The growth suppressing effects of girinimbine on hepg2 involve induction of apoptosis and cell cycle arrest

Molecules

Volumn 16, Issue 8, 2011, Pages 7155-7170

  Syam, Suvitha ^a   Abdul, Ahmad Bustamam ^a   Sukari, Mohd Aspollah ^a   Mohan, Syam ^b   Abdelwahab, Siddig Ibrahim ^b   Wah, Tang Sook ^a  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Anticancer; Apoptosis; Carbazole alkaloid; Cell cycle arrest; Girinimbine; Pyranocarbazole

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; CASP3 PROTEIN, HUMAN; CASPASE 3; GIRINIMBINE; GROWTH INHIBITOR; LACTATE DEHYDROGENASE;

APOPTOSIS; ARTICLE; CELL CYCLE CHECKPOINT; CELL CYCLE G0 PHASE; CELL PROLIFERATION; CELL SHAPE; CELL STRAIN HEPG2; CELL SURVIVAL; CHEMISTRY; CULTURE MEDIUM; DNA FRAGMENTATION; DRUG EFFECT; DRUG SCREENING; ENZYME ASSAY; HUMAN; METABOLISM;

ALKALOIDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CASPASE 3; CELL CYCLE CHECKPOINTS; CELL PROLIFERATION; CELL SHAPE; CELL SURVIVAL; CULTURE MEDIA, CONDITIONED; DNA FRAGMENTATION; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME ASSAYS; G0 PHASE; GROWTH INHIBITORS; HEP G2 CELLS; HUMANS; L-LACTATE DEHYDROGENASE;

EID: 80052244679     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16087155     Document Type: Article

References (37)

