Isolation and identification of an antiproliferative substance from fructose-tyrosine Maillard reaction products

Food Chemistry

Volumn 130, Issue 3, 2012, Pages 547-551

  Hwang, In Guk ^a   Kim, Hyun Young ^b   Lee, Sang Hoon ^b   Woo, Koan Sik ^a   Ban, Jung Ok ^b   Hong, Jin Tae ^b   Yu, Kwang Won ^c   Lee, Junsoo ^b   Jeong, Heon Sang ^b  

^a National Institute of Animal Science   (South Korea)

^b Chungbuk National University   (South Korea)

^c Chungju National University   (South Korea)

Author keywords

2,4 Bis(p hydroxyphenyl) 2 butenal; Antiproliferative effect; Fructose tyrosine MRPs; Maillard reaction

Indexed keywords

ANTI-PROLIFERATIVE; ANTIPROLIFERATIVE EFFECT; BUTENAL; DOSE-DEPENDENT MANNER; ETHYL ACETATES; FRUCTOSE-TYROSINE MRPS; HUMAN CANCER CELLS; ISOLATED COMPOUNDS; ISOLATION AND IDENTIFICATION; MAILLARD REACTION; MAILLARD REACTION PRODUCTS; RP-HPLC; SILICA GEL COLUMN CHROMATOGRAPHY; SPECTROSCOPIC METHOD;

AMINO ACIDS; CELL CULTURE; CELLS; COLUMN CHROMATOGRAPHY; DISEASES; GLYCOSYLATION; GROWTH KINETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PURIFICATION; REACTION PRODUCTS; SILICA; SILICA GEL; SPECTROSCOPIC ANALYSIS;

FRUCTOSE;

2,4 BIS(4 HYDROXYPHENYL) 2 BUTENAL; ACETIC ACID ETHYL ESTER; CROTONALDEHYDE; FRUCTOSE; FRUCTOSE TYROSINE MAILLARD REACTION PRODUCT; SILICA GEL; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CELL GROWTH; CELL PROLIFERATION; GEL CHROMATOGRAPHY; GLYCATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; SPECTROSCOPY;

EID: 80052754485     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2011.07.068     Document Type: Article

References (26)

