Identification of a cytotoxic molecule in heat-modified citrus pectin

Carbohydrate Polymers

Volumn 137, Issue , 2016, Pages 39-51

  Leclere, Lionel ^a   Fransolet, Maude ^a   Cambier, Pierre ^a   El Bkassiny, Sandy ^a   Tikad, Abdellatif ^a   Dieu, Marc ^a   Vincent, Stéphane P ^a   Van Cutsem, Pierre ^a   Michiels, Carine ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

4,5 Dihydroxy 2 cyclopenten 1 one; Cancer; Cytotoxic activity; Fragmented pectin

Indexed keywords

CELL DEATH; CYTOTOXICITY; DISEASES; HEAT TREATMENT; MASS SPECTROMETRY; MOLECULES;

4,5-DIHYDROXY-2-CYCLOPENTEN-1-ONE; ANTICANCER PROPERTIES; CANCER; CYTOTOXIC ACTIVITIES; ETHANOL PRECIPITATION; FRAGMENTED PECTIN; MASS SPECTROMETRY ANALYSIS; OLIGOGALACTURONIC ACIDS;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; PECTIN;

CELL DEATH; CHEMISTRY; DRUG EFFECTS; HEAT; HEP-G2 CELL LINE; HUMAN; MOLECULAR WEIGHT; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL DEATH; CELL LINE, TUMOR; CYCLOPENTANES; HEP G2 CELLS; HOT TEMPERATURE; HUMANS; MOLECULAR WEIGHT; PECTINS;

EID: 84945903067     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.10.055     Document Type: Article

References (37)

