Procyanidins negatively affect the activity of the phosphatases of regenerating liver

PLoS ONE

Volumn 10, Issue 7, 2015, Pages

  Stadlbauer, Sven ^a   Rios, Pablo ^a   Ohmori, Ken ^b   Suzuki, Keisuke ^b   Köhn, Maja ^a  

^a EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHIN; EPICATECHIN; EPICATECHIN GALLATE; EPIGALLOCATECHIN; EPIGALLOCATECHIN GALLATE; GALLIC ACID; PHOSPHATASE; PHOSPHATASE OF REGENERATING LIVER; PHOSPHATASE OF REGENERATING LIVER 1; PHOSPHATASE OF REGENERATING LIVER 3; POLYPHENOL; PROCYANIDIN; UNCLASSIFIED DRUG; CELL CYCLE PROTEIN; MEMBRANE PROTEIN; PHOSPHOPROTEIN PHOSPHATASE; PROANTHOCYANIDIN; PROTEIN TYROSINE PHOSPHATASE; PTP4A1 PROTEIN, HUMAN; PTP4A3 PROTEIN, HUMAN; TUMOR PROTEIN;

ARTICLE; CELL MIGRATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG TARGETING; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; PHENOTYPE; POLYPHARMACOLOGY; PROTEIN EXPRESSION; PROTEIN FAMILY; ANTAGONISTS AND INHIBITORS; DRUG EFFECTS; FLOW CYTOMETRY; HEK293 CELL LINE; LIVER REGENERATION; WOUND HEALING;

CATECHIN; CELL CYCLE PROTEINS; FLOW CYTOMETRY; HEK293 CELLS; HUMANS; LIVER REGENERATION; MEMBRANE PROTEINS; NEOPLASM PROTEINS; PHOSPHOPROTEIN PHOSPHATASES; PROANTHOCYANIDINS; PROTEIN TYROSINE PHOSPHATASES; WOUND HEALING;

EID: 84942155736     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0134336     Document Type: Article

References (50)