1. J.O. Ban, I.G. Hwang, T.M. Kim, B.Y. Hwang, U.S. Lee, and H.S. Jeong Anti-proliferate and pro-apoptotic effects of 2,3-dihydro-3,5-dihydroxy-6- methyl-4H-pyranone through inactivation of NF-κB in human colon cancer cells Archives of Pharmacal Research 30 2007 1455 1463
2. J.O. Ban, D.Y. Yuk, K.S. Woo, T.Y. Kim, U.S. Lee, and H.S. Jeong Inhibition of cell growth and induction of apoptosis via inactivation of NF-κB by a sulfur compound isolated from garlic in human colon cancer cells Journal of Pharmacological Sciences 104 2007 374 383
3. R.J. Bold, P.M. Termuhlen, and D.J. McConkey Apoptosis, cancer, and cancer therapy Journal of Surgical Oncology 6 1997 133 142
4. Y.L. Cheng, S.C. Lee, S.Z. Lin, W.L. Chang, Y.L. Chen, and N.M. Tasi Anti-proliferative activity of Bupleurum scrozonerifolium in A549 human lung cancer cells in vitro and in vivo Cancer Letters 222 2005 183 193
5. K. Hiramoto, R. Aso-o, H. Ni-iyama, S. Hikage, T. Kato, and K. Kikugawa DNA strand break by 2,5-dimethyl-4-hydroxy-3(2H)-furanone, a fragrant compound in various foodstuffs Mutation Research 359 1996 17 24 (Pubitemid 26031090)
6. M.L. Hooper, N. Toft, S. Webb, and C.C. Bird Apoptosis and carcinogenesis British Journal of Cancer 80 1999 34 37 (Pubitemid 29389605)
7. I.G. Hwang, H.Y. Kim, K.S. Woo, J. Lee, and H.S. Jeong Biological activities of Maillard reaction products (MRPs) in a sugar-amino acid model system Food Chemistry 126 2011 221 227
8. I.G. Hwang, K.S. Woo, D.J. Kim, J.T. Hong, B.Y. Hwang, and Y.R. Lee Isolation and identification of an antioxidant substance from heated garlic (Allium sativum L.) Food Science and Biotechnology 16 2007 963 966
9. I.G. Hwang, K.S. Woo, T.M. Kim, D.J. Kim, M.H. Yang, and H.S. Jeong Change of physicochemical characteristics of Korean pear (Pyrus pyrifolia Nakai) juice with heat treatment conditions Korean Journal of Food Science and Technology 38 2006 342 347
10. Jeong, H.S., Woo, K.S., Hwang, I.G., Kim, D.J., Hong, J.T. 2008. Synthetic methods of thiacremonone. Korean Patent Application No. 20080089028.
11. H. Jing, and D. Kitts Antioxidant activity of sugar-lysine Maillard reaction products in cell free and cell culture systems Archives of Biochemistry and Biophysics 429 2004 154 163 (Pubitemid 39099250)
12. A.D. Kinghorn, N.R. Farnsworth, D.D. Soejarto, G.A. Cordell, S.M. Swanson, and J.M. Pezzuto Novel strategies for the discovery of plant-derived anticancer agents Pharmaceutical Biology 41 2003 53 67 (Pubitemid 39564233)
13. O.C. Kwon, K.S. Woo, T.M. Kim, D.J. Kim, J.T. Hong, and H.S. Jeong Physicochemical characteristics of garlic (Allium sativum L.) on the high temperature and pressure treatment Korean Journal of Food Science and Technology 38 2006 331 336
14. J.Y. Lee, W.I. Hwang, and S.T. Lim Antioxidant and anticancer activities of organic extracts from Platycodon grandiflorum A De Candolle roots. Journal of Ethnopharmacology 93 2004 409 415
15. W. Lertittikul, S. Benjakul, and M. Tanake Characteristics and antioxidative of Maillard reaction products from a porcine plasma protein-glucose model system as influenced by pH Food Chemistry 100 2007 669 677 (Pubitemid 43928367)
16. X. Li, K. Hiramoto, M. Yoshida, T. Kato, and K. Kikugawa Identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) with DNA breaking activity in soy sauce Food and Chemical Toxicology 36 1998 305 314 (Pubitemid 28255343)
17. M.N. Maillard, C. Billaud, Y.N. Chow, C. Ordonaud, and J. Nicolas Free radical scavenging, inhibition of polyphenoloxidase activity and copper chelating properties of model Maillard systems LWT-Food Science and Technology 40 2007 1434 1444 (Pubitemid 46745297)
18. L. Manzocco, S. Calligaris, D. Mastrocola, M.C. Nicoli, and C.R. Lerici Review of non-enzymatic browning and antioxidant capacity in processed foods Trends in Food Science & Technology 11 2001 340 346
19. D. Marko, M. Habermeyer, M. Kemény, U. Weyand, E. Niederberger, and O. Frank Maillard reaction products modulating the growth of human tumor cells in vitro Chemical Research in Toxicology 16 2003 48 55 (Pubitemid 36139410)
20. D. Marko, M. Kemény, E. Bernady, M. Habermeyer, U. Weyand, and S. Meiers Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product Food and Chemical Toxicology 40 2002 9 18 (Pubitemid 33132136)
21. F. Morales, and S. Jiménez-Pérez Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence Food Chemistry 72 2001 119 125
22. J. Rufián-Henares, and F. Morales Angiotensin-I converting enzyme inhibitory activity of coffee melanoidins Journal of Agricultural and Food Chemistry 55 2007 1480 1485
23. J. Rufián-Henares, and F. Morales Functional properties of melanoidins: In vitro antioxidant, antimicrobial and antihypertens e activities Food Research International 40 2007 995 1002 (Pubitemid 47223699)
24. J. Wu, Y. Wu, and B.B. Yang Anticancer activity of Hemsleya amabilis extract Life Science 71 2002 2161 2170
25. G.C. Yen, and L.C. Tsai Antimutagenicity of a partially fractionated Maillard reaction product Food Chemistry 47 1993 11 15
26. Y. Yilmaz, and R. Toledo Antioxidant activity of water-soluble Maillard reaction products Food Chemistry 93 2005 273 278 (Pubitemid 40724513)