1. Barshack, I.; Meiri, E.; Rosenwald, S.; Lebanony, D.; Bronfeld, M.; Aviel-Ronen, S.; Rosenblatt, K.; Polak-Charcon, S.; Leizerman, I.; Ezagouri, M. Differential diagnosis of hepatocellular carcinoma from metastatic tumors in the liver using microRNA expression. Int. J. Biochem. Cell Biol. 2010, 42, 1355-1362.
2. Capocaccia, R.; Sant, M.; Berrino, F.; Simonetti, A.; Santi, V.; Trevisani F. Hepatocellular carcinoma: Trends of incidence and survival in Europe and the United States at the end of the 20th century. Am. J. Gastroenterol. 2007, 102, 1661-1670. (Pubitemid 47206702)
3. Yuen, M.F.; Hou, J.L.; Chutaputti, A. Hepatocellular carcinoma in the Asia pacific region. J. Gastroenterol. Hepatol. 2009, 24, 346-353.
4. Ferenci, P.; Fried, M.; Labrecque, D.; Bruix, J.; Sherman, M.; Omata, M.; Heathcote, J.; Piratsivuth, T.; Kew, M.; Otegbayo, J.A. Hepatocellular Carcinoma (HCC): A Global Perspective. J. Clin. Gastroenterol. 2010, 44, 239-245.
5. Guglielmi, A.; Ruzzenente, A.; Valdegamberi, A.; Pachera, S.; D'Onofrio, M.C.T.; Martone, E.; Nicoli, P.; Iacono, C. Radiofrequency ablation versus surgical resection for the treatment of hepatocellular carcinoma in cirrhosis. J. Gastrointest. Surg. 2008, 12, 192-198.
6. Chen, L.; Yuan, Y.F.; Li, Y.; Chan, T.H.M.; Zheng, B.J.; Huang, J.; Guan, X.Y. Clinical significance of CHD1L in hepatocellular carcinoma and therapeutic potentials of virus-mediated CHD1L depletion. Gut 2011, 60, 534-543.
7. Knolker, H.J.; Reddy, K.R. Isolation and synthesis of biologically active carbazole alkaloids. Chem. Rev. 2002, 102, 4303-4428.
8. Itoigawa, M.; Kashiwada, Y.; Ito, C.; Furukawa, H.; Tachibana, Y.; Bastow, K.F.; Lee, K.H. Carbazole alkaloid murrayaquinone A and related synthetic carbazolequinones as cytotoxic agents. J .Nat Prod. 2000, 63, 893-897.
9. Asche, C.; Demeunynck, M. Antitumor carbazoles. Anticancer Agents Med. Chem. 2007, 7, 247-267. (Pubitemid 46403587)
10. Knolker, H. Occurrence, biological activity, and convergent organometallic synthesis of carbazole alkaloids. Top. Curr. Chem. 2005, 24, 115-148. (Pubitemid 44423486)
11. Cui, C.B.; Yan, S.Y.; Cai, B.; Yao, X.S. Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena dunniana Levl. J. Asian Nat Prod. Res. 2002, 4, 233-241. (Pubitemid 35285339)
12. Joshi, B.S.; Kamat, V.N.; Gawad, D.H.; Govindachari, T.R. Structure and synthesis of heptaphylline. Phytochemistry 1972, 11, 2065-2071.
13. Joseph, S.; Peter, K.V. Curry leaf (Murraya koenigii), perennial, nutritious, leafy vegetable. Econ. Bot. 1985, 39, 68-73.
14. Adebajo, A.C.; Ayoola, O.F.; Iwalewa, E.O.; Akindahunsi, A.A.; Omisore, N.O.A.; Adewunmi, C.O.; Adenowo, T.K. Anti-trichomonal, biochemical and toxicological activities of methanolic extract and some carbazole alkaloids isolated from the leaves of Murraya koenigii growing in Nigeria. Phytomedicine 2006, 13, 246-254. (Pubitemid 43255324)
15. Ko, F.N.; Lee, Y.S.; Wu, T.S.; Teng, C.M. Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia. Biochem. Pharmacol. 1994, 48, 353-360.
16. Thevissen, K.; Marchand, A.; Chaltin, P.; Meert, E.M.K.; Cammue, B. Antifungal carbazoles. Curr. Med. Chem. 2009, 16, 2205-2211.
17. Wang, S.; Cai, B.; Cui, C.; Yan, S.; Wu, C. Study on induction of apoptosis by girinimbine in HCT-15 cell in vitro. Chin. J. Pharm. Anal. 2008, 28, 176-181.
18. Wang, S.; Cai, B.; Cui, C. Induction of apoptosis by girinimbine in K562 cell. Chin. Tradit Herb. Drugs 2007, 38, 1677-1680.
19. Abubakar, N.H.; Sukari, M.A.; Rahmani, M.; Sharif, M.A.; Khalid, K.; Yusof, U.K. Chemical Constituents from Stem Barks and Roots of Murraya koenigii (Rutaceae). MJAS 2007, 11, 173-176.
20. Rowinsky, E.K.; Donehower, R.C. Paclitaxel (taxol). N. Eng. J. Med. 1995, 332, 1004-1014.
21. Rosenkranz, V.; Wink, M. Alkaloids induce programmed cell death in bloodstream forms of Trypanosomes (Trypanosoma b. Brucei). Molecules 2008, 13, 2462-2473.
22. Khan, B.A.; Abraham, A.; Lelamma, S. Murraya koenigii and Brassica juncea-Alterations on lipid profile in 1-2 dimethyl hydrazine induced colon carcinogenesis. Invest. New Drugs 1996, 14, 365-369. (Pubitemid 27075443)
23. Haslizawati, A.B.N. Chemical constituents, bioactivity and HPLC profiling of microwave-assisted normal extraction of Murraya koenigii. Masters thesis, Universiti Putra Malaysia, Selangor, Malaysia, 30 April 2010.
24. Roy, M.K.; Thalang, V.N.; Trakoontivakorn, G.; Nakahara, K. Mahanine, a carbazole alkaloid from Micromelum minutum, inhibits cell growth and induces apoptosis in U937 cells through a mitochondrial dependent pathway. Br. J. Pharmacol. 2005, 145, 145-155. (Pubitemid 40756519)
25. Kok, Y.Y. Cytotoxicity of mahanimbine, murryafoline A and S-benzyldithiocarbazate on human leukemic cell line. Masters thesis, Universiti Putra Malaysia, Selangor, Malaysia, 23 November 2010.
26. Jiang, H.; Zhang, L.; Kuo, J.; Kuo, K.; Gautam, S.C.; Groc, L.; Rodriguez, A.I.; Koubi, D.; Hunter, T.J.; Corcoran, G.B. Resveratrol-induced apoptotic death in human U251 glioma cells. Mol. Cancer Ther. 2005, 4, 554-561. (Pubitemid 40601836)
27. Liu, J.; Shen, H.M.; Ong, C.N. Salvia miltiorrhiza inhibits cell growth and induces apoptosis in human hepatoma HepG2 cells. Cancer Lett. 2000, 153, 85-93. (Pubitemid 30209848)
28. Zain, W.N. Antiproliferative properties of Clausine-B against cancer cell lines. Malays. J. Med. Sci. 2009, 16, 31-36.
29. Fink, S.L.; Cookson, B.T. Apoptosis, pyroptosis, and necrosis: mechanistic description of dead and dying eukaryotic cells. Infect. Immun. 2005, 73, 1907-1916. (Pubitemid 40470787)
30. Kuo, P.L.; Hsu, Y.L.; Chang, C.H.; Lin, C.C. The mechanism of ellipticine-induced apoptosis and cell cycle arrest in human breast MCF-7 cancer cells. Cancer Lett. 2005, 223, 293-301.
31. Kuo, P.L.; Hsu, Y.L.; Kuo, Y.C.; Chang, C.H.; Lin, C.C. The anti-proliferative inhibition of ellipticine in human breast MDA-MB-231 cancer cells is through cell cycle arrest and apoptosis induction. Anti-cancer Drug. 2005, 16, 789-795.
32. Kerr, J.F.R.; Wyllie, A.H.; Currie, A.R. Apoptosis: A basic biological phenomenon with wide-ranging implications in tissue kinetics. Br. J. Cancer. 1972, 26, 239-257.
33. Jänicke, R.U.; Sprengart, M.L.; Wati, M.R.; Porter, A.G. Caspase-3 is required for DNA fragmentation and morphological changes associated with apoptosis. J. Biol. Chem. 1998, 273, 9357-9360. (Pubitemid 28183012)
34. Collins, J.A.; Schandl, C.A.; Young, K.K.; Vesely, J.; Willingham, M.C. Major DNA Fragmentation Is a Late Event in Apoptosis. J. Histochem. Cytochem. 1997, 45, 923-934. (Pubitemid 27284016)
35. Ito, C.; Itoigawa, M.; Nakao, K.; Murata, T.; Tsuboi, M.; Kaneda, N.; Furukawa, H. Induction of apoptosis by carbazole alkaloids isolated from Murraya koenigii. Phytomedicine 2006, 13, 359-365.
36. Elankumaran, S.; Rockemann, D.; Samal, S.K. Newcastle disease virus exerts oncolysis by both intrinsic and extrinsic caspase-dependent pathways of cell death. J. Virol. 2006, 80, 7522-7534. (Pubitemid 44092574)
37. Liger, F.; Popowycz, F.; Besson, T.; Picot, L.; Galmarini, C.M.; Joseph, B. Synthesis and antiproliferative activity of clausine E, mukonine, and koenoline bioisosteres. Bioorg. Med. Chem. 2007, 15, 5615-5619. (Pubitemid 46970819)