Supercritical carbon dioxide extraction of aromatic turmerone from Curcuma longa Linn. Induces apoptosis through reactive oxygen species-triggered intrinsic and extrinsic pathways in human hepatocellular carcinoma HepG2 cells

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 38, 2012, Pages 9620-9630

  Cheng, Shao Bin ^a,b   Wu, Li Chen ^c   Hsieh, Yun Chih ^a   Wu, Chi Hao ^a   Chan, Yu Ju ^a,c   Chang, Li Hsun ^d   Chang, Chieh Ming J ^d   Hsu, Shih Lan ^a,b,c   Teng, Chieh Lin ^a,b   Wu, Chun Chi ^b,e  

^a TAICHUNG VETERANS GENERAL HOSPITAL   (Taiwan)

^b CHUNG SHAN MEDICAL UNIVERSITY   (Taiwan)

^c NATIONAL CHI NAN UNIVERSITY   (Taiwan)

^d NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^e CHUNG SHAN MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

Author keywords

apoptosis; ar turmerone; Curcuma; hepatocellular carcinoma cells; reactive oxygen species

Indexed keywords

ANNEXINS; ANTI-PROLIFERATIVE; ANTI-TUMOR ACTIVITIES; ANTIPROLIFERATIVE ACTIVITIES; AR-TURMERONE; BAX TRANSLOCATION; C-JUN N-TERMINAL KINASE; CASPASE ACTIVATION; CASPASE INHIBITORS; CASPASE-3; CURCUMA; CURCUMA LONGA; CYTOCHROME C; DEATH RECEPTOR 4; DNA FRAGMENTATION; ERK ACTIVATION; EXTRACELLULAR; FUROSEMIDES; HEPATOCELLULAR CARCINOMA; HEPATOCELLULAR CARCINOMA CELL; HEPG2 CELLS; INHIBITORY CONCENTRATION; LIQUID-SOLID CHROMATOGRAPHY; MITOCHONDRIAL DYSFUNCTION; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRIAL TRANSLOCATION; MOLECULAR MECHANISM; P53 UP-REGULATED MODULATOR OF APOPTOSIS; POTENTIAL EFFECTS; REACTIVE OXYGEN; REACTIVE OXYGEN SPECIES; SUPERCRITICAL CARBON DIOXIDE EXTRACTION; SUPERCRITICAL CARBON DIOXIDES; TURMERIC OIL;

AROMATIC COMPOUNDS; CARBON DIOXIDE; CELL CULTURE; CELL PROLIFERATION; DRUG PRODUCTS; ENZYME ACTIVITY; LIQUID CHROMATOGRAPHY; MITOCHONDRIA; OXYGEN; PHOSPHORYLATION; SUPERCRITICAL FLUID EXTRACTION;

CELL DEATH;

ANTINEOPLASTIC AGENT; APOPTOSIS REGULATORY PROTEIN; AR TURMERONE; AR-TURMERONE; BAX PROTEIN, HUMAN; BBC3 PROTEIN, HUMAN; CARBON DIOXIDE; CASPASE; CYTOCHROME C; FAS LIGAND; FASLG PROTEIN, HUMAN; KETONE; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE KINASE 4; ONCOPROTEIN; PROTEIN BAX; REACTIVE OXYGEN METABOLITE; SESQUITERPENE;

APOPTOSIS; ARTICLE; CELL STRAIN HEPG2; CHEMISTRY; CURCUMA; DRUG EFFECT; DRUG SCREENING; HUMAN; LIVER CELL CARCINOMA; LIVER TUMOR; METABOLISM; METHODOLOGY; MITOCHONDRIAL MEMBRANE POTENTIAL; PATHOLOGY; SIGNAL TRANSDUCTION; SUPERCRITICAL FLUID CHROMATOGRAPHY; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; APOPTOSIS REGULATORY PROTEINS; BCL-2-ASSOCIATED X PROTEIN; CARBON DIOXIDE; CARCINOMA, HEPATOCELLULAR; CASPASES; CELL LINE, TUMOR; CHROMATOGRAPHY, SUPERCRITICAL FLUID; CURCUMA; CYTOCHROMES C; DRUG SCREENING ASSAYS, ANTITUMOR; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FAS LIGAND PROTEIN; HEP G2 CELLS; HUMANS; KETONES; LIVER NEOPLASMS; MAP KINASE KINASE 4; MEMBRANE POTENTIAL, MITOCHONDRIAL; PROTO-ONCOGENE PROTEINS; REACTIVE OXYGEN SPECIES; SESQUITERPENES; SIGNAL TRANSDUCTION;

CURCUMA; CURCUMA LONGA;

EID: 84866721021     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf301882b     Document Type: Article

References (43)

