Perillyl alcohol (BioDeep_00000229770)

Main id: BioDeep_00000000641

 

human metabolite PANOMIX_OTCML-2023 blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


1-cyclohexene-1-methanol, 4-(1-methylethenyl)-, (4S)-

化学式: C10H16O (152.12010859999998)
中文名称: 紫苏醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C(C)[C@@H]1CC=C(CC1)CO
InChI: InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3

描述信息

Perillyl alcohol is a limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender. It has a role as a plant metabolite and a volatile oil component.
Perillyl alcohol is a natural product found in Trachyspermum anethifolium, Geum heterocarpum, and other organisms with data available.
Perillyl Alcohol is a naturally occurring monoterpene related to limonene with antineoplastic activity. Perillyl alcohol inhibits farnesyl transferase and geranylgeranyl transferase, thereby preventing post-translational protein farnesylation and isoprenylation and activation of oncoproteins such as p21-ras, and arresting tumor cells in the G1 phase of the cell cycle. (NCI04)
Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID: 9855569) [HMDB]. p-Mentha-1,8-dien-7-ol is found in many foods, some of which are caraway, ginger, german camomile, and sweet bay.
Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID:9855569).
A limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender.
C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor
D000970 - Antineoplastic Agents
D004791 - Enzyme Inhibitors
(S)-(?)-Perillyl alcohol is a monoterpene found in lavender, inhibits farnesylation of Ras, upregulates the mannose-6-phosphate receptor and induces apoptosis. Anti-cancer activity[1].
(S)-(?)-Perillyl alcohol is a monoterpene found in lavender, inhibits farnesylation of Ras, upregulates the mannose-6-phosphate receptor and induces apoptosis. Anti-cancer activity[1].
Perillyl alcohol, a monoterpene,?is active in inducing apoptosis in tumor cells without affecting normal cells[1].
Perillyl alcohol, a monoterpene,?is active in inducing apoptosis in tumor cells without affecting normal cells[1].

同义名列表

51 个代谢物同义名

1-cyclohexene-1-methanol, 4-(1-methylethenyl)-, (4S)-; (+/-)-1-CYCLOHEXENE-1-METHANOL, 4-(1-METHYLETHENYL)-; (S)-[4-(1-Propen-2-yl)-1-cyclohexen-1-yl]methanol; Cyclohex-1-ene-1-methanol, 4-(1-methylethenyl)-; [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol; (4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol; 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-; cyclohex-1-ene-1-methanol, 4(1-methylethenyl); 4-(1-Methylethenyl)-1-cyclohexene-1-methanol; (4-(prop-1-en-2-yl)cyclohex-1-enyl)methanol; 1-Hydroxymethyl-4-isopropenyl-1-cyclohexene; (4-Isopropenyl-1-cyclohexen-1-yl)methanol; (4-prop-1-en-2-ylcyclohexen-1-yl)methanol; 4-Isopropenylcyclohex-1-en-1-ylmethanol; 4-isopropenyl-cyclohex-1-ene-1-methanol; 4-isopropenyl-cyclohex-1-enylmethanol; 4-Isopropenyl-1-cyclohexene-methanol; 4-Isopropenyl-1-cyclohexene carbinol; P-MENTHA-1,8-DIEN-7-OL [FHFI]; perilla alcohol, (S)-isomer; perilla alcohol, (R)-isomer; (-)-p-mentha-1,8-dien-7-ol; Para-mentha-1,8-dien-7-ol; (S)-(?)-Perillyl alcohol; (S)-(-)-Perillyl alcohol; STERCOBILINHYDROCHLORIDE; dihydrocuminyl alcoholn; BENCYNOATEHYDROCHLORIDE; PERILLYL ALCOHOL [INCI]; p-mentha-1,8-dien-7-ol; dihydrocuminyl alcohol; (+/-)-PERILLYL ALCOHOL; Dihydrocuminic alcohol; 1,8-p-Menthadien-7-ol; (-)-Perillyl alcohol; (S)-perillyl alcohol; Dl-perillyl alcohol; (-)-Perillylalcohol; Hydrocumin alcohol; Perillyl alcohol; Spectrum3_001974; Perillic alcohol; Spectrum2_000838; perilla alcohol; UNII:319R5C7293; 1-perillalcohol; perill alcohol; KBio3_002951; Iso-carveol; Isocarveol; Perillol



