7α-hydroxy-β-sitosterol from Chisocheton tomentosus induces apoptosis via dysregulation of cellular Bax/Bcl-2 ratio and cell cycle arrest by downregulating ERK1/2 activation

Evidence-based Complementary and Alternative Medicine

Volumn 2012, Issue , 2012, Pages

  Tasyriq, Mohammad ^a   Najmuldeen, Ibrahim A ^b   In, Lionel L A ^a   Mohamad, Khalit ^a   Awang, Khalijah ^a   Hasima, Noor ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b UNIVERSITY OF ZAKHO   (Iraq)

Author keywords

[No Author keywords available]

Indexed keywords

7 ALPHA HYDROXY BETA SITOSTEROL; ANTINEOPLASTIC AGENT; CYTOCHROME C; HERBACEOUS AGENT; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; PROCASPASE 3; PROCASPASE 9; PROTEIN BAX; PROTEIN BCL 2; SITOSTEROL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL; CELL CYCLE ARREST; CELL VIABILITY; CHISOCHETON TOMENTOSUS; CONTROLLED STUDY; CYTOTOXICITY; DOWN REGULATION; DRUG EFFECT; ENZYME ACTIVATION; HUMAN; HUMAN CELL; MEDICINAL PLANT; MELIACEAE; MITOCHONDRION; PRIORITY JOURNAL;

EID: 84867817828     PISSN: 1741427X     EISSN: 17414288     Source Type: Journal    
DOI: 10.1155/2012/765316     Document Type: Article

References (49)

