Identification and anti-human glioblastoma activity of tagitinin C from tithonia diversifolia methanolic extract

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 6, 2011, Pages 2347-2355

  Lee, Ming Yi ^a   Liao, May Hua ^b   Tsai, Yung Nuan ^c   Chiu, Kong Hwa ^d   Wen, Hsiao Chuan ^b  

^a CHANG GUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

^b YUANPEI UNIVERSITY   (Taiwan)

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^d NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

1H NMR; apoptosis; autophagy; tagitinin C; Tithonia diversifolia methanolic extract (TDM)

Indexed keywords

1H NMR; APOPTOSIS; AUTOPHAGY; TAGITININ C; TITHONIA DIVERSIFOLIA METHANOLIC EXTRACT (TDM);

CELL DEATH; RESONANCE; SILICA; SILICA GEL;

NUCLEAR MAGNETIC RESONANCE;

ANTINEOPLASTIC AGENT; METHANOL; PLANT EXTRACT; SESQUITERPENE; TAGITININ;

APOPTOSIS; ARTICLE; ASTERACEAE; AUTOPHAGY; CHEMISTRY; DRUG EFFECT; GLIOBLASTOMA; HUMAN; PATHOPHYSIOLOGY; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; ASTERACEAE; AUTOPHAGY; CELL LINE, TUMOR; GLIOBLASTOMA; HUMANS; METHANOL; PLANT EXTRACTS; SESQUITERPENES;

TITHONIA DIVERSIFOLIA;

EID: 79952762714     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf105003n     Document Type: Article

References (33)

