(-)-Perillyl alcohol

(-)-perillyl alcohol is a lipid of Prenol Lipids (PR) class. The involved functions are known as Cell Cycle Progression, Cell Cycle, Cell Proliferation, Apoptosis and Isoprenylation. (-)-perillyl alcohol often locates in Cytoplasm, Membrane and Plasma membrane. The associated genes with (-)-Perillyl alcohol are JUN gene, Candidate Disease Gene, IL24 gene, BCL2L1 gene and CFB gene. The related experimental models are Transgenic Model.

Cross Reference

Introduction

To understand associated biological information of (-)-Perillyl alcohol, we collected biological information of abnormalities, associated pathways, cellular/molecular locations, biological functions, related genes/proteins, lipids and common seen animal/experimental models with organized paragraphs from literatures.

What diseases are associated with (-)-Perillyl alcohol?

There are no associated biomedical information in the current reference collection.

Possible diseases from mapped MeSH terms on references

We collected disease MeSH terms mapped to the references associated with (-)-Perillyl alcohol

MeSH term MeSH ID Detail
Adenocarcinoma D000230 166 associated lipids
Lung Neoplasms D008175 171 associated lipids
Pancreatic Neoplasms D010190 77 associated lipids
Mammary Neoplasms, Experimental D008325 67 associated lipids
Body Weight D001835 333 associated lipids
Edema D004487 152 associated lipids
Esophageal Neoplasms D004938 20 associated lipids
Precancerous Conditions D011230 48 associated lipids
Prostatic Neoplasms D011471 126 associated lipids
Brain Neoplasms D001932 15 associated lipids
Per page 10 20 50 | Total 22

PubChem Associated disorders and diseases

What pathways are associated with (-)-Perillyl alcohol

Lipid pathways are not clear in current pathway databases. We organized associated pathways with (-)-Perillyl alcohol through full-text articles, including metabolic pathways or pathways of biological mechanisms.

Related references are published most in these journals:

Pathway name Related literatures
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PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with (-)-Perillyl alcohol?

Related references are published most in these journals:

Location Cross reference Weighted score Related literatures
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What functions are associated with (-)-Perillyl alcohol?


Related references are published most in these journals:

Function Cross reference Weighted score Related literatures

What lipids are associated with (-)-Perillyl alcohol?

There are no associated biomedical information in the current reference collection.

What genes are associated with (-)-Perillyl alcohol?

Related references are published most in these journals:


Gene Cross reference Weighted score Related literatures

What common seen animal models are associated with (-)-Perillyl alcohol?

Transgenic Model

Transgenic Model are used in the study 'A phase 2a study of topical perillyl alcohol cream for chemoprevention of skin cancer.' (Stratton SP et al., 2010).

Related references are published most in these journals:

Model Cross reference Weighted score Related literatures
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NCBI Entrez Crosslinks

