Myrtenal, a natural monoterpene, down-regulates TNF-α expression and suppresses carcinogen-induced hepatocellular carcinoma in rats

Molecular and Cellular Biochemistry

Volumn 369, Issue 1-2, 2012, Pages 183-193

  Hari Babu, Lingaiah ^a   Perumal, Srinivasan ^a   Balasubramanian, Maruthaiveeran Periyasamy ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Diethylnitrosamine; Hepatocellular carcinoma; Monoterpene; Myrtenal; TNF

Indexed keywords

ALPHA FETOPROTEIN; ANTINEOPLASTIC AGENT; CARCINOEMBRYONIC ANTIGEN; CYTOCHROME B5; CYTOCHROME B5 REDUCTASE; CYTOCHROME P450; DIETHYLNITROSAMINE; GLUCURONOSYLTRANSFERASE; GLUTATHIONE TRANSFERASE; MALONALDEHYDE; MYRTENAL; PHENOBARBITAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; TERPENE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BODY WEIGHT; CANCER INHIBITION; CELL STRUCTURE; CONTROLLED STUDY; DOWN REGULATION; IMMUNOBLOTTING; LIPID PEROXIDATION; LIVER; LIVER CELL CARCINOMA; LIVER MICROSOME; LIVER WEIGHT; MALE; NONHUMAN; PROTEIN EXPRESSION; RAT; TRANSMISSION ELECTRON MICROSCOPY; UPREGULATION;

ANIMALS; CARCINOGENS; CARCINOMA, HEPATOCELLULAR; DIETHYLNITROSAMINE; GENE EXPRESSION REGULATION, NEOPLASTIC; LIPID PEROXIDATION; LIVER; NEOPLASMS, EXPERIMENTAL; RATS; TERPENES; TUMOR NECROSIS FACTOR-ALPHA;

ANIMALIA; RATTUS;

EID: 84865659623     PISSN: 03008177     EISSN: 15734919     Source Type: Journal    
DOI: 10.1007/s11010-012-1381-0     Document Type: Article

References (66)

