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Chemical Compound Review

Glidsafe     (4R)-1-methyl-4-prop-1-en-2- yl-cyclohexene

Synonyms: Refchole, Carvene, Citrene, Glidesafe, Kautschiin, ...
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Disease relevance of C06099

  • In these experiments D-limonene and D-carvone were tested and reduced forestomach tumor formation by slightly over 60% and pulmonary adenoma formation by about 35% [1].
  • We have shown that d-limonene induces the regression of advanced rat mammary adenocarcinomas [2].
  • No toxicity was evident in these rats even at the highest d-limonene dose [3].
  • d-Limonene was found to be effective in reducing the average number of rat mammary carcinomas that developed in 7,12-dimethylbenz[a]anthracene-treated rats when the terpene was fed during the initiation or during the promotion/progression stage of carcinogenesis [4].
  • However, in rats given both sodium chloride and d-limonene, the incidence of gastric cancers, the labeling index and ODC activity were significantly lower and the apoptotic index was significantly higher than in rats given sodium chloride alone [5].

High impact information on C06099

  • Quercetin, d-limonene, and all-trans retinoic acid each had no effect on spontaneous tumor development in p53-/- mice [6].
  • The presence of alpha 2u-globulin is necessary for d-limonene promotion of male rat kidney tumors [7].
  • In a 2-year carcinogenesis bioassay, d-limonene (dL) induced kidney tumors in male F344 rats, but not in female F344 rats or either sex of mice, d-Limonene-1,2-oxide, a metabolite of dL, has been shown to bind reversibly the male rat-specific urinary protein, alpha2u-globulin (alpha 2u-G), lysosomal degradation than alpha 2u-G alone [7].
  • Selective inhibition of isoprenylation of 21-26-kDa proteins by the anticarcinogen d-limonene and its metabolites [8].
  • With administration of sufficient doses of d-limonene to male rats, this protein has been found to accumulate excessively in the P2 segment cells of renal proximal tubules, resulting in hyaline droplet formation as a manifestation of protein overload [9].

Chemical compound and disease context of C06099


Biological context of C06099

  • This proposed mechanism has been supported by additional information, including negative genotoxicity tests for d-limonene and its oxide metabolites, experimentally verified tumor promotion, and enhanced cell proliferation primarily in P2 segment tubule cells in male F344 rats, but no such effects in the alpha 2U-g-deficient NBR rat [9].
  • The results of isotopically sensitive branching experiments of competitive and noncompetitive design were consistent with a nondissociative kinetic mechanism, indicating that (4R)-limonene has sufficient freedom of motion within the active site of CYP71D18 to allow formation of either the trans-3- or cis-6-hydroxylated product [15].
  • Pharmacokinetics of perillic acid in humans after a single dose administration of a citrus preparation rich in d-limonene content [16].
  • Comparative analysis of percutaneous absorption enhancement by d-limonene and oleic acid based on a skin diffusion model [17].
  • Further studies with large sample sizes are needed to more completely evaluate the interrelationships between peel intake, bioavailability of d-limonene, and other lifestyle factors [18].

