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Isolation and Structure Determination of an Imidazo-pyrimidine, 5-Chlorocavernicolin, Maleimide oximes and Nucleosides from a Marine Sponge Extract  

Kulkarni, Roshan R. (College of Pharmacy, Chungnam National University)
Kim, Jang Hoon (College of Pharmacy, Chungnam National University)
Kim, Young Ho (College of Pharmacy, Chungnam National University)
Oh, Sangtaek (Department of Bio and Fermentation Convergence Technology, Kookmin University)
Na, MinKyun (College of Pharmacy, Chungnam National University)
Publication Information
Natural Product Sciences / v.21, no.1, 2015 , pp. 25-29 More about this Journal
Abstract
In a continuation of our studies to discover bioactive secondary metabolites from marine sources, we further investigated samples from a tryptamine and phenyl-alkane producing sponge, which resulted in the isolation of four uncommon small molecules and five nucleosides. Their structures were determined to be 7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one (1), 5-chlorocavernicolin (2), maleimide-5-oxime (3), 3-methylmaleimide-5-oxime (4), uridine (5), 2'-deoxyuridine (6), thymidine (7), adenine (8), and adenosine (9) by spectroscopic analyses. The isolated compounds were evaluated for inhibitory activity against soluble epoxide hydrolase (sEH) as well as the Wnt/${\beta}$-catenine signaling pathway.
Keywords
Imidazo-pyrimidine; 5-Chlorocavernicolin; Maleimide-5-oxime; Nucleoside; Soluble epoxide hydrolase; Wnt/${\beta}$-catenine signaling;
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1 Park, S.; Gwak, J.; Cho, M.; Song, T.; Won, J.; Kim, D. -E.; Shin, J. -G.; Oh, S. Mol. Pharmacol. 2006, 70, 960-966.   DOI   ScienceOn
2 Durmus, S.; Garrison, J. C.; Panzner, M. J.; Tessier, C. A.; Youngs, W. J. Tetrahedron 2005, 61, 97-101.   DOI   ScienceOn
3 Lira, N. S.; Montes, R. C.; Tavares, J. F.; da Silva, M. S.; da Cunha, E. V. L.; de Athayde-Filho, P. F.; Rodrigues, L. C.; da Silva Dias, C.; Barbosa-Filho, J. M. Mar. Drugs 2011, 9, 2316-2368.   DOI
4 Leal, M. C.; Puga, J.; Serodio, J.; Gomes, N. C. M.; Calado, R. PLoS ONE 2012, 7, e30580. doi:10.1371/journal.pone.0030580.   DOI
5 Bao, L.; Deng, A.; Li, Z.; Du, G.; Qin, H. Zhongguo Zhong Yao Za Zhi. 2010, 35, 598-601.
6 Kijjoa, A.; Bessa, J.; Wattanadilok, R.; Sawangwong, P.; Nascimento, M. S. J.; Pedro, M.; Silva, A. M. S.; Eaton, G.; Van Soest, R.; Herz, W. Z. Naturforsch. 2005, 60b, 904-908.
7 Perdicaris, S.; Vlachogianni, T.; Valavanidis, A. Nat. Prod. Chem. Res. 2013, 1, 114 doi:10.4172/2329-6836.1000115.   DOI
8 Kingston, D. G. I. J. Nat. Prod. 2011, 74, 496-511.   DOI   ScienceOn
9 Montaser, R.; Luesch, H. Future Med. Chem. 2011, 3, 1475-1489.   DOI   ScienceOn
10 Kochanowska, A. J.; Rao, K. V.; Childress, S.; El-Alfy, A.; Matsumoto, R. R.; Kelly, M.; Stewart, G. S.; Sufka, K. J.; Hamann, M. T. J. Nat. Prod. 2008, 71, 186-189.   DOI   ScienceOn
11 Hwang, I. H.; Oh, J.; Kochanowska-Karamyan, A.; Doerksen, R. J.; Na, M.; Hamann, M. T. Tetrahedron Lett. 2013, 54, 3872-3876.   DOI   ScienceOn
12 Zhu, F.; Han, B.; Kumar, P.; Liu, X.; Ma, X.; Wei, X.; Huang, L.; Guo, Y.; Han, L.; Zheng, C.; Chen, Y. Nucleic Acids Res. 2010, 38(database issue), D787-D791.   DOI   ScienceOn
13 Hammock, B. D.; Wagner, K.; Inceoglu, B. Pain Manage. 2011, 1, 383-386.   DOI   ScienceOn
14 Pillarisetti, S.; Khanna, I. Inflamm. Allergy Drug Targets 2012, 11, 143-158.   DOI
15 Shen, H. C.; Hammock, B. D. J. Med. Chem. 2012, 55, 1789-1808.   DOI   ScienceOn
16 Park, S.; Yun, E.; Hwang, I. H.; Yoon, S.; Kim, D.-E.; Kim, J. S.; Na, M.; Song, G. -Y., Oh, S. Mar. Drugs 2014, 12, 3231-3244.   DOI   ScienceOn
17 Mayer, A. M. S.; Glaser, K. B.; Cuevas, C.; Jacobs, R. S.; Kem, W.; Little, R. D.; McIntosh, J. M.; Newman, D. J.; Potts, B. C.; Shuster, D. E. Trends Pharmacol. Sci. 2010, 31, 255-265.   DOI   ScienceOn
18 Wattanadilok, R.; Sawangwong, P.; Rodrigues, C.; Cidade, H.; Pinto, M.; Pinto, E.; Silva, A.; Kijjoa, A. Mar. Drugs 2007, 5, 40-51.   DOI
19 Ciminiello, P.; Costantino, V.; Fattorusso, E.; Magno, S.; Mangoni, A. J. Nat. Prod. 1994, 57, 705-712.   DOI   ScienceOn