Chemo-protective and regenerative effects of diarylheptanoids from the bark of black alder (Alnus glutinosa) in human normal keratinocytes

Fitoterapia

Volumn 105, Issue , 2015, Pages 169-176

  Dinić, Jelena ^a   Randelović, Teodora ^a   Stanković, Tijana ^a   Dragoj, Miodrag ^a   Isaković, Aleksandra ^b   Novaković, Miroslav ^a   Pešić, Milica ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Cell motility; Chemoprotection; Curcumin; Diarylheptanoid; DNA damage; Doxorubicin

Indexed keywords

1,7 DI(4 HYDROXYPHENYL) 3 HEPTANONE 5 O BETA D GLUCOPYRANOSIDE; 1,7 DI(4 HYDROXYPHENYL) 5 O BETA D [6 (E P COUMAROYLGLUCOPYRANOSYL)]HEPTANE 3 ONE; ANTINEOPLASTIC AGENT; DOXORUBICIN; F ACTIN; HEPTANE DERIVATIVE; HISTONE H2AX; UNCLASSIFIED DRUG; 5-1,7-DI(4-HYDROXYPHENYL)-5-O-(6-(P-COUMAROYLGLUCOPYRANOSYL))HEPTANE-3-ONE; DNA ADDUCT; DOXORUBICIN-DNA; GLUCOSIDE; PLATYPHYLLOSIDE 1,7-DI(4-HYDROXYPHENYL)-3-HEPTANONE-5-O-GLUCOPYRANOSIDE; PROTECTIVE AGENT;

ALNUS GLUTINOSA; APOPTOSIS; ARTICLE; AUTOPHAGY; BARK; CELL DEATH; CELL MIGRATION; CELL MOTILITY; CELL REGENERATION; CELL SURVIVAL; CHEMOPROPHYLAXIS; CONTROLLED STUDY; DIET SUPPLEMENTATION; DNA DAMAGE; DRUG EFFECT; DRUG ISOLATION; GROWTH INHIBITION; HUMAN; HUMAN CELL; KERATINOCYTE; MEDICINAL PLANT; MELANOMA CELL; PRIORITY JOURNAL; SKIN PROTECTION; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DNA ADDUCT; DRUG EFFECTS; ILEX; ISOLATION AND PURIFICATION;

ALNUS GLUTINOSA;

CELL DEATH; CELL LINE; DIARYLHEPTANOIDS; DNA ADDUCTS; DNA DAMAGE; DOXORUBICIN; GLUCOSIDES; HUMANS; ILEX; KERATINOCYTES; MOLECULAR STRUCTURE; PLANT BARK; PROTECTIVE AGENTS;

EID: 84937539499     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2015.07.003     Document Type: Article

References (57)