1. Schütte, K.; Bornschein, J.; Malfertheiner, P. Hepatocellular carcinoma-epidemiological trends and risk factors Dig. Dis. 2009, 27, 80-92
2. Wilhelm, S. M.; Adnane, L.; Newell, P.; Villanueva, A.; Llovet, J. M.; Lynch, M. Preclinical overview of sorafenib, a multikinase inhibitor that targets both Raf and VEGF and PDGF receptor tyrosine kinase signaling Mol. Cancer Ther. 2008, 7, 3129-3140
3. Kane, R. C.; Farrell, A. T.; Saber, H.; Tang, S.; Williams, G.; Jee, J. M.; Liang, C.; Booth, B.; Chidambaram, N.; Morse, D. Sorafenib for the treatment of advanced renal cell carcinoma Clin. Cancer Res. 2006, 12, 7271-7278
4. Singh, G.; Kapoor, I. P. S.; Singh, P.; de Heluani, C. S.; de Lampasona, M. P.; Catalan, C. A. N. Comparative study of chemical composition and antioxidant activity of fresh and dry rhizomes of turmeric (Curcuma longa Linn.) Food Chem. Toxicol. 2010, 48, 1026-1031
5. Anand, P.; Sundaram, C.; Jhurani, S.; Kunnumakkara, A. B.; Aggarwal, B. B. Curcumin and cancer: an "old-age" disease with an "age-old" solution Cancer Lett. 2008, 267, 133-164
6. Ammon, H.; Wahl, M. A. Pharmacology of Curcuma longa Planta Med. 1991, 57, 1-7
7. Yue, G. G. L.; Chan, B. C. L.; Hon, P. M.; Lee, M. Y. H.; Fung, K. P.; Leung, P. C.; Lau, C. Evaluation of in vitro anti-proliferative and immunomodulatory activities of compounds isolated from Curcuma longa Food Chem. Toxicol. 2010, 48, 2011-2020
8. Bar-Sela, G.; Epelbaum, R.; Schaffer, M. Curcumin as an anti-cancer agent: review of the gap between basic and clinical applications Curr. Med. Chem. 2010, 17, 190-197
9. Ramsewak, R.; DeWitt, D.; Nair, M. Cytotoxicity, antioxidant and anti-inflammatory activities of curcumins I-III from Curcuma longa Phytomedicine 2000, 7, 303-308
10. Polasa, K.; Raghuram, T. C.; Krishna, T. P.; Krishnaswamy, K. Effect of turmeric on urinary mutagens in smokers Mutagenesis 1992, 7, 107-109
11. Martins, A.; Salgueiro, L.; Goncalves, M.; da Cunha, A. P.; Vila, R.; Canigueral, S.; Mazzoni, V.; Tomi, F.; Casanova, J. Essential oil composition and antimicrobial activity of three Zingiberaceae from S. Tome e Principe Planta Med. 2001, 67, 580-584
12. Wuthi-Udomlert, M.; Grisanapan, W.; Luanratana, O.; Caichompoo, W. Antifungal activity of Curcuma longa grown in Thailand Southeast Asian J. Trop. Med. Public Health 2000, 31, 178-182
13. Hail, N., Jr.; Lotan, R. Cancer chemoprevention and mitochondria: targeting apoptosis in transformed cells via the disruption of mitochondrial bioenergetics/redox state Mol. Nutr. Food Res. 2009, 53, 49-67
14. Manzan, A. C.; Toniolo, F. S.; Bredow, E.; Povh, N. P. Extraction of essential oil and pigments from Curcuma longa [L] by steam distillation and extraction with volatile solvents J. Agric. Food Chem. 2003, 51, 6802-6807
15. Byun, J. Y.; Kim, M. J.; Eum, D. Y.; Yoon, C. H.; Seo, W. D.; Park, K. H.; Hyun, J. W.; Lee, Y. S.; Lee, J. S.; Yoon, M. Y. Reactive oxygen species-dependent activation of Bax and poly (ADP-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid pristimerin in human cervical cancer cells Mol. Pharmacol. 2009, 76, 734-744
16. Li, Y. H.; Chung, H. C.; Liu, S. L.; Chao, T. H.; Chen, J. C. A novel inhibitory effect of Antrodia camphorata extract on vascular smooth muscle cell migration and neointima formation in mice Int. Heart J. 2009, 50, 207-220
17. Cheng, J.; Chang, G.; Wu, W.; Liu, W.; Yang, Z.; Meng, F.; Xu, K.; Li, L.; Zhu, D.; Zhu, C. A controlled clinical study between hepatic arterial infusion with embolized curcuma aromatic oil and chemical drugs in treating primary liver cancer Chin. J. Integ. Med. 2001, 7, 141-141
18. 2 + turmerones J. Supercrit. Fluids 2007, 43, 276-282
19. Chang, L.; Jong, T.; Huang, H.; Nien, Y.; Chang, C. Supercritical carbon dioxide extraction of turmeric oil from Curcuma longa Linn and purification of turmerones Sep. Purif. Technol. 2006, 47, 119-125
20. Gupta, S. Molecular signaling in death receptor and mitochondrial pathways of apoptosis (review) Int. J. Oncol. 2003, 22, 15-20
21. Jurgensmeier, J. M.; Xie, Z.; Deveraux, Q.; Ellerby, L.; Bredesen, D.; Reed, J. C. Bax directly induces release of cytochrome c from isolated mitochondria Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4997-5002