1. Takanashi, M. U.S. Patent 5,773,004, 1998.
2. Rungeler, P.; Lyss, G.; Castro, V.; Mora, G.; Pahl, H. L.; Merfort, I. Study of three sesquiterpene lactones from Tithonia diversifolia on their anti-inflammatory activity using the transcription factor NF-κB and enzymes of the arachidonic acid pathway as targets Planta Med. 1998, 64, 588-593 (Pubitemid 28481467)
3. Tona, L.; Kambu, K.; Mesia, K.; Cimanga, K.; Apers, S.; De Bruyne, T.; Pieters, L.; Totte, J.; Vlietinck, A. J. Biological screening of traditional preparations from some medicinal plants used as antidiarrhoeal in Kinshasa, Congo Phytomedicine 1999, 6, 59-66 (Pubitemid 129632495)
4. Tona, L.; Kambu, K.; Ngimbi, N.; Mesia, K.; Penge, O.; Lusakibanza, M.; Cimanga, K.; De Bruyne, T.; Apers, S.; Totte, J.; Pieters, L.; Vlietinck, A. J. Antiamoebic and spasmolytic activities of extracts from some antidiarrhoeal traditional preparations used in Kinshasa, Congo Phytomedicine 2000, 7, 31-38 (Pubitemid 30191126)
5. Lin, C. C.; Lin, M. L.; Lin, J. M. The antiinflammatory and liver protective effect of Tithonia diversifolia (Hemsl.) gray and Dicliptera chinensis Juss. extracts in rats Phytother. Res. 1993, 7, 305-309
6. Kuo, Y. H.; Lin, B. Y. Five new taraxastane-type triterpenes from the aerial roots of Ficus microcarpa Chem. Pharm. Bull. 1999, 47, 498-500
7. Kuo, Y. H.; Chen, C. H. Sesquiterpenes from the leaves of Tithonia diversifolia J. Nat. Prod. 1998, 61, 827-828
8. Kuo, Y. H.; Chen, C. H. Diversifolol sesquiterpenes from the leaves of Tithonia diversifolia Chem. Pharm. Bull. 1997, 45, 1223-1224
9. Bordoloi, M.; Barua, N. C.; Ghosh, A. C. An artemisinic acid analogue from Tithonia diversifolia Phytochemistry 1996, 1, 557-559
10. Baruah, N. C.; Sarma, J. C.; Barua, N. C.; Sarma, S.; Sharma, R. P. Germination and growth inhibitory sesquiterpene lactones and a flavone from Tithonia diversifolia Phytochemistry 1994, 36, 29-36 (Pubitemid 2079038)
11. Schuster, A.; Stokes, S.; Papastergiou, F.; Castro, V.; Poveda, L.; Jakupovic, J. Sesquiterpene lactones from two Tithonia species Phytochemistry 1992, 31, 3139-3141
12. Chowdury, P. K.; Barua, N. C.; Sharma, R. P.; Thyagarajan, G.; Herz, W. Structure of deacetylviguiestenin (tagitinin E). An addendum J. Org. Chem. 1980, 5, 535-536
13. Baruah, N. C.; Sharma, R. P.; Madhusudanan, K. P.; Thyagarajan, G.; Herz, W.; Murari, R. Sesquiterpene lactones of Tithonia diversifolia. Stereochemistry of the tagitinins and related compounds J. Org. Chem. 1979, 44, 1831-1835
14. Gu, J. Q.; Gills, J. J.; Park, E. J.; Mata-Greenwood, E.; Hawthorne, M. E.; Axelrod, F.; Chavez, P. I.; Fong, H. H.; Mehta, R. G.; Pezzuto, J. M.; Kinghorn, A. D. Sesquiterpenoids from Tithonia diversifolia with potential cancer chemopreventive activity J. Nat. Prod. 2002, 65, 532-536 (Pubitemid 34456938)
15. Kuroda, M.; Yokosuka, A.; Kobayashi, R.; Jitsuno, M.; Kando, H.; Nosaka, K.; Ishii, H.; Yamori, T.; Mimaki, Y. Sesquiterpenoids and flavonoids from the aerial parts of Tithonia diversifolia and their cytotoxic activity Chem. Pharm. Bull. 2007, 55, 1240-1244 (Pubitemid 47344981)
16. Kroemer, G.; Martin, S. J. Caspase-independent cell death Nat. Med. 2005, 11, 725-730 (Pubitemid 41021204)
17. Huang, Q.; Wu, Y. T.; Tan, H. L.; Ong, C. N.; Shen, H. M. A novel function of poly(ADP-ribose) polymerase-1 in modulation of autophagy and necrosis under oxidative stress Cell Death Differ. 2009, 16, 264-277
18. Klionsky, D. J.; Ohsumi, Y. Vacuolar import of proteins and organelles from the cytoplasm Annu. Rev. Cell Dev. Biol. 1999, 15, 1-32 (Pubitemid 32250369)
19. Dunn, W. J. Autophagy and related mechanisms of lysosomemediated protein degradation Trends Cell Biol. 1994, 4, 139-143
20. Kim, J.; Klionsky, D. J. Autophagy, cytoplasm-to-vacuole targeting pathway, and pexophagy in yeast and mammalian cells Annu. Rev. Biochem. 2000, 69, 303-342
21. Seglen, P. O.; Bohley, P. Autophagy and other vacuolar protein degradation mechanisms Experientia 1992, 48, 158-172
22. Klionsky, D. J.; Emr, S. D. Autophagy as a regulated pathway of cellular degradation Science 2000, 290, 1717-1721 (Pubitemid 32004796)
23. Dunn, W. A., Jr. Studies on the mechanisms of autophagy: Formation of the autophagic vacuole J. Cell Biol. 1991, 110, 1923-1933
24. Fengsrud, M.; Roos, N.; Berg, T.; Liou, W.; Slot, J. W.; Seglen, P. O. Ultrastructural and immunocytochemical characterization of autophagic vacuoles in isolated hepatocytes: Effects of vinblastine and asparagine on vacuole distributions Exp. Cell Res. 1995, 221, 504-519
25. Klionsky, D. J. The molecular machinery of autophagy: Unanswered questions J. Cell Sci. 2005, 118, 7-18 (Pubitemid 40277100)
26. Klionsky, D. J.; Cregg, J. M.; Dunn, W. A. J.; Emr, S. D.; Sakai, Y.; Sandoval, I. V.; Sibirny, A.; Subramani, S.; Thumm, M.; Veenhuis, M.; Ohsumi, Y. A unified nomenclature for yeast autophagy-related genes Dev. Cell 2003, 5, 539-545 (Pubitemid 37243044)
27. Prick, T.; Thumm, M.; Kohrer, K.; Haussinger, D.; Vom Dahl, S. In yeast, loss of Hog1 leads to osmosensitivity of autophagy Biochem. J. 2006, 394, 153-161 (Pubitemid 43259665)
28. Philipp, A. J.; Tony, W. C. All-you-can-eat: Autophagy in neurodegeneration and neuroprotection Mol. Neurodegener. 2009, 4, 16-38
29. Liao, M. H.; Lin, W. C.; Wen, H. C.; Pu, H. F. Tithonia diversifolia and its main active component tagitinin C induce survivin inhibition and G2/M arrest in human malignant glioblastoma cells Fitoterapia 2010, 10.1016/j.fitote.2010. 11.002
30. Takao, K.; Yasuko, K.; Hideaki, I.; Seiji, K.; Isabelle, G. Induction of autophagic cell death in malignant glioma cells by arsenic trioxide Cancer Res. 2003, 63, 2103-2108
31. Boya, P.; Gonzalez-Polo, R. A.; Casares, N.; Perfettini, J. L.; Dessen, P.; Larochette, N.; Me'tivier, D.; Meley, D.; Souquere, S.; Yoshimori, T.; Pierron, G.; Codogno, P.; Kroemer, G. Inhibition of macroautophagy triggers apoptosis Mol. Cell. Biol. 2005, 25, 1025-1040 (Pubitemid 40165810)
32. Gonzalez-Polo, R. A.; Boya, P.; Pauleau, A. L.; Jalil, A.; Larochette, N.; Souquere, S.; Eskelinen, E. L.; Pierron, G.; Saftig, P.; Kroemer, G. The apoptosis/autophagy paradox: Autophagic vacuolization before apoptotic death J. Cell Sci. 2005, 118, 3091-3102 (Pubitemid 41149913)
33. Wong, C. H.; Iskandar, K. B.; Yadav, S. K.; Hirpara, J. L.; Loh, T.; Pervaiz, S. Simultaneous induction of non-canonical autophagy and apoptosis in cancer cells by ROS-dependent ERK and JNK activation PLoS One 2010, 5, 1-12