1. Mabberly D. J., Pannell C. M., Meliaceae in Tree Flora of Malaya 1989 4 Kuala Lumpur, Malaysia Forest Research Institute Malaysia
2. Awang K., Lim C. S., Mohamad K., Morita H., Hirasawa Y., Takeya K., Thoison O., Hadi A. H. A., Erythrocarpines A-E, new cytotoxic limonoids from Chisocheton erythrocarpus. Bioorganic & Medicinal Chemistry 2007 15 17 5997 6002 2-s2.0-34447249291 10.1016/j.bmc.2007.05.049 (Pubitemid 47043463)
3. Najmuldeen I. A., Hadi A. H. A., Awang K., Mohamad K., Ketuly K. A., Mukhtar M. R., Chong S. L., Chan G., Nafiah M. A., Weng N. S., Shirota O., Hosoya T., Nugroho A. E., Morita H., Chisomicines A-C, limonoids from Chisocheton ceramicus. Journal of Natural Products 2011 74 5 1313 1317 2-s2.0-79957825831 10.1021/np200013g
4. Mohamad K., Hirasawa Y., Litaudon M., Awang K., Hadi A. H. A., Takeya K., Ekasari W., Widyawaruyanti A., Zaini N. C., Morita H., Ceramicines B-D, new antiplasmodial limonoids from Chisocheton ceramicus. Bioorganic & Medicinal Chemistry 2009 17 2 727 730 2-s2.0-58749091074 10.1016/j.bmc.2008.11.048
5. 1 Planta Medica 1987 53 254 255 10.1055/s-2006-962695 (Pubitemid 17094895)
6. Agbedahunsi J. M., Fakoya F. A., Adesanya S. A., Studies on the anti-inflammatory and toxic effects of the stem bark of Khaya ivorensis (Meliaceae) on rats. Phytomedicine 2004 11 6 504 508 2-s2.0-4744368589 10.1016/j.phymed.2003.07.009 (Pubitemid 39312626)
7. Oliver-Bever B., Medicinal Plants in Tropical West Africa 1986 Cambridge, UK Cambridge University Press
8. Omar S., Zhang J., MacKinnon S., Leaman D., Durst T., Philogene B. J., Arnason J. T., Sanchez-Vindas P. E., Poveda L., Tamez P. A., Pezzuto J. M., Traditionally-used antimalarials from the Meliaceae. Current Topics in Medicinal Chemistry 2003 3 2 133 139 2-s2.0-0038546591
9. Nagoor N. H., Shah Jehan Muttiah N., Lim C. S., In L. L. A., Mohammad K., Awang K., Regulation of apoptotic effects by erythrocarpine E, a cytotoxic limonoid from Chisocheton erythrocarpus in HSC-4 human oral cancer cells. PLoS One 2011 6 8 e23661 2-s2.0-80051776653 10.1371/journal.pone.0023661
10. Rubis B., Paszel A., Kaczmarek M., Rudzinska M., Jelen H., Rybczynska M., Beneficial or harmful influence of phytosterols on human cells? British Journal of Nutrition 2008 100 6 1183 1191 2-s2.0-56349104802 10.1017/S0007114508981423
11. Paniagua-Pérez R., Madrigal-Bujaidar E., Reyes-Cadena S., Álvarez-González I., Sánchez-Chapul L., Pérez-Gallaga J., Hernández N., Flores-Mondragón G., Velasco O., Cell protection induced by beta-sitosterol: inhibition of genotoxic damage, stimulation of lymphocyte production, and determination of its antioxidant capacity. Archives of Toxicology 2008 82 9 615 622 2-s2.0-50649123243 10.1007/s00204-007-0277-3
12. Ju Y. H., Clausen L. M., Allred K. F., Almada A. L., Helferich W. G., β -sitosterol, β -sitosterol glucoside, and a mixture of β -sitosterol and β -sitosterol glucoside modulate the growth of estrogen-responsive breast cancer cells in vitro and in ovariectomized athymic mice. Journal of Nutrition 2004 134 5 1145 1151 2-s2.0-2442574038 (Pubitemid 38619954)
13. Kurban S., Erko F., Erko S, Quantum chemical treatment of β -sitosterol molecule. Pharmaceutical Biology 2010 48 6 637 642 2-s2.0-77952949784 10.3109/13880200903229106
14. Woyengo T. A., Ramprasath V. R., Jones P. J. H., Anticancer effects of phytosterols. European Journal of Clinical Nutrition 2009 63 7 813 820 2-s2.0-67650245083 10.1038/ejcn.2009.29
15. Sudhamalla B., Gokara M., Ahalawat N., Amooru D. G., Subramanyam R., Molecular dynamics simulation and binding studies of β -sitosterol with human serum albumin and its biological relevance. Journal of Physical Chemistry B 2010 114 27 9054 9062 2-s2.0-77954507346 10.1021/jp102730p
16. Ryan E., Chopra J., McCarthy F., Maguire A. R., O'Brien N. M., Qualitative and quantitative comparison of the cytotoxic and apoptotic potential of phytosterol oxidation products with their corresponding cholesterol oxidation products. British Journal of Nutrition 2005 94 3 443 451 2-s2.0-26044448563 10.1079/BJN20051500 (Pubitemid 41404288)
17. Hovenkamp E., Demonty I., Plat J., Lütjohann D., Mensink R. P., Trautwein E. A., Biological effects of oxidized phytosterols: a review of the current knowledge. Progress in Lipid Research 2008 47 1 37 49 2-s2.0-36749086632 10.1016/j.plipres.2007.10.001 (Pubitemid 350216621)
