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Chemical Compound Review

L-Limonen     (4S)-1-methyl-4-prop-1-en-2- yl-cyclohexene

Synonyms: l-Limonene, beta-Limonene, Limonene, L-, S-(-)-Limonene, Limonene, (-)-, ...
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Disease relevance of C00521


Psychiatry related information on C00521

  • As expected, limonene administration increased the latency period and lowered the frequency of mammary carcinoma development as compared to controls [5].
  • Responses to food frequency and dietary behavior questionnaires indicated a pattern of diet selection and food preferences that were consistent with a dietary origin for the limonene in these patients [6].

High impact information on C00521

  • Nine cDNA isolates expressed sesquiterpene synthase activity, and GC-MS analysis of the products identified germacrene C with smaller amounts of germacrene A, B, and D. None of the expressed proteins was active with geranylgeranyl diphosphate; however, one truncated protein converted geranyl diphosphate to the monoterpene limonene [7].
  • Search of the GenBank data base with the deduced translation product revealed 42% identity and 65% similarity with 5-epi-aristolochene synthase from tobacco and 31% identity and 53% similarity with limonene synthase from spearmint [8].
  • On the basis of these observations, it was hypothesized that a possible mechanism by which limonene exerts its effects on the chemoprevention and regression of mammary tumors involves the inhibition of protein isoprenylation of the small G protein p21 [5].
  • These studies are consistent with the above studies in that limonene is effective in preventing mammary carcinomas with activated ras [5].
  • In addition, dietary limonene has been shown to be capable of preventing the development and causing the regression of chemically induced mammary carcinomas, many of which contain activated ras oncogenes [5].

Chemical compound and disease context of C00521


Biological context of C00521


Anatomical context of C00521


Associations of C00521 with other chemical compounds


Gene context of C00521

  • CYP2C9 may be more important than CYP2C19 in catalyzing limonene oxidations in human liver microsomes, since levels of the former protein are more abundant than CYP2C19 in these human samples [20].
  • Interestingly, human CYP2B6 did not catalyze limonene oxidations, whereas rat CYP2B1 had high activities in catalyzing limonene oxidations [20].
  • Western blot analysis has shown inhibition of YY1 protein in NDEA induced liver tumor samples in comparison to normal and both NDEA and limonene treated samples [21].
  • Limonene has chemotherapeutic activity against chemically induced rat mammary carcinomas, many of which contain activated ras genes [16].
  • Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation [22].

Analytical, diagnostic and therapeutic context of C00521

  • Limonene chemoprevention of mammary carcinoma induction following direct in situ transfer of v-Ha-ras [5].
  • Furthermore, polyclonal antibodies raised against the angiosperm limonene synthase did not detectably cross-react with any proteins in extracts from either lodgepole pine or grand fir by immunoblotting analysis [23].
  • At week 16, quantitative histologic analysis showed that oral administration of 1% or 2% limonene resulted in significant reductions in the number and mean area of GST-P-positive hepatic foci and the number of cellular alteration foci, neoplastic nodules and hepatocellular carcinomas [17].
  • In solution both enantiomers of limonene induce significant changes in the visible and circular dichroism (CD) spectra of [Co2(1)], while a different behavior is observed in the case of the enantiomeric pair of trans-1,2-diaminocyclohexane [24].
  • Reversibility studies showed that the post-recovery passive flux of LHRH through 5% limonene in EtOH/iontophoresis treated epidermis was significantly (p < 0.05) decreased but did not significantly recover to the baseline flux (i.e., flux through control epidermis) [25].


