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Isolation, Docking and Cytotoxicity Evaluation Against Cholangiocarcinoma of Labdanes from Curcuma petiolata
Corresponding Author(s) : Chavi Yenjai
Asian Journal of Chemistry,
Vol. 26 No. 14 (2014): Vol 26 Issue 14
Abstract
Labdanes 1-4, stigmasterol (5) and vanillin (6) were isolated from the rhizomes of Curcuma petiolata. Compounds 2-4 exhibited strong to moderate cytotoxicity against cholangiocarcinoma cell lines. Compound 3 showed strong cytotoxicity with IC50 values ranging from 5-11 μg/mL. The molecular modeling was studied using the AutoDock 4 program. The docking results reveal that 3 interacted with EGFR through the 2 H-bond at Gln767 and Met769 with binding energy of -6.89 kcal/mol.
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- B. Sripa and C. Pairojkul, Curr. Opin. Gastroenterol., 24, 349 (2008); doi:10.1097/MOG.0b013e3282fbf9b3.
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References
B. Sripa and C. Pairojkul, Curr. Opin. Gastroenterol., 24, 349 (2008); doi:10.1097/MOG.0b013e3282fbf9b3.
L.K. Sampson, S.M. Vickers, W. Ying and J.O. Phillips, Cancer Res., 57, 1743 (1997).
W. Loilome, P. Yongvanit, C. Wongkham, N. Tepsiri, B. Sripa, P. Sithithaworn, S. Hanai and M. Miwa, Mol. Carcinog., 45, 279 (2006); doi:10.1002/mc.20094.
U. Songsiang, S. Pitchuanchom, C. Boonyarat, C. Hahnvajanawong and C. Yenjai, Eur. J. Med. Chem., 45, 3794 (2010); doi:10.1016/j.ejmech.2010.05.029.
U. Songsiang, T. Thongthoom, P. Zeekpudsa, V. Kukongviriyapan, C. Boonyarat, J. Wangboonskul and C. Yenjai, Sci. Asia, 38, 75 (2012); doi:10.2306/scienceasia1513-1874.2012.38.075.
S. Pitchuanchom, C. Boonyarat, S. Forli, J.A. Olson and C. Yenjai, Comput. Biol. Med., 42, 106 (2012); doi:10.1016/j.compbiomed.2011.10.014.
D. Yoshikawa, H. Ojima, M. Iwasaki, N. Hiraoka, T. Kosuge, S. Kasai, S. Hirohashi and T. Shibata, Br. J. Cancer, 98, 418 (2008); doi:10.1038/sj.bjc.6604129.
J. Stamos, M.X. Sliwkowdki and C. Eigenbrot, J. Biol. Chem., 277, 46265 (2002); doi:10.1074/jbc.M207135200.
X. Lin, S. Ji, R. Li, Y. Dong, X. Qiao, H. Hu, W. Yang, D. Guo, P. Tu and M. Ye, J. Nat. Prod., 75, 2121 (2012); doi:10.1021/np300551g.
G.N. Roth, A. Chandra and M.G. Nair, J. Nat. Prod., 61, 542 (1998); doi:10.1021/np970459f.
N. Chimnoi, C. Sarasuk, N. Khunnawutmanotham, P. Intachote, S. Seangsai, B. Saimanee, S. Pisutjaroenpong, C. Mahidol and S. Techasakul, Phytochem. Lett., 2, 184 (2009); doi:10.1016/j.phytol.2009.06.003.
L.G. Mahaira, C. Tsimplouli, N. Sakellaridis, K. Alevizopoulos, C. Demetzos, Z. Han, P. Pantazis and K. Dimas, Eur. J. Pharmacol., 666, 173 (2011); doi:10.1016/j.ejphar.2011.04.065.
P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney and M.R. Boyd, J. Natl. Cancer Inst., 82, 1107 (1990); doi:10.1093/jnci/82.13.1107.
S.J. Weiner, P.A. Kollman, D.A. Case, U.C. Singh, C. Ghio, G. Alagona, S. Profeta and P. Weiner, J. Am. Chem. Soc., 106, 765 (1984); doi:10.1021/ja00315a051.
(a) G.M. Morris, D.S. Goodsell, R. Huey and A.J. Olson, J. Comput. Aided Mol. Des., 10, 293 (1996); doi:10.1007/BF00124499.; (b) G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew and A.J. Olson, J. Comput. Chem., 19, 1639 (1998); doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B.
J. Gasteiger and M. Marsili, Tetrahedron, 36, 3219 (1980); doi:10.1016/0040-4020(80)80168-2.
P.S. Hema and M.S. Nair, Biochem. Syst. Ecol., 37, 52 (2009); doi:10.1016/j.bse.2009.01.001.
H. Itokawa, M. Morita and S. Mihashi, Chem. Pharm. Bull. (Tokyo), 28, 3452 (1980); doi:10.1248/cpb.28.3452.
D.B. Alan Sheeja and M.S. Nair, Biochem. Syst. Ecol., 44, 264 (2012); doi:10.1016/j.bse.2012.06.008.
P.V. Kiem, N.T.K. Thuy, H.L.T. Anh, N.X. Nhiem, C.V. Minh, P.H. Yen, N.K. Ban, D.T. Hang, B.H. Tai, N.V. Tuyen, V.B. Mathema, Y.S. Koh and Y.H. Kim, Bioorg. Med. Chem. Lett., 21, 7460 (2011); doi:10.1016/j.bmcl.2011.09.129.