1. M. Bauer-Marinovic, F. Taugner, S. Florian, and H. Glatt Toxicity studies with 5-hydroxymethylfurfural and its metabolite 5-sulphooxymethylfurfural in wild-type mice and transgenic mice expressing human sulphotransferases 1A1 and 1A2 Archives of Toxicology 86 2012 701 711 10.1007/s00204-012-0807-5
2. S.S. Bharate, and S.B. Bharate Non-enzymatic browning in citrus juice: Chemical markers, their detection and ways to improve product quality Journal of Food Science and Technology 2012 10.1007/s13197-012-0718-8. 10.3389/fphar.2013.00128
3. D. Chauhan, G. Li, K. Podar, T. Hideshima, P. Neri, D. He, and et al. A novel carbohydrate-based therapeutic GCS-100 overcomes bortezomib resistance and enhances dexamethasone-induced apoptosis in multiple myeloma cells Cancer Research 65 2005 8350 8358 10.1158/0008-5472.CAN-05-0163
4. C. Chen, W. Ye, C. lLiu, and S.W. Schnelle 2′-Fluoro-3-deazaaristeromycin Tetrahedron 68 2012 3908 3914
5. H. Cheng, S. Li, Y. Fan, X. Gao, M. Hao, J. Wang, and et al. Comparative studies of the antiproliferative effects of ginseng polysaccharides on HT-29 human colon cancer cells Medical Oncology 28 2011 175 181 10.1007/s12032-010-9449-8
6. H. Cheng, Z. Zhang, J. Leng, D. Liu, M. Hao, X. Gao, and et al. The inhibitory effects and mechanisms of rhamnogalacturonan I pectin from potato on HT-29 colon cancer cell proliferation and cell cycle progression International Journal of Food Sciences and Nutrition 64 2013 36 43 10.3109/09637486.2012.694853
7. G.M. Cragg, and D.J. Newman Plants as a source of anti-cancer agents Journal of Ethnopharmacology 100 2005 72 79 10.1016/j.jep.2005.05.011
8. G.M. Cragg, and D.J. Newman Natural products: A continuing source of novel drug leads Biochimica et Biophysica Acta 1830 2013 3670 3695 10.1016/j.bbagen.2013.02.008
9. J.T. de Oliveira, A.J. de Matos, J. Gomes, M. Vilanova, V. Hespanhol, A. Manninen, and et al. Coordinated expression of galectin-3 and galectin-3-binding sites in malignant mammary tumors: Implications for tumor metastasis Glycobiology 20 2010 1341 1352 10.1093/glycob/cwq103
10. B. Diez-Dacal, and D. Perez-Sala A-class prostaglandins: Early findings and new perspectives for overcoming tumor chemoresistance Cancer Letters 320 2012 150 157 10.1016/j.canlet.2012.03.003
11. A. Fortuna-Costa, A.M. Gomes, E.O. Kozlowski, M.P. Stelling, and M.S. Pavao Extracellular galectin-3 in tumor progression and metastasis Frontiers in Oncology 4 2014 138 10.3389/fonc.2014.00138
12. X. Gao, Y. Zhi, T. Zhang, H. Xue, X. Wang, A.D. Foday, and et al. Analysis of the neutral polysaccharide fraction of MCP and its inhibitory activity on galectin-3 Glycoconjugate Journal 29 2012 159 165 10.1007/s10719-012-9382-5
13. J. Harholt, A. Suttangkakul, and H. Vibe Scheller Biosynthesis of pectin Plant Physiology 153 2010 384 395 10.1104/pp.110.156588
14. K. Hiramoto, A. Ishihara, N. Sakui, S. Daishima, and K. Kikugawa Formation of hydroxyfuranone and hydroxypyranone derivatives with DNA-breaking activity in the Maillard reaction of glucose and albumin under physiological conditions Biological & Pharmaceutical Bulletin 21 1998 102 104
15. A. Ibartz, D. Garza, and J. Pagan Nonenzymatic browning of selected fruit juices affected by d-galacturonic acid International Journal of Food Science & Technology 43 2008 908 914 10.3389/fphar.2013.00128
16. H. Inohara, and A. Raz Effects of natural complex carbohydrate (citrus pectin) on murine melanoma cell properties related to galectin-3 functions Glycoconjugate Journal 11 1994 527 532
17. C.L. Jackson, T.M. Dreaden, L.K. Theobald, N.M. Tran, T.L. Beal, M. Eid, and et al. Pectin induces apoptosis in human prostate cancer cells: Correlation of apoptotic function with pectin structure Glycobiology 17 2007 805 819 10.1093/glycob/cwm054
18. H.J. Kang, C. Jo, J.H. Kwon, J.H. Son, B.J. An, and M.W. Byun Antioxidant and cancer cell proliferation inhibition effect of citrus pectin-oligosaccharide prepared by irradiation Journal of Medicinal Food 9 2006 313 320 10.1089/jmf.2006.9.313
19. F. Klepper, E.-M. Jahn, V. Hickmann, and T. Carell Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate Angewandte Chemie International Edition 46 2007 23 27