1. M Barthelman W Chen HL Gensler C Huang Z Dong GT Bowden 1998 Inhibitory effects of perillyl alcohol on UVB-induced murine skin cancer and AP-1 transactivation Cancer Res 58 711 716 9485025 1:CAS:528:DyaK1cXht1anur0%3D (Pubitemid 28099482)
2. JD Haag MN Gould 1994 Mammary carcinoma regression induced by perillyl alcohol, a hydroxylated analog of limonene Cancer Chemother Pharmacol 34 477 483 7923558 10.1007/BF00685658 1:CAS:528:DyaK2MXis1Onu7k%3D (Pubitemid 24306046)
3. LW Wattenberg JB Coccia 1991 Inhibition of 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone carcinogenesis in mice by d-limonene and citrus fruit oils Carcinogenesis 12 115 117 1988170 10.1093/carcin/12.1.115 1:CAS:528: DyaK3MXhtFCks7s%3D
4. MJ Stark YD Burke JH McKinzie AS Ayoubi PL Crowell 1995 Chemotherapy of pancreatic cancer with the monoterpene perillyl alcohol Cancer Lett 96 15 21 7553603 10.1016/0304-3835(95)03912-G 1:CAS:528:DyaK2MXotFCmsL0%3D
5. JJ Mills RS Chari IJ Boyer MN Gould RL Jirtle 1995 Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol Cancer Res 55 979 983 7867007 1:CAS:528:DyaK2MXktVGitL4%3D
6. BS Reddy CX Wang H Samaha R Lubet VE Steele GJ Kelloff CV Rao 1997 Chemoprevention of colon carcinogenesis by dietary perillyl alcohol Cancer Res 57 420 425 9012468 1:CAS:528:DyaK2sXhtVKhsr8%3D (Pubitemid 27081658)
7. F Karp CA Mihaliak JL Harris R Croteau 1990 Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint, (Mentha spectat), and perilla (Perilla frutescens) leaves Arch Biochem Biophys 276 219 226 2297225 10.1016/0003- 9861(90)90029-X 1:CAS:528:DyaK3cXhvFGgs7k%3D (Pubitemid 20041836)
8. DJ McGarvey R Croteau 1995 Terpenoid metabolism Plant Cell 7 1015 1026 7640522 1:CAS:528:DyaK2MXnt1Sgt7w%3D
9. CE Elson 1995 Suppression of mevalonate pathway activities by dietary isoprenoids: protective roles in cancer and cardiovascular disease J Nutr 125 1666S 1672S 7782923 1:CAS:528:DyaK2MXmt1ahsro%3D
10. Y Yamamoto M Hosokawa H Kurihara T Maoka K Miyashita 2008 Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells Bioorg Med Chem Lett 18 4044 4046 18556205 10.1016/j.bmcl.2008.05.113 1:CAS:528:DC%2BD1cXosleqt70%3D
11. GH Ripple MN Gould RZ Arzoomanian D Alberti C Feierabend K Simon K Binger KD Tutsch M Pomplun A Wahamaki R Marnocha G Wilding HH Bailey 2000 Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day Clin Cancer Res 6 390 396 10690515 1:CAS:528:DC%2BD3cXhs1aksLg%3D (Pubitemid 30111455)
12. D Samaila BJ Toy RC Wang JA Elegbede 2004 Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro Anticancer Res 24 3089 3095 15517920 1:CAS:528:DC%2BD2cXhtVSjsLnL (Pubitemid 39407190)
13. HH Bailey D Levy LS Harris JC Schink F Foss P Beatty S Wadler 2002 A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96 Gynecol Oncol 85 464 468 12051875 10.1006/gyno.2002.6647 1:CAS:528:DC%2BD38XktlWqsbc%3D (Pubitemid 34651886)
14. M Xu HS Floyd SM Greth WC Chang K Lohman R Stoyanova GL Kucera TE Kute MC Willingham MS Miller 2004 Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: potential mechanisms for its chemotherapeutic effects Toxicol Appl Pharmacol 195 232 246 14998688 10.1016/j.taap.2003.11.013 1:CAS:528:DC%2BD2cXhslels74%3D (Pubitemid 38293154)
15. PJM Boon DVD Boon GL Mulder 2000 Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat Toxicol Appl Pharmacol 167 55 62 10936079 10.1006/taap.2000.8988 1:CAS:528: DC%2BD3cXlsVKksLY%3D (Pubitemid 30663088)
16. MM Cruz Silva ML Melo M Parolin D Tessaro S Riva B Danieli 2004 Tetrahedron Asymmetry 15 21 27 10.1016/j.tetasy.2003.11.003 1:CAS:528: DC%2BD3sXhtVSiu7zK (Pubitemid 38032729)