1. Jankun J, Swiercz R, Skrzypczak-Jankun E (1997) Why drinking green tea could prevent cancer. Nature 387: 561. PMID: 9177339
2. Hara Y (2001) Green Tea. Boca Raton: CRC Press.
3. Nakayama M, Suzuki K, Toda M, Okubo S, Hara Y, Shimamura T (1993) Inhibition of the infectivity of influenza virus by tea polyphenols. Antiviral Res 21: 289-299. PMID: 8215301
4. Song J-M, Lee K-H, Seong B-L (2005) Antiviral effect of catechins in green tea on influenza virus. Antiviral Res 68: 66-74. PMID: 16137775
5. Gupta S, Hastak K, Ahmad N, Lewin JS, Mukhtar H (2001) Inhibition of prostate carcinogenesis in TRAMP mice by oral infusion of green tea polyphenols. Proc Natl Acad Sci 98: 10350-10355. PMID: 11504910
6. Ahmad N, Feyes DK, Agarwal R, Mukhtar H, Nieminen A-L (1997) Green Tea Constituent Epigallocatechin-3-Gallate and Induction of Apoptosis and Cell Cycle Arrest in Human Carcinoma Cells. J. Natl Cancer Inst 89: 1881-1886. PMID: 9414176
7. Khan N, Afaq F, Saleem M, Ahmad N, Mukhtar H (2006) Targeting Multiple Signaling Pathways by Green Tea Polyphenol (-)-Epigallocatechin-3-Gallate. Cancer Res 66: 2500-2505. PMID: 16510563
8. Siddiqui IA, Asim M, Hafeez BB, Adhami VM, Tarapore RS, Mukhtar H (2011) Green tea polyphenol EGCG blunts androgen receptor function in prostate cancer. FASEB J 25: 1198-1207. doi: 10.1096/fj. 10-167924 PMID: 21177307
9. Quideau S, Deffieux D, Douat-Casassus C, Pouységu L (2011) Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis. Angew. Chem Int Ed 50: 586-621.
10. Ohmori K (2011) Synthetic challenge to ubiquitous natural products from plant origin: flavan-derived polyphenols. Chem Rec 11: 252-259. doi: 10.1002/tcr.201100026 PMID: 21898781
11. Deziel BA, Patel K, Neto C, Gottschall-Pass K, Hurta RA (2010) Proanthocyanidins from the American Cranberry (Vaccinium macrocarpon) inhibit matrix metalloproteinase-2 and matrix metalloproteinase-9 activity in human prostate cancer cells via alterations in multiple cellular signalling pathways. J Cell Biochem 111: 742-754. doi: 10.1002/jcb.22761 PMID: 20626034
12. Singh AP, Singh RK, Kim KK, Satyan KS, Nussbaum R, Torres M et al. (2009) Cranberry proanthocyanidins are cytotoxic to human cancer cells and sensitize platinum-resistant ovarian cancer cells to paraplatin. Phytother Res 23: 1066-1074. doi: 10.1002/ptr.2667 PMID: 19172579
13. Nandakumar V, Singh T, Katiyar SK (2008) Multi-targeted prevention and therapy of cancer by proanthocyanidins. Cancer Lett 269: 378-387. doi: 10.1016/j.canlet.2008.03.049 PMID: 18457915
14. Gopalakrishnan A, Xu C, Nair S, Chen C, Hebbar V, Kong AN (2006) Modulation of activator protein-1 (AP-1) and MAPK pathway by flavonoids in human prostate cancer PC3 cells. Arch Pharm Res 29: 633-644. PMID: 16964758
15. Ferreira D, Coleman CM (2011) Towards the Synthesis of Proanthocyanidins: Half a Century of Innovation. Planta Med 77: 1071-1085. doi: 10.1055/s-0030-1270908 PMID: 21412691
16. Chen X-X, Shi Y, Chai W-M, Feng H-L, Zhuang J-X, Chen QX (2014) Condensed Tannins from Ficus virens as Tyrosinase Inhibitors: Structure, Inhibitory Activity and Molecular Mechanism. PLoS ONE 9: e91809. doi: 10.1371/journal.pone.0091809 PMID: 24637701
17. Stadlbauer S, Ohmori K, Hattori F, Suzuki K (2012) A new synthetic strategy for catechin-class polyphenols: concise synthesis of (-)-epicatechin and its 3-O-gallate. Chem Commun 48: 8425-8427.
18. Ohmori K, Yano T, Suzuki K (2010) General synthesis of epi-series catechins and their 3-gallates: reverse polarity strategy. Org Biomol Chem 8: 2693-2696. doi: 10.1039/c003464a PMID: 20386808