All references with (-)-Perillyl alcohol

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Per page 10 20 50 100 | Total 165
Authors Title Published Journal PubMed Link
Pan J et al. [Constituents of essential oils from leaves, stems, and fruits of Perilla frutescens (L.) Britt]. 1992 Zhongguo Zhong Yao Za Zhi pmid:1418538
Khan AQ et al. Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NFκ-B activation and proinflammatory cytokine production. 2011 Toxicology pmid:20923693
Chan NL et al. Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells. 2006 Toxicol. Appl. Pharmacol. pmid:16307765
Xu M et al. Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: potential mechanisms for its chemotherapeutic effects. 2004 Toxicol. Appl. Pharmacol. pmid:14998688
Boon PJ et al. Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat. 2000 Toxicol. Appl. Pharmacol. pmid:10936079
da Fonseca CO et al. Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas. 2008 Surg Neurol pmid:18295834
da Fonseca CO et al. Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol. 2006 Surg Neurol pmid:16427438
Da Fonseca CO et al. Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review. 2006 Surg Neurol pmid:17145324
Ripple GH and Wilding G Drug development in prostate cancer. 1999 Semin. Oncol. pmid:10597732
Song X et al. Temozolomide-perillyl alcohol conjugate induced reactive oxygen species accumulation contributes to its cytotoxicity against non-small cell lung cancer. 2016 Sci Rep pmid:26949038
Bisson JF et al. Anti-inflammatory senescence actives 5203-L molecule to promote healthy aging and prolongation of lifespan. 2008 Rejuvenation Res pmid:18370605
Rajesh D and Howard SP Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells. 2003 Prostate pmid:12886519
Ansari MA et al. Anticandidal Effect and Mechanisms of Monoterpenoid, Perillyl Alcohol against Candida albicans. 2016 PLoS ONE pmid:27627759
Courdavault V et al. CaaX-prenyltransferases are essential for expression of genes involvedin the early stages of monoterpenoid biosynthetic pathway in Catharanthus roseus cells. 2005 Plant Mol. Biol. pmid:15952070
Xie L et al. Therapeutic effect of TMZ-POH on human nasopharyngeal carcinoma depends on reactive oxygen species accumulation. 2016 Oncotarget pmid:26625208
Zweibel J et al. Clinical trials referral resource. Clinical trials with perillyl alcohol. 1997 Oncology (Williston Park, N.Y.) pmid:9436188
Clark SS Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells. 2006 Oncology pmid:16439861
Fernandes J et al. Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells. 2005 Oncol. Rep. pmid:15809762
Koyama M et al. Perillyl alcohol causes G1 arrest through p15(INK4b) and p21(WAF1/Cip1) induction. 2013 Oncol. Rep. pmid:23233050
Lewis KA and Hohl RJ Modulation of RAS expression in human malignant cells by dietary supplements. 1997 Nutrition pmid:9357036
Zhou W et al. Components of lemon essential oil attenuate dementia induced by scopolamine. 2009 Nutr Neurosci pmid:19356307
Magkouta S et al. Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma. 2009 Nutr Cancer pmid:19838938
Loutrari H et al. Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis. 2006 Nutr Cancer pmid:16965245
Stratton SP et al. Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer. 2008 Nutr Cancer pmid:18444166
Bardon S et al. Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines. 1998 Nutr Cancer pmid:9824849
Kiran I Microbial hydroxylation of S-(-)-perillyl alcohol by Fusarium heterosporium. 2011 Nat Prod Commun pmid:22312710
Wróblewska A The epoxidation of limonene over the TS-1 and Ti-SBA-15 catalysts. 2014 Molecules pmid:25460313
Hui Z et al. Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives. 2014 Molecules pmid:24858099
Garcia DG et al. The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor. 2010 Mol. Cell. Biochem. pmid:20689980
Sundin T et al. Disruption of an hTERT-mTOR-RAPTOR protein complex by a phytochemical perillyl alcohol and rapamycin. 2013 Mol. Cell. Biochem. pmid:23283642
Lebedeva IV et al. Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis. 2008 Mol. Cancer Ther. pmid:18645014
Cho HY et al. Perillyl alcohol for the treatment of temozolomide-resistant gliomas. 2012 Mol. Cancer Ther. pmid:22933703
Chen TC et al. A novel temozolomide-perillyl alcohol conjugate exhibits superior activity against breast cancer cells in vitro and intracranial triple-negative tumor growth in vivo. 2014 Mol. Cancer Ther. pmid:24623736
Garcia DG et al. Na/K-ATPase as a target for anticancer drugs: studies with perillyl alcohol. 2015 Mol. Cancer pmid:25976744