17. H Marica Lindmark I Dan V Tomas V Irena H Hans-Erik S Kristina 2004 Transformation of terpenes using a Picea abies suspension culture J Biotechnol 107 173 184 10.1016/j.jbiotec.2003.10.009 (Pubitemid 38058678)
18. JB Vibha K Choudhary Singh Mangal MS Rathore NS Shekhawat 2009 A study on pharmacokinetics and therapeutic efficacy of Glycyrrhiza glabra. A Miracle Medicinal Herb Bot Res Int 2 157 163
19. MAL Holguín FO Holguín S Micheletto S Goehle JA Simon MA O'Connell 2008 Chemotypic variation of essential oils in the medicinal plant, Anemopsis californica Phytochemistry 69 919 927 18177907 10.1016/j.phytochem. 2007.11.006
20. D Kaufmann AK Dogra M Wink 2011 Myrtenal inhibits acetylcholinesterase, a known Alzheimer target J Pharm Pharmacol 63 10 1368 1371 21899553 10.1111/j.2042-7158.2011.01344.x 1:CAS:528:DC%2BC3MXht1CitrrI
21. T Ishida 2005 Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells Chem Biodivers 2 5 569 590 17192005 10.1002/cbdv.200590038 1:CAS:528:DC%2BD2MXkvF2ktLc%3D (Pubitemid 40790439)
22. A Dullin F Dufrasne M Gelbcke R Gust 2004 Enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)butane]platinum(II) complexes: synthesis and antitumor activity against MCF-7 and MDA-MB 231 breast cancer and LnCaP/FGC prostate cancer cell lines Arch Pharm 337 12 654 667 10.1002/ardp.200400621 1:CAS:528:DC%2BD2MXltlCrtw%3D%3D (Pubitemid 40101063)
23. T Ishida M Toyota Y Asakawa 1989 Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (±)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (±)-carvone in rabbits Xenobiotica 19 843 855 2815827 10.3109/00498258909043145 1:CAS:528:DyaL1MXls1yrt70%3D (Pubitemid 19213053)
24. S Sivalokanathan M Ilayaraja MP Balasubramanian 2006 Antioxidant activity of Terminalia arjuna bark extract on N-nitrosodiethylamine induced hepatocellular carcinoma in rats Mol Cell Biochem 281 87 93 16328960 10.1007/s11010-006-0433-8 1:CAS:528:DC%2BD2MXht1Oqsb3M (Pubitemid 43040127)
25. L Hari Babu N Nandakumar T Rengarajan S Perumal MP Balasubramanian 2012 Myrtenal ameliorates diethylnitrosamine-induced hepatocarcinogenesis through the activation of tumor suppressor protein p53 and regulation of lysosomal and mitochondrial enzymes Fundam Clin Pharmacol 10.1111/j.1472-8206.2012.01039.x
26. S Sell FF Beckar 1978 Alpha-fetoprotein J Natl Cancer Inst 60 19 26 75267 1:CAS:528:DyaE1cXhtVajtbo%3D (Pubitemid 8287163)
27. GM Macnab JM Urbanowicz JM Kew 1978 Carcinoembryonic antigen in hepatocellular cancer Br J Cancer 38 51 54 80223 10.1038/bjc.1978.162 1:CAS:528:DyaE1MXktFWr
28. OH Lowry NJ Rosebrough AJ Farr AL Randall 1951 Protein measurement with Folins' phenol reagent J Biol Chem 193 262 275
29. 2+ with endoplasmic reticulum of rat liver: a standardized procedure for the isolation of rat liver microsomes Anal Biochem 48 53 61 4339370 10.1016/0003-2697(72)90169-8 1:CAS:528:DyaE38XktlWhtL4%3D
30. JR Wright, et al. 1981 Cytosolic factors which affect microsomal lipid peroxidation in lung and liver Arch Biochem Biophys 206 296 304 7224639 10.1016/0003-9861(81)90095-3 1:CAS:528:DyaL3MXpvVersw%3D%3D (Pubitemid 11102033)
31. T Omura R Sato 1964 The carbon monoxide-binding pigment of liver microsomes J Biol Chem 239 2379 2385 14209972 1:CAS:528:DyaF2cXktF2gur8%3D
32. AH Philips RG Langdon 1962 Hepatic triphosphopyridine nucleotide-cytochromec reductase: isolation, characterization and kinetic studies J Biol Chem 237 2652 2669
33. P Strittmatter SF Velick 1956 A microsomal cytochrome reductase specific for di phosphor pyridine nucleotide J Biol Chem 221 277 286 13345817 1:CAS:528:DyaG28XnsVegtQ%3D%3D
