Asian Pacific Journal of Cancer Prevention

  • 제14권6호
  • /
  • Pages.3735-3742
  • /
  • 2013
  • /
  • 1513-7368(pISSN)
  • /
  • 2476-762X(eISSN)
아시아태평양암예방학회 (Asian Pacific Journal of Cancer Prevention)
권호 표지
DOI QR코드

DOI QR Code

Identification of Proapoptopic, Anti-Inflammatory, Anti-Proliferative, Anti-Invasive and Anti-Angiogenic Targets of Essential Oils in Cardamom by Dual Reverse Virtual Screening and Binding Pose Analysis

  • 발행 : 2013.06.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Background: Cardamom (Elettaria cardamom), also known as "Queen of Spices", has been traditionally used as a culinary ingredient due to its pleasant aroma and taste. In addition to this role, studies on cardamom have demonstrated cancer chemopreventive potential in in vitro and in vivo systems. Nevertheless, the precise poly-pharmacological nature of naturally occurring chemo-preventive compounds in cardamom has still not been fully demystified. Methods:In this study, an effort has been made to identify the proapoptopic, anti-inflammatory, anti-proliferative, anti-invasive and anti-angiogenic targets of Cardamom's bioactive principles (eucalyptol, alpha-pinene, beta-pinene, d-limonene and geraniol) by employing a dual reverse virtual screening protocol. Experimentally proven target information of the bioactive principles was annotated from bioassay databases and compared with the virtually screened set of targets to evaluate the reliability of the computational identification. To study the molecular interaction pattern of the anti-tumor action, molecular docking simulation was performed with Auto Dock Pyrx. Interaction studies of binding pose of eucalyptol with Caspase 3 were conducted to obtain an insight into the interacting amino acids and their inter-molecular bondings. Results:A prioritized list of target proteins associated with multiple forms of cancer and ranked by their Fit Score (Pharm Mapper) and descending 3D score (Reverse Screen 3D) were obtained from the two independent inverse screening platforms. Molecular docking studies exploring the bioactive principle targeted action revealed that H- bonds and electrostatic interactions forms the chief contributing factor in inter-molecular interactions associated with anti-tumor activity. Eucalyptol binds to the Caspase 3 with a specific framework that is well-suited for nucleophilic attacks by polar residues inside the Caspase 3 catalytic site. Conclusion:This study revealed vital information about the poly-pharmacological anti-tumor mode-of-action of essential oils in cardamom. In addition, a probabilistic set of anti-tumor targets for cardamom was generated, which can be further confirmed by in vivo and in vitro experiments.