Luján HD et al. Isoprenylation of proteins in the protozoan Giardia lamblia. 1995 Mol. Biochem. Parasitol. pmid:8538683
Alonso-Gutierrez J et al. Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production. 2013 Metab. Eng. pmid:23727191
Cerda SR et al. Enhancement of sterol synthesis by the monoterpene perillyl alcohol is unaffected by competitive 3-hydroxy-3-methylglutaryl-CoA reductase inhibition. 1999 Lipids pmid:10405975
Elegbede JA et al. Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro. 2003 Life Sci. pmid:14511768
Sahin MB et al. Perillyl alcohol selectively induces G0/G1 arrest and apoptosis in Bcr/Abl-transformed myeloid cell lines. 1999 Leukemia pmid:10516760
Clark SS et al. 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. 2002 Leukemia pmid:11840288
Si MS and Imagawa DK Prenylation inhibitors to treat proliferative renal disease. 2000 Lancet pmid:10791545
O'Shaughnessy JA Chemoprevention of breast cancer. 1996 JAMA pmid:8614122
Matos JM et al. A pilot study of perillyl alcohol in pancreatic cancer. 2008 J. Surg. Res. pmid:18498869
Fulton GJ et al. Oral monoterpene therapy (perillyl alcohol) reduces vein graft intimal hyperplasia. 1997 J. Surg. Res. pmid:9202658
de Saldanha da Gama Fischer J et al. Chemo-resistant protein expression pattern of glioblastoma cells (A172) to perillyl alcohol. 2011 J. Proteome Res. pmid:20806975
Loutrari H et al. Perillyl alcohol is an angiogenesis inhibitor. 2004 J. Pharmacol. Exp. Ther. pmid:15210838
Wiseman DA et al. Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and farnesol is mediated by p21(Cip1) and p27(Kip1) in human pancreatic adenocarcinoma cells. 2007 J. Pharmacol. Exp. Ther. pmid:17138864
Crowell PL Prevention and therapy of cancer by dietary monoterpenes. 1999 J. Nutr. pmid:10082788
Duelund L et al. Influence of the active compounds of Perilla frutescens leaves on lipid membranes. 2012 J. Nat. Prod. pmid:22272932
Nandurkar NS et al. The identification of perillyl alcohol glycosides with improved antiproliferative activity. 2014 J. Med. Chem. pmid:25121720
Holstein SA and Hohl RJ Monoterpene regulation of Ras and Ras-related protein expression. 2003 J. Lipid Res. pmid:12671036
Cornelissen S et al. Cell physiology rather than enzyme kinetics can determine the efficiency of cytochrome P450-catalyzed C-H-oxyfunctionalization. 2011 J. Ind. Microbiol. Biotechnol. pmid:21559976
Chen Y and Hu D Effects of POH in combination with STI571 on the proliferation and apoptosis of K562 cells. 2004 J. Huazhong Univ. Sci. Technol. Med. Sci. pmid:15165112
Fischer Jde S et al. Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol. 2008 J. Exp. Ther. Oncol. pmid:19227008
Fischer Jde S et al. Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549. 2006 J. Exp. Ther. Oncol. pmid:17024970
Zhang Z et al. Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. 1999 J. Chromatogr. B Biomed. Sci. Appl. pmid:10379660
Clinical development plan: l-perillyl alcohol. 1996 J. Cell. Biochem. Suppl. pmid:9154174
Lantry LE et al. Chemopreventive effect of perillyl alcohol on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced tumorigenesis in (C3H/HeJ X A/J)F1 mouse lung. 1997 J. Cell. Biochem. Suppl. pmid:9591189
Unlu S et al. Perillyl alcohol, an inhibitor of geranylgeranyl transferase, induces apoptosis of immortalized human vascular smooth muscle cells in vitro. 2000 J. Cardiovasc. Pharmacol. pmid:10672871
da Fonseca CO et al. Efficacy of monoterpene perillyl alcohol upon survival rate of patients with recurrent glioblastoma. 2011 J. Cancer Res. Clin. Oncol. pmid:20401670
da Silveira Fd et al. Analysis of EGF+61A>G polymorphism and EGF serum levels in Brazilian glioma patients treated with perillyl alcohol-based therapy. 2012 J. Cancer Res. Clin. Oncol. pmid:22481252
Bassi AM et al. Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo. 2005 J. Biomed. Sci. pmid:15959631
Hohl RJ and Lewis K Differential effects of monoterpenes and lovastatin on RAS processing. 1995 J. Biol. Chem. pmid:7615555
Rajesh D et al. Perillyl alcohol as a radio-/chemosensitizer in malignant glioma. 2003 J. Biol. Chem. pmid:12805388
Fischer Jde S et al. Dynamic proteomic overview of glioblastoma cells (A172) exposed to perillyl alcohol. 2010 J Proteomics pmid:20083244
Hua HY et al. High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats. 2008 J Pharm Biomed Anal pmid:18849133
Gupta A et al. An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation. 2005 J Pharm Biomed Anal pmid:15740902
