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Chemical Compound Review

CHEMBL236687     [(4S)-4-prop-1-en-2-yl-1...

Synonyms: SureCN569985, CHEBI:10782, bmse000559, KST-1A2232, NSC-641066, ...
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Disease relevance of Perilla alcohol


High impact information on Perilla alcohol


Chemical compound and disease context of Perilla alcohol


Biological context of Perilla alcohol

  • Our studies also indicate that the colon tumors of animals fed perillyl alcohol exhibited increased apoptosis as compared to those fed the control diet [3].
  • PURPOSE: Perillyl alcohol (POH) displays preventive and therapeutic activity against a wide variety of tumor models, and it has been suggested that this might be associated with the ability of POH to interfere with Ras prenylation [12].
  • We conducted a phase I dose-escalation trial of perillyl alcohol (POH; NSC 641066) given p.o. on a continuous four times a day basis to characterize the maximum tolerated dose, toxicities, pharmacokinetic profile, and antitumor activity [13].
  • In this study, the monoterpene perillyl alcohol (POH) was found to induce transient expression of the c-jun and c-fos genes transcriptionally [14].
  • Although R- and S-limonene are only weak inhibitors of the isoprenylation enzymes, their major metabolites, perillic acid and perillyl alcohol, are more potent inhibitors, with IC50 values in the low mM range [15].

