(-)-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
Loading... please refresh the page if content is not showing up.

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
Loading... please refresh the page if content is not showing up.

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
Loading... please refresh the page if content is not showing up.

NCBI Entrez Crosslinks

All references with (-)-Perillyl alcohol

Download all related citations
Per page 10 20 50 100 | Total 165
Authors Title Published Journal PubMed Link
pmid:28594456
pmid:28233648
pmid:28314870
pmid:24125633
pmid:29129690
pmid:28450161
pmid:28044940
pmid:27394002
pmid:27220072
pmid:26475687
pmid:25497898
pmid:25240714
pmid:27325307
pmid:27890582
pmid:
Belanger JT Perillyl alcohol: applications in oncology. 1998 Altern Med Rev pmid:9855569
Karlson J et al. Inhibition of tumor cell growth by monoterpenes in vitro: evidence of a Ras-independent mechanism of action. 1996 Anticancer Drugs pmid:8826611
Yeruva L et al. Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin. 2010 Anticancer Drugs pmid:19820395
Samaila D et al. Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro. 2004 Sep-Oct Anticancer Res. pmid:15517920
DA Fonseca CO et al. Long-term outcome in patients with recurrent malignant glioma treated with Perillyl alcohol inhalation. 2013 Anticancer Res. pmid:24324108
Burke YD et al. Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention. 2002 Nov-Dec Anticancer Res. pmid:12530055
Stayrook KR et al. Effects of the antitumor agent perillyl alcohol on H-Ras vs. K-Ras farnesylation and signal transduction in pancreatic cells. 1998 Mar-Apr Anticancer Res. pmid:9615726
d'Alessio PA et al. Skin repair properties of d-Limonene and perillyl alcohol in murine models. 2014 Antiinflamm Antiallergy Agents Med Chem pmid:24160248
van Beilen JB et al. Biocatalytic production of perillyl alcohol from limonene by using a novel Mycobacterium sp. cytochrome P450 alkane hydroxylase expressed in Pseudomonas putida. 2005 Appl. Environ. Microbiol. pmid:15811996
Peffley DM et al. Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor cells. 2007 Arch. Biochem. Biophys. pmid:17601486
da Fonseca CO et al. Ras pathway activation in gliomas: a strategic target for intranasal administration of perillyl alcohol. 2008 Jul-Aug Arch. Immunol. Ther. Exp. (Warsz.) pmid:18726148
D'Alincourt Salazar M et al. Intranasal administration of perillyl alcohol activates peripheral and bronchus-associated immune system in vivo. 2014 Arch. Immunol. Ther. Exp. (Warsz.) pmid:24257817
Imamura M et al. Perillyl alcohol suppresses antigen-induced immune responses in the lung. 2014 Biochem. Biophys. Res. Commun. pmid:24309112
Ren Z et al. Inhibition of type I and type II geranylgeranyl-protein transferases by the monoterpene perillyl alcohol in NIH3T3 cells. 1997 Biochem. Pharmacol. pmid:9296357
Sundin T et al. The isoprenoid perillyl alcohol inhibits telomerase activity in prostate cancer cells. 2012 Biochimie pmid:22902867
Yamamoto Y et al. Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells. 2008 Bioorg. Med. Chem. Lett. pmid:18556205
Cornelissen S et al. Whole-cell-based CYP153A6-catalyzed (S)-limonene hydroxylation efficiency depends on host background and profits from monoterpene uptake via AlkL. 2013 Biotechnol. Bioeng. pmid:23239244
Kim D and Ortiz de Montellano PR Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system. 2009 Biotechnol. Lett. pmid:19458919
Jung HJ et al. Calcium blockers decrease the bortezomib resistance in mantle cell lymphoma via manipulation of tissue transglutaminase activities. 2012 Blood pmid:22294726
Yuri T et al. Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo. 2004 Breast Cancer Res. Treat. pmid:15026623
Murren JR et al. Phase I study of perillyl alcohol in patients with refractory malignancies. 2002 Mar-Apr Cancer Biol. Ther. pmid:12170772
Bailey HH et al. A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days. 2004 Cancer Chemother. Pharmacol. pmid:15205914
Bailey HH et al. Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer. 2008 Cancer Chemother. Pharmacol. pmid:17885756
Azzoli CG et al. A phase I trial of perillyl alcohol in patients with advanced solid tumors. 2003 Cancer Chemother. Pharmacol. pmid:12695855
Morgan-Meadows S et al. Phase I trial of perillyl alcohol administered four times daily continuously. 2003 Cancer Chemother. Pharmacol. pmid:12904896
Lluria-Prevatt M et al. Effects of perillyl alcohol on melanoma in the TPras mouse model. 2002 Cancer Epidemiol. Biomarkers Prev. pmid:12050099
Yeruva L et al. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. 2007 Cancer Lett. pmid:17888568
Chung BH et al. Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells. 2006 Cancer Lett. pmid:16029925
Ren Z and Gould MN Inhibition of ubiquinone and cholesterol synthesis by the monoterpene perillyl alcohol. 1994 Cancer Lett. pmid:8149348
