Geraniol and limonene interaction with 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase for their role as cancer chemo-preventive agents

Journal of Proteomics and Bioinformatics

Volumn 2, Issue 11, 2009, Pages 466-474

  Pattanayak, Madhumita ^a,b   Seth, P K ^c   Smita, Suchi ^d   Gupta, Shailendra K ^a,d  

^a Indian Institute of Toxicological Research   (India)

^b CENTRE FOR CELLULAR AND MOLECULAR BIOLOGY   (India)

^c Biotech Park   (India)

^d UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Cancer chemo preventive agents; Docking; Geraniol; HMG CoA reductase; Limonene

Indexed keywords

CITRUS; OCIMUM; RODENTIA;

EID: 75749129919     PISSN: None     EISSN: 0974276X     Source Type: Journal    
DOI: 10.4172/jpb.1000107     Document Type: Article

References (30)

1. Alonso WR, Rajaonarivony JI, Gershenzon J, Croteau R (1992) Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita) and spearmint (Mentha spicata). J Biol Chem 267: 7582-7.
2. Asamoto M, Ota T, Toriyama-Baba H, Hokaiwado N, Naito A, et al. (2002) Mammary carcinomas induced in human c-Ha-ras proto-oncogene transgenic rats are estrogen-independent but responsive to d-limonene treatment. Jpn J Cancer Res 93: 32-5.
3. Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, et al. (1983) CHARMM: A program for macromolecular energy minimization and dynamics calculations. J Comput Chem 4: 187-217.
4. Carnesecchi S, Bras-Gonçalves R, Bradaia A, Zeisel M, Gossé F, et al. (2004) Geraniol, a component of plant essential oils, modulates DNA synthesis and potentiates 5-fluorouracil efficacy on human colon tumor xenografts. Cancer Lett 215: 53-9.
5. Chander SK, Lansdown AG, Luqmani YA, Gomm JJ, Coope RC, et al. (1994) Effectiveness of combined limonene and 4-hydroxyandrostenedione in the treatment of NMU-induced rat mammary tumours. Br J Cancer 69: 879-82.
6. Clarke S (1992) Protein isoprenylation and methylation at carboxyl-terminal cysteine residues. Annu Rev Biochem 61: 355-86.
7. Crowell PL (1999) Prevention and therapy of cancer by dietary monoterpenes. J Nutr 129: 775S-778S.
8. Elegbede JA, Maltzman TH, Verma AK, Tanner MA, Elson CE, et al. (1986) Mouse skin tumor promoting activity of orange peel oil and d-limonene: a re-evaluation. Carcinogenesis 7: 2047-9.
9. Elson CE, Maltzman TH, Boston JL, Tanner MA, Gould MN (1988) Anti-carcinogenic activity of d-limonene during the initiation and promotion/progression stages of DMBA-induced rat mammary carcinogenesis. Carcinogenesis 9: 331-2.
10. Genser B, Grammer TB, Stojakovic T, Siekmeier R, März W (2008) Effect of HMG CoA reductase inhibitors on lowdensity lipoprotein cholesterol and C-reactive protein: systematic review and meta-analysis. Int J Clin Pharmacol Ther 46: 497-510.
11. Gould MN, Moore CJ, Zhang R, Wang B, Kennan WS, et al. (1994) Limonene chemoprevention of mammary carcinoma induction following direct in situ transfer of v-Ha-ras. Cancer Res 54: 3540-3543.
12. Iijima Y, Davidovich-Rikanati R, Fridman E, Gang DR, Bar E, et al. (2004) The Biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of Basil. Plant Physiol 136: 3724-3736.
13. Istvan ES, Deisenhofer J (2001) Structural mechanism for statin inhibition of HMG-CoA reductase. Science 292: 1160-4.
14. Jain AN (1996) Scoring noncovalent protein-ligand interactions: a continuous differentiable function tuned to compute binding affinities. J Comput Aided Mol Des 10: 427-40.
15. Kawamori T, Tanaka T, Hirose Y, Ohnishi M, Mori H (1996) Inhibitory effects of d-limonene on the development of colonic aberrant crypt foci induced by azoxymethane in F344 rats. Carcinogenesis. 17: 369-372.
16. Kjonaas R, Croteau R (1983) Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha Piperita and other Mentha species. Arch Biochem Biophys 220: 79-89.
17. Kodama R, Yano T, Furukawa K, Noda K, Ide H (1976) Studies on the metabolism of d-limonene (p-mentha-1,8-diene). IV. Isolation and characterization of new metabolites and species differences in metabolism. Xenobiotica 6: 377-89.
18. Krammer A, Kirchhoff PD, Jiang X, Venkatachalam CM, Waldman M (2005) LigScore: a novel scoring function for predicting binding affinities. J Mol Graph Model 23: 395-407.
19. Loza-Tavera H (1999) Monoterpenes in essential oils. Biosynthesis and properties. Adv Exp Med Biol 464: 49-62.
20. Lu XG, Zhan LB, Feng BA, Qu MY, Yu LH, et al. (2004) Inhibition of growth and metastasis of human gastric cancer implanted in nude mice by d-limonene. World J Gastroenterol 10: 2140-4.
21. McGarvey DJ, Croteau R (1995) Terpenoid metabolism. Plant Cell 7: 1015-1026.
22. Muegge I, Martin YC (1999) A general and fast scoring function for protein-ligand interactions: a simplified potential approach. J Med Chem 42: 791-804.
23. National Toxicology Program (1990) NTP Toxicology and Carcinogenesis Studies of d-Limonene (CAS No. 5989-27-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies). Natl Toxicol Program Tech Rep Ser 347: 1-165.
24. Peffley DM, Gayen AK (2003) Plant-derived monoterpenes suppress hamster kidney cell 3-hydroxy-3-methylglutaryl coenzyme a reductase synthesis at the post-transcriptional level. J Nutr 133: 38-44.
25. Polo MP, de Bravo MG (2006) Effect of geraniol on fattyacid and mevalonate metabolism in the human hepatoma cell line Hep G2. Biochem Cell Biol 84: 102-11.
26. Raphael TJ, Kuttan G (2003) Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells. J Exp Clin Cancer Res 22: 419-24.
27. Salim EI, Wanibuchi H, Morimura K, Wei M, Mitsuhashi M, et al. (2003) Carcinogenicity of dimethylarsinic acid in p53 heterozygous knockout and wild-type C57BL/6J mice. Carcinogenesis 24: 335-42.
28. Singletery K (2000) Diet, natural products and cancer chemoprevention. J Nutr 130: 465S-466S
29. Swanson KM, Hohl RJ (2006) Anti-cancer therapy: targeting the mevalonate pathway. Curr Cancer Drug Targets 6: 15-37.
30. Venkatachalam CM, Jiang X, Oldfield T, Waldman M (2003) LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites. J Mol Graph Model 21: 289-307.