19. Liu Y, Li X, Lin G, Xiang Z, Xiang J, Zhao M et al. (2008) Synthesis of Catechins via Thiourea/AuCl3-Catalyzed Cycloalkylation of Aryl Epoxides. J Org Chem 73: 4625-4629. doi: 10.1021/jo8005649 PMID: 18498193
20. Dennis EG, Jeffery DW, Johnston MR, Perkins MV, Smith PA (2012) Procyanidin oligomers. A new method for 4!8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy. Tetrahedron 68: 340-348.
21. Ohmori K, Shono T, Hatakoshi Y, Yano T, Suzuki K (2011) Integrated synthetic strategy for higher catechin oligomers. Angew Chem Int Ed Engl 50: 4862-4867. doi: 10.1002/anie.201007473 PMID: 21472924
22. Ohmori K, Ushimaru N, Suzuki K (2004) Oligomeric catechins: an enabling synthetic strategy by orthogonal activation and C(8) protection. Proc Natl Acad Sci 101: 12002-12007. PMID: 15141082
23. Kozikowski AP, Tückmantel W, Böttcher G, Romanczyk LJ (2003) Studies in Polyphenol Chemistry and Bioactivity. 4.1 Synthesis of Trimeric, Tetrameric, Pentameric, and Higher Oligomeric Epicatechin-Derived Procyanidins Having All-4β,8-Interflavan Connectivity and Their Inhibition of Cancer Cell Growth through Cell Cycle Arrest1. J Org Chem 68: 1641-1658. PMID: 12608775
24. Ito Y, Ohmori K, Suzuki K (2014) Annulation Approach to Doubly Linked (A-type) Oligocatechins: Syntheses of (+)-Procyanidin A2 and (+)-Cinnamtannin B1. Angew Chem Int Ed Engl 53: 10129-10133. doi: 10.1002/anie.201405600 PMID: 25070773
25. Fujii W, Toda K, Kawaguchi K, Kawahara S-i, Katoh M, Hattori Y et al. (2013) Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation. Tetrahedron 69: 3543-3550.
26. Park YC, Rimbach G, Saliou C, Valacchi G, Packer L (2000) Activity of monomeric, dimeric, and trimeric flavonoids on NO production, TNF-α secretion, and NF-κB-dependent gene expression in RAW 264.7 macrophages. FEBS Lett 465: 93-97. PMID: 10631311
27. Kiss A, Becsi B, Kolozsvari B, Komaromi I, Kover KE, Erdodi F (2013) Epigallocatechin-3-gallate and penta-O-galloyl-beta-D-glucose inhibit protein phosphatase-1. FEBS J 280: 612-626. doi: 10.1111/j. 1742-4658.2012.08498.x PMID: 22260360
28. Li X, Wilmanns M, Thornton J, Köhn M (2013) Elucidating Human Phosphatase-Substrate Networks. Sci Signal 6: rs10. doi: 10.1126/scisignal.2003203 PMID: 23674824
29. Rios P, Li X, Köhn M (2013) Molecular mechanisms of the PRL phosphatases. FEBS J 280: 505-524. doi: 10.1111/j.1742-4658.2012.08565.x PMID: 22413991
30. Qian F, Li YP, Sheng X, Zhang ZC, Song R, DongWet al. (2007) PRL-3 siRNA inhibits the metastasis of B16-BL6 mouse melanoma cells in vitro and in vivo. Mol Med 13: 151-159. PMID: 17592549
31. Bessette D, Qiu D, Pallen C (2008) PRL PTPs: mediators and markers of cancer progression. Cancer Metastasis Rev 27: 231-252. doi: 10.1007/s10555-008-9121-3 PMID: 18224294
32. Saha S, Bardelli A, Buckhaults P, Velculescu VE, Rago C, Croix B St et al. (2001) A Phosphatase Associated with Metastasis of Colorectal Cancer. Science 294: 1343-1346. PMID: 11598267
33. Rios P, Nunes-Xavier CE, Tabernero L, Köhn M, Pulido R (2014) Dual-specificity phosphatases as molecular targets for inhibition in human disease. Antioxid Redox Signal 20: 2251-2273. doi: 10.1089/ars.2013.5709 PMID: 24206177
34. Wang Y, Lazo JS (2012) Metastasis-associated phosphatase PRL-2 regulates tumor cell migration and invasion. Oncogene 31: 818-827. doi: 10.1038/onc.2011.281 PMID: 21765462
