Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene

PLoS ONE

Volumn 6, Issue 8, 2011, Pages

  Cárdenas, Casimiro ^a   Quesada, Ana R ^a,b   Medina, Miguel A ^a,b  

^a UNIVERSITY OF MÁLAGA   (Spain)

^b CENTRO DE INVESTIGACIÓN BIOMÉDICA EN RED DE ENFERMEDADES RARAS CIBERER   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOXYGENASE 2; GELATINASE A; KAHWEOL; MATRIGEL; MONOCYTE CHEMOTACTIC PROTEIN 1; UROKINASE; ANGIOGENESIS INHIBITOR; ANTIINFLAMMATORY AGENT; DITERPENE;

ANIMAL CELL; ANTIANGIOGENIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL GROWTH; CELL INVASION; CELL MEMBRANE POTENTIAL; CELL MIGRATION; CELL PROLIFERATION; CELL VIABILITY; CELLULAR DISTRIBUTION; CHEMICAL STRUCTURE; CHICKEN; CHORIOALLANTOIS; COFFEE; CONTROLLED STUDY; ENDOTHELIUM CELL; EX VIVO STUDY; EXTRACELLULAR MATRIX; HUMAN; HUMAN CELL; IN VITRO STUDY; MICROTUBULE; MOUSE; NONHUMAN; PROTEIN EXPRESSION; PROTEIN TARGETING; QUAIL; VASCULAR RING; ZEBRA FISH; ZYMOGRAPHY; ANGIOGENESIS; ANIMAL; AORTA; APOPTOSIS; C57BL MOUSE; CELL CULTURE; CELL MOTION; CHEMISTRY; CHICK EMBRYO; CYTOLOGY; DOSE RESPONSE; DRUG EFFECT; METABOLISM; PHYSIOLOGY; VASCULARIZATION;

DANIO RERIO; PHASIANIDAE;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTI-INFLAMMATORY AGENTS; AORTA; APOPTOSIS; CELL MOVEMENT; CELL PROLIFERATION; CELLS, CULTURED; CHEMOKINE CCL2; CHICK EMBRYO; CHORIOALLANTOIC MEMBRANE; COFFEE; CYCLOOXYGENASE 2; DITERPENES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOTHELIAL CELLS; HUMANS; MATRIX METALLOPROTEINASE 2; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; NEOVASCULARIZATION, PHYSIOLOGIC; QUAIL; UROKINASE-TYPE PLASMINOGEN ACTIVATOR; ZEBRAFISH;

EID: 79961227890     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0023407     Document Type: Article

References (47)

