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Chemical Compound Review

CPD-8984     (2R,3S)-2,3-diphenyloxirane

Synonyms: CCRIS 2080, CHEBI:50004, KST-1A1987, OR9373, LMPK13090030, ...
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Disease relevance of cis-Stilbene oxide


High impact information on cis-Stilbene oxide


Anatomical context of cis-Stilbene oxide

  • Microsomes catalysed the hydratation of benzo(a)pyrene-4,5-oxide and cis-stilbene oxide at the same extent, whatever the sex, although the specific activity was 10 times lower than in liver [8].
  • Conjugation of cis-stilbene oxide with glutathione in skin and liver proceeded at essentially similar rates, as the specific activity of glutathione S-transferase in skin was only two times less than that measured in hepatic cytosol [8].
  • Hydrolysis of both cis-stilbene oxide and benzo[a]pyrene 4,5-oxide was highest in testis followed by liver greater than lung greater than kidney [9].
  • 2. To examine the effects of these amino acid alterations on EPHX1 function, EPHX1 cDNA constructs of wild-type and five variants were transfected into COS-1 cells, and their hydrolytic activities for cis-stilbene oxide were determined in vitro [10].

Associations of cis-Stilbene oxide with other chemical compounds


Gene context of cis-Stilbene oxide

  • Using the purified protein preparations, rates of cSO and BaPO hydrolysis for the reference protein, Y113/H139, were approximately 2-fold greater than those measured with the other EPHX1 allelic variants [16].
  • In particular, the relative specific activity of all three enzymes decreased in the light mitochondrial (peroxisomal) cell fraction, and an increase of a mEH-like activity (benzo[a]pyrene-4,5-oxide and cis-stilbene oxide hydrolysis) in the cytosol occurred [17].
  • Microsomal epoxide hydrolase activity towards cis-stilbene oxide was increased up to three-fold and cytosolic glutathione S-transferase activity towards 1-chloro-2, 4-dinitrobenzene reached twice the control value [18].
  • Pretreatment with buthionine sulfoximine (BSO), an inhibitor of GSH synthesis, enhanced MT synthesis itself as well as that induced by TSO and cis-stilbene oxide (CSO) [19].
  • The subcellular and organ distributions of microsomal epoxide hydrolases measured with cis-stilbene oxide and cholesterol 5,6 alpha-epoxide as substrates have been investigated [20].

