2-Deprenyl-Rheediaxanthone B Isolated from Metaxya rostrata Induces Active Cell Death in Colorectal Tumor Cells

PLoS ONE

Volumn 8, Issue 6, 2013, Pages

  Kainz, Kerstin P ^a,b   Krenn, Liselotte ^b   Erdem, Zeynep ^a   Kaehlig, Hanspeter ^b   Zehl, Martin ^b   Bursch, Wilfried ^a   Berger, Walter ^a   Marian, Brigitte ^a  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEPRENYLRHEEDIAXANTHONE; ATR PROTEIN; CASPASE 2; CASPASE 3; PLANT MEDICINAL PRODUCT; PROTEIN BCL 2; PROTEIN BCL XL; PROTEIN FOXM1; TRANSCRIPTION FACTOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CELL CYCLE G2 PHASE; CELL CYCLE S PHASE; CELL DEATH; CELL VIABILITY; CHROMOSOME CONDENSATION; COLORECTAL CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOWN REGULATION; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG SENSITIVITY; DRUG STRUCTURE; ENZYME ACTIVATION; IC 50; MEDICINAL PLANT; METAXYA ROSTRATA; MITOSIS; UPREGULATION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BLOTTING, WESTERN; CACO-2 CELLS; CASPASE 2; CELL CYCLE; CELL LINE; CELL SURVIVAL; COLORECTAL NEOPLASMS; FERNS; HCT116 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MEMBRANE POTENTIAL, MITOCHONDRIAL; PLANT EXTRACTS;

FILICOPHYTA; METAXYA ROSTRATA; METAXYACEAE;

EID: 84878941755     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0065745     Document Type: Article

References (44)