  1. Limonene-induced regression of mammary carcinomas. Haag, J.D., Lindstrom, M.J., Gould, M.N. Cancer Res. (1992) [Pubmed]
  2. Catalytic mechanism of limonene epoxide hydrolase, a theoretical study. Hopmann, K.H., Hallberg, B.M., Himo, F. J. Am. Chem. Soc. (2005) [Pubmed]
  3. In vitro comparison of different gall stone dissolution solvents. Vergunst, H., Terpstra, O.T., Nijs, H.G., Steen, G. Gut (1991) [Pubmed]
  4. 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]
  5. Limonene chemoprevention of mammary carcinoma induction following direct in situ transfer of v-Ha-ras. Gould, M.N., Moore, C.J., Zhang, R., Wang, B., Kennan, W.S., Haag, J.D. Cancer Res. (1994) [Pubmed]
  6. Limonene in expired lung air of patients with liver disease. Friedman, M.I., Preti, G., Deems, R.O., Friedman, L.S., Munoz, S.J., Maddrey, W.C. Dig. Dis. Sci. (1994) [Pubmed]
  7. Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. Colby, S.M., Crock, J., Dowdle-Rizzo, B., Lemaux, P.G., Croteau, R. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  8. Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants. Mau, C.J., West, C.A. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Human metabolism of the experimental cancer therapeutic agent d-limonene. Crowell, P.L., Elson, C.E., Bailey, H.H., Elegbede, A., Haag, J.D., Gould, M.N. Cancer Chemother. Pharmacol. (1994) [Pubmed]
  10. Volatile organic compounds in the exhaled breath of young patients with cystic fibrosis. Barker, M., Hengst, M., Schmid, J., Buers, H.J., Mittermaier, B., Klemp, D., Koppmann, R. Eur. Respir. J. (2006) [Pubmed]
  11. Antimutagenic effect of essential oil of sage (Salvia officinalis L.) and its monoterpenes against UV-induced mutations in Escherichia coli and Saccharomyces cerevisiae. Vuković-Gacić, B., Nikcević, S., Berić-Bjedov, T., Knezević-Vukcević, J., Simić, D. Food Chem. Toxicol. (2006) [Pubmed]
  12. The synthesis of l-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells. Chen, J., Lu, M., Jing, Y., Dong, J. Bioorg. Med. Chem. (2006) [Pubmed]
  13. Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor. Mars, A.E., Gorissen, J.P., van den Beld, I., Eggink, G. Appl. Microbiol. Biotechnol. (2001) [Pubmed]
  14. 4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase. Colby, S.M., Alonso, W.R., Katahira, E.J., McGarvey, D.J., Croteau, R. J. Biol. Chem. (1993) [Pubmed]
  15. Stereoselective carveol dehydrogenase from Rhodococcus erythropolis DCL14. A novel nicotinoprotein belonging to the short chain dehydrogenase/reductase superfamily. van der Werf, M.J., van der Ven, C., Barbirato, F., Eppink, M.H., de Bont, J.A., van Berkel, W.J. J. Biol. Chem. (1999) [Pubmed]
  16. 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]
  17. 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]
  18. Perillyl alcohol selectively induces G0/G1 arrest and apoptosis in Bcr/Abl-transformed myeloid cell lines. Sahin, M.B., Perman, S.M., Jenkins, G., Clark, S.S. Leukemia (1999) [Pubmed]
  19. Effects of monoterpenoids on in vivo DMBA-DNA adduct formation and on phase I hepatic metabolizing enzymes. Maltzman, T.H., Christou, M., Gould, M.N., Jefcoate, C.R. Carcinogenesis (1991) [Pubmed]
  20. Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. Miyazawa, M., Shindo, M., Shimada, T. Drug Metab. Dispos. (2002) [Pubmed]
  21. 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]
  22. 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]
  23. Monoterpene synthases of Pinus contorta and related conifers. A new class of terpenoid cyclase. Savage, T.J., Hatch, M.W., Croteau, R. J. Biol. Chem. (1994) [Pubmed]
  24. Preparation and self-assembly of chiral porphyrin diads on the gold electrodes of quartz crystal microbalances: a novel potential approach to the development of enantioselective chemical sensors. Paolesse, R., Monti, D., La Monica, L., Venanzi, M., Froiio, A., Nardis, S., Di Natale, C., Martinelli, E., D'Amico, A. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  25. Mechanism of transport enhancement of LHRH through porcine epidermis by terpenes and iontophoresis: permeability and lipid extraction studies. Bhatia, K.S., Singh, J. Pharm. Res. (1998) [Pubmed]
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