1. N.R. Farnsworth, and D.D. Soejarto Potential consequences of plant extinction in the United States on the current and future availability of prescription drugs Econ. Bot. 3 1985 231 240
2. G.A. Cordell Recent developments in the study of biologically active natural products ACGC Chem. Commun. 2002 31 63
3. S.C. Sati, N. Sati, and O.P. Sati Bioactive constituents and medicinal importance of genus Alnus Pharmacogn. Rev. 5 2011 174 183
4. C. O'Rourke, M. Byres, A. Delazar, Y. Kumarasamy, L. Nahar, F. Stewart, and et al. Hirsutanonol, oregonin and genkwanin from the seeds of Alnus glutinosa (Betulaceae) Biochem. Syst. Ecol. 749-52 2005
5. Y. Kumarasamy, P.J. Cox, M. Jaspars, L. Nahar, and S.D. Sarker Bioactivity of hirsutanolol, oregonin and genkwanin, isolated from the seeds of Alnus glutinosa (Betulaceae) Nat. Prod. Commun. 641-4 2006
6. M. Novakovic, M. Stankovic, I. Vuckovic, N. Todorovic, S. Trifunovic, V. Tesevic, and et al. Diarylheptanoids from Alnus glutinosa bark and their chemoprotective effect on human lymphocytes DNA Planta Med. 79 2013 499 505
7. M. Novakovic, M. Pesic, S. Trifunovic, I. Vuckovic, N. Todorovic, A. Podolski-Renic, and et al. Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells Phytochemistry 97 2014 46 54
8. S. Brand, D. Holscher, A. Schierhorn, A. Svatos, J. Schroder, and B. Schneider A type III polyketide synthase from Wachendorfia thyrsiflora and its role in diarylheptanoid and phenylphenalenone biosynthesis Planta 224 2006 413 428
9. T. Munde, S. Brand, W. Hidalgo, R.K. Maddula, A. Svatos, and B. Schneider Biosynthesis of tetraoxygenated phenylphenalenones in Wachendorfia thyrsiflora Phytochemistry 91 2013 165 176
10. B.B. Aggarwal, and K.B. Harikumar Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases Int. J. Biochem. Cell Biol. 41 2009 40 59
11. S.C. Gupta, S. Patchva, W. Koh, and B.B. Aggarwal Discovery of curcumin, a component of golden spice, and its miraculous biological activities Clin. Exp. Pharmacol. Physiol. 39 2012 283 299
12. M.S. Baliga, N. Joseph, M.V. Venkataranganna, A. Saxena, V. Ponemone, and R. Fayad Curcumin, an active component of turmeric in the prevention and treatment of ulcerative colitis: preclinical and clinical observations Food Funct. 3 2012 1109 1117
13. K.N. Chidambara Murthy, G.K. Jayaprakasha, and B.S. Patil Citrus limonoids and curcumin additively inhibit human colon cancer cells Food Funct. 4 2013 803 810
14. Q.A. Nazari, Y. Takada-Takatori, T. Hashimoto, A. Imaizumi, Y. Izumi, A. Akaike, and et al. Potential protective effect of highly bioavailable curcumin on an oxidative stress model induced by microinjection of sodium nitroprusside in mice brain Food Funct. 5 2014 984 989
15. H. Matsuda, A. Ishikado, N. Nishida, K. Ninomiya, H. Fujiwara, Y. Kobayashi, and et al. Hepatoprotective, superoxide scavenging, and antioxidative activities of aromatic constituents from the bark of Betula platyphylla var. japonica Bioorg. Med. Chem. Lett. 8 1998 2939 2944
16. N.H. Tung, S.K. Kim, J.C. Ra, Y.Z. Zhao, D.H. Sohn, and Y.H. Kim Antioxidative and hepatoprotective diarylheptanoids from the bark of Alnus japonica Planta Med. 76 2010 626 629
17. Y.C. Lai, C.K. Chen, W.W. Lin, and S.S. Lee A comprehensive investigation of anti-inflammatory diarylheptanoids from the leaves of Alnus formosana Phytochemistry 73 2012 84 94
18. N.H. Tung, H.J. Kwon, J.H. Kim, J.C. Ra, Y. Ding, J.A. Kim, and et al. Anti-influenza diarylheptanoids from the bark of Alnus japonica Bioorg. Med. Chem. Lett. 20 2010 1000 1003
19. S.E. Choi, K.H. Kim, J.H. Kwon, S.B. Kim, H.W. Kim, and M.W. Lee Cytotoxic activities of diarylheptanoids from Alnus japonica Arch. Pharm. Res. 31 2008 1287 1289