키워드

참고문헌

  1. Aggarwal BB, Shishodia S, Sandur SK, et al (2006). Inflammation and cancer: how hot is the link? Biochem Pharmacol, 72, 1605-21. https://doi.org/10.1016/j.bcp.2006.06.029
  2. al-Zuhair H, el-Sayeh B, Ameen HA, et al (1996). Pharmacological studies of cardamom oil in animals. Pharmacol Res, 34, 79-82. https://doi.org/10.1006/phrs.1996.0067
  3. Aneja KR, Joshi R (2009). Antimicrobial activity of Amomum subulatum and Elettaria cardamomum against dental caries causing pathogens, Ethnobotanical Leaflets, 13, 840-9.
  4. Bhattacharjee B, Vijayasarathy S, Karunakar P, et al (2012). Comparative reverse screening approach to identify potential anti-neoplastic targets of saffron functional components and binding mode. Asian Pac J Cancer Prev, 13, 5605-11. https://doi.org/10.7314/APJCP.2012.13.11.5605
  5. Bianco C, Tortora G, Bianco R, et al (2002). Enhancement of antitumor activity of ionizing radiation by combined treatment with the selective epidermal growth factor receptor-tyrosine kinase inhibitor ZD1839 (Iressa). Clin Cancer Res, 8, 3250-8.
  6. Bruzzo J, Chiarella P, Fernandez G, et al (2007). Systemic inflammation and experimental cancer in a murine model. Medicina (B Aires), 67, 469-74.
  7. Chang HY, Yang X (2000). Proteases for cell suicide: functions and regulation of caspases. Microbiol Mol Bio Rev, 64, 821-46. https://doi.org/10.1128/MMBR.64.4.821-846.2000
  8. Chen YZ, Ung CY (2001). Prediction of potential toxicity and side effect protein targets of a small molecule by a ligandprotein inverse docking approach. J Mol Graph Model, 20, 199-18. https://doi.org/10.1016/S1093-3263(01)00109-7
  9. Ciardiello F, Caputo R, Borriello G, et al (2002). ZD1839 (IRESSA), an EGFR-selective tyrosine kinase inhibitor, enhances taxane activity in bcl-2 overexpressing, multidrugresistant MCF-7 ADR human breast cancer cells. Int J Cancer, 98, 463-9.
  10. Delaquis PJ, Stanich K, Girard B, et al (2002). Antimicrobial activity of individual and mixed fractions of dill, cilantro, coriander and eucalyptus essential oils. Int J Food Microbiol, 74, 101-9. https://doi.org/10.1016/S0168-1605(01)00734-6
  11. de Jong JS, van Diest PJ, van der Valk P, et al (2001). Expression of growth factors, growth factor receptors and apoptosis related proteins in invasive breast cancer: relation to apoptotic rate. Breast Cancer Res Treat, 66, 201-8. https://doi.org/10.1023/A:1010650305100
  12. Driscoll JS (1984). The preclinical new drug research program of the National Cancer Institute. Cancer Treat, 68, 63-76.
  13. Djenane D, Yanguela J, Montanes L, et al (2011). Antimicrobial activity of pistacia lentiscus and satureja montana essential oils against listeria monocytogenes CECT 935 using laboratory media: efficacy and synergistic potential in minced beef. Food Control, 22, 1046-53. https://doi.org/10.1016/j.foodcont.2010.12.015
  14. Duchen MR (2004). Mitochondria in health and disease: perspectives on a new mitochondrial biology. Mol Aspects Med, 25, 365-451. https://doi.org/10.1016/j.mam.2004.03.001
  15. Elder JT, Fisher GJ, Lindquist PB, et al (1989). Overexpression of transforming growth factor alpha in psoriatic epidermis. Science, 243, 811-4. https://doi.org/10.1126/science.2916128
  16. Elder LT, Klein SB, Tavakkol A, et al (1990). Growth factor and proto-oncogene expression in psoriasis. J Invest Dermatol, 95, 7-9. https://doi.org/10.1111/1523-1747.ep12505653
  17. Espina L, Somolinos M, Loran S, et al (2011). Chemical composition of commercial citrus fruit essential oils and evaluation of their antimicrobial activity acting alone or in combined processes. Food Control, 22, 896-902. https://doi.org/10.1016/j.foodcont.2010.11.021
  18. Fang-jun L, Song-bai G, Chu-zhong L, et al (2008). Antitumor activity of F90, an epidermal growth factor receptor tyrosine kinase inhibitor, on glioblastoma cell line SHG-44. Chin Med J, 121, 1702-6.
  19. Griffiths DE (2005). Psi-screen, an in vitro toxicity test system: applications in the bioassay of perfumes and fragrance chemicals. Altern Lab Anim, 33, 471-86.
  20. Hajduk PJ, Huth JR, Tse C (2005). Predicting protein druggability. Drug Discov Today, 10, 1675-82. https://doi.org/10.1016/S1359-6446(05)03624-X
  21. Hamzaa R, Osman N (2012). Using of coffee and cardamom mixture to ameliorate oxidative stress induced in $\gamma$-irradiated rats. Biochemistry and Analytical Biochemistry, 1, 113-9.
  22. Hashim S, Aboobaker VS, Madhubala R, Bhattacharya RK, Rao AR (1994). Modulatory effects of essential oils from spices on the formation of DNA adduct by aflatoxin B1 in vitro. Nutr Cancer, 21, 169-75. https://doi.org/10.1080/01635589409514314
  23. Huang CM, Elmets CA, Tang DC, et al (2004). Proteomics reveals that proteins expressed during the early stage of Bacillus anthracis infection are potential targets for the development of vaccines and drugs. Genomics Proteomics Bioinforma, 3, 143-1.
  24. Janne PA, Taffaro ML, Salgia R, et al (2002). Inhibition of epidermal growth factor receptor signaling in malignant pleural mesothelioma. Cancer Res, 62, 5242-7.
