The importance of polymerization and galloylation for the antiproliferative properties of procyanidin-rich natural extracts

FEBS Journal

Volumn 274, Issue 18, 2007, Pages 4802-4811

  Lizarraga, D ^a   Lozano, C ^b   Briede J J ^c   Van Delft, J H ^c   Tourino S ^b   Centelles, J J ^a   Torres, J L ^b   Cascante, M ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^c MAASTRICHT UNIVERSITY   (Netherlands)

Author keywords

Antiproliferative; Apoptosis; Cell cycle; Colon cancer; Scavenger capacity

Indexed keywords

DNA FRAGMENT; PINE TREE EXTRACT; PLANT EXTRACT; PROCYANIDIN; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; VITIS VINIFERA EXTRACT;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG MECHANISM; HUMAN; HUMAN CELL; PINE; POLYMERIZATION; PRIORITY JOURNAL; SCAVENGING SYSTEM;

ANIMALS; APOPTOSIS; BIFLAVONOIDS; BIOPOLYMERS; CATECHIN; CELL CYCLE; CELL LINE; CELL PROLIFERATION; HT29 CELLS; HUMANS; MOLECULAR STRUCTURE; PINUS; PLANT BARK; PROANTHOCYANIDINS; RATS; TISSUE EXTRACTS; VITIS;

PINUS PINASTER; VITACEAE; VITIS VINIFERA;

EID: 34548459466     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2007.06010.x     Document Type: Article

References (52)