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

23 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Eswara Rao Puppala, Siddhi Jain, Pritam Saha, Mahesh Rachamalla, Syamprasad Np, Sai Sudha Yalamarthi, Md Abubakar, Antra Chaudhary, D Chamundeswari, Murty Usn, Jagadeesh Kumar Gangasani, V G M Naidu. Perillyl alcohol attenuates rheumatoid arthritis via regulating TLR4/NF-κB and Keap1/Nrf2 signaling pathways: A comprehensive study onin-vitro and in-vivo experimental models. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Mar; 97(?):153926. doi: 10.1016/j.phymed.2022.153926. [PMID: 35030388]
  • Marcela de Oliveira Silva, Graziella Ribeiro de Sousa, Sarah Capelupe Simões, Patrícia Nicolucci, Edwin Tamashiro, Fabiano Saggioro, Ricardo Santos de Oliveira, María Sol Brassesco. Perillyl alcohol for pediatric TP53- and RAS-mutated SHH-medulloblastoma: an in vitro and in vivo translational pre-clinical study. Child's nervous system : ChNS : official journal of the International Society for Pediatric Neurosurgery. 2021 07; 37(7):2163-2175. doi: 10.1007/s00381-021-05115-w. [PMID: 33885911]
  • Arlindo César Matias Pereira, Brenda Lorena Sánchez-Ortíz, Ester Lopes de Melo, Lorane Izabel da Silva Hage-Melim, Raphaelle Sousa Borges, Xuebo Hu, José Carlos Tavares Carvalho. Perillyl alcohol decreases the frequency and severity of convulsive-like behavior in the adult zebrafish model of acute seizures. Naunyn-Schmiedeberg's archives of pharmacology. 2021 06; 394(6):1177-1190. doi: 10.1007/s00210-021-02050-0. [PMID: 33515278]
  • Soodeh Rajabi, Hamid Najafipour, Saeideh Jafarinejad-Farsangi, Siyavash Joukar, Ahmad Beik, Majid Askaripour, Elham Jafari, Zohreh Safi. Quercetin, Perillyl Alcohol, and Berberine Ameliorate Right Ventricular Disorders in Experimental Pulmonary Arterial Hypertension: Effects on miR-204, miR-27a, Fibrotic, Apoptotic, and Inflammatory Factors. Journal of cardiovascular pharmacology. 2021 06; 77(6):777-786. doi: 10.1097/fjc.0000000000001015. [PMID: 34016844]
  • Juliane da Silva Santos, Camila Diedrich, Christiane Schineider Machado, Clovis Orlando da Fonseca, Najeh Maissar Khalil, Rubiana Mara Mainardes. Intranasal administration of perillyl alcohol-loaded nanoemulsion and pharmacokinetic study of its metabolite perillic acid in plasma and brain of rats using ultra-performance liquid chromatography/tandem mass spectrometry. Biomedical chromatography : BMC. 2021 Apr; 35(4):e5037. doi: 10.1002/bmc.5037. [PMID: 33238042]
  • Geetika Nehra, Shannon Andrews, Joan Rettig, Michael N Gould, Jill D Haag, Steven P Howard, Robert G Thorne. Intranasal administration of the chemotherapeutic perillyl alcohol results in selective delivery to the cerebrospinal fluid in rats. Scientific reports. 2021 03; 11(1):6351. doi: 10.1038/s41598-021-85293-4. [PMID: 33737566]
  • Chao Sun, Xianjuan Dong, Rubing Zhang, Congxia Xie. Effectiveness of recombinant Escherichia coli on the production of (R)-(+)-perillyl alcohol. BMC biotechnology. 2021 01; 21(1):3. doi: 10.1186/s12896-020-00662-7. [PMID: 33419424]