18. Otaegui-Arrazola A., Menéndez-Carreo M., Ansorena D., Astiasarán I., Oxysterols: a world to explore. Food and Chemical Toxicology 2010 48 12 3289 3303 2-s2.0-78049441228 10.1016/j.fct.2010.09.023
19. Bradford P. G., Awad A. B., Phytosterols as anticancer compounds. Molecular Nutrition & Food Research 2007 51 2 161 170 2-s2.0-34250890634 10.1002/mnfr.200600164 (Pubitemid 47083247)
20. Bradford P. G., Awad A. B., Modulation of signal transduction in cancer cells by phytosterols. BioFactors 2010 36 4 241 247 2-s2.0-78149476478 10.1002/biof.97
21. Rubis B., Polrolniczak A., Knula H., Potapinska O., Kaczmarek M., Rybczynska M., Phytosterols in physiological concentrations target multidrug resistant cancer cells. Medicinal Chemistry 2010 6 4 184 190 2-s2.0-78650205004
22. Awad A. B., Chinnam M., Fink C. S., Bradford P. G., β -Sitosterol activates Fas signaling in human breast cancer cells. Phytomedicine 2007 14 11 747 754 2-s2.0-35148820279 10.1016/j.phymed.2007.01.003 (Pubitemid 47539097)
23. Moon D. O., Lee K. J., Choi Y. H., Kim G. Y., β -Sitosterol-induced- apoptosis is mediated by the activation of ERK and the downregulation of Akt in MCA-102 murine fibrosarcoma cells. International Immunopharmacology 2007 7 8 1044 1053 2-s2.0-34250213261 10.1016/j.intimp.2007.03.010 (Pubitemid 46900910)
24. Moon D. O., Kim M. O., Choi Y. H., Kim G. Y., β -Sitosterol induces G2/M arrest, endoreduplication, and apoptosis through the Bcl-2 and PI3K/Akt signaling pathways. Cancer Letters 2008 264 2 181 191 2-s2.0-42749090904 10.1016/j.canlet.2008.01.032
25. Park C., Moon D. O., Rhu C. H., Choi B. T., Lee W. H., Kim G. Y., Choi Y. H., β -Sitosterol induces anti-proliferation and apoptosis in human leukemic U937 cells through activation of caspase-3 and induction of Bax/Bcl-2 ratio. Biological & Pharmaceutical Bulletin 2007 30 7 1317 1323 2-s2.0-34447115675 10.1248/bpb.30.1317 (Pubitemid 47037662)
26. Park C., Moon D. O., Ryu C. H., Choi B. T., Lee W. H., Kim G. Y., Choi Y. H., β -Sitosterol sensitizes MDA-MB-231 cells to TRAIL-induced apoptosis. Acta Pharmacologica Sinica 2008 29 3 341 348 2-s2.0-39849092986 10.1111/j.1745-7254.2008.00761.x (Pubitemid 351316993)
27. O'Callaghan Y. C., Foley D. A., O'Connell N. M., Mccarthy F. O., Maguire A. R., O'Brien N. M., Cytotoxic and apoptotic effects of the oxidized derivatives of stigmasterol in the u937 human monocytic cell line. Journal of Agricultural and Food Chemistry 2010 58 19 10793 10798 2-s2.0-78049246727 10.1021/jf1023017
28. Roussi S., Winter A., Gosse F., Werner D., Zhang X., Marchioni E., Geoffroy P., Miesch M., Raul F., Different apoptotic mechanisms are involved in the antiproliferative effects of 7 β -hydroxysitosterol and 7 β -hydroxycholesterol in human colon cancer cells. Cell Death and Differentiation 2005 12 2 128 135 2-s2.0-13544257455 10.1038/sj.cdd.4401530 (Pubitemid 40220643)
29. Roussi S., Gossé F., Aoudé-Werner D., Zhang X., Geoffroy P., Miesch M., Marchioni E., Raul F., Perturbation of polyamine metabolism and its relation to cell death in human colon cancer cells treated by 7 β -hydroxycholesterol and 7 β -hydroxysitosterol. International Journal of Oncology 2006 29 6 1549 1554 2-s2.0-39049183720
30. Roussi S., Gossé F., Aoudé-Werner D., Zhang X., Marchioni E., Geoffroy P., Miesch M., Raul F., Mitochondrial perturbation, oxidative stress and lysosomal destabilization are involved in 7 β -hydroxysitosterol and 7 β -hydroxycholesterol triggered apoptosis in human colon cancer cells. Apoptosis 2007 12 1 87 96 2-s2.0-33845733075 10.1007/s10495-006-0485-y (Pubitemid 46009506)
31. Najmuldeen I. A., Hadi A. H. A., Mohamad K., Awang K., Nasab M. F., Ketuly K. A., Mukhtar M. R., Morita H., Steroids from Chisocheton tomentosus. Malaysian Journal of Science 2011 30 2 144 153 2-s2.0-80054093138
32. Gebäck T., Schulz M. M. P., Koumoutsakos P., Detmar M., TScratch: a novel and simple software tool for automated analysis of monolayer wound healing assays. BioTechniques 2009 46 4 265 274 2-s2.0-67650504966 10.2144/000113083