1. Parkin DM (2004) International variation. Oncogene 23, 6329 6340.
2. Potter JD, Slattery ML, Bostick RM Gapstur SM (1993) Colon cancer: a review of the epidemiology. Epidemiol Rev 15, 499 545.
3. Steinmetz KA Potter JD (1991) Vegetables, fruit, and cancer. I. Epidemiology. Cancer Causes Control 2, 325 357.
4. Park OJ Surh YJ (2004) Chemopreventive potential of epigallocatechin gallate and genistein: evidence from epidemiological and laboratory studies. Toxicol Lett 150, 43 56.
5. Bruce WR, Giacca A Medline A (2000) Possible mechanisms relating diet and risk of colon cancer. Cancer Epidemiol Biomarkers Prev 9, 1271 1279.
6. Hietanen E, Bartsch H, Bereziat JC, Camus AM, McClinton S, Eremin O, Davidson L Boyle P (1994) Diet and oxidative stress in breast, colon and prostate cancer patients: a case-control study. Eur J Clin Nutr 48, 575 586.
7. Theodoratou E, Kyle J, Cetnarskyj R, Farrington SM, Tenesa A, Barnetson R, Porteous M, Dunlop M Campbell H (2007) Dietary flavonoids and the risk of colorectal cancer. Cancer Epidemiol Biomarkers Prev 16, 684 693.
8. Mukhtar H Ahmad N (1999) Green tea in chemoprevention of cancer. Toxicol Sci 52, 111 117.
9. Lee KW, Lee HJ Lee CY (2004) Vitamins, phytochemicals, diets, and their implementation in cancer chemoprevention. Crit Rev Food Sci Nutr 44, 437 452.
10. Witschi H, Espiritu I, Ly M, Uyeminami D, Morin D Raabe OG (2004) Chemoprevention of tobacco smoke-induced lung tumors by inhalation of an epigallocatechin gallate (EGCG) aerosol: a pilot study. Inhal Toxicol 16, 763 770.
11. Delmas D, Lancon A, Colin D, Jannin B Latruffe N (2006) Resveratrol as a chemopreventive agent: a promising molecule for fighting cancer. Curr Drug Targets 7, 423 442.
12. Hakimuddin F, Paliyath G Meckling K (2006) Treatment of mcf-7 breast cancer cells with a red grape wine polyphenol fraction results in disruption of calcium homeostasis and cell cycle arrest causing selective cytotoxicity. J Agric Food Chem 54, 7912 7923.
13. Sime S Reeve VE (2004) Protection from inflammation, immunosuppression and carcinogenesis induced by UV radiation in mice by topical Pycnogenol. Photochem Photobiol 79, 193 198.
14. Kumar N, Shibata D, Helm J, Coppola D Malafa M (2007) Green tea polyphenols in the prevention of colon cancer. Front Biosci 12, 2309 2315.
15. McKay DL Blumberg JB (2007) A review of the bioactivity of south African herbal teas: rooibos (Aspalathus linearis) and honeybush (Cyclopia intermedia). Phytother Res 21, 1 16.
16. Wright TI, Spencer JM Flowers FP (2006) Chemoprevention of nonmelanoma skin cancer. J Am Acad Dermatol 54, 933 946 quiz 947 950.
17. Tan XHD, Li S, Han Y, Zhang Y Zhou D (2000) Differences of four catechins in cell cycle arrest and induction of apoptosis in LoVo cells. Cancer Lett 158, 1 6.
18. Kozikowski AP, Tuckmantel W, Bottcher G Romanczyk LJ Jr. (2003) Studies in polyphenol chemistry and bioactivity. 4 (1) Synthesis of trimeric, tetrameric, pentameric, and higher oligomeric epicatechin-derived procyanidins having all-4beta,8-interflavan connectivity and their inhibition of cancer cell growth through cell cycle arrest. J Org Chem 68, 1641 1658.
19. Nakamuta M, Higashi N, Kohjima M, Fukushima M, Ohta S, Kotoh K, Kobayashi N Enjoji M (2005) Epigallocatechin-3-gallate, a polyphenol component of green tea, suppresses both collagen production and collagenase activity in hepatic stellate cells. Int J Mol Med 16, 677 681.
20. Shi J, Yu J, Pohorly JE Kakuda Y (2003) Polyphenolics in grape seeds - biochemistry and functionality. J Med Food 6, 291 299.
21. Siddiqui IA, Adhami VM, Saleem M Mukhtar H (2006) Beneficial effects of tea and its polyphenols against prostate cancer. Mol Nutr Food Res 50, 130 143.
22. Zhang Q, Tang X, Lu Q, Zhang Z, Rao J Le AD (2006) Green tea extract and (-)-epigallocatechin-3-gallate inhibit hypoxia- and serum-induced HIF-1alpha protein accumulation and VEGF expression in human cervical carcinoma and hepatoma cells. Mol Cancer Ther 5, 1227 1238.
23. Prieur CRJ, Cheynier V Moutounet M (1994) Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36, 781 784.
24. Souquet J-MCV, Brossaud F Moutounet M (1996) Polymeric proanthocyanidins from grape skins. Phytochemistry 43, 509 512.
25. Rohdewald P (2002) A review of the French maritime pine bark extract (Pycnogenol), a herbal medication with a diverse clinical pharmacology. Int J Clin Pharmacol Ther 40, 158 168.
26. Tourino S, Selga A, Jimenez A, Julia L, Lozano C, Lizarraga D, Cascante M Torres JL (2005) Procyanidin fractions from pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells. J Agric Food Chem 53, 4728 4735.
27. Gonthier MP, Donovan JL, Texier O, Felgines C, Remesy C Scalbert A (2003) Metabolism of dietary procyanidins in rats. Free Radic Biol Med 35, 837 844.