  • Soodeh Rajabi, Hamid Najafipour, Saeideh Jafarinejad Farsangi, Siyavash Joukar, Ahmad Beik, Maryam Iranpour, Zeinab Kordestani. Perillyle alcohol and Quercetin ameliorate monocrotaline-induced pulmonary artery hypertension in rats through PARP1-mediated miR-204 down-regulation and its downstream pathway. BMC complementary medicine and therapies. 2020 Jul; 20(1):218. doi: 10.1186/s12906-020-03015-1. [PMID: 32660602]
  • Daniela Carneiro de Lima, Silvana Vianna Rodrigues, Gilson Teles Boaventura, Hee-Yeon Cho, Thomas C Chen, Axel H Schönthal, Clovis Orlando Da Fonseca. Simultaneous measurement of perillyl alcohol and its metabolite perillic acid in plasma and lung after inhalational administration in Wistar rats. Drug testing and analysis. 2020 Feb; 12(2):268-279. doi: 10.1002/dta.2722. [PMID: 31800149]
  • Zeeshan Fatima, Saif Hameed. Lipidomic Insight of Anticandidal Perillyl Alcohol and Sesamol Induced Candida Membrane Disruption: Implications of Lipid Alteration, Impaired Fluidity and Flippase Activity. Infectious disorders drug targets. 2020; 20(6):784-797. doi: 10.2174/1871526519666191023125020. [PMID: 31657691]
  • Monika Kopečná, Miloslav Macháček, Anna Nováčková, Georgios Paraskevopoulos, Jaroslav Roh, Kateřina Vávrová. Esters of terpene alcohols as highly potent, reversible, and low toxic skin penetration enhancers. Scientific reports. 2019 10; 9(1):14617. doi: 10.1038/s41598-019-51226-5. [PMID: 31601936]
  • Navneet Kaur, Khushminder Kaur Chahal, Amit Kumar, Ravinder Singh, Urvashi Bhardwaj. Antioxidant activity of Anethum graveolens L. essential oil constituents and their chemical analogues. Journal of food biochemistry. 2019 04; 43(4):e12782. doi: 10.1111/jfbc.12782. [PMID: 31353585]
  • Adriana A Marin Rodriguez, Leonardo J M Carvalho, Emilia A Kimura, Alejandro M Katzin. Perillyl alcohol exhibits in vitro inhibitory activity against Plasmodium falciparum and protects against experimental cerebral malaria. International journal of antimicrobial agents. 2018 Mar; 51(3):370-377. doi: 10.1016/j.ijantimicag.2017.08.025. [PMID: 28843818]
  • Malgorzata Miastkowska, Monika Konieczna, Elwira Lason, Malgorzata Tabaszewska, Elzbieta Sikora, Jan Ogonowski. The Release of Perillyl Alcohol from the Different Kind of Vehicles. Current pharmaceutical biotechnology. 2018; 19(7):573-580. doi: 10.2174/1389201019666180730165330. [PMID: 30062959]
  • Yixiao Xu, Wantie Wang, Keke Jin, Qifan Zhu, Hongzhou Lin, Minye Xie, Dexuan Wang. Perillyl alcohol protects human renal tubular epithelial cells from hypoxia/reoxygenation injury via inhibition of ROS, endoplasmic reticulum stress and activation of PI3K/Akt/eNOS pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Nov; 95(?):662-669. doi: 10.1016/j.biopha.2017.08.129. [PMID: 28886525]
  • Aline C Gomes, Angélica L Mello, Manuel G Ribeiro, Diogo G Garcia, Clovis O Da Fonseca, Marcela D'Alincourt Salazar, Axel H Schönthal, Thereza Quirico-Santos. Perillyl alcohol, a pleiotropic natural compound suitable for brain tumor therapy, targets free radicals. Archivum immunologiae et therapiae experimentalis. 2017 Aug; 65(4):285-297. doi: 10.1007/s00005-017-0459-5. [PMID: 28314870]
  • Lukas Schmidt, Thomas Göen. R-Limonene metabolism in humans and metabolite kinetics after oral administration. Archives of toxicology. 2017 Mar; 91(3):1175-1185. doi: 10.1007/s00204-016-1751-6. [PMID: 27325307]
