5'-phosphatase 1 (SHIP1) and SHIP2 inhibition in cancer. Mol Med. 2012;18:65-75 pubmed publisher
    ..In conclusion, this study shows that inhibition of SHIP1 and SHIP2 may have broad clinical application in the treatment of multiple tumor types. ..
  42. Roitman M, Wescott S, Cone J, McLane M, Wolfe H. MSI-1436 reduces acute food intake without affecting dopamine transporter activity. Pharmacol Biochem Behav. 2010;97:138-43 pubmed publisher
    ..Thus, over a time course when MSI-1436 suppresses food intake it does not affect DAT function. The results support MSI-1436 as an anti-obesity treatment which spares DAT. ..
  43. Sharma K, Lal B. An experimental and theoretical approach to 5alpha-cholestan-6-spiro-1',2',4'-triazolidine-3'-one. J Steroid Biochem Mol Biol. 2007;107:270-6 pubmed
    ..Stability and feasibility of all the optimized structures were supported by their respective fundamental frequencies and energy minima. ..
  44. Hussainzada N, Da Silva T, Zhang E, Swaan P. Conserved aspartic acid residues lining the extracellular loop 1 of sodium-coupled bile acid transporter ASBT Interact with Na+ and 7alpha-OH moieties on the ligand cholestane skeleton. J Biol Chem. 2008;283:20653-63 pubmed publisher
  45. Fine J, Sorensen P. Isolation and biological activity of the multi-component sea lamprey migratory pheromone. J Chem Ecol. 2008;34:1259-67 pubmed publisher
    ..Finally, the mixture of all three components was as attractive as larval water to adult sea lampreys in laboratory mazes. It is believed that these steroids are the principal components of the pheromone. ..
  46. Greube A, Muller K, Töpfer Petersen E, Herrmann A, Muller P. Interaction of fibronectin type II proteins with membranes: the stallion seminal plasma protein SP-1/2. Biochemistry. 2004;43:464-72 pubmed
    ..The data are discussed with regard to similarities and species-specific differences of the function of seminal Fn type II proteins in the genesis of sperm cells. ..
  47. Vandenberg A, Bales B, Salikhov K, Peric M. Bimolecular encounters and re-encounters (cage effect) of a spin-labeled analogue of cholestane in a series of n-alkanes: effect of anisotropic exchange integral. J Phys Chem A. 2012;116:12460-9 pubmed publisher
    ..Thus, B(dip) and ?(RE) form common curves when plotted vs V(0)/V(f). As a result, the fractional broadening by DD occurs at an order of magnitude higher values of T/? for CSL compared with pDT. ..
  48. Ali Z, Smillie T, Khan I. Cholestane steroid glycosides from the rhizomes of Dioscorea villosa (wild yam). Carbohydr Res. 2013;370:86-91 pubmed publisher
    ..The structures of the isolated compounds were determined using spectroscopic and chemical methods including 1D and 2D NMR. The antimicrobial action of most of these compounds was tested against five fungal and five bacterial strains. ..
  49. Kim H, Jadhav J, Jung S, Kwak J. Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates. Bioorg Med Chem Lett. 2013;23:4315-8 pubmed publisher
    ..3?,7?-Di(pyridylmethyl)amino-5?-cholestane 10 showed the highest potency in these series toward the Gram-positive bacteria, Staphylococcus epidermidis 887E, with the lowest MIC value of 1 ?g/mL. ..
  50. Georgiou C, Constantinou M, Kapnissi Christodoulou C. Sample preparation: a critical step in the analysis of cholesterol oxidation products. Food Chem. 2014;145:918-26 pubmed publisher
    ..according to recovery, precision and simplicity. ..
  51. Deo A, Bandiera S. 3-ketocholanoic acid is the major in vitro human hepatic microsomal metabolite of lithocholic acid. Drug Metab Dispos. 2009;37:1938-47 pubmed publisher
  52. Li T, Li Y, Liang X. Studies of the synthesis of biomarkers. X. Synthesis of 13,17-secodiacholestanes. Steroids. 1992;57:67-71 pubmed
    ..On Clemmensen reduction, the diones (5a and 5b) yielded the target molecule 6. The structure of an unknown biomarker was shown to be different from the proposed 6 by gas chromatographic/mass spectrometric comparison. ..
  53. Zheng D, Zhou L, Guan Y, Chen X, Zhou W, Chen X, et al. Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1-->4-linked analogue and their antitumor activities. Bioorg Med Chem Lett. 2010;20:5439-42 pubmed publisher
    ..Their cytotoxic activities were evaluated by the standard MTT assay. Compound 1 showed potent cytotoxicity against five types of human tumor cells, with IC50 ranging between 1.3 and 73 nM...