1. Bellisle F, Diplock AR, Hornstra G, Koletzko B, Roberfroid M, et al. (1998) Functional food in Europe. British Journal of Nutrition 80: S1-S93.
2. Spiller MA, (1984) The chemical components of coffee. Prog Clin Biol Res 158: 91-147.
3. Bengis RO, Anderson RJ, (1932) The chemistry of coffee bean. I. Concerning the unsapnifiable matter of the coffee bean oil. Extraction and properties of kahweol. J Biol Chem 97: 99-113.
4. Giovannucci E, (1998) Meta-analysis of coffee consumption and risk of colorectal cancer. Am J Epidemiol 147: 1043-1052.
5. Larsson SC, Wolk A, (2007) Coffee consumption and risk of liver cancer: a meta-analysis. Gastroenterology 132: 1740-1745.
6. Lee KJ, Jeong HG, (2007) Protective effects of kahweol and cafestol against hydrogen peroxide-induced oxidative stress and DNA damage. Toxicol Lett 173: 80-87.
7. Hanahan D, Weinberg RA, (2000) The hallmarks of cancer. Cell 100: 57-70.
8. Muñoz-Chápuli R, Quesada AR, Medina MA, (2004) Angiogenesis and signal transduction in endothelial cells. Cell Mol Life Sci 61: 2224-2243.
9. Quesada AR, Muñoz-Chápuli R, Medina MA, (2006) Anti-angiogenic drugs: from bench to clinical trials. Med Res Rev 26: 483-530.
10. Rodríguez-Nieto S, González-Iriarte M, Carmona R, Muñoz-Chápuli R, Medina MA, et al. (2002) Antiangiogenic activity of aeroplysinin-1, a brominated compound isolated from a marine sponge. Faseb J 16: 261-263.
11. Castro ME, González-Iriarte M, Barrero AF, Salvador-Tormo N, Muñoz-Chápuli R, et al. (2004) Study of puupehenone and related compounds as inhibitors of angiogenesis. Int J Cancer 110: 31-38.
12. Martínez-Poveda B, Quesada AR, Medina MA, (2005) Hyperforin, a bio-active compound of St. John's Wort, is a new inhibitor of angiogenesis targeting several key steps of the process. Int J Cancer 117: 775-780.
13. Cárdenas C, Quesada AR, Medina MA, (2006) Evaluation of the anti-angiogenic effect of aloe-emodin. Cell Mol Life Sci 63: 3083-3089.
14. Martínez-Poveda B, Muñoz-Chápuli R, Rodríguez-Nieto S, Quintela JM, Fernández A, et al. (2007) IB05204, a dichloropyridodithienotriazine, inhibits angiogenesis in vitro and in vivo. Mol Cancer Ther 6: 2675-2685.
15. González-Iriarte M, Carmona R, Pérez-Pomares JM, Macías D, Medina MA, et al. (2003) A modified chorioallantoic membrane assay allows for specific detection of endothelial apoptosis induced by antiangiogenic substances. Angiogenesis 6: 251-254.
16. Medina MA, Muñoz-Chápuli R, Quesada AR, (2007) Challenges of antiangiogenic cancer therapy: trials and errors, and renewed hope. J Cell Mol Med 11: 374-382.
17. Quesada AR, Medina MA, Muñoz-Chápuli R, Ponce AL, (2010) Do not say ever never more: the ins and outs of antiangiogenic therapies. Curr Pharm Des 16: 3932-3957.
18. Quesada AR, Medina MA, Alba E, (2007) Playing only one instrument may be not enough: limitations and future of the antiangiogenic treatment of cancer. Bioessays 29: 1159-1168.
19. Martínez-Poveda B, Quesada AR, Medina MA, (2005) Hypericin in the dark inhibits key steps of angiogenesis in vitro. Eur J Pharmacol 516: 97-103.
20. Rodríguez-Nieto S, Chavarría T, Martínez-Poveda B, Sánchez-Jiménez F, Quesada AR, et al. (2002) Anti-angiogenic effects of homocysteine on cultured endothelial cells. Biochem Biophys Res Commun 293: 497-500.
21. Cárdenas C, Quesada AR, Medina MA, (2004) Effects of ursolic acid on different steps of the angiogenic process. Biochem Biophys Res Commun 320: 402-408.
22. Ingber D, Fujita T, Kishimoto S, Sudo K, Kanamaru T, et al. (1990) Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth. Nature 348: 555-557.
23. Rodríguez-Nieto S, Medina MA, Quesada AR, (2001) A re-evaluation of fumagillin selectivity towards endothelial cells. Anticancer Res 21: 3457-3460.
24. Igura K, Ohta T, Kuroda Y, Kaji K, (2001) Resveratrol and quercetin inhibit angiogenesis in vitro. Cancer Lett 171: 11-16.