  • Luciana Nalone Andrade, Ricardo Guimarães Amaral, Grace Anne Azevedo Dória, Cecília Santos Fonseca, Tayane Kayane Mariano da Silva, Ricardo Luiz Cavalcante Albuquerque Júnior, Sara Maria Thomazzi, Lázaro Gomes do Nascimento, Adriana Andrade Carvalho, Damião Pergentino de Sousa. In Vivo Anti-Tumor Activity and Toxicological Evaluations of Perillaldehyde 8,9-Epoxide, a Derivative of Perillyl Alcohol. International journal of molecular sciences. 2016 Jan; 17(1):. doi: 10.3390/ijms17010032. [PMID: 26742032]
  • Moiz A Ansari, Zeeshan Fatima, Saif Hameed. Anticandidal Effect and Mechanisms of Monoterpenoid, Perillyl Alcohol against Candida albicans. PloS one. 2016; 11(9):e0162465. doi: 10.1371/journal.pone.0162465. [PMID: 27627759]
  • Rizwana Tabassum, Kumar Vaibhav, Pallavi Shrivastava, Andleeb Khan, Mohd Ejaz Ahmed, Mohammad Ashafaq, M Badruzzaman Khan, Farah Islam, Mohammed M Safhi, Fakhrul Islam. Perillyl alcohol improves functional and histological outcomes against ischemia-reperfusion injury by attenuation of oxidative stress and repression of COX-2, NOS-2 and NF-κB in middle cerebral artery occlusion rats. European journal of pharmacology. 2015 Jan; 747(?):190-9. doi: 10.1016/j.ejphar.2014.09.015. [PMID: 25240714]
  • Patrizia A d'Alessio, Massoud Mirshahi, Jean-Francois Bisson, Marie C Bene. Skin repair properties of d-Limonene and perillyl alcohol in murine models. Anti-inflammatory & anti-allergy agents in medicinal chemistry. 2014 Mar; 13(1):29-35. doi: 10.2174/18715230113126660021. [PMID: 24160248]
  • Tabetha Sundin, Dennis Peffley, Patricia Hentosh. eIF4E-Overexpression imparts perillyl alcohol and rapamycin-mediated regulation of telomerase reverse transcriptase. Experimental cell research. 2013 Aug; 319(13):2103-2112. doi: 10.1016/j.yexcr.2013.05.029. [PMID: 23747720]
  • M M Silva, C O Da Fonseca, R Moura-Neto, J F Carvalho, T Quirico-Santos, M G Carvalho. Influence of GSTM1 and GSTT1 polymorphisms on the survival rate of patients with malignant glioma under perillyl alcohol-based therapy. Genetics and molecular research : GMR. 2013 May; 12(2):1621-30. doi: 10.4238/2013.may.14.2. [PMID: 23765968]
  • Florence Lefranc, Zhanjie Xu, Patricia Burth, Véronique Mathieu, Germain Revelant, Mauro Velho de Castro Faria, Caroline Noyon, Diogo Gomes Garcia, Damien Dufour, Céline Bruyère, Cassiano Felippe Gonçalves-de-Albuquerque, Pierre Van Antwerpen, Bernard Rogister, Stéphanie Hesse, Gilbert Kirsch, Robert Kiss. 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K(+)-ATPase and Ras oncogene activity in cancer cells. European journal of medicinal chemistry. 2013 May; 63(?):213-23. doi: 10.1016/j.ejmech.2013.01.046. [PMID: 23474907]
  • Francisco das Chagas Abreu da Silveira, Bruno de Almeida Lopes, Clovis Orlando da Fonseca, Thereza Quirico-Santos, Izabel Christina Nunes de Palmer Paixão, Lidia Maria da Fonte de Amorim. Analysis of EGF+61A>G polymorphism and EGF serum levels in Brazilian glioma patients treated with perillyl alcohol-based therapy. Journal of cancer research and clinical oncology. 2012 Aug; 138(8):1347-54. doi: 10.1007/s00432-012-1203-5. [PMID: 22481252]
  • Lars Duelund, Arnaud Amiot, Alexandra Fillon, Ole G Mouritsen. Influence of the active compounds of Perilla frutescens leaves on lipid membranes. Journal of natural products. 2012 Feb; 75(2):160-6. doi: 10.1021/np200713q. [PMID: 22272932]
