Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves

Fitoterapia

Volumn 83, Issue 6, 2012, Pages 1000-1007

  Dolečková, Iva ^a   Rárová, Lucie ^b   Grúz, Jiří ^a,b   Vondrusová, Magdaléna ^a   Strnad, Miroslav ^a,b   Kryštof, Vladimír ^a  

^a INSTITUTE OF EXPERIMENTAL BOTANY   (Czech Republic)

^b PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Antiangiogenic; Antiproliferative; Eupatorin; Flavonoids; Kinase inhibitor; Orthosiphon stamineus

Indexed keywords

CHLOROFORM; EUPATORIN; ORTHOSIPHON STAMINEUS EXTRACT; PLANT EXTRACT; PROTEIN KINASE; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL MIGRATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG MECHANISM; ENDOTHELIUM CELL; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; NONHUMAN; ORTHOSIPHON STAMINEUS; PLANT LEAF; PRIORITY JOURNAL;

ANGIOGENESIS INHIBITORS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL MOVEMENT; CELL PROLIFERATION; FLAVONES; FLAVONOIDS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; INHIBITORY CONCENTRATION 50; ORTHOSIPHON; PHYTOTHERAPY; PLANT EXTRACTS; PLANT LEAVES; PROTEIN KINASES;

ORTHOSIPHON STAMINEUS;

EID: 84863988727     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2012.06.002     Document Type: Article

References (37)

