Chebulagic acid, a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula Retz., induces apoptosis in COLO-205 cell line

Journal of Ethnopharmacology

Volumn 124, Issue 3, 2009, Pages 506-512

  Reddy, D Bharat ^a   Reddy, T C M ^a   Jyotsna, G ^a   Sharan, Satish ^a   Priya, Nalini ^a   Lakshmipathi, V ^a   Reddanna, Pallu ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Anti oxidant; Apoptosis; Chebulagic acid; COX LOX dual inhibitor; Terminalia chebula Retz.

Indexed keywords

ALCOHOL; CHEBULAGIC ACID; CYCLOOXYGENASE 2; LIPOXYGENASE; TERMINALIA CHEBULA EXTRACT; WATER;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; ENZYME INHIBITION; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INFRARED SPECTROMETRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; RADIATION PROTECTION;

ANTIOXIDANTS; APOPTOSIS; ARACHIDONATE 5-LIPOXYGENASE; BENZOPYRANS; BIPHENYL COMPOUNDS; BLOTTING, WESTERN; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DNA FRAGMENTATION; FLOW CYTOMETRY; FREE RADICAL SCAVENGERS; FREE RADICALS; FRUIT; GLUCOSIDES; HUMANS; INDICATORS AND REAGENTS; LIPOXYGENASE INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PICRATES; SPECTROPHOTOMETRY, INFRARED; TERMINALIA;

TERMINALIA CHEBULA;

EID: 67650664952     PISSN: 03788741     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jep.2009.05.022     Document Type: Article

References (37)

