Curcuminoids from Curcuma longa and their inhibitory activities on influenza A neuraminidases

Food Chemistry

Volumn 134, Issue 1, 2012, Pages 21-28

  Dao, Trong Tuan ^a   Nguyen, Phi Hung ^a   Won, Ho Keun ^b   Kim, Eun Hee ^b   Park, Junsoo ^c   Won, Boo Yeon ^a   Oh, Won Keun ^a  

^a Chosun University   (South Korea)

^b Choongang Vaccine Laboratory   (South Korea)

^c Yonsei University Wonju   (South Korea)

Author keywords

Curcuma longa; Curcuminoids; Influenza A; Neuraminidase inhibitors; Oseltamivir resistance

Indexed keywords

CURCUMA LONGA; CURCUMINOIDS; INFLUENZA A; NEURAMINIDASE; OSELTAMIVIR;

METHANOL;

VIRUSES;

1 (4 HYDROXY 3 METHOXYPHENYL) 7 (3,4 DIHYDROXYPHENYL) 1,6 HEPTADIENE 3,5 DIONE; 1 (4 HYDROXYPHENYL) 7 (3,4 DIHYDROXYPHENYL) 1,6 HEPTADIENE 3,5 DIONE; 1,5 BIS(4 HYDROXYPHENYL) 1,4 PENTADIENE 3 ONE; 1,5 DIHYDROXY 1,7 BIS(4 HYDROXYL 3 METHOXYPHENYL) 4,6 HEPTADIENE 3 ONE; 1,5 DIHYDROXY 1,7 BIS(4 HYDROXYPHENYL) 4,6 HEPTADIENE 3 ONE; 5 HYDROXY 1,7 BIS(4 HYDROXYPHENYL) 4,6 HEPTADIENE 3 ONE; CURCUMA LONGA EXTRACT; CURCUMALONGIN A; CURCUMALONGIN B; CURCUMALONGIN C; CURCUMIN; DEMETHOXYCURCUMIN; DIDEMETHOXYCURCUMIN; DINORCURCUMIN; METHANOL; OSELTAMIVIR; UNCLASSIFIED DRUG; VIRUS SIALIDASE;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CURCUMA LONGA; DRUG ISOLATION; DRUG POTENTIATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; INFLUENZA VIRUS A H1N1; INFLUENZA VIRUS A H9N2; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RHIZOME; SOLVENT EXTRACTION; VIRUS STRAIN;

CURCUMA LONGA; ORTHOMYXOVIRIDAE;

EID: 84862806835     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.02.015     Document Type: Article

References (28)