  25. Ka H, Park HJ, Jung HJ et al (2003). Cinnamaldehyde induces apoptosis by ROS-mediated mitochondrial permeability transition in human promeolcytic leukaemia HL-60 cell. Cancer Lett, 196, 143-52. https://doi.org/10.1016/S0304-3835(03)00238-6
  26. Kinnings SL, Jackson RM (2011). ReverseScreen3D: a structurebased ligand matching method to identify protein targets. J Chem Inf Model, 51, 624-34. https://doi.org/10.1021/ci1003174
  27. Kinnings SL, Jackson RM (2009). LigMatch: a multiple structure-based ligand matching method for 3D virtual screening. J Chemical Information and Modeling, 49, 2056-66. https://doi.org/10.1021/ci900204y
  28. Kodama R, Noda K, Ide H (1976). Studies on the metabolism of d-limonene (p-mentha-1,8-diene). II: the metabolic fate of d-limonene in rabbits. Xenobiotica, 4, 85-95.
  29. Kodama R, Yano T, Furukawa K, et al (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. https://doi.org/10.3109/00498257609151649
  30. Li H, Gao Z, Kang L, et al (2006). TarFisDock: a web server for identifying drug targets with docking approach. Nucleic Acids Res, 34, 219-24. https://doi.org/10.1093/nar/gkl114
  31. Lin JH, Lu AY (1997). Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev, 49, 403-49.
  32. Misharina T, Terenina M, Krikunova N (2011). Inhibition of 2-hexenal autooxidation by essential oils from clove bud, laurel, cardamom, nutmeg and mace. Chemistry and Chemical Technology, 5, 161-4.
  33. Moteki H, Hibasami H, Yamada Y, et al (2002). Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line. Oncol Rep, 9, 757-60.
  34. Mangal M, Sagar P, Singh H, et al (2013). NPACT: naturally occurring plant-based anti-cancer compound-activity-target database. Nucleic Acids Res, 41, 1124-9. https://doi.org/10.1093/nar/gks1045
  35. Mitsuo Miyazawa, Masaki Shindo ,Tsutomu Shimada (2001). Oxidation of 1,8-Cineole, the monoterpene cyclic ether originated from eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes. Drug Metabolism and Disposition, 29, 200-05.
  36. Nagy M, Lacroute F, Thomas D (1992). Divergent evolution of pyrimidine biosynthesis between anaerobic and aerobic yeasts. Proct Natl Acad Sci, 89, 8966-70. https://doi.org/10.1073/pnas.89.19.8966
  37. Nair S, Nagar R, Gupta R(1998). Antioxidant phenolics and flavonoids in common Indian foods. J Assoc Physicians India, 46, 708-10.
  38. Nicholson D, Thornberry NA(2004). Caspase-3 and caspase-7. In 'Handbook of Proteolytic Enzymes', Eds Barrett AJ, Rawlings ND and Woessner JF, 2nd edn, Elsevier, London. 1298-2.
  39. Padmakumari Amma KP, Rani MP, Sasidharan I, et al (2010). Chemical composition, flavonoid - phenolic contents and radical scavenging activity of four major varieties of cardamom. Int J Biol Med Res, 1, 20-4.
  40. Persidis A (1998). Proteomics: an ambitious drug development platform attempts to link gene sequence to expressed phenotype under various physiological states. Nat Biotechnol, 16, 393-4. https://doi.org/10.1038/nbt0498-393
  41. Pons JL, Labesse G (2009). -TOME-2: a new pipeline for comparative modeling of protein-ligand complexes. Nucl Acids Res, 37, 485-91. https://doi.org/10.1093/nar/gkp368
  42. Rakoff-Nahoum S (2006). Why cancer and inflammation?.Yale J Biol Med Cancer, 79, 123-30.
  43. Rawils J, Knecht W, Diekert K, et al (2000). Requirements for the mitochondrial input and localization of dihydroorotate dehydrogenase. Eur J Biochem, 267, 2079-87. https://doi.org/10.1046/j.1432-1327.2000.01213.x
  44. Raychaudhuri S (2010). How can we kill cancer cells: Insights from the computational models of apoptosis. World J Clin Oncol, 1 24-8. https://doi.org/10.5306/wjco.v1.i1.24
  45. Trott O, Olson AJ (2010). AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem, 31, 455-1.
  46. Vermeulen K, Van Bockstaele DR, Berneman ZN (2003). The cell cycle: a review of regulation, deregulation and therapeutic targets in cancer. Cell Prolif, 36, 131-49. https://doi.org/10.1046/j.1365-2184.2003.00266.x
  47. Watters D and Lavin M, Eds (1999). 'Signaling Pathways in Apoptosis' Hardwood Academic Publishers, Amsterdam, The Netherlands.
  48. Wang JC, Chu PY, Chen CM, et al (2012). idTarget: a webserver for identifying protein targets of small chemical molecules with robust scoring functions and a divide-and-conquer docking approach. Nucleic Acids Research, 40, 393-9. https://doi.org/10.1093/nar/gks496
  49. Wang Y, Xiao J, Suzek TO, et al (2012). PubChem's BioAssay Database. Nucleic Acids Res, 40, 400-12.
  50. Yadav VR, Prasad S, Sung B, et al (2010). Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins (Basel), 2, 2428-66. https://doi.org/10.3390/toxins2102428
  51. Ye H, Ye L, Kang H, et al (2010). HIT: linking herbal active ingredients to targets. Nucleic Acids Res, 39, 1055-9.
  52. Zheng R, Chen TS, Lu T (2011). A Comparative Reverse Docking Strategy to Identify Potential Antineoplastic Targets of Tea Functional Components and Binding Mode. Int J Mol Sci, 12, 5200-12. https://doi.org/10.3390/ijms12085200
  53. Zhou H, Beevers CS, Huang S (2011). Targets of curcumin. Curr Drug Targets, 12, 332-47. https://doi.org/10.2174/138945011794815356