1. K. Tran Medicinal plants in Viet Nam 1990 Science and Technology Publishing House Hanoi
2. J.H. Chin, H.H. Abas, and I. Sabariah Toxicity study of Orthosiphon stamineus Benth (Misai Kucing) on Sprague Dawley rats Trop Biomed 25 2008 9 16
3. N.K. Olah, L. Radu, C. Mogosan, D. Hanganu, and S. Gocan Phytochemical and pharmacological studies on Orthosiphon stamineus Benth. (Lamiaceae) hydroalcoholic extracts J Pharm Biomed Anal 33 2003 117 123 (Pubitemid 37297524)
4. M.F. Yam, R. Basir, M.Z. Asmawi, and Z. Ismail Antioxidant and hepatoprotective effects of Orthosiphon stamineus Benth. standardized extract Am J Chin Med 35 2007 115 126 (Pubitemid 46206527)
5. M.F. Yam, V. Lim, I.M. Salman, O.Z. Ameer, L.F. Ang, and N. Rosidah HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves Molecules 15 2010 4452 4466
6. Y. Tezuka, P. Stampoulis, A.H. Banskota, S. Awale, K.Q. Tran, and I. Saiki Constituents of the Vietnamese medicinal plant Orthosiphon stamineus Chem Pharm Bull (Tokyo) 48 2000 1711 1719
7. R.J. Nijveldt, N.E. van, D.E. van Hoorn, P.G. Boelens, N.K. van, and P.A. van Leeuwen Flavonoids: a review of probable mechanisms of action and potential applications Am J Clin Nutr 74 2001 418 425 (Pubitemid 32880250)
8. S. Kuntz, U. Wenzel, and H. Daniel Comparative analysis of the effects of flavonoids on proliferation, cytotoxicity, and apoptosis in human colon cancer cell lines Eur J Nutr 38 1999 133 142 (Pubitemid 29352529)
9. J.A. Beutler, E. Hamel, A.J. Vlietinck, A. Haemers, P. Rajan, and J.N. Roitman Structure-activity requirements for flavone cytotoxicity and binding to tubulin J Med Chem 41 1998 2333 2338 (Pubitemid 28285735)
10. J. Mojzis, L. Varinska, G. Mojzisova, I. Kostova, and L. Mirossay Antiangiogenic effects of flavonoids and chalcones Pharmacol Res 57 2008 259 265
11. D.R. Ferry, A. Smith, J. Malkhandi, D.W. Fyfe, P.G. deTakats, and D. Anderson Phase I clinical trial of the flavonoid quercetin: pharmacokinetics and evidence for in vivo tyrosine kinase inhibition Clin Cancer Res 2 1996 659 668 (Pubitemid 26133468)
12. T.S. Lin, A.S. Ruppert, A.J. Johnson, B. Fischer, N.A. Heerema, and L.A. Andritsos Phase II study of flavopiridol in relapsed chronic lymphocytic leukemia demonstrating high response rates in genetically high-risk disease J Clin Oncol 27 2009 6012 6018
13. B. Lazarevic, G. Boezelijn, L.M. Diep, K. Kvernrod, O. Ogren, and H. Ramberg Efficacy and safety of short-term genistein intervention in patients with localized prostate cancer prior to radical prostatectomy: a randomized, placebo-controlled, double-blind phase 2 clinical trial Nutr Cancer 63 2011 889 898
14. F. Teillet, A. Boumendjel, J. Boutonnat, and X. Ronot Flavonoids as RTK inhibitors and potential anticancer agents Med Res Rev 28 2008 715 745
15. R.P. Singh, and R. Agarwal Natural flavonoids targeting deregulated cell cycle progression in cancer cells Curr Drug Targets 7 2006 345 354 (Pubitemid 43744850)
16. T. Nagao, F. Abe, J. Kinjo, and H. Okabe Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship Biol Pharm Bull 25 2002 875 879 (Pubitemid 40022116)
17. V. Androutsopoulos, R.R. Arroo, J.F. Hall, S. Surichan, and G.A. Potter Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism Breast Cancer Res 10 2008 R39
18. A.L. Salmela, J. Pouwels, A. Kukkonen-Macchi, S. Waris, P. Toivonen, and K. Jaakkola The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis Exp Cell Res 318 2012 578 592
19. R. Jorda, L. Havlicek, I.W. Mcnae, M.D. Walkinshaw, J. Voller, and A. Sturc Pyrazolo[4,3-d]pyrimidine bioisostere of roscovitine: evaluation of a novel selective inhibitor of cyclin-dependent kinases with antiproliferative activity J Med Chem 54 2011 2980 2993
20. J. Bain, L. Plater, M. Elliott, N. Shpiro, C.J. Hastie, and H. McLauchlan The selectivity of protein kinase inhibitors: a further update Biochem J 408 2007 297 315
21. S. Zahler, J. Liebl, R. Furst, and A.M. Vollmar Anti-angiogenic potential of small molecular inhibitors of cyclin dependent kinases in vitro Angiogenesis 13 2010 239 249
22. C. Crosio, G.M. Fimia, R. Loury, M. Kimura, Y. Okano, and H. Zhou Mitotic phosphorylation of histone H3: spatio-temporal regulation by mammalian Aurora kinases Mol Cell Biol 22 2002 874 885 (Pubitemid 34053065)
23. B. Perez-Cadahia, B. Drobic, and J.R. Davie H3 phosphorylation: dual role in mitosis and interphase Biochem Cell Biol 87 2009 695 709
24. C. Prigent, and S. Dimitrov Phosphorylation of serine 10 in histone H3, what for? J Cell Sci 116 2003 3677 3685 (Pubitemid 37185297)
25. S. Hauf, R.W. Cole, S. LaTerra, C. Zimmer, G. Schnapp, and R. Walter The small molecule Hesperadin reveals a role for Aurora B in correcting kinetochore-microtubule attachment and in maintaining the spindle assembly checkpoint J Cell Biol 161 2003 281 294 (Pubitemid 36529847)
26. C. Ditchfield, V.L. Johnson, A. Tighe, R. Ellston, C. Haworth, and T. Johnson Aurora B couples chromosome alignment with anaphase by targeting BubR1, Mad2, and Cenp-E to kinetochores J Cell Biol 161 2003 267 280 (Pubitemid 36529846)
27. M. Scheffner, J.M. Huibregtse, R.D. Vierstra, and P.M. Howley The Hpv-16 E6 and E6-Ap complex functions as a ubiquitin-protein ligase in the ubiquitination of P53 Cell 75 1993 495 505 (Pubitemid 23335075)
28. D.T. Terrano, M. Upreti, and T.C. Chambers Cyclin-dependent kinase 1-mediated Bcl-xL/Bcl-2 phosphorylation acts as a functional link coupling mitotic arrest and apoptosis Mol Cell Biol 30 2010 640 656
29. I.B. Roninson, E.V. Broude, and B.D. Chang If not apoptosis, then what? Treatment-induced senescence and mitotic catastrophe in tumor cells Drug Resist Updat 4 2001 303 313 (Pubitemid 34456384)
30. O. Tounekti, G. Pron, J. Belehradek Jr., and L.M. Mir Bleomycin, an apoptosis-mimetic drug that induces two types of cell death depending on the number of molecules internalized Cancer Res 53 1993 5462 5469 (Pubitemid 23342168)
31. R.B. Lock, and L. Stribinskiene Dual modes of death induced by etoposide in human epithelial tumor cells allow Bcl-2 to inhibit apoptosis without affecting clonogenic survival Cancer Res 56 1996 4006 4012 (Pubitemid 26284752)
32. K. Torres, and S.B. Horwitz Mechanisms of Taxol-induced cell death are concentration dependent Cancer Res 58 1998 3620 3626 (Pubitemid 28376560)
33. M. Castedo, J.L. Perfettini, T. Roumier, A. Valent, H. Raslova, and K. Yakushijin Mitotic catastrophe constitutes a special case of apoptosis whose suppression entails aneuploidy Oncogene 23 2004 4362 4370 (Pubitemid 38850415)
34. H.B. Sahib, A.F. Aisha, M.F. Yam, M.Z. Asmawi, Z. Ismail, and S.M. Salhimi Anti-angiogenic and anti oxidant properties of Orthosiphon stamineus Benth. methanolic leaves extract Int J Pharmacol 5 2009 162 167
35. M.B.K. Ahamed, A.F.A. Aisha, Z.D. Nassar, J.M. Siddiqui, Z. Ismail, and S.M.S. Omani Cat's whiskers tea (Orthosiphon stamineus) extract inhibits growth of colon tumor in nude mice and angiogenesis in endothelial cells via suppressing VEGFR phosphorylation Nutr Cancer 64 2012 89 99
36. A.K. Olsson, A. Dimberg, J. Kreuger, and L. Claesson-Welsh VEGF receptor signalling - in control of vascular function Nat Rev Mol Cell Biol 7 2006 359 371
37. G. Neufeld, T. Cohen, S. Gengrinovitch, and Z. Poltorak Vascular endothelial growth factor (VEGF) and its receptors FASEB J 13 1999 9 22 (Pubitemid 29038270)