Cytotoxic activity of rearranged drimane meroterpenoids against colon cancer cells via down-regulation of β-catenin expression

Journal of Natural Products

Volumn 78, Issue 3, 2015, Pages 453-461

  Hwang, In Hyun ^a   Oh, Joonseok ^b   Zhou, Wei ^d   Park, Seoyoung ^e   Kim, Joo Hyun ^e   Chittiboyina, Amar G ^c   Ferreira, Daneel ^b   Song, Gyu Yong ^d   Oh, Sangtaek ^e   Na, Minkyun ^d   Hamann, Mark T ^b  

^a E11 SSH   (United States)

^b School of Pharmacy   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d Chungnam National University   (South Korea)

^e Kookmin University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

17 HYDROXY 19 METHOXY 20 OXO 16 [(5,8,9 TRIMETHYL 4 METHYLENEDECAHYDRONAPHHTHALEN 9 YL)METHYL]CYCLOPENT 18 ENE 17 CARBOXYLATE; 17 HYDROXY 19 METHOXY 20 OXO 16 [(5,8,9 TRIMETHYL 4 METHYLENEDECAHYDRONAPHTHALEN 9 YL)METHYL]CYCLOPENT 18 ENE 17 CARBOXYLATE; 18 METHOXY 22 METHYL 16 [(5,8,9 TRIMETHYL 4 METHYLENEDECAHYDRONAPHTHALEN 9 YL)METHYL]BENZO[D]OXAZOL 17 OL; 18 METHOXY 22 METHYL 16 [(5,8,9TRIMETHYL 4 METHYLENEDECAHYDRONAPHTHALEN 9 YL)METHYL]BENZO[D]OXAZOL 17 OL; 18 METHOXY 22,22 DIMETHYL 16 [(5,8,9 TRIMETHYL 4 METHYLENEDECAHYDRONAPHTHALEN 9 YL)METHYL]BENZO[D]OXAZOL 17(2H) ONE; 20 ETHOXY 17 HYDROXY 16 [(5,8,9 TRIMETHYL 4 METHYLENEDECAHYDRONAPHTHALEN 9 YL)METHYL]CYCLOHEXA 16,19 DIENNE 18,21 DIONE; ANTINEOPLASTIC AGENT; BETA CATENIN; SESQUITERPENOID; UNCLASSIFIED DRUG; DRIMANE; SESQUITERPENE; TERPENE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; COLON CANCER; CONTROLLED STUDY; DOWN REGULATION; EMBRYO; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; METABOLITE; OXIDATION REDUCTION POTENTIAL; PROTEIN DEGRADATION; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; SMENOSPONGIA AUREA; SMENOSPONGIA CEREBRIFORMIS; SPONGE (PORIFERA); STEREOCHEMISTRY; VERONGULA RIGIDA; CHEMICAL STRUCTURE; CHEMISTRY; COLONIC NEOPLASMS; DRUG EFFECTS; DRUG SCREENING; GENETICS; ISOLATION AND PURIFICATION;

SMENOSPONGIA; VERONGULA;

ANTINEOPLASTIC AGENTS; BETA CATENIN; COLONIC NEOPLASMS; DOWN-REGULATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; SESQUITERPENES; TERPENES;

EID: 84925937450     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500843m     Document Type: Article

References (26)