  • Sabita N Saldanha, Trygve O Tollefsbol. The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes. Journal of oncology. 2012; 2012(?):192464. doi: 10.1155/2012/192464. [PMID: 22187555]
  • Abdul Quaiyoom Khan, Sana Nafees, Sarwat Sultana. Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NFκ-B activation and proinflammatory cytokine production. Toxicology. 2011 Jan; 279(1-3):108-14. doi: 10.1016/j.tox.2010.09.017. [PMID: 20923693]
  • Ompal Singh, Zakia Khanam, Neelam Misra, Manoj Kumar Srivastava. Chamomile (Matricaria chamomilla L.): An overview. Pharmacognosy reviews. 2011 Jan; 5(9):82-95. doi: 10.4103/0973-7847.79103. [PMID: 22096322]
  • Diogo G Garcia, Lidia M F Amorim, Mauro V de Castro Faria, Aline S Freire, Ricardo E Santelli, Clóvis O Da Fonseca, Thereza Quirico-Santos, Patricia Burth. The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor. Molecular and cellular biochemistry. 2010 Dec; 345(1-2):29-34. doi: 10.1007/s11010-010-0556-9. [PMID: 20689980]
  • Sujata Maiti Choudhury, Malaya Gupta, Upal Kanti Majumder. Antineoplastic activities of MT81 and its structural analogue in Ehrlich ascites carcinoma-bearing Swiss Albino mice. Oxidative medicine and cellular longevity. 2010 Jan; 3(1):61-70. doi: 10.4161/oxim.3.1.10495. [PMID: 20716929]
  • Laxmi Yeruva, Casey Hall, John Abiodun Elegbede, Stephen W Carper. Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin. Anti-cancer drugs. 2010 Jan; 21(1):1-9. doi: 10.1097/cad.0b013e32832a68ad. [PMID: 19820395]
  • Panagiotis Moulos, Olga Papadodima, Aristotelis Chatziioannou, Heleni Loutrari, Charis Roussos, Fragiskos N Kolisis. A transcriptomic computational analysis of mastic oil-treated Lewis lung carcinomas reveals molecular mechanisms targeting tumor cell growth and survival. BMC medical genomics. 2009 Dec; 2(?):68. doi: 10.1186/1755-8794-2-68. [PMID: 20003503]
  • Wenjun Zhou, Syuichi Fukumoto, Hidehiko Yokogoshi. Components of lemon essential oil attenuate dementia induced by scopolamine. Nutritional neuroscience. 2009 Apr; 12(2):57-64. doi: 10.1179/147683009x388832. [PMID: 19356307]
  • Justyna Szumiło. [Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies]. Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego. 2009 Feb; 26(152):156-61. doi: . [PMID: 19388525]
  • Sophia Magkouta, Georgios T Stathopoulos, Ioannis Psallidas, Andreas Papapetropoulos, Fragiskos N Kolisis, Charis Roussos, Heleni Loutrari. Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma. Nutrition and cancer. 2009; 61(5):640-8. doi: 10.1080/01635580902825647. [PMID: 19838938]
  • Hai-Ying Hua, Yong-Xing Zhao, Lin Liu, Qi-Xia Ye, Shi-Wen Ge. High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats. Journal of pharmaceutical and biomedical analysis. 2008 Dec; 48(4):1201-5. doi: 10.1016/j.jpba.2008.08.015. [PMID: 18849133]
  • Roland J W Meesters, Mike Duisken, Heike Jähnigen, Juliane Hollender. Sensitive determination of monoterpene alcohols in urine by HPLC-FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Nov; 875(2):444-50. doi: 10.1016/j.jchromb.2008.09.024. [PMID: 18845490]
  • Jesus M Matos, C Max Schmidt, Howard J Thomas, Oscar W Cummings, Eric A Wiebke, James A Madura, Loehrer J Patrick, P L Crowell. A pilot study of perillyl alcohol in pancreatic cancer. The Journal of surgical research. 2008 Jun; 147(2):194-9. doi: 10.1016/j.jss.2008.02.005. [PMID: 18498869]