34. WH Habig MJ Pabst WB Jakoby 1974 Glutathione S-transferase, the first enzymatic step in mercapturic acid formation J Biol Chem 249 7130 7139 4436300 1:CAS:528:DyaE2MXltlahtg%3D%3D
35. S Hollman O Touster 1962 Alterations in tissue levels of UDP-glucose dehydrogenase, UDP-glucuronic acid pyrophosphatase and glucuronyl transferase induced by substances influencing the production of ascorbic acid Biochim Biophys Acta 62 338 352 10.1016/0006-3002(62)90048-3
36. GFX David J Herbert CDS Wright 1973 The ultrastructure of the pineal ganglion in the ferret J Anat 115 79 97 4728267 1:CAS:528:DyaE3sXlt1Cjt7c%3D
37. K Yamada I Yamamiya H Utsumi 2006 In vivo detection of free radicals induced by diethylnitrosamine in rat liver tissue Free Radic Biol Med 40 2040 2046 16716904 10.1016/j.freeradbiomed.2006.01.031 1:CAS:528:DC%2BD28XkvVyju7k%3D (Pubitemid 43728859)
38. AS Yu EB Keeffe 2003 Management of hepatocellular carcinoma Rev Gastroenterol Disord 3 8 24 12684589 1:CAS:528:DC%2BD3sXps1Cqt7w%3D (Pubitemid 36335933)
39. V Sivaramakrishnan P Shilpa V Kumar SN Devaraj 2008 Attenuation of N-nitrosodiethylamine-induced hepatocellular carcinogenesis by a novel flavonol-morin Chem Biol Interact 171 79 88 17950263 10.1016/j.cbi.2007.09.003 1:CAS:528:DC%2BD2sXhsVSrsL%2FJ (Pubitemid 350191846)
40. S Sell F Becker HL Leffert K Osborn J Salman B Lombardi J Shinozuka Reddy E Roushlahti J Sala-Trepat 1983 α-Fetoprotein as a marker for early events and carcinoma development during chemical hepatocarcinogenesis Environ Sci Res 29 271 293 1:CAS:528:DyaL2cXjtVCqsA%3D%3D
41. FF Becker S Sell 1979 Differences in serum α-fetoprotein concentrations during the carcinogenic sequences resulting from exposure to diethylnitrosamine or acetaminofluorene Cancer Res 39 1437 1442 85483 1:CAS:528:DyaE1MXks12lt7k%3D (Pubitemid 9172654)
42. R Zimmer P Thomas 2001 Mutations in the carcinoembryonic antigen gene in colorectal cancer patients: implications on liver metastasis Cancer Res 61 2822 2826 11306451 1:CAS:528:DC%2BD3MXivFGrurs%3D (Pubitemid 32691918)
43. P Janani K Sivakumari A Geetha B Ravisankar C Parthasarathy 2011 Chemopreventive effect of bacoside A on N-nitrosodiethylamine-induced hepatocarcinogenesis in rats J Cancer Res Clin Oncol 136 759 770 10.1007/s00432-009-0715-0
44. H Esterbauer RJ Schaur Zollner 1991 Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes Free Rad Biol Med 11 81 128 1937131 10.1016/0891-5849(91)90192-6 1:CAS:528:DyaK3MXmsFSnsbo%3D (Pubitemid 121003917)
45. J Torel J Cillard P Cillard 1986 Antioxidant activity of flavonoids and reactivity with peroxyl radical Phytochemistry 25 383 385 10.1016/S0031-9422(00) 85485-0 1:CAS:528:DyaL28Xht1art7g%3D
46. Hietanen E, Ahotupa M, Bartsch H (1987) Lipid peroxidation and chemically induced cancer in rats fed lipid rich diet. In: Lapis K, Kcharst S (eds) Carcinogenesis and tumor progression, vol 4. Akadémiai Kiadó, Budapest, pp 9-16
47. W Scholz K Schutze W Kunz M Schwartz 1990 Phenobarbital enhances the formation of reactive oxygen in neoplastic rat liver nodules Cancer Res 50 7015 7022 2208168 1:CAS:528:DyaK3MXltFw%3D (Pubitemid 20361107)
48. IF Benzie 1996 Lipid peroxidation: a review of causes, consequences, measurement and dietary influences Int J Food Sci Nutr 47 233 261 8735779 10.3109/09637489609012586 1:CAS:528:DyaK28XjslGms7o%3D (Pubitemid 26154906)
49. Flohe L, Beckmann R, Giertz H, Loschen G (1985) Oxygen centered free radicals a mediators of inflammation. In: Sies H (ed) Oxidative stress. Academic Press, New York, p 405
50. LJ Marnett 1994 DNA adducts of alpha, beta-unsaturated aldehydes and dicarbonyl compounds IARC Sci Publ 125 151 163 7806310 1:CAS:528: DyaK2MXjtV2ksLs%3D