Anatomical context of Perilla alcohol


Associations of Perilla alcohol with other chemical compounds


Gene context of Perilla alcohol


Analytical, diagnostic and therapeutic context of Perilla alcohol


  1. Activation of the transforming growth factor beta signaling pathway and induction of cytostasis and apoptosis in mammary carcinomas treated with the anticancer agent perillyl alcohol. Ariazi, E.A., Satomi, Y., Ellis, M.J., Haag, J.D., Shi, W., Sattler, C.A., Gould, M.N. Cancer Res. (1999) [Pubmed]
  2. Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway. Berchtold, C.M., Chen, K.S., Miyamoto, S., Gould, M.N. Cancer Res. (2005) [Pubmed]
  3. Chemoprevention of colon carcinogenesis by dietary perillyl alcohol. Reddy, B.S., Wang, C.X., Samaha, H., Lubet, R., Steele, V.E., Kelloff, G.J., Rao, C.V. Cancer Res. (1997) [Pubmed]
  4. Inhibitory effects of perillyl alcohol on UVB-induced murine skin cancer and AP-1 transactivation. Barthelman, M., Chen, W., Gensler, H.L., Huang, C., Dong, Z., Bowden, G.T. Cancer Res. (1998) [Pubmed]
  5. Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. Liston, B.W., Nines, R., Carlton, P.S., Gupta, A., Aziz, R., Frankel, W., Stoner, G.D. Cancer Res. (2003) [Pubmed]
  6. In situ detection of neoplastic transformation and chemopreventive effects in rat esophagus epithelium using angle-resolved low-coherence interferometry. Wax, A., Yang, C., Müller, M.G., Nines, R., Boone, C.W., Steele, V.E., Stoner, G.D., Dasari, R.R., Feld, M.S. Cancer Res. (2003) [Pubmed]
  7. Biocatalytic production of perillyl alcohol from limonene by using a novel Mycobacterium sp. cytochrome P450 alkane hydroxylase expressed in Pseudomonas putida. van Beilen, J.B., Holtackers, R., Lüscher, D., Bauer, U., Witholt, B., Duetz, W.A. Appl. Environ. Microbiol. (2005) [Pubmed]
  8. Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines. Bardon, S., Picard, K., Martel, P. Nutrition and cancer. (1998) [Pubmed]
  9. Inhibition of ubiquinone and cholesterol synthesis by the monoterpene perillyl alcohol. Ren, Z., Gould, M.N. Cancer Lett. (1994) [Pubmed]
  10. Oral monoterpene therapy (perillyl alcohol) reduces vein graft intimal hyperplasia. Fulton, G.J., Barber, L., Svendsen, E., Hagen, P.O., Davies, M.G. J. Surg. Res. (1997) [Pubmed]
  11. Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention. Burke, Y.D., Ayoubi, A.S., Werner, S.R., McFarland, B.C., Heilman, D.K., Ruggeri, B.A., Crowell, P.L. Anticancer Res. (2002) [Pubmed]
  12. Anti-leukemia effect of perillyl alcohol in Bcr/Abl-transformed cells indirectly inhibits signaling through Mek in a Ras- and Raf-independent fashion. Clark, S.S., Zhong, L., Filiault, D., Perman, S., Ren, Z., Gould, M., Yang, X. Clin. Cancer Res. (2003) [Pubmed]
  13. Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. Ripple, G.H., Gould, M.N., Arzoomanian, R.Z., Alberti, D., Feierabend, C., Simon, K., Binger, K., Tutsch, K.D., Pomplun, M., Wahamaki, A., Marnocha, R., Wilding, G., Bailey, H.H. Clin. Cancer Res. (2000) [Pubmed]
  14. Induction of AP-1 activity by perillyl alcohol in breast cancer cells. Satomi, Y., Miyamoto, S., Gould, M.N. Carcinogenesis (1999) [Pubmed]
  15. Inhibition of protein prenylation by metabolites of limonene. Hardcastle, I.R., Rowlands, M.G., Barber, A.M., Grimshaw, R.M., Mohan, M.K., Nutley, B.P., Jarman, M. Biochem. Pharmacol. (1999) [Pubmed]
  16. Insulin promotes phosphorylation and activation of geranylgeranyltransferase II. Studies with geranylgeranylation of rab-3 and rab-4. Goalstone, M.L., Leitner, J.W., Golovchenko, I., Stjernholm, M.R., Cormont, M., Le Marchand-Brustel, Y., Draznin, B. J. Biol. Chem. (1999) [Pubmed]
  17. Induction of the apoptosis-promoting protein Bak by perillyl alcohol in pancreatic ductal adenocarcinoma relative to untransformed ductal epithelial cells. Stayrook, K.R., McKinzie, J.H., Burke, Y.D., Burke, Y.A., Crowell, P.L. Carcinogenesis (1997) [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. Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes. Miyazawa, M., Shindo, M., Shimada, T. Chem. Res. Toxicol. (2002) [Pubmed]
  20. Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat. Boon, P.J., van der Boon, D., Mulder, G.J. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  21. Cancer chemoprevention and therapy by monoterpenes. Gould, M.N. Environ. Health Perspect. (1997) [Pubmed]
  22. Cytotoxicity of perillyl alcohol against cancer cells is potentiated by hyperthermia. Ahn, K.J., Lee, C.K., Choi, E.K., Griffin, R., Song, C.W., Park, H.J. Int. J. Radiat. Oncol. Biol. Phys. (2003) [Pubmed]
  23. The chemoprevention of cancer by mevalonate-derived constituents of fruits and vegetables. Elson, C.E., Yu, S.G. J. Nutr. (1994) [Pubmed]
  24. Genetic and cellular changes in colorectal cancer: proposed targets of chemopreventive agents. Greenwald, P., Kelloff, G.J., Boone, C.W., McDonald, S.S. Cancer Epidemiol. Biomarkers Prev. (1995) [Pubmed]
  25. The state-of-the-art in chemoprevention of skin cancer. Stratton, S.P., Dorr, R.T., Alberts, D.S. Eur. J. Cancer (2000) [Pubmed]
  26. 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]
  27. Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells. Chung, B.H., Lee, H.Y., Lee, J.S., Young, C.Y. Cancer Lett. (2006) [Pubmed]
  28. Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells. Clark, S.S. Oncology (2006) [Pubmed]
  29. Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes. Liu, K., Liang, C., Liang, Z., Tus, K., Wakeland, E.K. J. Immunol. (2005) [Pubmed]
  30. Antileukemia activity of perillyl alcohol (POH): uncoupling apoptosis from G0/G1 arrest suggests that the primary effect of POH on Bcr/Abl-transformed cells is to induce growth arrest. Clark, S.S., Perman, S.M., Sahin, M.B., Jenkins, G.J., Elegbede, J.A. Leukemia (2002) [Pubmed]
  31. Induction of cytostasis in mammary carcinoma cells treated with the anticancer agent perillyl alcohol. Shi, W., Gould, M.N. Carcinogenesis (2002) [Pubmed]
  32. Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells. Rajesh, D., Howard, S.P. Prostate (2003) [Pubmed]
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