Gelb MH et al. The inhibition of protein prenyltransferases by oxygenated metabolites of limonene and perillyl alcohol. 1995 Cancer Lett. pmid:7767906
Shi W and Gould MN Induction of differentiation in neuro-2A cells by the monoterpene perillyl alcohol. 1995 Cancer Lett. pmid:7656215
Stark MJ et al. Chemotherapy of pancreatic cancer with the monoterpene perillyl alcohol. 1995 Cancer Lett. pmid:7553603
Bardon S et al. Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression. 2002 Cancer Lett. pmid:12175534
Stratton SP et al. A phase 2a study of topical perillyl alcohol cream for chemoprevention of skin cancer. 2010 Cancer Prev Res (Phila) pmid:20103724
Clifford JL and DiGiovanni J The promise of natural products for blocking early events in skin carcinogenesis. 2010 Cancer Prev Res (Phila) pmid:20103730
Berchtold CM et al. Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway. 2005 Cancer Res. pmid:16166337
Lebedeva IV et al. Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol. 2008 Cancer Res. pmid:18768668
Barthelman M et al. Inhibitory effects of perillyl alcohol on UVB-induced murine skin cancer and AP-1 transactivation. 1998 Cancer Res. pmid:9485025
Reddy BS et al. Chemoprevention of colon carcinogenesis by dietary perillyl alcohol. 1997 Cancer Res. pmid:9012468
Mills JJ et al. Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol. 1995 Cancer Res. pmid:7867007
Ariazi EA et al. 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. 1999 Cancer Res. pmid:10213501
Liston BW et al. Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. 2003 Cancer Res. pmid:12750258
Stayrook KR et al. Induction of the apoptosis-promoting protein Bak by perillyl alcohol in pancreatic ductal adenocarcinoma relative to untransformed ductal epithelial cells. 1997 Carcinogenesis pmid:9276644
Satomi Y et al. Induction of AP-1 activity by perillyl alcohol in breast cancer cells. 1999 Carcinogenesis pmid:10506111
Shi W and Gould MN Induction of cytostasis in mammary carcinoma cells treated with the anticancer agent perillyl alcohol. 2002 Carcinogenesis pmid:11756234
Löw-Baselli A et al. Failure to demonstrate chemoprevention by the monoterpene perillyl alcohol during early rat hepatocarcinogenesis: a cautionary note. 2000 Carcinogenesis pmid:11023545
Wei X et al. Perillyl alcohol inhibits TCR-mediated [Ca(2+)](i) signaling, alters cell shape and motility, and induces apoptosis in T lymphocytes. 2000 Cell. Immunol. pmid:10805968
Chaudhary SC et al. Perillyl alcohol attenuates Ras-ERK signaling to inhibit murine skin inflammation and tumorigenesis. 2009 Chem. Biol. Interact. pmid:19161993
Miyazawa M et al. Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes. 2002 Chem. Res. Toxicol. pmid:11800592
Seifert A et al. An efficient route to selective bio-oxidation catalysts: an iterative approach comprising modeling, diversification, and screening, based on CYP102A1. 2011 Chembiochem pmid:21591046
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
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
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
Prado R et al. Nonmelanoma skin cancer chemoprevention. 2011 Dermatol Surg pmid:21895847
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
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
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
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
Sundin T et al. eIF4E-Overexpression imparts perillyl alcohol and rapamycin-mediated regulation of telomerase reverse transcriptase. 2013 Exp. Cell Res. pmid:23747720
Lantry LE et al. Chemopreventive efficacy of promising farnesyltransferase inhibitors. 2000 Exp. Lung Res. pmid:11195470
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
Opdyke DL Monographs on fragrance raw materials. 1981 Food Cosmet Toxicol pmid:7286874
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
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
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
Meadows SM et al. Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer. 2002 Int J Gastrointest Cancer pmid:12794248
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
Farazuddin M et al. Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles. 2012 Int J Nanomedicine pmid:22275821
Gupta A and Myrdal PB Development of a perillyl alcohol topical cream formulation. 2004 Int J Pharm pmid:14706249
Del Toro-Arreola S et al. Effect of D-limonene on immune response in BALB/c mice with lymphoma. 2005 Int. Immunopharmacol. pmid:15778119
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
Ahn KJ et al. Cytotoxicity of perillyl alcohol against cancer cells is potentiated by hyperthermia. 2003 Int. J. Radiat. Oncol. Biol. Phys. pmid:14529788
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
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
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