22. Kuwana, T.; Newmeyer, D. D. Bcl-2-family proteins and the role of mitochondria in apoptosis Curr. Opin. Cell. Biol. 2003, 15, 691-699
23. Wang, Q. F.; Chiang, C. W.; Wu, C. C.; Cheng, C. C.; Hsieh, S. J.; Chen, J. C.; Hsieh, Y. C.; Hsu, S. L. Gypenosides induce apoptosis in human hepatoma Huh-7 cells through a calcium/reactive oxygen species-dependent mitochondrial pathway Planta Med. 2007, 73, 535-544
24. Simon, H. U.; Haj-Yehia, A.; Levi-Schaffer, F. Role of reactive oxygen species (ROS) in apoptosis induction Apoptosis 2000, 5, 415-418
25. Hsieh, Y. C.; Rao, Y. K.; Wu, C. C.; Huang, C. Y.; Geethangili, M.; Hsu, S. L.; Tzeng, Y. M. Methyl antcinate A from Antrodia camphorata induces apoptosis in human liver cancer cells through oxidant-mediated cofilin- and Bax-triggered mitochondrial pathway Chem. Res. Toxicol. 2010, 23, 1256-1267
26. Gaestel, M. MAPKAP kinases-MKs - two's company, three's a crowd Nat. Rev. Mol. Cell. Biol. 2006, 7, 120-130
27. Park, S. Y.; Jin, M. L.; Kim, Y. H.; Lee, S. J. Aromatic-turmerone inhibits α-MSH and IBMX-induced melanogenesis by inactivating CREB and MITF signaling pathways Arch. Dermatol. Res. 2011, 1-8
28. Lee, Y. Activation of apoptotic protein in U937 cells by a component of turmeric oil BMB Rep. 2009, 42, 96-100
29. Karbowski, M.; Norris, K. L.; Cleland, M. M.; Jeong, S. Y.; Youle, R. J. Role of Bax and Bak in mitochondrial morphogenesis Nature 2006, 443, 658-662
30. Gross, A.; McDonnell, J. M.; Korsmeyer, S. J. BCL-2 family members and the mitochondria in apoptosis Gene Dev. 1999, 13, 1899-1911
31. Lee, Y. Activation of apoptotic protein in U937 cells by a component of turmeric oil BMB Rep. 2009, 42, 96-100
32. Fulda, S.; Debatin, K. Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy Oncogene 2006, 25, 4798-4811
33. Kim, R.; Emi, M.; Tanabe, K. Role of mitochondria as the gardens of cell death Cancer Chemother. Pharm. 2006, 57, 545-553
34. Verrax, J.; Pedrosa, R. C.; Beck, R.; Dejeans, N.; Taper, H.; Calderon, P. B. In situ modulation of oxidative stress: a novel and efficient strategy to kill cancer cells Curr. Med. Chem. 2009, 16, 1821-1830
35. Georgakilas, A. Detection of clustered DNA lesions: biological and clinical applications World J. Biol. Chem. 2011, 2, 173-176
36. Plotnikov, A.; Zehorai, E.; Procaccia, S.; Seger, R. The MAPK cascades: signaling components, nuclear roles and mechanisms of nuclear translocation Biochim. Biophys. Acta-Mol. Cell Res. 2011, 1813, 1619-1633
37. Peyssonnaux, C.; Eychène, A. The Raf/MEK/ERK pathway: new concepts of activation Biol. Cell 2001, 93, 53-62
38. Kim, M. J.; Choi, S. Y.; Park, I. C.; Hwang, S. G.; Kim, C.; Choi, Y. H.; Kim, H.; Lee, K. H.; Lee, S. J. Opposing roles of c-Jun NH2-terminal kinase and p38 mitogen-activated protein kinase in the cellular response to ionizing radiation in human cervical cancer cells Mol. Cancer Res. 2008, 6, 1718-1731
39. An, W. W.; Wang, M. W.; Tashiro, S.; Onodera, S.; Ikejima, T. Mitogen-activated protein kinase-dependent apoptosis in norcan-tharidin-treated A375-S2 cells is proceeded by the activation of protein kinase C Chin. Med. J. (Engl.) 2005, 118, 198-203
40. Kang, Y. H.; Lee, S. J. The role of p38 MAPK and JNK in arsenic trioxide-induced mitochondrial cell death in human cervical cancer cells J. Cell. Physiol. 2008, 217, 23-33
41. Persons, D. L.; Yazlovitskaya, E. M.; Cui, W.; Pelling, J. C. Cisplatin-induced activation of mitogen-activated protein kinases in ovarian carcinoma cells: inhibition of extracellular signal-regulated kinase activity increases sensitivity to cisplatin Clin. Cancer Res. 1999, 5, 1007-1014
42. Chang, L. H.; Jong, T. T.; Huang, H. S.; Nien, Y. F.; Chang, C. M. J. Supercritical carbon dioxide extraction of turmeric oil from Curcuma longa Linn and purification of turmerones Sep. Purif. Technol. 2006, 47, 119-125
43. Hsu, Y. T.; Wolter, K. G.; Youle, R. J. Cytosol-to-membrane redistribution of Bax and Bcl-X(L) during apoptosis Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3668-3672