1. H.P. Ammon, and M.A. Wahl Pharmacology of Curcuma longa Planta Medica 57 1991 1 7
2. J. Beigel, and M. Bray Current and future antiviral therapy of severe seasonal and avian influenza Antiviral Research 78 2008 91 102
3. D.Y. Chen, J.H. Shien, L. Tiley, S.S. Chiou, S.Y. Wang, and T.J. Chang Curcumin inhibits influenza virus infection and haemagglutination activity Food Chemistry 119 2010 1346 1351
4. P.M. Colman New antivirals and drug resistance Annual Review of Biochemistry 78 2009 95 118
5. G. Comte, D.P. Allais, A.J. Chulia, J. Vercauteren, and C. Delage Two furanone glucoside derivatives from Juniperus phoenicea Phytochemistry 41 1996 1329 1332
6. T.T. Dao, B.T. Tung, P.H. Nguyen, P.T. Thuong, S.S. Yoo, and E.H. Kim C-methylated flavonoids from Cleistocalyx operculatus and their inhibitory effects on novel influenza A (H1N1) neuraminidase Journal of Natural Products 73 2010 1636 1642
7. E. De Clercq Antiviral agents active against influenza A viruses Nature Reviews Drug Discovery 5 2006 1015 1025
8. J. Gershenzon, and T.J. Mabry Furanoheliangolides from Helianthus schweinitzii Phytochemistry 23 1984 2557 2559
9. U. Grienke, M. Schmidtke, J. Kirchmair, K. Pfarr, P. Wutzler, and R. Dürrwald Antiviral potential and molecular insight into neuraminidase inhibiting diarylheptanoids from Alpinia katsumadai Journal of Medicinal Chemistry 53 2010 778 786
10. H.C. Hung, C.P. Tseng, J.M. Yang, Y.W. Ju, S.N. Tseng, and Y.F. Chen Aurintricarboxylic acid inhibits influenza virus neuraminidase Antiviral Research 81 2009 123 131
11. A.C. Hurt, J.K. Holien, M.W. Parker, and I.G. Barr Oseltamivir resistance and the H274Y neuraminidase mutation in seasonal, pandemic and highly pathogenic influenza viruses Drugs 69 2009 2523 2531
12. G.K. Jayaprakasha, L.J.M. Rao, and K.K. Sakariah Improved HPLC method for the determination of curcumin, demethoxycurcumin, and bisdemethoxycurcumin Journal of Agricultural and Food Chemistry 50 2002 3668 3672
13. W. Li, S. Wang, J. Feng, Y. Xiao, X. Xue, and H. Zhang Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa Magnetic Resonance in Chemistry 47 2009 902 908
14. T. Masuda, A. Jitoe, J. Isobe, N. Nakatani, and S. Yonemori Anti-oxidative and anti-inflammatory curcumin-related phenolics from rhizomes of Curcuma domestica Phytochemistry 32 1993 1557 1560
15. S. Miriyala, M. Panchatcharam, and P. Rengarajulu Cardioprotective effects of curcumin Advances in Experimental Medicine and Biology 595 2007 359 377
16. T.N.A. Nguyen, T.T. Dao, B.T. Tung, H. Choi, E. Kim, and J. Park Influenza A (H1N1) neuraminidase inhibitors from Vitis amurensis Food Chemistry 124 2011 437 443
17. y mice Journal of Agricultural and Food Chemistry 53 2005 959 963
18. S.Y. Park, and D.S. Kim Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: A drug discovery effort against Alzheimer's disease Journal of Natural Products 65 2002 1227 1231
19. J. Ravindran, S. Prasad, and B.B. Aggarwal Curcumin and cancer cells: How many ways can curry kill tumour cells selectively? The AAPS Journal 11 2009 495 510
20. R.R. Regoes, and S. Bonhoeffer Emergence of drug-resistant influenza virus: Population dynamical considerations Science 312 2006 389 391
21. D.M. Ryan, J. Ticehurst, and M.H. Dempsey GG167 (4-guanidino-2,4-dideoxy- 2,3-dehydro-N-acetylneuraminic acid) is a potent inhibitor of influenza virus in ferrets Antimicrobial Agents and Chemotherapy 39 1995 2583 2584
22. A. Simon, D.P. Allais, J.L. Duroux, J.P. Basly, S.F. Durand, and C. Delage Inhibitory effect of curcuminoids on MCF-7 cell proliferation and structure-activity relationships Cancer Letters 129 1998 111 116
23. D.F. Smee, B.L. Hurst, M.H. Wong, E.B. Tarbet, Y.S. Babu, and K. Klumpp Combinations of oseltamivir and peramivir for the treatment of influenza A (H1N1) virus infections in cells culture and in mice Antiviral Research 88 2010 38 44
24. N.H. Tung, H.J. Kwon, J.H. Kim, J.C. Ra, Y. Ding, and J.A. Kim Anti-influenza diarylheptanoids from the bark of Alnus japonica Bioorganic and Medicinal Chemistry Letters 20 2010 1000 1003
25. S. Venkateswarlu, M.S. Ramachandra, and G.V. Subbaraju Synthesis and biological evaluation of polyhydroxycurcuminoids Bioorganic and Medicinal Chemistry 13 2005 6374 6380
26. Y. Xie, J. Gong, M. Li, H. Fang, and W. Xu The medicinal potential of influenza virus surface proteins: Hemagglutinin and neuraminidase Current Medicinal Chemistry 18 2011 1050 1066
27. H. Yamakoshi, H. Ohori, C. Kudo, A. Sato, N. Kanoh, and C. Ishioka Structure-activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof Bioorganic and Medicinal Chemistry 18 2010 1083 1092
28. J. Zhang, K. Yu, W. Zhu, and H. Jiang Neuraminidase pharmacophore model derived from diverse classes of inhibitors Bioorganic and Medicinal Chemistry Letters 16 2006 3009 3014