  • Howard H Bailey, Steven Attia, Richard R Love, Terri Fass, Rick Chappell, Kendra Tutsch, Linda Harris, Alcee Jumonville, Richard Hansen, Gary R Shapiro, James A Stewart. Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer. Cancer chemotherapy and pharmacology. 2008 Jun; 62(1):149-57. doi: 10.1007/s00280-007-0585-6. [PMID: 17885756]
  • Juliana de Saldanha da Gama Fischer, Paulo Costa Carvalho, Ana Gisele da Costa Neves-Ferreira, Clovis Orlando da Fonseca, Jonas Perales, Maria da Gloria da Costa Carvalho, Gilberto Barbosa Domont. Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol. Journal of experimental therapeutics & oncology. 2008; 7(4):285-90. doi: NULL. [PMID: 19227008]
  • Tamanna Jahangir, Sarwat Sultana. Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model. Evidence-based complementary and alternative medicine : eCAM. 2007 Dec; 4(4):439-45. doi: 10.1093/ecam/nel104. [PMID: 18227911]
  • Laxmi Yeruva, Keon J Pierre, Abiodun Elegbede, Robert C Wang, Stephen W Carper. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer letters. 2007 Nov; 257(2):216-26. doi: 10.1016/j.canlet.2007.07.020. [PMID: 17888568]
  • Dennis M Peffley, Catherine Sharma, Patricia Hentosh, Robbie D Buechler. Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor cells. Archives of biochemistry and biophysics. 2007 Sep; 465(1):266-73. doi: 10.1016/j.abb.2007.05.022. [PMID: 17601486]
  • Nguyen Thi Lan Phi, Chieko Nishiyama, Hyang-Sook Choi, Masayoshi Sawamura. Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil. Bioscience, biotechnology, and biochemistry. 2006 Aug; 70(8):1832-8. doi: 10.1271/bbb.50705. [PMID: 16926494]
  • Heleni Loutrari, Sophia Magkouta, Anastasia Pyriochou, Vasiliki Koika, Fragiskos N Kolisis, Andreas Papapetropoulos, Charis Roussos. Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis. Nutrition and cancer. 2006; 55(1):86-93. doi: 10.1207/s15327914nc5501_11. [PMID: 16965245]
  • Jan B van Beilen, René Holtackers, Daniel Lüscher, Ulrich Bauer, Bernard Witholt, Wouter A Duetz. Biocatalytic production of perillyl alcohol from limonene by using a novel Mycobacterium sp. cytochrome P450 alkane hydroxylase expressed in Pseudomonas putida. Applied and environmental microbiology. 2005 Apr; 71(4):1737-44. doi: 10.1128/aem.71.4.1737-1744.2005. [PMID: 15811996]
  • Vincent Courdavault, Martine Thiersault, Martine Courtois, Pascal Gantet, Audrey Oudin, Pierre Doireau, Benoit St-Pierre, Nathalie Giglioli-Guivarc'h. CaaX-prenyltransferases are essential for expression of genes involvedin the early stages of monoterpenoid biosynthetic pathway in Catharanthus roseus cells. Plant molecular biology. 2005 Apr; 57(6):855-70. doi: 10.1007/s11103-005-3095-0. [PMID: 15952070]
  • Abhishek Gupta, Steven P Stratton, Paul B Myrdal. An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation. Journal of pharmaceutical and biomedical analysis. 2005 Mar; 37(3):447-52. doi: 10.1016/j.jpba.2004.02.039. [PMID: 15740902]
  • M O Omolo, D Okinyo, I O Ndiege, W Lwande, A Hassanali. Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2005 Mar; 12(3):241-6. doi: 10.1016/j.phymed.2003.10.004. [PMID: 15830848]
  • Amitabha Ray. Cancer preventive role of selected dietary factors. Indian journal of cancer. 2005 Jan; 42(1):15-24. doi: 10.4103/0019-509x.15095. [PMID: 15805687]
  • J Grassmann. Terpenoids as plant antioxidants. Vitamins and hormones. 2005; 72(?):505-35. doi: 10.1016/s0083-6729(05)72015-x. [PMID: 16492481]