20. J.X. Liu, D.L. Di, X.N. Wei, and Y. Han Cytotoxic diarylheptanoids from the pericarps of walnuts (Juglans regia) Planta Med. 74 2008 754 759
21. Y. Sun, K. Tabata, H. Matsubara, S. Kitanaka, T. Suzuki, and K. Yasukawa New cytotoxic diarylheptanoids from the rhizomes of Alpinia officinarum Planta Med. 74 2008 427 431
22. V. Mshvildadze, J. Legault, S. Lavoie, C. Gauthier, and A. Pichette Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera Phytochemistry 68 2007 2531 2536
23. J. Dinic, M. Novakovic, A. Podolski-Renic, S. Stojkovic, B. Mandic, V. Tesevic, and et al. Antioxidative activity of diarylheptanoids from the bark of black alder (Alnus glutinosa) and their interaction with anticancer drugs Planta Med. 80 2014 1088 1096
24. T.C. Chou, and P. Talalay Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors Adv. Enzyme Regul. 22 1984 27 55
25. H. Mizutani, S. Tada-Oikawa, Y. Hiraku, M. Kojima, and S. Kawanishi Mechanism of apoptosis induced by doxorubicin through the generation of hydrogen peroxide Life Sci. 76 2005 1439 1453
26. S. Wang, E.A. Konorev, S. Kotamraju, J. Joseph, S. Kalivendi, and B. Kalyanaraman Doxorubicin induces apoptosis in normal and tumor cells via distinctly different mechanisms. Intermediacy of H(2)O(2)- and p53-dependent pathways J. Biol. Chem. 279 2004 25535 25543
27. Y.W. Eom, M.A. Kim, S.S. Park, M.J. Goo, H.J. Kwon, S. Sohn, and et al. Two distinct modes of cell death induced by doxorubicin: apoptosis and cell death through mitotic catastrophe accompanied by senescence-like phenotype Oncogene 24 2005 4765 4777
28. E.L. Eskelinen, and P. Saftig Autophagy: a lysosomal degradation pathway with a central role in health and disease Biochim. Biophys. Acta 1793 2009 664 673
29. F. Aredia, and A.I. Scovassi Manipulation of autophagy in cancer cells: an innovative strategy to fight drug resistance Future Med. Chem. 5 2013 1009 1021
30. P. Kumar, D.M. Zhang, K. Degenhardt, and Z.S. Chen Autophagy and transporter-based multi-drug resistance Cells 1 2012 558 575
31. G. Marino, M. Niso-Santano, E.H. Baehrecke, and G. Kroemer Self-consumption: the interplay of autophagy and apoptosis Nat. Rev. Mol. Cell Biol. 15 2014 81 94
32. Z. Yang, and D.J. Klionsky Mammalian autophagy: core molecular machinery and signaling regulation Curr. Opin. Cell Biol. 22 2010 124 131
33. H. Nakatogawa Two ubiquitin-like conjugation systems that mediate membrane formation during autophagy Essays Biochem. 55 2013 39 50
34. Y. Kabeya, N. Mizushima, A. Yamamoto, S. Oshitani-Okamoto, Y. Ohsumi, and T. Yoshimori LC3, GABARAP and GATE16 localize to autophagosomal membrane depending on form-II formation J. Cell Sci. 117 2004 2805 2812
35. G. Warnes Measurement of autophagy by flow cytometry Curr. Protoc. Cytom. 68 2014 (9 45 1-9 10)
36. E. Shvets, and Z. Elazar Flow cytometric analysis of autophagy in living mammalian cells Methods Enzymol. 452 2009 131 141
37. P. Hundeshagen, A. Hamacher-Brady, R. Eils, and N.R. Brady Concurrent detection of autolysosome formation and lysosomal degradation by flow cytometry in a high-content screen for inducers of autophagy BMC Biol. 9 2011 38
38. J. Cao, Y. Liu, L. Jia, H.M. Zhou, Y. Kong, G. Yang, and et al. Curcumin induces apoptosis through mitochondrial hyperpolarization and mtDNA damage in human hepatoma G2 cells Free Radic. Biol. Med. 43 2007 968 975
39. M. Roy, D. Sinha, S. Mukherjee, and J. Biswas Curcumin prevents DNA damage and enhances the repair potential in a chronically arsenic-exposed human population in West Bengal, India Eur. J. Cancer Prev. 20 2011 123 131