51. Timbrell (1991) Principles of biochemical toxicology, 2nd edn. Taylor and Francis, London
52. B Testa B Jenner 1976 The concept of regioselectivity in drug metabolism J Pharm Pharmacol 28 731 744 62048 10.1111/j.2042-7158.1976.tb04038.x 1:CAS:528:DyaE2sXltVehsA%3D%3D
53. ME Varnes JE Biaglow 1979 Interactions of the carcinogen 4-nitroquinoline 1-oxide with the non-protein thiols of mammalian cells Cancer Res 39 2960 2965 110443 1:CAS:528:DyaE1MXltFygtL8%3D (Pubitemid 9226902)
54. AK Bansal M Bansal G Soni D Bhatnagar 2005 Protective role of vitamin E pretreatment on N-nitrosodiethylamine induced oxidative stress in rat liver Chem Biol Interact 156 101 111 16144695 10.1016/j.cbi.2005.08.001 1:CAS:528:DC%2BD2MXhtVymsL3K (Pubitemid 41406233)
55. M Sreepriya G Bali 2005 Chemopreventive effects of embelin and curcumin against N-nitrosodiethylamine/phenobarbital-induced hepatocarcinogenesis in Wistar rats Fitoterapia 76 549 555 16009505 10.1016/j.fitote.2005.04.014 1:CAS:528:DC%2BD2MXpslyis7Y%3D (Pubitemid 41749743)
56. GMM Rao CHV Rao P Pushpangadan S Annie 2006 Hepatoprotective effects of rubiadin, a major constituent of Rubia cordifolia Linn J Ethnopharmacol 103 484 490 16213120 10.1016/j.jep.2005.08.073 1:CAS:528:DC%2BD28XovVSqtw%3D%3D (Pubitemid 43143388)
57. Bergmeyer HU, Bernt E (1974) Aminotransferases and related enzymes. In: Bergmeyer HU (ed) Methods of enzymatic analysis, vol 2, 2nd edn. Academic Press, New York, pp 735-763
58. George SG (1994) Enzymology and molecular biology of phase II xenobiotic-conjugating enzymes in the fish. In: Malins DC, Ostrander GK (eds) Aquatic toxicology: molecular biochemical and cellular perspectives. Lewis Publishers, CRC Press, New York, pp 37-85
59. RH Erickson DA Zakim 1978 Preparation and properties of a phospholipid-free form of microsomal UDP glucuronyl transferase Biochemistry 17 3706 3711 100135 10.1021/bi00611a005 1:CAS:528:DyaE1cXlsF2gsr0%3D (Pubitemid 9022577)
60. ILC Chapple 1997 Reactive oxygen species and antioxidants in inflammatory diseases J Clin Periodontol 24 287 296 9178107 10.1111/j.1600-051X.1997. tb00760.x 1:CAS:528:DyaK2sXjt1Glu7s%3D (Pubitemid 127731526)
61. A Thorburn 2004 Death receptor-induced cell killing Cell Signal 16 139 144 14636884 10.1016/j.cellsig.2003.08.007 1:CAS:528:DC%2BD3sXptVWmtr4%3D (Pubitemid 37431163)
62. EY Choi HJ Hwang IH Kim TJ Nam 2009 Protective effects of a polysaccharide from Hizikia fusiformis against ethanol toxicity in rats Food Chem Toxicol 47 134 139 19026708 10.1016/j.fct.2008.10.026 1:CAS:528: DC%2BD1MXksVejsA%3D%3D
63. BS Yang YJ Ma Y Wang LY Chen MR Bi BZ Yan L Bai H Zhou FX Wang 2007 Protective effect and mechanism of stronger neo-minophagen C against fulminant hepatic failure World J Gastroenterol 13 462 466 17230620 1:CAS:528: DC%2BD2sXitFGgtbw%3D (Pubitemid 46178985)
64. L Leifeld J Nattermann M Fielenbach V Schmitz T Sauerbruch U Spengler 2006 Intrahepatic activation of caspases in human fulminant hepatic failure Liver Int 26 872 879 16911471 10.1111/j.1478-3231.2006.01300.x 1:CAS:528:DC%2BD28XhtVegsrjK (Pubitemid 44165256)
65. G Ramakrishnan HR Raghavendran Vinodhkumar T Devaki 2006 Suppression of N-nitrosodiethylamine induced hepatocarcinogenesis by silymarin in rats Chem Biol Interact 161 104 114 16643877 10.1016/j.cbi.2006.03.007 1:CAS:528:DC%2BD28XltFOqsL8%3D (Pubitemid 43776629)
66. S Pathak ARK Bukhsh 2007 Assessment of hepatocellular damage and hematological alterations in mice chronically fed p-dimethyl aminoazobenzene and Phenobarbital Exp Mol Pathol 83 104 111 17189631 10.1016/j.yexmp.2006.10.003 1:CAS:528:DC%2BD2sXmtVOrtr8%3D (Pubitemid 46842956)