Analytical, diagnostic and therapeutic context of cis-Stilbene oxide


  1. Characterization and cDNA cloning of a clofibrate-inducible microsomal epoxide hydrolase in Drosophila melanogaster. Taniai, K., Inceoglu, A.B., Yukuhiro, K., Hammock, B.D. Eur. J. Biochem. (2003) [Pubmed]
  2. Assessment of possible protective roles of selenium, zinc, and cis-stilbene oxide against acute T-2 toxin poisoning: a preliminary report. Yazdanpanah, H., Roshanzamir, F., Shafaghi, B., Faizi, M., Elhami, M., Rasekh, H.R. Nat. Toxins (1997) [Pubmed]
  3. Human glutathione S-transferase deficiency as a marker of susceptibility to epoxide-induced cytogenetic damage. Wiencke, J.K., Kelsey, K.T., Lamela, R.A., Toscano, W.A. Cancer Res. (1990) [Pubmed]
  4. Biochemical evidence for the involvement of tyrosine in epoxide activation during the catalytic cycle of epoxide hydrolase. Yamada, T., Morisseau, C., Maxwell, J.E., Argiriadi, M.A., Christianson, D.W., Hammock, B.D. J. Biol. Chem. (2000) [Pubmed]
  5. Immunochemical comparison of human and rhesus monkey liver microsomal and the hepatocellular carcinoma-induced human serum epoxide hydrolases (preneoplastic antigens): basis for an enzyme-linked immunoabsorbent assay. Moody, D.E., Hammock, B.D., Ruebner, B.H., Hillman, D.W., Hillman, J.H. Carcinogenesis (1989) [Pubmed]
  6. Induction of hepatic heme oxygenase and changes in cytochrome P-450s in response to oxidative stress produced by stilbenes and stilbene oxides in rats. Oguro, T., Kaneko, E., Numazawa, S., Imaoka, S., Funae, Y., Yoshida, T. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  7. Kinetic parameters of lymphocyte microsomal epoxide hydrolase in carbamazepine hypersensitive patients. Assessment by radiometric HPLC. Davis, C.D., Pirmohamed, M., Kitteringham, N.R., Allott, R.L., Smith, D., Park, B.K. Biochem. Pharmacol. (1995) [Pubmed]
  8. Characterization of distinct forms of cytochromes P-450, epoxide metabolizing enzymes and UDP-glucuronosyltransferases in rat skin. Pham, M.A., Magdalou, J., Totis, M., Fournel-Gigleux, S., Siest, G., Hammock, B.D. Biochem. Pharmacol. (1989) [Pubmed]
  9. Effect of dietary clofibrate on epoxide hydrolase activity in tissues of mice. Loury, D.N., Moody, D.E., Kim, B.W., Hammock, B.D. Biochem. Pharmacol. (1985) [Pubmed]
  10. Non-synonymous single nucleotide alterations in the microsomal epoxide hydrolase gene and their functional effects. Maekawa, K., Itoda, M., Hanioka, N., Saito, Y., Murayama, N., Nakajima, O., Soyama, A., Ishida, S., Ozawa, S., Ando, M., Sawada, J. Xenobiotica (2003) [Pubmed]
  11. Epoxide hydrolysis in the cytosol of rat liver, kidney, and testis. Measurement in the presence of glutathione and the effect of dietary clofibrate. Moody, D.E., Silva, M.H., Hammock, B.D. Biochem. Pharmacol. (1986) [Pubmed]
  12. Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: studies with cis-stilbene oxide, carbamazepine 10, 11-epoxide and naphthalene. Kitteringham, N.R., Davis, C., Howard, N., Pirmohamed, M., Park, B.K. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  13. Human liver cytosolic epoxide hydrolases. Schladt, L., Thomas, H., Hartmann, R., Oesch, F. Eur. J. Biochem. (1988) [Pubmed]
  14. Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides. Bellucci, G., Chiappe, C., Ingrosso, G. Chirality. (1994) [Pubmed]
  15. Subcellular distribution, catalytic properties and partial purification of epoxide hydrolase in the human adrenal gland. Papadopoulos, D., Seidegård, J., Georgellis, A., Rydström, J. Chem. Biol. Interact. (1985) [Pubmed]
  16. Functional analysis of human microsomal epoxide hydrolase genetic variants. Hosagrahara, V.P., Rettie, A.E., Hassett, C., Omiecinski, C.J. Chem. Biol. Interact. (2004) [Pubmed]
  17. Epoxide metabolism in the liver of mice treated with clofibrate (ethyl-alpha-(p-chlorophenoxyisobutyrate], a peroxisome proliferator. Moody, D.E., Loury, D.N., Hammock, B.D. Toxicol. Appl. Pharmacol. (1985) [Pubmed]
  18. Selective induction of rat liver phase II enzymes by N-heterocycle analogues of phenanthrene: a response exhibiting high correlation between UDP-glucuronosyltransferase and microsomal epoxide hydrolase activities. Franklin, M.R., Slawson, M.H., Moody, D.E. Xenobiotica (1993) [Pubmed]
  19. Induction of metallothionein synthesis by glutathione depletion after trans- and cis-stilbene oxide administration in rats. Sato, M., Sasaki, M., Oguro, T., Kuroiwa, Y., Yoshida, T. Chem. Biol. Interact. (1995) [Pubmed]
  20. Subcellular and organ distribution of cholesterol epoxide hydrolase in the rat. Aström, A., Eriksson, M., Eriksson, L.C., Birberg, W., Pilotti, A., DePierre, J.W. Biochim. Biophys. Acta (1986) [Pubmed]
  21. Expression and activity of microsomal epoxide hydrolase in follicles isolated from mouse ovaries. Cannady, E.A., Dyer, C.A., Christian, P.J., Sipes, I.G., Hoyer, P.B. Toxicol. Sci. (2002) [Pubmed]
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