40. M. Srinivasan, N. Rajendra Prasad, and V.P. Menon Protective effect of curcumin on gamma-radiation induced DNA damage and lipid peroxidation in cultured human lymphocytes Mutat. Res. 611 2006 96 103
41. J. Cao, L. Jia, H.M. Zhou, Y. Liu, and L.F. Zhong Mitochondrial and nuclear DNA damage induced by curcumin in human hepatoma G2 cells Toxicol. Sci. 91 2006 476 483
42. F.A. Fornari, J.K. Randolph, J.C. Yalowich, M.K. Ritke, and D.A. Gewirtz Interference by doxorubicin with DNA unwinding in MCF-7 breast tumor cells Mol. Pharmacol. 45 1994 649 656
43. Y. Pommier, E. Leo, H. Zhang, and C. Marchand DNA topoisomerases and their poisoning by anticancer and antibacterial drugs Chem. Biol. 17 2010 421 433
44. B. Pang, X. Qiao, L. Janssen, A. Velds, T. Groothuis, R. Kerkhoven, and et al. Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin Nat. Commun. 4 2013 1908
45. S. Jaamaa, T.M. Af Hallstrom, A. Sankila, V. Rantanen, H. Koistinen, U.H. Stenman, and et al. DNA damage recognition via activated ATM and p53 pathway in nonproliferating human prostate tissue Cancer Res. 70 2010 8630 8641
46. F. Zhou, H. Mei, Q. Wu, and R. Jin Expression of histone H2AX phosphorylation and its potential to modulate adriamycin resistance in K562/A02 cell line J. Huazhong Univ. Sci. Technolog. Med. Sci. 31 2011 154 158
47. E.U. Kurz, P. Douglas, and S.P. Lees-Miller Doxorubicin activates ATM-dependent phosphorylation of multiple downstream targets in part through the generation of reactive oxygen species J. Biol. Chem. 279 2004 53272 53281
48. S. Prasad, A.K. Tyagi, and B.B. Aggarwal Recent developments in delivery, bioavailability, absorption and metabolism of curcumin: the golden pigment from golden spice Cancer Res. Treat. 46 2014 2 18
49. Y. Ji, X.T. Li, and G.Q. Chen Interactions between a poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate) terpolyester and human keratinocytes Biomaterials 29 2008 3807 3814
50. J.L. Garcia, A. Asadinezhad, J. Pachernik, M. Lehocky, I. Junkar, P. Humpolicek, and et al. Cell proliferation of HaCaT keratinocytes on collagen films modified by argon plasma treatment Molecules 15 2010 2845 2856
51. B. Lehmann HaCaT cell line as a model system for vitamin D3 metabolism in human skin J. Invest. Dermatol. 108 1997 78 82
52. E. Boelsma, M.C. Verhoeven, and M. Ponec Reconstruction of a human skin equivalent using a spontaneously transformed keratinocyte cell line (HaCaT) J. Invest. Dermatol. 112 1999 489 498
53. N. Maas-Szabowski, A. Starker, and N.E. Fusenig Epidermal tissue regeneration and stromal interaction in HaCaT cells is initiated by TGF-alpha J. Cell Sci. 116 2003 2937 2948
54. V. Meineke, K. Muller, R. Ridi, N. Cordes, F.M. Kohn, A. Mayerhofer, and et al. Development and evaluation of a skin organ model for the analysis of radiation effects Strahlenther. Onkol. 180 2004 102 108
55. Q.Y. Chen, Y. Zheng, D.M. Jiao, F.Y. Chen, H.Z. Hu, Y.Q. Wu, and et al. Curcumin inhibits lung cancer cell migration and invasion through Rac1-dependent signaling pathway J. Nutr. Biochem. 25 2014 177 185
56. S.S. Lin, K.C. Lai, S.C. Hsu, J.S. Yang, C.L. Kuo, J.P. Lin, and et al. Curcumin inhibits the migration and invasion of human A549 lung cancer cells through the inhibition of matrix metalloproteinase-2 and -9 and Vascular Endothelial Growth Factor (VEGF) Cancer Lett. 285 2009 127 133
57. J. Tello Velasquez, M.E. Watts, M. Todorovic, L. Nazareth, E. Pastrana, J. Diaz-Nido, and et al. Low-dose curcumin stimulates proliferation, migration and phagocytic activity of olfactory ensheathing cells PLoS One 9 2014 e111787