28. Kuhnle G, Spencer JP, Schroeter H, Shenoy B, Debnam ES, Srai SK, Rice-Evans C Hahn U (2000) Epicatechin and catechin are O-methylated and glucuronidated in the small intestine. Biochem Biophys Res Commun 277, 507 512.
29. Rechner AR, Smith MA, Kuhnle G, Gibson GR, Debnam ES, Srai SK, Moore KP Rice-Evans CA (2004) Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Free Radic Biol Med 36, 212 225.
30. Meselhy MR, Nakamura N Hattori M (1997) Biotransformation of (-)-epicatechin 3-O-gallate by human intestinal bacteria. Chem Pharm Bull (Tokyo) 45, 888 893.
31. Salucci M, Stivala LA, Maiani G, Bugianesi R Vannini V (2002) Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). Br J Cancer 86, 1645 1651.
32. Stagos D, Kazantzoglou G, Magiatis P, Mitaku S, Anagnostopoulos K Kouretas D (2005) Effects of plant phenolics and grape extracts from Greek varieties of Vitis vinifera on mitomycin C and topoisomerase I-induced nicking of DNA. Int J Mol Med 15, 1013 1022.
33. Subirade I, Fernandez Y, Periquet A Mitjavila S (1995) Catechin protection of 3T3 Swiss fibroblasts in culture under oxidative stress. Biol Trace Elem Res 47, 313 319.
34. Cao Z Li Y (2004) Potent induction of cellular antioxidants and phase 2 enzymes by resveratrol in cardiomyocytes: protection against oxidative and electrophilic injury. Eur J Pharmacol 489, 39 48.
35. Alanko J, Riutta A, Holm P, Mucha I, Vapaatalo H Metsa-Ketela T (1999) Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties. Free Radic Biol Med 26, 193 201.
36. Azam S, Hadi N, Khan NU Hadi SM (2004) Prooxidant property of green tea polyphenols epicatechin and epigallocatechin-3-gallate: implications for anticancer properties. Toxicol In Vitro 18, 555 561.
37. Halliwell B Gutteridge JM (1992) Biologically relevant metal ion-dependent hydroxyl radical generation. An update. FEBS Lett 307, 108 112.
38. Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M Telser J (2007) Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 39, 44 84.
39. Mathers JC (2002) Pulses and carcinogenesis: potential for the prevention of colon, breast and other cancers. Br J Nutr 88 (Suppl. 3 S273 S279.
40. Witte JS, Longnecker MP, Bird CL, Lee ER, Frankl HD Haile RW (1996) Relation of vegetable, fruit, and grain consumption to colorectal adenomatous polyps. Am J Epidemiol 144, 1015 1025.
41. Manju V Nalini N (2005) Chemopreventive efficacy of ginger, a naturally occurring anticarcinogen during the initiation, post-initiation stages of 1,2-dimethylhydrazine-induced colon cancer. Clin Chim Acta 358, 60 67.
42. Zou DM, Brewer M, Garcia F, Feugang JM, Wang J, Zang R, Liu H Zou C (2005) Cactus pear: a natural product in cancer chemoprevention. Nutr J 4, 25 37.
43. Joshi SS, Kuszynski CA Bagchi D (2001) The cellular and molecular basis of health benefits of grape seed proanthocyanidin extract. Curr Pharm Biotechnol 2, 187 200.
44. Depeint F, Gee JM, Williamson G Johnson IT (2002) Evidence for consistent patterns between flavonoid structures and cellular activities. Proc Nutr Soc 61, 97 103.
45. Fiuza SM, Gomes C, Teixeira LJ, Girao da Cruz MT, Cordeiro MN, Milhazes N, Borges F Marques MP (2004) Phenolic acid derivatives with potential anticancer properties - a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids. Bioorg Med Chem 12, 3581 3589.
46. Brusselmans K, Vrolix R, Verhoeven G Swinnen JV (2005) Induction of cancer cell apoptosis by flavonoids is associated with their ability to inhibit fatty acid synthase activity. J Biol Chem 280, 5636 5645.
47. Lozano C, Torres JL, Julia L, Jimenez A, Centelles JJ Cascante M (2005) Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells. FEBS Lett 579, 4219 4225.
48. Kokura S, Yoshida N, Sakamoto N, Ishikawa T, Takagi T, Higashihara H, Nakabe N, Handa O, Naito Y Yoshikawa T (2005) The radical scavenger edaravone enhances the anti-tumor effects of CPT-11 in murine colon cancer by increasing apoptosis via inhibition of NF-kappaB. Cancer Lett 229, 223 233.
49. Zielinska-Przyjemska M Wiktorowicz K (2006) An in vitro study of the protective effect of the flavonoid silydianin against reactive oxygen species. Phytother Res 20, 115 119.
50. Torres JL, Varela B, Garcia MT, Carilla J, Matito C, Centelles JJ, Cascante M, Sort X Bobet R (2002) Valorization of grape (Vitis vinifera) byproducts. Antioxidant and biological properties of polyphenolic fractions differing in procyanidin composition and flavonol content. J Agric Food Chem 50, 7548 7555.
51. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65, 55 63.
52. Selga A Torres JL (2005) Efficient preparation of catechin thio conjugates by one step extraction/depolymerization of pine (Pinus pinaster) bark procyanidins. J Agric Food Chem 53, 7760 7765.