25. Shimamura M, Hazato T, Ashino H, Yamamoto Y, Iwasaki E, et al. (2001) Inhibition of angiogenesis by humulone, a bitter acid from beer hop. Biochem Biophys Res Commun 289: 220-224.
26. Kim HG, Hwang YP, Jeong HG, (2009) Kahweol blocks STAT3 phosphorylation and induces apoptosis in human lung adenocarcinoma A549 cells. Toxicol Lett 187: 28-34.
27. Kim MS, Lee YM, Moon EJ, Kim SE, Lee JJ, et al. (2000) Anti-angiogenic activity of torilin, a sesquiterpene compound isolated from Torilis japonica. Int J Cancer 87: 269-275.
28. Liotta LA, Steeg PS, Stetler-Stevenson WG, (1991) Cancer metastasis and angiogenesis: an imbalance of positive and negative regulation. Cell 64: 327-336.
29. Binder BR, Mihaly J, Prager GW, (2007) uPAR-uPA-PAI-1 interactions and signaling: a vascular biologist's view. Thromb Haemost 97: 336-342.
30. Kessenbrock K, Plaks V, Werb Z, (2010) Matrix metalloproteinases: regulators of the tumor microenvironment. Cell 141: 52-67.
31. Bourboulia D, Stetler-Stevenson WG, (2010) Matrix metalloproteinases (MMPs) and tissue inhibitors of metalloproteinases (TIMPs): Positive and negative regulators in tumor cell adhesion. Semin Cancer Biol 20: 161-168.
32. Pepper MS, Belin D, Montesano R, Orci L, Vassalli JD, (1990) Transforming growth factor-beta 1 modulates basic fibroblast growth factor-induced proteolytic and angiogenic properties of endothelial cells in vitro. J Cell Biol 111: 743-755.
33. Stetler-Stevenson WG, (1999) Matrix metalloproteinases in angiogenesis: a moving target for therapeutic intervention. J Clin Invest 103: 1237-1241.
34. Egeblad M, Werb Z, (2002) New functions for the matrix metalloproteinases in cancer progression. Nat Rev Cancer 2: 161-174.
35. Rabbani SA, (1998) Metalloproteases and urokinase in angiogenesis and tumor progression. In Vivo 12: 135-142.
36. Mazar AP, Henkin J, Goldfarb RH, (1999) The urokinase plasminogen activator system in cancer: implications for tumor angiogenesis and metastasis. Angiogenesis 3: 15-32.
37. Rakic JM, Maillard C, Jost M, Bajou K, Masson V, et al. (2003) Role of plasminogen activator-plasmin system in tumor angiogenesis. Cell Mol Life Sci 60: 463-473.
38. Kim JY, Jung KS, Jeong HG, (2004) Suppressive effects of the kahweol and cafestol on cyclooxygenase-2 expression in macrophages. FEBS Lett 569: 321-326.
39. Futagami S, Hiratsuka T, Shindo T, Hamamoto T, Tatsuguchi A, et al. (2008) COX-2 and CCR2 induced by CD40 ligand and MCP-1 are linked to VEGF production in endothelial cells. Prostaglandins Leukot Essent Fatty Acids 78: 137-146.
40. Totzke G, Schulze-Osthoff K, Janicke RU, (2003) Cyclooxygenase-2 (COX-2) inhibitors sensitize tumor cells specifically to death receptor-induced apoptosis independently of COX-2 inhibition. Oncogene 22: 8021-8030.
41. Friberg E, Orsini N, Mantzoros CS, Wolk A, (2009) Coffee drinking and risk of endometrial cancer--a population-based cohort study. Int J Cancer 125: 2413-2417.
42. Nkondjock A, (2009) Coffee consumption and the risk of cancer: an overview. Cancer Lett 277: 121-125.
43. Kubota Y, Kleinman HK, Martin GR, Lawley TJ, (1988) Role of laminin and basement membrane in the morphological differentiation of human endothelial cells into capillary-like structures. J Cell Biol 107: 1589-1598.
44. Serbedzija GN, Flynn E, Willett CE, (1999) Zebrafish angiogenesis: a new model for drug screening. Angiogenesis 3: 353-359.
45. Cross LM, Cook MA, Lin S, Chen JN, Rubinstein AL, (2003) Rapid analysis of angiogenesis drugs in a live fluorescent zebrafish assay. Arterioscler Thromb Vasc Biol 23: 911-912.
46. Masson VV, Devy L, Grignet-Debrus C, Bernt S, Bajou K, et al. (2002) Mouse Aortic Ring Assay: A New Approach of the Molecular Genetics of Angiogenesis. Biol Proced Online 4: 24-31.
47. Nicosia RF, Ottinetti A, (1990) Growth of microvessels in serum-free matrix culture of rat aorta. A quantitative assay of angiogenesis in vitro. Lab Invest 63: 115-122.