Tao L and Pereira MA Quantification of carvone, cineole, perillaldehyde, perillyl alcohol and sobrerol by isocratic high-performance liquid chromatography. 1998 J Chromatogr A pmid:9468652
Liu G et al. Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer. 2003 Invest New Drugs pmid:14578686
Da Fonseca CO et al. Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol. 2009 Invest New Drugs pmid:19139816
Ahn KJ et al. Cytotoxicity of perillyl alcohol against cancer cells is potentiated by hyperthermia. 2003 Int. J. Radiat. Oncol. Biol. Phys. pmid:14529788
Teruszkin Balassiano I et al. Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model. 2002 Int. J. Mol. Med. pmid:12430008
Del Toro-Arreola S et al. Effect of D-limonene on immune response in BALB/c mice with lymphoma. 2005 Int. Immunopharmacol. pmid:15778119
Gupta A and Myrdal PB Development of a perillyl alcohol topical cream formulation. 2004 Int J Pharm pmid:14706249
Farazuddin M et al. Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles. 2012 Int J Nanomedicine pmid:22275821
Chen TC et al. Perillyl Alcohol and Its Drug-Conjugated Derivatives as Potential Novel Methods of Treating Brain Metastases. 2016 Int J Mol Sci pmid:27598140
Andrade LN et al. In Vivo Anti-Tumor Activity and Toxicological Evaluations of Perillaldehyde 8,9-Epoxide, a Derivative of Perillyl Alcohol. 2016 Int J Mol Sci pmid:26742032
Meadows SM et al. Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer. 2002 Int J Gastrointest Cancer pmid:12794248
Sultana S et al. Perillyl alcohol as a protective modulator against rat hepatocarcinogenesis via amelioration of oxidative damage and cell proliferation. 2013 Hum Exp Toxicol pmid:23536516
Alison M Promoting apoptosis. 1995 Hum Exp Toxicol pmid:7576838
Bailey HH et al. A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96. 2002 Gynecol. Oncol. pmid:12051875
Silva MM et al. Influence of GSTM1 and GSTT1 polymorphisms on the survival rate of patients with malignant glioma under perillyl alcohol-based therapy. 2013 Genet. Mol. Res. pmid:23765968
Opdyke DL Monographs on fragrance raw materials. 1981 Food Cosmet Toxicol pmid:7286874
Bicas JL et al. Evaluation of the antioxidant and antiproliferative potential of bioflavors. 2011 Food Chem. Toxicol. pmid:21540069
Bhatia SP et al. Fragrance material review on p-mentha-1,8-dien-7-ol. 2008 Food Chem. Toxicol. pmid:18640209
Lantry LE et al. Chemopreventive efficacy of promising farnesyltransferase inhibitors. 2000 Exp. Lung Res. pmid:11195470
Sundin T et al. eIF4E-Overexpression imparts perillyl alcohol and rapamycin-mediated regulation of telomerase reverse transcriptase. 2013 Exp. Cell Res. pmid:23747720
Kennedy S et al. Effect of antiproliferative agents on vascular function in normal and in vitro balloon-injured porcine coronary arteries. 2003 Eur. J. Pharmacol. pmid:14637181
Russell J and Ling CC Studies with cytotoxic agents suggest that apoptosis is not a major determinant of clonogenic death in neuroblastoma cells. 2003 Eur. J. Cancer pmid:14522384
Lefranc F et al. 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K(+)-ATPase and Ras oncogene activity in cancer cells. 2013 Eur J Med Chem pmid:23474907
Phillips LR et al. Pharmacokinetics of active drug metabolites after oral administration of perillyl alcohol, an investigational antineoplastic agent, to the dog. 1995 Drug Metab. Dispos. pmid:7587953
Miyazawa M et al. Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. 2002 Drug Metab. Dispos. pmid:11950794
Prado R et al. Nonmelanoma skin cancer chemoprevention. 2011 Dermatol Surg pmid:21895847
Sarkar S et al. Chemoprevention gene therapy (CGT) of pancreatic cancer using perillyl alcohol and a novel chimeric serotype cancer terminator virus. 2014 Curr. Mol. Med. pmid:24236457
Clark SS et al. Anti-leukemia effect of perillyl alcohol in Bcr/Abl-transformed cells indirectly inhibits signaling through Mek in a Ras- and Raf-independent fashion. 2003 Clin. Cancer Res. pmid:14555523
Stearns V et al. A pilot surrogate end point biomarker trial of perillyl alcohol in breast neoplasia. 2004 Clin. Cancer Res. pmid:15569989
Ripple GH et al. Phase I clinical trial of perillyl alcohol administered daily. 1998 Clin. Cancer Res. pmid:9607573
Hudes GR et al. Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies. 2000 Clin. Cancer Res. pmid:10955786
Ripple GH et al. Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. 2000 Clin. Cancer Res. pmid:10690515
Gómez-Contreras PC et al. In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression. 2006 Chemotherapy pmid:17008791