  • Howard H Bailey, George Wilding, Kendra D Tutsch, Rhoda Z Arzoomanian, Dona Alberti, Chris Feierabend, Kris Simon, Rebecca Marnocha, Sarah A Holstein, Jan Stewart, Kriste A Lewis, Raymond J Hohl. A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days. Cancer chemotherapy and pharmacology. 2004 Oct; 54(4):368-76. doi: 10.1007/s00280-004-0788-z. [PMID: 15205914]
  • Samira Golshani, Fariba Karamkhani, Hamid Reza Monsef-Esfehani, Mohammad Abdollahi. Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2004 Apr; 7(1):76-9. doi: . [PMID: 15144738]
  • Sarah A Holstein, Raymond J Hohl. Monoterpene regulation of Ras and Ras-related protein expression. Journal of lipid research. 2003 Jun; 44(6):1209-15. doi: 10.1194/jlr.m300057-jlr200. [PMID: 12671036]
  • Christopher G Azzoli, Vincent A Miller, Kenneth K Ng, Lee M Krug, David R Spriggs, William P Tong, Elyn R Riedel, Mark G Kris. A phase I trial of perillyl alcohol in patients with advanced solid tumors. Cancer chemotherapy and pharmacology. 2003 Jun; 51(6):493-8. doi: 10.1007/s00280-003-0599-7. [PMID: 12695855]
  • Dennis M Peffley, Apurba K Gayen. Plant-derived monoterpenes suppress hamster kidney cell 3-hydroxy-3-methylglutaryl coenzyme a reductase synthesis at the post-transcriptional level. The Journal of nutrition. 2003 Jan; 133(1):38-44. doi: 10.1093/jn/133.1.38. [PMID: 12514264]
  • Frank Sandner, Jennifer Fornara, Wolfgang Dott, Juliane Hollender. Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Nov; 780(2):225-30. doi: 10.1016/s1570-0232(02)00469-5. [PMID: 12401347]
  • John R Murren, Giuseppe Pizzorno, Susan A DiStasio, Anne McKeon, Kathleen Peccerillo, Ashwin Gollerkari, Walter McMurray, Barbara A Burtness, Thomas Rutherford, Xin Li, Peter T C Ho, Alan Sartorelli. Phase I study of perillyl alcohol in patients with refractory malignancies. Cancer biology & therapy. 2002 Mar; 1(2):130-5. doi: 10.4161/cbt.57. [PMID: 12170772]
  • S S Clark, S M Perman, M B Sahin, G J Jenkins, J A Elegbede. 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. Leukemia. 2002 Feb; 16(2):213-22. doi: 10.1038/sj.leu.2402369. [PMID: 11840288]
  • P J Boon, D van der Boon, G J Mulder. Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat. Toxicology and applied pharmacology. 2000 Aug; 167(1):55-62. doi: 10.1006/taap.2000.8988. [PMID: 10936079]
  • G R Hudes, C E Szarka, A Adams, S Ranganathan, R A McCauley, L M Weiner, C J Langer, S Litwin, G Yeslow, T Halberr, M Qian, J M Gallo. Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research. 2000 Aug; 6(8):3071-80. doi: . [PMID: 10955786]
  • M S Si, D K Imagawa. Prenylation inhibitors to treat proliferative renal disease. Lancet (London, England). 2000 Apr; 355(9213):1460. doi: 10.1016/s0140-6736(05)74654-7. [PMID: 10791545]
  • S Unlu, C D Mason, M Schachter, A D Hughes. Perillyl alcohol, an inhibitor of geranylgeranyl transferase, induces apoptosis of immortalized human vascular smooth muscle cells in vitro. Journal of cardiovascular pharmacology. 2000 Feb; 35(2):341-4. doi: 10.1097/00005344-200002000-00025. [PMID: 10672871]
  • G H Ripple, M N Gould, R Z Arzoomanian, D Alberti, C Feierabend, K Simon, K Binger, K D Tutsch, M Pomplun, A Wahamaki, R Marnocha, G Wilding, H H Bailey. Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. Clinical cancer research : an official journal of the American Association for Cancer Research. 2000 Feb; 6(2):390-6. doi: . [PMID: 10690515]