피인용 문헌

  1. Identification of a Potential Anticancer Target of Danshensu by Inverse Docking vol.15, pp.1, 2014, https://doi.org/10.7314/APJCP.2014.15.1.111
  2. A Potential Target of Tanshinone IIA for Acute Promyelocytic Leukemia Revealed by Inverse Docking and Drug Repurposing vol.15, pp.10, 2014, https://doi.org/10.7314/APJCP.2014.15.10.4301
  3. Inhibitory Effects of α-Pinene on Hepatoma Carcinoma Cell Proliferation vol.15, pp.7, 2014, https://doi.org/10.7314/APJCP.2014.15.7.3293
  4. Antitumor Activity of Monoterpenes Found in Essential Oils vol.2014, pp.1537-744X, 2014, https://doi.org/10.1155/2014/953451
  5. Inhibitory Effect of α-Pinene on SGC-7901 Cell Proliferation and the Mechanism of ATM Kinase Signaling Pathway vol.06, pp.01, 2015, https://doi.org/10.4236/cm.2015.61004
  6. Exploring the anti-proliferative activity of Pelargonium sidoides DC with in silico target identification and network pharmacology vol.21, pp.4, 2017, https://doi.org/10.1007/s11030-017-9769-0
  7. Cardamom supplementation improves inflammatory and oxidative stress biomarkers in hyperlipidemic, overweight, and obese pre-diabetic women: a randomized double-blind clinical trial vol.97, pp.15, 2017, https://doi.org/10.1002/jsfa.8414
  8. vol.32, pp.3, 2018, https://doi.org/10.1080/14786419.2017.1346643
  9. Essential oils used in aromatherapy: A systemic review vol.5, pp.8, 2015, https://doi.org/10.1016/j.apjtb.2015.05.007
  10. Reverse pharmacophore mapping and molecular docking studies for discovery of GTPase HRas as promising drug target for bis-pyrimidine derivatives vol.12, pp.1, 2018, https://doi.org/10.1186/s13065-018-0475-5
  11. Green cardamom increases Sirtuin-1 and reduces inflammation in overweight or obese patients with non-alcoholic fatty liver disease: a double-blind randomized placebo-controlled clinical trial vol.15, pp.1, 2018, https://doi.org/10.1186/s12986-018-0297-4
  12. -Limonene Enhances Differentiation and 2-Deoxy-D-Glucose Uptake in 3T3-L1 Preadipocytes by Activating the Akt Signaling Pathway vol.2018, pp.1741-4288, 2018, https://doi.org/10.1155/2018/4573254
  13. Reverse Screening Methods to Search for the Protein Targets of Chemopreventive Compounds vol.6, pp.2296-2646, 2018, https://doi.org/10.3389/fchem.2018.00138
  14. Camphor white oil induces tumor regression through cytotoxic T cell-dependent mechanisms pp.08991987, 2019, https://doi.org/10.1002/mc.22965