20. L.M. Koharudin, H. Liu, R. Di Maio, R.B. Kodali, S.H. Graham, and A.M. Gronenborn Cyclopentenone prostaglandin-induced unfolding and aggregation of the Parkinson disease-associated UCH-L1 Proceedings of the National Academy of Sciences of the United States of America 107 2010 6835 6840 10.1073/pnas.1002295107
21. Koyama, N., Sagawa, H., Kobayashi, E., Enoki, T., Wu, H.-K., Nishiyama, E. et al. (2000). Cyclopentenones, process for preparing the seame, and the use thereof. US patent, 6,087, 401.
22. S.M. Kral, and R.F. McFeeters Pectin hydrolysis: Effect of temperature, degree of methylation, pH, and calcium on hydrolysis rates Journal of Agricultural and Food Chemistry 46 1998 1311 1315 10.3389/fphar.2013.00128
23. L. Leclere, M. Fransolet, F. Cote, P. Cambier, T. Arnould, P. Van Cutsem, and et al. Heat-modified citrus pectin induces apoptosis-like cell death and autophagy in HepG2 and A549 cancer cells PLoS ONE 10 2015 e0115831 10.1371/journal.pone.0115831
24. L. Leclere, P. Van Cutsem, and C. Michiels Anti-cancer activities of pH- or heat-modified pectin Frontiers in Pharmacology 4 2013 128 10.3389/fphar.2013.00128
25. H. Liu, W. Li, M. Ahmad, M.E. Rose, T.M. Miller, M. Yu, and et al. Increased generation of cyclopentenone prostaglandins after brain ischemia and their role in aggregation of ubiquitinated proteins in neurons Neurotoxicity Research 24 2013 191 204 10.1007/s12640-013-9377-4
26. D. Marko, M. Habermeyer, M. Kemeny, U. Weyand, E. Niederberger, O. Frank, and et al. Maillard reaction products modulating the growth of human tumor cells in vitro Chemical Research in Toxicology 16 2003 48 55 10.1021/tx025531a
27. D. Marko, M. Kemeny, E. Bernady, M. Habermeyer, U. Weyand, S. Meiers, and et al. 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 (an international journal published for the British Industrial Biological Research Association)
28. D. Mohnen Pectin structure and biosynthesis Current Opinion in Plant Biology 11 2008 266 277 10.1016/j.pbi.2008.03.006
29. J.E. Mullally, P.J. Moos, K. Edes, and F.A. Fitzpatrick Cyclopentenone prostaglandins of the J series inhibit the ubiquitin isopeptidase activity of the proteasome pathway The Journal of Biological Chemistry 276 2001 30366 30373 10.1074/jbc.M102198200
30. T. Nakayachi, E. Yasumoto, K. Nakano, S.R. Morshed, K. Hashimoto, H. Kikuchi, and et al. Structure-activity relationships of alpha, beta-unsaturated ketones as assessed by their cytotoxicity against oral tumor cells Anticancer Research 24 2004 737 742
31. P. Nangia-Makker, V. Hogan, Y. Honjo, S. Baccarini, L. Tait, R. Bresalier, and et al. Inhibition of human cancer cell growth and metastasis in nude mice by oral intake of modified citrus pectin Journal of the National Cancer Institute 94 2002 1854 1862
32. A.M. Palmer, and V. Jager Pyrrolidine N-oxides by stereoselective addition of grignard and lithium compounds to 4,5-dideoxy-2,3-O-isopropylidene-d-erythro-4-pentenose N-benzyl nitrone and subsequent cope-house cyclization European Journal of Organic Chemistry 2001 2001 1293 1308
33. F.J. Sanchez-Gomez, E. Cernuda-Morollon, K. Stamatakis, and D. Perez-Sala Protein thiol modification by 15-deoxy-delta12,14-prostaglandin J2 addition in mesangial cells: Role in the inhibition of pro-inflammatory genes Molecular Pharmacology 66 2004 1349 1358 10.1124/mol.104.002824
34. A.B. Smith, Q. Han, P.A.S. Breslin, and G.K. Beauchamp Synthesis and assignment of absolute conformation of (-)-oleocanthal: A potent naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils Organic Letters 7 2005 23 27
35. T. Sugahara, H. Fukada, and Y. Iwabuchi Total synthesis and absolute stereochemistry of pentenocin B, a novel interleukin-1 beta converting enzyme inhibitor Journal of Organic Chemistry 69 2004 1744 1747
36. M. Yang, W. Ye, and S. Schneller Preparation of carbocyclic S-adenosylazamethionine accompanied by a practical synthesis of (-)-aristeromycin Journal of Organic Chemistry 69 2004 3993 3996
37. B.M. Yapo, P. Lerouge, J.F. Thibault, and M.C. Ralet Pectins from citrus peel cell walls contain homogalacturonans homogenous with respect to molar mass, rhamnogalacturon I and rhamnogalacturonan II Carbohydrate Polymers 69 2007 426 435 10.3389/fphar.2013.00128