Anatomical context of C06099


Associations of C06099 with other chemical compounds


Gene context of C06099


Analytical, diagnostic and therapeutic context of C06099


  1. Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Wattenberg, L.W., Sparnins, V.L., Barany, G. Cancer Res. (1989) [Pubmed]
  2. Increased mannose 6-phosphate/insulin-like growth factor II receptor and transforming growth factor beta 1 levels during monoterpene-induced regression of mammary tumors. Jirtle, R.L., Haag, J.D., Ariazi, E.A., Gould, M.N. Cancer Res. (1993) [Pubmed]
  3. Inhibition of DMBA-induced mammary cancer by the monoterpene d-limonene. Elegbede, J.A., Elson, C.E., Qureshi, A., Tanner, M.A., Gould, M.N. Carcinogenesis (1984) [Pubmed]
  4. Anti-carcinogenic activity of d-limonene during the initiation and promotion/progression stages of DMBA-induced rat mammary carcinogenesis. Elson, C.E., Maltzman, T.H., Boston, J.L., Tanner, M.A., Gould, M.N. Carcinogenesis (1988) [Pubmed]
  5. Attenuation by d-limonene of sodium chloride-enhanced gastric carcinogenesis induced by N-methyl-N'-nitro-N-nitrosoguanidine in Wistar rats. Yano, H., Tatsuta, M., Iishi, H., Baba, M., Sakai, N., Uedo, N. Int. J. Cancer (1999) [Pubmed]
  6. Chemoprevention of spontaneous tumorigenesis in p53-knockout mice. Hursting, S.D., Perkins, S.N., Haines, D.C., Ward, J.M., Phang, J.M. Cancer Res. (1995) [Pubmed]
  7. The presence of alpha 2u-globulin is necessary for d-limonene promotion of male rat kidney tumors. Dietrich, D.R., Swenberg, J.A. Cancer Res. (1991) [Pubmed]
  8. Selective inhibition of isoprenylation of 21-26-kDa proteins by the anticarcinogen d-limonene and its metabolites. Crowell, P.L., Chang, R.R., Ren, Z.B., Elson, C.E., Gould, M.N. J. Biol. Chem. (1991) [Pubmed]
  9. Risk assessment of d-limonene: an example of male rat-specific renal tumorigens. Hard, G.C., Whysner, J. Crit. Rev. Toxicol. (1994) [Pubmed]
  10. The prevention of nitrosomethylurea-induced mammary tumors by d-limonene and orange oil. Maltzman, T.H., Hurt, L.M., Elson, C.E., Tanner, M.A., Gould, M.N. Carcinogenesis (1989) [Pubmed]
  11. Modulation of the mevalonate pathway and cell growth by pravastatin and d-limonene in a human hepatoma cell line (Hep G2). Kawata, S., Nagase, T., Yamasaki, E., Ishiguro, H., Matsuzawa, Y. Br. J. Cancer (1994) [Pubmed]
  12. Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells. Duetz, W.A., Fjällman, A.H., Ren, S., Jourdat, C., Witholt, B. Appl. Environ. Microbiol. (2001) [Pubmed]
  13. Perception of noxious compounds by contact chemoreceptors of the blowfly, Phormia regina: putative role of an odorant-bindingpProtein. Ozaki, M., Takahara, T., Kawahara, Y., Wada-Katsumata, A., Seno, K., Amakawa, T., Yamaoka, R., Nakamura, T. Chem. Senses (2003) [Pubmed]
  14. Comparison of short-term renal effects due to oral administration of decalin or d-limonene in young adult male Fischer-344 rats. Kanerva, R.L., Ridder, G.M., Lefever, F.R., Alden, C.L. Food Chem. Toxicol. (1987) [Pubmed]
  15. Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. Wüst, M., Croteau, R.B. Biochemistry (2002) [Pubmed]
  16. Pharmacokinetics of perillic acid in humans after a single dose administration of a citrus preparation rich in d-limonene content. Chow, H.H., Salazar, D., Hakim, I.A. Cancer Epidemiol. Biomarkers Prev. (2002) [Pubmed]
  17. Comparative analysis of percutaneous absorption enhancement by d-limonene and oleic acid based on a skin diffusion model. Koyama, Y., Bando, H., Yamashita, F., Takakura, Y., Sezaki, H., Hashida, M. Pharm. Res. (1994) [Pubmed]
  18. Citrus peel use is associated with reduced risk of squamous cell carcinoma of the skin. Hakim, I.A., Harris, R.B., Ritenbaugh, C. Nutrition and cancer. (2000) [Pubmed]