33. Najmuldeen I. A., Hadi A. H. A., Awang K., Mohamad K., Ng S. W., 17-(5-Ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13, 14,15,16,17-tetra-deca-hydro-1H-cyclo-penta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae). Acta Crystallographica Section E 2008 64 11 o2163 2-s2.0-55749091629 10.1107/S1600536808033163
34. Guerriero A., D'Ambrosio M., Pietra F., Debitus C., Ribes O., Pteridines, sterols, and indole derivatives from the lithistid sponge Corallistes undulatus of the coral sea. Journal of Natural Products 1993 56 11 1962 1970 2-s2.0-0027421681 (Pubitemid 23348571)
35. Cui E. J., Park J. H., Park H. J., Chung I. S., Kim J. Y., Yeon S. W., Baek N. I., Isolation of sterols from cowpea (Vigna sinensis) seeds and their promotion activity on HO-1. Journal of Applied Biological Chemistry 2011 54 3 362 366 2-s2.0-79960544976 10.3839/jksabc.2011.057
36. Schroeder G., Rohmer M., Beck J. P., Anton R., 7-Oxo-, 7 α -hydroxy- and 7 β -hydroxysterols from Euphorbia fischeriana. Phytochemistry 1980 19 10 2213 2215 2-s2.0-0000960653
37. Chaurasia N., Wichtl M., Sterols and steryl glycosides from Urtica dioica. Journal of Natural Products 1987 50 5 881 885 2-s2.0-0000635135
38. Newman D. J., Cragg G. M., Natural products as sources of new drugs over the 30 years from 1981 to 2010. Journal of Natural Products 2012 75 3 311 335 10.1021/np200906s
39. O'Shea S. H., Schwarz J., Kosyk O., Ross P. K., Ha M. J., Wright F. A., Rusyn I., In vitro screening for population variability in chemical toxicity. Toxicological Sciences 2011 119 2 398 407 2-s2.0-78751684725 10.1093/toxsci/kfq322
40. Koschutnig K., Heikkinen S., Kemmo S., Lampi A. M., Piironen V., Wagner K. H., Cytotoxic and apoptotic effects of single and mixed oxides of β -sitosterol on HepG2-cells. Toxicology in Vitro 2009 23 5 755 762 2-s2.0-67649344133 10.1016/j.tiv.2009.03.007
41. Misharin A. Y., Mehtiev A. R., Morozevich G. E., Tkachev Y. V., Timofeev V. P., Synthesis and cytotoxicity evaluation of 22,23-oxygenated stigmastane derivatives. Bioorganic & Medicinal Chemistry 2008 16 3 1460 1473 2-s2.0-38849085288 10.1016/j.bmc.2007.10.056 (Pubitemid 351191765)
42. Yuste L., Esparís-Ogando A., Santos E., Pandiella A., Overexpression of RasN17 fails to neutralize endogenous ras in MCF7 breast cancer cells. Journal of Biochemistry 2005 137 6 731 739 2-s2.0-22344443619 10.1093/jb/mvi092 (Pubitemid 41003557)
43. Ley R., Balmanno K., Hadfield K., Weston C., Cook S. J., Activation of the ERK1/2 signaling pathway promotes phosphorylation and proteasome-dependent degradation of the BH3-only protein, Bim. Journal of Biological Chemistry 2003 278 21 18811 18816 2-s2.0-0038482050 10.1074/jbc.M301010200 (Pubitemid 36799262)
44. Fiddes R. J., Janes P. W., Sivertsen S. P., Sutherland R. L., Musgrove E. A., Daly R. J., Inhibition of the MAP kinase cascade blocks heregulin-induced cell cycle progression in T-47D human breast cancer cells. Oncogene 1998 16 21 2803 2813 2-s2.0-0032575091 (Pubitemid 28279347)
45. Petros A. M., Olejniczak E. T., Fesik S. W., Structural biology of the Bcl-2 family of proteins. Biochimica et Biophysica Acta 2004 1644 2-3 83 94 2-s2.0-1442310957 10.1016/j.bbamcr.2003.08.012 (Pubitemid 38281265)
46. Hoetelmans R. W. M., van Slooten H. J., Keijzer R., Erkeland S., van de Velde C. J. H., van Dierendonck J. H., Bcl-2 and Bax proteins are present in interphase nuclei of mammalian cells. Cell Death and Differentiation 2000 7 4 384 392 2-s2.0-0034119019 (Pubitemid 30209666)
47. Androutsopoulos V. P., Ruparelia K. C., Papakyriakou A., Filippakis H., Tsatsakis A. M., Spandidos D. A., Anticancer effects of the metabolic products of the resveratrol analogue, DMU-212: structural requirements for potency. European Journal of Medicinal Chemistry 2011 46 6 2586 2595 2-s2.0-79955589531 10.1016/j.ejmech.2011.03.049
48. Hsuuw Y. D., Chan W. H., Epigallocatechin gallate dose-dependently induces apoptosis or necrosis in human MCF-7 cells. Annals of the New York Academy of Sciences 2007 1095 428 440 2-s2.0-34247892269 10.1196/annals.1397.046 (Pubitemid 47092473)
49. Inoue S., Browne G., Melino G., Cohen G. M., Ordering of caspases in cells undergoing apoptosis by the intrinsic pathway. Cell Death and Differentiation 2009 16 7 1053 1061 2-s2.0-67549118622 10.1038/cdd.2009.29