  • E Elmore, T T Luc, H R Li, J A Buckmeier, V E Steele, G J Kelloff, J L Redpath. Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. Anticancer research. 2000 Jan; 20(1A):27-32. doi: NULL. [PMID: 10769631]
  • S R Cerda, J Wilkinson, S K Branch, S A Broitman. Enhancement of sterol synthesis by the monoterpene perillyl alcohol is unaffected by competitive 3-hydroxy-3-methylglutaryl-CoA reductase inhibition. Lipids. 1999 Jun; 34(6):605-15. doi: 10.1007/s11745-999-0405-5. [PMID: 10405975]
  • Z Zhang, H Chen, K K Chan, T Budd, R Ganapathi. Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. Journal of chromatography. B, Biomedical sciences and applications. 1999 May; 728(1):85-95. doi: 10.1016/s0378-4347(99)00065-1. [PMID: 10379660]
  • G H Ripple, M N Gould, J A Stewart, K D Tutsch, R Z Arzoomanian, D Alberti, C Feierabend, M Pomplun, G Wilding, H H Bailey. Phase I clinical trial of perillyl alcohol administered daily. Clinical cancer research : an official journal of the American Association for Cancer Research. 1998 May; 4(5):1159-64. doi: . [PMID: 9607573]
  • G J Fulton, L Barber, E Svendsen, P O Hagen, M G Davies. Oral monoterpene therapy (perillyl alcohol) reduces vein graft intimal hyperplasia. The Journal of surgical research. 1997 Apr; 69(1):128-34. doi: 10.1006/jsre.1997.5047. [PMID: 9202658]
  • Y D Burke, M J Stark, S L Roach, S E Sen, P L Crowell. Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol. Lipids. 1997 Feb; 32(2):151-6. doi: 10.1007/s11745-997-0019-y. [PMID: 9075204]
  • L E Lantry, Z Zhang, F Gao, K A Crist, Y Wang, G J Kelloff, R A Lubet, M You. Chemopreventive effect of perillyl alcohol on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced tumorigenesis in (C3H/HeJ X A/J)F1 mouse lung. Journal of cellular biochemistry. Supplement. 1997; 27(?):20-5. doi: 10.1002/(sici)1097-4644(1997)27+<20::aid-jcb6>3.0.co;2-3. [PMID: 9591189]
  • S A Broitman, J Wilkinson, S Cerda, S K Branch. Effects of monoterpenes and mevinolin on murine colon tumor CT-26 in vitro and its hepatic "metastases" in vivo. Advances in experimental medicine and biology. 1996; 401(?):111-30. doi: 10.1007/978-1-4613-0399-2_9. [PMID: 8886130]
  • H D Luján, M R Mowatt, G Z Chen, T E Nash. Isoprenylation of proteins in the protozoan Giardia lamblia. Molecular and biochemical parasitology. 1995 Jun; 72(1-2):121-7. doi: 10.1016/0166-6851(94)00070-4. [PMID: 8538683]
  • C E Elson, S G Yu. The chemoprevention of cancer by mevalonate-derived constituents of fruits and vegetables. The Journal of nutrition. 1994 May; 124(5):607-14. doi: 10.1093/jn/124.5.607. [PMID: 8169651]
  • Z Ren, M N Gould. Inhibition of ubiquinone and cholesterol synthesis by the monoterpene perillyl alcohol. Cancer letters. 1994 Jan; 76(2-3):185-90. doi: 10.1016/0304-3835(94)90396-4. [PMID: 8149348]
  • J D Haag, M N Gould. Mammary carcinoma regression induced by perillyl alcohol, a hydroxylated analog of limonene. Cancer chemotherapy and pharmacology. 1994; 34(6):477-83. doi: 10.1007/bf00685658. [PMID: 7923558]
  • J Pan, Z Xu, L Ji, Z Zhao, X Tang. [Constituents of essential oils from leaves, stems, and fruits of Perilla frutescens (L.) Britt]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1992 Mar; 17(3):164-5, 192. doi: ". [PMID: 1418538]