1. Peterson C, (2011) Drug therapy of cancer. Eur J Clin Pharmacol 67(5): 437-47.
2. Newman DJ, Cragg GM, (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70(3): 461-477.
3. Kim J, Park EJ, (2002) Cytotoxic anticancer candidates from natural resources. Curr Med Chem Anticancer Agents 2(4): 485-537.
4. Macdonald JS, Astrow AB, (2001) Adjuvant therapy of colon cancer. Semin Oncol 28(1): 30-40.
5. Ragnhammar P, Hafstrom L, Nygren P, Glimelius B, (2001) A systematic overview of chemotherapy effects in colorectal cancer. Acta Oncol 40(2-3): 282-308.
6. Eng C, (2010) The evolving role of monoclonal antibodies in colorectal cancer: early presumptions and impact on clinical trial development. Oncologist 15(1): 73-84.
7. Fearon ER, Vogelstein B, (1990) A genetic model for colorectal tumorigenesis. Cell 61(5): 759-67.
8. Krajewska M, Moss SF, Krajewski S, Song K, Holt PR, et al. (1996) Elevated expression of Bcl-XL and reduced Bak in primary colorectal adenocarcinomas. Cancer Res 56(10): 2422-2427.
9. Partik G, Kahl-Rainer P, Sedivy R, Ellinger A, Bursch W, et al. (1998) Apoptosis in human colorectal tumours: ultrastructure and quantitative studies on tissue localization and association with bak expression. Virchows Arch 432(5): 415-426.
10. Hinoshita E, Uchiumi T, Taguchi K, Kinukawa N, Tsuneyoshi M, et al. (2000) Increased expression of an ATP-binding cassette superfamily transporter, multidrug resistance protein 2, in human colorectal carcinomas. Clin Cancer Res 6(6): 2401-2407.
11. Peng KC, Cluzeaud F, Bens M, Duong Van Huyen JP, Wioland MA, et al. (1999) Tissue and cell distribution of the multidrug resistance-associated protein (MRP) in mouse intestine and kidney. J Histochem Cytochem 47(6): 757-768.
12. Pekarek B (2003) Die Heilpflanzen in den Hausgärten von La Gamba. Diploma thesis University of Natural Resources and Life Sciences, Vienna.
13. Kalabis J, Patterson MJ, Enders GH, Marian B, Iozzo RV, et al. (2003) Stimulation of human colonic epithelial cells by leukemia inhibitory factor is dependent on collagen-embedded fibroblasts in organotypic culture. FASEB J 17(9): 1115-1117.
14. Richter M, Jurek D, Wrba F, Kaserer K, Wurzer G, et al. (2002) Cells obtained from colorectal microadenomas mirror early premalignant growth patterns in vitro. Eur J Cancer 38(14): 1937-1945.
15. Hausott B, Greger H, Marian B, (2004) Flavaglines: a group of efficient growth inhibitors block cell cycle progression and induce apoptosis in colorectal cancer cells. Int J Cancer 109(6): 933-940.
16. Monache FD, Botta B, Nicoletti M, de Barros Coelho JS, de Andrade Lyra FD, (1981) Three New Xanthones and Macluraxanthone from Rheedia benthamiana Pl. Triana (Guttiferae). J. Chem. Soc. 1: 484-488.
17. Hay AE, Helesbeux JJ, Duval O, Labaied M, Grellier P, et al. (2004) Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii. Life Sci 75(25): 3077-3085.
18. Rath G, Potterat O, Mavi S, Hostettmann K, (1996) Xanthones from Hypericum roeperanum. Phytochemistry 43(2): 513-520.
19. Lavaud A, Soleti R, Hay AE, Richomme P, Guilet D, et al. (2012) Paradoxical effects of polyphenolic compounds from Clusiaceae on angiogenesis. Biochem Pharmacol 83(4): 514-523.
20. Virtbauer J, Krenn L, Kahlig H, Hufner A, Donath O, et al. (2008) Chemical and pharmacological investigations of Metaxya rostrata. Z Naturforsch C 63(7-8): 469-475.
21. Boutros R, Dozier C, Ducommun B, (2006) The when and wheres of Cdc25 phosphatases. Curr Opin Cell Biol 18(2): 185-191.
22. Wang IC, Chen YJ, Hughes D, Petrovic V, Major ML, P et al, (2005) Forkhead box M1 regulates the transcriptional network of genes essential for mitotic progression and genes encoding the SCF (Skp2-Cks1) ubiquitin ligase. Mol Cell Biol 25(24): 10875-10894.
23. Wei Y, Yu L, Bowen J, Gorovsky MA, Allis CD, (1999) Phosphorylation of histone H3 is required for proper chromosome condensation and segregation. Cell 97(1): 99-109.
24. Portugal J, Mansilla S, Bataller M, (2010) Mechanisms of drug-induced mitotic catastrophe in cancer cells. Curr Pharm Des 16(1): 69-78.
25. Singh R, George J, Shukla Y, (2010) Role of senescence and mitotic catastrophe in cancer therapy. Cell Div 5: 4.
26. Castanheiro RAP, Silva AMS, Campos NAN, Nascimento MSJ, Pinto MMM, (2009) Antitumor activity of some prenylated xanthones. Pharmaceuticals 2: 33-43.
27. Niu S-L, Li Z-L, Ji F, Liu G-Y, Zhao N, et al. (2012) Xanthones from the stem bark of Garcinia bracteata with growth inhibitory effects against HL-60 cells. Phytochemistry 77: 280-286.
28. Kiang LC, Tho LY, Lim CH, Lim YM, Shah SA, et al. (2011) Synthesis and SAR study of prenylated xanthone analogues as HeLa and MDA-MB-231 cancer cell inhibitors. Letters in Drug Design & Discovery 8: 523-528.
29. Akao Y, Nakagawa Y, Iinuma M, Nozawa Y, (2008) Anti-cancer effects of xanthones from pericarps of mangosteen. Int J Mol Sci 9(3): 355-370.
30. Matsumoto K, Akao Y, Yi H, Ohguchi K, Ito T, et al. (2004) Preferential target is mitochondria in alpha-mangostin-induced apoptosis in human leukemia HL60 cells. Bioorg Med Chem 12(22): 5799-5806.
31. Watanapokasin R, Jarinthanan F, Nakamura Y, Sawasjirakij N, Jaratrungtawee A, et al. (2011) Effects of alpha-mangostin on apoptosis induction of human colon cancer. World J Gastroenterol 17(16): 2086-2095.
32. Cheng JH, Huang AM, Hour TC, Yang SC, Pu YS, et al. (2011) Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS. Eur J Med Chem 46(4): 1222-1231.
33. Ding L, Liu B, Qi LL, Zhou QY, Hou Q, et al. (2009) Anti-proliferation, cell cycle arrest and apoptosis induced by a natural xanthone from Gentianopsis paludosa Ma, in human promyelocytic leukemia cell line HL-60 cells. Toxicol In Vitro 23(3): 408-417.
34. Krajarng A, Nakamura Y, Suksamrarn S, Watanapokasin R, (2011) alpha-Mangostin induces apoptosis in human chondrosarcoma cells through downregulation of ERK/JNK and Akt signaling pathway. J Agric Food Chem 59(10): 5746-5754.
35. Nakagawa Y, Iinuma M, Naoe T, Nozawa Y, Akao Y, (2007) Characterized mechanism of alpha-mangostin-induced cell death: caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells. Bioorg Med Chem 15(16): 5620-5628.
36. Chao AC, Hsu YL, Liu CK, Kuo PL, (2011) alpha-Mangostin, a dietary xanthone, induces autophagic cell death by activating the AMP-activated protein kinase pathway in glioblastoma cells. J Agric Food Chem 59(5): 2086-2096.
37. Palmeira A, Paiva A, Sousa E, Seca H, Almeida GM, et al. (2010) Insights into the in vitro antitumor mechanism of action of a new pyranoxanthone. Chem Biol Drug Des 76(1): 43-58.
38. Batova A, Altomare D, Chantarasriwong O, Ohlsen KL, Creek KE, et al. (2010) The synthetic caged garcinia xanthone cluvenone induces cell stress and apoptosis and has immune modulatory activity. Mol Cancer Ther 9(11): 2869-2878.
39. Shen R, Wang P, Tang N, (2010) Cytotoxic activity and DNA-binding properties of xanthone derivatives. J Fluoresc 20(6): 1287-1297.
40. Harper JW, Elledge SJ, (2007) The DNA damage response: ten years after. Mol Cell 28(5): 739-745.
41. García-Rivera D, Delgado R, Bougarne N, Haegeman G, Vanden Berghe W, (2011) Gallic acid indanone and mangiferin xanthone are strong determinants of immunosuppressive anti-tumour effects of Mangifera indica L. bark in MDA-MB231 breast cancer cells. Cancer Letters 305(1): 21-31.
42. Raychaudhuri P, Park HJ, (2011) FoxM1: A Master Regulator of Tumor Metastasis. Cancer Research 71(13): 4329-4333.
43. De Bruin EC, Medema JP, (2008) Apoptosis and non-apoptotic deaths in cancer development and treatment response. Cancer Treat Rev 34(8): 737-749.
44. Ianzini F, Bertoldo A, Kosmacek EA, Phillips SL, Mackey MA, (2006) Lack of p53 function promotes radiation-induced mitotic catastrophe in mouse embryonic fibroblast cells. Cancer Cell Int 6: 11.