  19. Inhibition by d-limonene of experimental hepatocarcinogenesis in Sprague-Dawley rats does not involve p21(ras) plasma membrane association. Kaji, I., Tatsuta, M., Iishi, H., Baba, M., Inoue, A., Kasugai, H. Int. J. Cancer (2001) [Pubmed]
  20. Inhibitory effects of d-limonene on the development of colonic aberrant crypt foci induced by azoxymethane in F344 rats. Kawamori, T., Tanaka, T., Hirose, Y., Ohnishi, M., Mori, H. Carcinogenesis (1996) [Pubmed]
  21. Metabolism of d-limonene by hepatic microsomes to non-mutagenic epoxides toward Salmonella typhimurium. Watabe, T., Hiratsuka, A., Isobe, M., Ozawa, N. Biochem. Pharmacol. (1980) [Pubmed]
  22. Biochemical basis for mouse resistance to hyaline droplet nephropathy: lack of relevance of the alpha 2u-globulin protein superfamily in this male rat-specific syndrome. Lehman-McKeeman, L.D., Caudill, D. Toxicol. Appl. Pharmacol. (1992) [Pubmed]
  23. Perillic acid inhibits Ras/MAP kinase-driven IL-2 production in human T lymphocytes. Schulz, S., Reinhold, D., Schmidt, H., Ansorge, S., Höllt, V. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  24. Prenylated proteins and lymphocyte proliferation: inhibition by d-limonene related monoterpenes. Schulz, S., Bühling, F., Ansorge, S. Eur. J. Immunol. (1994) [Pubmed]
  25. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone carcinogenesis in mice by D-limonene and citrus fruit oils. Wattenberg, L.W., Coccia, J.B. Carcinogenesis (1991) [Pubmed]
  26. Ciprofibrate represses alpha 2u-globulin expression in liver and inhibits d-limonene nephrotoxicity. Alvares, K., Subbarao, V., Rao, M.S., Reddy, J.K. Carcinogenesis (1996) [Pubmed]
  27. Involvement of YY1 and its correlation with c-myc in NDEA induced hepatocarcinogenesis, its prevention by d-limonene. Parija, T., Das, B.R. Mol. Biol. Rep. (2003) [Pubmed]
  28. d-limonene chemoprevention of hepatocarcinogenesis in AKR mice: inhibition of c-jun and c-myc. Giri, R.K., Parija, T., Das, B.R. Oncol. Rep. (1999) [Pubmed]
  29. The introduction of activated oncogenes to mammary cells in vivo using retroviral vectors: a new model for the chemoprevention of premalignant and malignant lesions of the breast. Gould, M.N. J. Cell. Biochem. Suppl. (1993) [Pubmed]
  30. Structure-activity relationships among monoterpene inhibitors of protein isoprenylation and cell proliferation. Crowell, P.L., Ren, Z., Lin, S., Vedejs, E., Gould, M.N. Biochem. Pharmacol. (1994) [Pubmed]
  31. Design of a gas chromatograph with parallel radioactivity and mass spectrometric detection. Application to the identification of the major metabolite of d-limonene associated with alpha 2u-globulin. Rodriguez, P.A., Takigiku, R., Lehman-McKeeman, L.D., Fey, M.L., Eddy, C.L., Caudill, D. J. Chromatogr. (1991) [Pubmed]
  32. Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene. Crowell, P.L., Kennan, W.S., Haag, J.D., Ahmad, S., Vedejs, E., Gould, M.N. Carcinogenesis (1992) [Pubmed]
  33. The p53 heterozygous knockout mouse as a model for chemical carcinogenesis in vascular tissue. Carmichael, N.G., Debruyne, E.L., Bigot-Lasserre, D. Environ. Health Perspect. (2000) [Pubmed]
  34. d-Limonene-induced male rat-specific nephrotoxicity: evaluation of the association between d-limonene and alpha 2u-globulin. Lehman-McKeeman, L.D., Rodriguez, P.A., Takigiku, R., Caudill, D., Fey, M.L. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  35. Phase I and pharmacokinetic study of D-limonene in patients with advanced cancer. Cancer Research Campaign Phase I/II Clinical Trials Committee. Vigushin, D.M., Poon, G.K., Boddy, A., English, J., Halbert, G.W., Pagonis, C., Jarman, M., Coombes, R.C. Cancer Chemother. Pharmacol. (1998) [Pubmed]
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