1. Barthakur N.N., and Arnold N.P. Nutritive value of the chebulic myrobalan (Terminalia chebula Retz.) and its potential as a food source. Food Chemistry 40 (1991) 213-219
2. Bradford M.M. A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of protein-dye-binding. Analytical Biochemistry 72 (1976) 248-254
3. Caroline C., and Catherine M. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. European Journal of Medicinal Chemistry 38 (2003) 645-659
4. Chattopadhyay R.R., and Bhattacharyya S.K. Terminalia chebula: an update. Pharmacognosy Reviews 1 (2007) 151-156
5. Cianchi F., Cortesini C., Magnelli L., Fanti E., Papucci L., Schiavone N., Messerini L., Vannacc A., Capaccioli S., Perna F., Lulli M., Fabbroni V., Perigli G., Bechi P., and Masini E. Inhibition of 5-lipoxygenase by MK886 augments the antitumor activity of celecoxib in human colon cancer cells. Molecular Cancer Therapeutics 5 (2006) 2716-2726
6. Copeland R.A., Williams J.M., Giannaras J., Nurnberg S., Covington M., Pinto D., Pick S., and Trzaskos J.M. Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase. Proceedings of National Academy of Sciences of United States of America 91 (1994) 11202-11206
7. Egan R.W., Paxton J., and Kuehl Jr. F.A. Mechanism for irreversible self-deactivation of prostaglandin synthetase. Journal of Biological Chemistry 251 (1976) 7329-7335
8. Elder D.J., Halton D.E., Hague A., and Paraskeva C. Induction of apoptotic cell death in human colorectal carcinoma cell lines by a cyclooxygenase-2 (COX-2)-selective nonsteroidal anti-inflammatory drug: independence from COX-2 protein expression. Clinical Cancer Research 3 (1997) 1679-1683
9. Ford-Hutchinson A.W., Bray M.A., Doig M.V., Shipley M.E., and Smith M.J.H. Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes. Nature 286 (1980) 264-265
10. Gandhi N.M., and Nair C.K.K. Radiation protection by Terminalia chebula: some mechanistic aspects. Molecular and Cellular Biochemistry 277 (2005) 43-48
11. Gao H., Huang Y.N., Xu P.Y., and Kawabata J. Inhibitory effect on a-glucosidase by the fruits of Terminalia chebula Retz. Food Chemistry 105 (2007) 628-634
12. Ghosh J., and Myers C.E. Inhibition of arachidonate 5-lipoxygenase triggers massive apoptosis in human prostate cancer cells. Proceedings of National Academy of Sciences United States of America 95 (1998) 13182-13187
13. Goossens L., Pommery N., and Hénichart J.P. COX-2/5-LOX dual acting anti-inflammatory drugs in cancer chemotherapy. Current Topics in Medicinal Chemistry 7 (2007) 283-296
14. Han Q., Song J., Qiao C., Wong L., and Xu H. Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography. Journal of Separation Science 29 (2006) 1653-1657
15. Hemler M., and Lands W.E. Purification of the cyclooxygenase that forms prostaglandins. Demonstration of two forms of iron in the holoenzyme. Journal of Biological Chemistry 251 (1976) 5575-5579
16. Herrmann M., Lorenz H.M., Voll R., Grünke M., Woith W., and Kalden J.R. A rapid and simple method for the isolation of apoptotic DNA fragments. Nucleic Acid Research 22 (1994) 5506-5507
17. Kirby A.J., and Schmidt R.J. The antioxidant activity of Chinese herbs for eczema and of placebo herbs-I. Journal of Ethnopharmacology 56 (1997) 103-108
18. Lee S.H., Ryu S.Y., Choi S.U., Lee C.O., No Z.S., Kim S.K., and Ahn J.W. Hydrolysable tannins and related compound having cytotoxic activity from the fruits of Terminalia chebula. Archives of Pharmacological Research 18 (1995) 118-120
19. Martel-Pelletier J., Lajeunesse D., Reboul P., and Pelletier J.-P. Therapeutic role of dual inhibitors of 5-LOX and COX, selective and non-selective non-steroidal anti-inflammatory drugs. Annals of the Rheumatic Diseases 62 (2003) 501-509
20. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods 65 (1983) 55-63
21. Naik G.H., Priyadarsini K.I., Naik D.B., Gangabhagirathi R., and Mohan H. Studies on the aqueous extract of Terminalia chebula as a potent antioxidant and a probable radioprotector. Phytomedicine 11 (2004) 530-538
22. Pagels W.R., Sachs R.J., Marnett L.J., Dewitt D.L., Day J.S., and Smith W.L. Immunochemical evidence for the involvement of prostaglandin H synthase in hydroperoxide-dependent oxidations by ram seminal vesicle microsomes. Journal of Biological Chemistry 258 (1983) 6517-6523
23. Pommery J., Pommery N., and Hénichart J.P. Modification of eicosanoid profile in human blood treated by dual COX/LOX inhibitors. Prostaglandins, Leukotrienes and Essential Fatty Acids 73 (2005) 411-417
24. Re R., Pellegrini N., Anna P., Ananth P., Yang M., and Catherine R.E. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine 26 (1999) 1231-1237
25. Reddanna P., Whelan J., Maddipati K.R., and Reddy C.C. Purification of arachidonate 5-lipoxygenase from potato tubers. Methods in Enzymology 187 (1990) 268-277
26. Reddy B.M., Rao N.K., Ramesh M., Appa Rao A.V.N., Lin L.J., Lin L.Z., and Cordell G.A. Chemical investigation of the fruits of Terminalia chebula. Pharmaceutical Biology 32 (1994) 352-356
27. Reddy C.M., Bhat V.B., Kiranmai G., Reddy M.N., Reddanna P., and Madyastha K.M. Selective inhibition of cyclooxygenase-2 by C-Phycocyanin, a biliprotein from Spirulina platensis. Biochemical and Biophysical Research Communications 277 (2000) 599-603
28. Reddy M.C., Subhashini J., Mahipal S.V., Bhat V.B., Srinivas Reddy P., Kiranmai G., Madyastha K.M., and Reddanna P. C-Phycocyanin, a selective cyclooxygenase-2 inhibitor, induces apoptosis in lipopolysaccharide-stimulated RAW 264.7 macrophages. Biochemical and Biophysical Research Communications 304 (2003) 385-392
29. Saleem A., Husheem M., Harkonen P., and Pihlaja K. Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit. Journal of Ethnopharmacology 81 (2002) 327-336
30. Shin T.Y., Jeong H.G., Kim D.K., Kim S.H., Lee J.K., Chae B.S., Kim J.H., Kong H.W., Lee C.M., Lee C., Park S.T., Lee E.J., Lin J.P., Kim H.M., and Lee Y.M. Inhibitory action of water soluble fraction of Terminalia chebula on systematic and local anaphylaxis. Journal of Ethnopharmacology 74 (2001) 133-140
31. Shishodia S., and Aggarwal B.B. Cyclooxygenase (COX)-2 inhibitor celecoxib abrogates activation of cigarette smoke-induced Nuclear Factor (NF)-κB by suppressing activation of I-κBα kinase in human non-small cell lung carcinoma correlation with suppression of cyclin D1, COX-2, and matrix metalloproteinase-9. Cancer Research 64 (2004) 5004-5012
32. Smith W.L., Garavito R.M., and DeWitt D.L. Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2. Journal of Biological Chemistry 271 (1996) 33157-33160
33. Sreekanth D., Arunasree M.K., Roy K.R., Chandramohan reddy T., Reddy G.V., and Reddanna P. Betanin, a betacyanin pigment purified from fruits of Opuntia ficus-indica induces apoptosis in human chronic myeloid leukemia cell line-K562. Phytomedicine 14 (2007) 739-746
34. Subhashini J., Mahipal S.V.K., Reddy M.C., Reddy M.M., Rachamallu A., and Reddanna P. Molecular mechanisms in C-Phycocyanin induced apoptosis in human chronic myeloid leukemia cell line-K562. Biochemistry and Pharmacology 68 (2004) 453-462
35. Ulbrich H., Soehnlein O., Xie X., Eriksson E.E., Lindbom L., Albrecht W., Laufer S., and Dannhardt G. Licofelone, a novel 5-LOX/COX-inhibitor, attenuates leukocyte rolling and adhesion on endothelium under flow. Biochemical Pharmacology 70 (2005) 30-36
36. Wang L., Chen W., Xie X., He Y., and BaI X. Celecoxib inhibits tumor growth and angiogenesis in an orthotopic implantation tumor model of human colon cancer. Experimental Oncology 30 (2008) 42-51
37. Ye Y.N., Wu W.K., Shin V.Y., Bruce I.C., Wong B.C., and Cho C.H. Dual inhibition of 5-LOX and COX-2 suppresses colon cancer formation promoted by cigarette smoke. Carcinogenesis 26 (2005) 827-834