35. Lu JW, Chang JG, Yeh KT, Chen RM, Tsai JJ, SuWWet al. (2012) Increased expression of PRL-1 protein correlates with shortened patient survival in human hepatocellular carcinoma. Clin Transl Oncol 14: 287-293. doi: 10.1007/s12094-012-0797-z PMID: 22484636
36. Hardy S, Wong NN, Muller WJ, Park M, Tremblay ML (2010) Overexpression of the protein tyrosine phosphatase PRL-2 correlates with breast tumor formation and progression. Cancer Res 70: 8959-8967. doi: 10.1158/0008-5472.CAN-10-2041 PMID: 20841483
37. He T, Liang N-c, Lin X-c, LiuW(2010) Effects of Seven Kinds of Flavanoids on Recombinant Human Protein Tyrosine Phosphatase. J Chin Med Mat 33: 771-774.
38. Sotoud H, Gribbon P, Ellinger B, Reinshagen J, Boknik P, Kattner L et al. (2013) Development of a colorimetric and a fluorescence phosphatase-inhibitor assay suitable for drug discovery approaches. J Biomol Screen 18: 899-909. doi: 10.1177/1087057113486000 PMID: 23606651
39. Wegner AM, McConnell JL, Blakely RD, Wadzinski BE (2007) An automated fluorescence-based method for continuous assay of PP2A activity. Methods Mol Biol 365: 61-69. PMID: 17200554
40. Li M, Hagerman AE (2014) Role of the Flavan-3-ol and Galloyl Moieties in the Interaction of (-)-Epigallocatechin Gallate with Serum Albumin. J Agric Food Chem 62: 3768-3775. doi: 10.1021/jf500246m PMID: 24712545
41. Nozaki A, Hori M, Kimura T, Ito H, Hatano T (2009) Interaction of Polyphenols with Proteins: Binding of (-)-Epigallocatechin Gallate to Serum Albumin, Estimated by Induced Circular Dichroism. Chem Pharm Bull 57: 224-228. PMID: 19182419
42. Trnková L, Boušová I, Staňková V, Dršata J (2011) Study on the interaction of catechins with human serum albumin using spectroscopic and electrophoretic techniques. J Mol Struct 985: 243-250.
43. Ma J, Li Z, Xing S, Ho W-TT, Fu X, Zhao ZJ (2011) Tea contains potent inhibitors of tyrosine phosphatase PTP1B. Biochem Biophys Res Comm 407: 98-102. doi: 10.1016/j.bbrc.2011.02.116 PMID: 21371422
44. Meyer C, Hoeger B, Temmerman K, Tatarek-Nossol M, Pogenberg V, Bernhagen J et al. (2014) Development of Accessible Peptidic Tool Compounds To Study the Phosphatase PTP1B in Intact Cells. ACS Chem Biol 9: 769-776. doi: 10.1021/cb400903u PMID: 24387659
45. Hoeger B, Diether M, Ballester PJ, Köhn M (2014) Biochemical evaluation of virtual screening methods reveals a cell-active inhibitor of the cancer-promoting phosphatases of regenerating liver. Eur J Med Chem 88: 89-100. doi: 10.1016/j.ejmech.2014.08.060 PMID: 25159123
46. Hemmersbach S, Brauer SS, Hüwel S, Galla H-J, Humpf H-U (2013) Transepithelial Permeability Studies of Flavan-3-ol-C-glucosides and Procyanidin Dimers and Trimers across the Caco-2 Cell Monolayer. J Agric Food Chem 61: 7932-7940. doi: 10.1021/jf402019f PMID: 23885956
47. Verstraeten SV, Fraga CG, Oteiza PI (2015) Interactions of flavan-3-ols and procyanidins with membranes: mechanisms and the physiological relevance. Food Funct. 6: 32-40. doi: 10.1039/c4fo00647j PMID: 25418533
48. Zimmerman MW, Homanics GE, Lazo JS (2013) Targeted Deletion of the Metastasis-Associated Phosphatase Ptp4a3 (PRL-3) Suppresses Murine Colon Cancer. PLoS ONE 8: e58300. doi: 10.1371/journal.pone.0058300 PMID: 23555575
49. Ohmori K, Takeda M, Higuchi T, Shono T, Suzuki K (2009) Stereocontolled Synthesis of (-)-Afzelechin: General Route to Catechin-class Polyphenols by Solving an SN2 vs. SN1 Problem. Chem Lett 38: 934-935.
50. McParland V, Varsano G, Li X, Thornton J, Baby J, Aravind A et al. (2011) The Metastasis-Promoting Phosphatase PRL-3 Shows Activity toward Phosphoinositides. Biochem 50: 7579-7590.