1. National Cancer Institute. http://seer.cancer.gov/ accessed on 4/10/ 2104.
2. Satoh, S.; Daigo, Y.; Furukawa, Y.; Kato, T.; Miwa, N.; Nishiwaki, T.; Kawasoe, T.; Ishiguro, H.; Fujita, M.; Tokino, T. Nat. Genet. 2000, 24, 245-250
3. Lepourcelet, M.; Chen, Y.-N. P.; France, D. S.; Wang, H.; Crews, P.; Petersen, F.; Bruseo, C.; Wood, A. W.; Shivdasani, R. A. Cancer Cell 2004, 5, 91-102
4. Gwak, J.; Oh, J.; Cho, M.; Bae, S. K.; Song, I.-S.; Liu, K.-H.; Jeong, Y.; Kim, D.-E.; Chung, Y.-H.; Oh, S. Mol. Pharmacol. 2011, 79, 1014-1022
5. Sharma, M.; Li, L.; Celver, J.; Killian, C.; Kovoor, A.; Seeram, N. P. J. Agric. Food Chem. 2009, 58, 3965-3969
6. Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discovery 2009, 8, 69-85
7. Lu, P.-H.; Chueh, S.-C.; Kung, F.-L.; Pan, S.-L.; Shen, Y.-C.; Guh, J.-H. Eur. J. Pharmacol. 2007, 556, 45-54
8. Du, L.; Zhou, Y.-D.; Nagle, D. G. J. Nat. Prod. 2013, 76, 1175-1181
9. Park, S.; Yun, E.; Hwang, I. H.; Yoon, S.; Kim, D.-E.; Kim, J.; Na, M.; Song, G.-Y.; Oh, S. Mar. Drugs 2014, 12, 3231-3244
10. Hamann, M. T. Curr. Pharm. Des. 2003, 9, 879-889
11. Hwang, I. H.; Oh, J.; Kochanowska-Karamyan, A.; Doerksen, R. J.; Na, M.; Hamann, M. T. Tetrahedron Lett. 2013, 54, 3872-3876
12. Nasu, S. S.; Yeung, B. K.; Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M.; Goins, K. J. Org. Chem. 1995, 60, 7290-7292
13. Menna, M.; Imperatore, C.; D'Aniello, F.; Aiello, A. Mar. Drugs 2013, 11, 1602-1643
14. Daletos, G.; de Voogd, N. J.; Müller, W. E.; Wray, V.; Lin, W.; Feger, D.; Kubbutat, M.; Aly, A. H.; Proksch, P. J. Nat. Prod. 2014, 77, 218-226
15. Rodríguez, J.; Quiñoá, E.; Riguera, R.; Peters, B. M.; Abrell, L. M.; Crews, P. Tetrahedron 1992, 48, 6667-6680
16. Salmoun, M.; Devijver, C.; Daloze, D.; Braekman, J. C.; Gomez, R.; De Kluijver, M.; Van Soest, R. J. Nat. Prod. 2000, 63, 452-456
17. Kushlan, D. M.; Faulkner, D. J.; Parkanyi, L.; Clardy, J. Tetrahedron 1989, 45, 3307-3312
18. Smith, S. G.; Goodman, J. M. J. Org. Chem. 2009, 74, 4597-4607
19. Smith, S. G.; Goodman, J. M. J. Am. Chem. Soc. 2010, 132, 12946-12959
20. Cho, M.; Gwak, J.; Park, S.; Won, J.; Kim, D.-E.; Yea, S. S.; Cha, I.-J.; Kim, T. K.; Shin, J.-G.; Oh, S. FEBS Lett. 2005, 579, 4213-4218
21. Zhou, W.; Oh, J.; Wonhwa, L.; Kwak, S.; Li, W.; Chittiboyina, A. G.; Ferreira, D.; Hamann, M. T.; Lee, S. H.; Bae, J.-S. Biochim. Biophys. Acta, Gen. Subj. 2014, 1840, 2042-2049
22. Park, S.; Gwak, J.; Cho, M.; Song, T.; Won, J.; Kim, D.-E.; Shin, J.-G.; Oh, S. Mol. Pharmacol. 2006, 70, 960-966
23. Ryu, M.-J.; Cho, M.; Song, J.-Y.; Yun, Y.-S.; Choi, I.-W.; Kim, D.-E.; Park, B.-S.; Oh, S. Biochem. Biophys. Res. Commun. 2008, 377, 1304-1308
24. Dignam, J. D.; Lebovitz, R. M.; Roeder, R. G. Nucleic Acids Res. 1983, 11, 1475-1489
25. Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114-1115
26. Carte, B.; Rose, C. B.; Faulkner, D. J. J. Org. Chem. 1985, 50, 2785-2787