Bioactivity guided isolation of anticancer constituents from leaves of Alnus sieboldiana (Betulaceae)

Phytomedicine

Volumn 18, Issue 6, 2011, Pages 491-498

  Ludwiczuk, A ^a,b   Saha, A ^a   Kuzuhara, T ^a   Asakawa, Y ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

Alnus sieboldiana; Cancer prevention; Flavonoids; Galangin; Quercetin; TNF inhibitors

Indexed keywords

ALNUS SIEBOLDIANA EXTRACT; ALNUSTINOL; ANTINEOPLASTIC AGENT; DEMETHOXYYANGONIN; DIHYDROKAWAIN; EPIGALLOCATECHIN GALLATE; GALANGIN; GALLIC ACID METHYL ESTER; HEXANE; KAWAIN; METHANOL; OKADAIC ACID; PINOBANKSINE; PINOCEMBRINE; PINOSYLVIN; PLANT EXTRACT; QUERCETIN; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA INHIBITOR; UNCLASSIFIED DRUG;

ALNUS SIEBOLDIANA; ARTICLE; BETULACEAE; CANCER INHIBITION; CELL VIABILITY; CYTOTOXICITY; DOSE RESPONSE; DRUG ISOLATION; GENE EXPRESSION; HUMAN; HUMAN CELL; LUNG NON SMALL CELL CANCER; MEDICINAL PLANT; PLANT LEAF; PRIORITY JOURNAL; REAL TIME POLYMERASE CHAIN REACTION;

ALNUS; ANTICARCINOGENIC AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; FLAVONOIDS; GALLIC ACID; HUMANS; LUNG NEOPLASMS; PHYTOTHERAPY; PLANT EXTRACTS; PLANT LEAVES; QUERCETIN; STILBENES; TUMOR NECROSIS FACTOR-ALPHA;

ALNUS SIEBOLDIANA; BETULACEAE;

EID: 79955002014     PISSN: 09447113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phymed.2010.10.005     Document Type: Article

References (64)

1. B.B. Aggarwal, and K. Natarajan Tumor necrosis factors: development during the last decade Eur. Cytokine Netw. 7 1996 93 124 (Pubitemid 26144548)
2. Y. Asakawa Chemical constituents of Alnus firma (Betulaceae). I. Phenyl propane derivatives isolated from Alnus firma Bull. Chem. Soc. Jpn. 43 1970 2223 2229
3. Y. Asakawa Chemical constituents of Alnus sieboldiana (Betulaceae). II. The isolation and structure of flavonoids and stilbenes Bull. Chem. Soc. Jpn. 44 1971 2761 2766
4. Y. Asakawa, F. Genjida, S. Hayashi, and T. Matsuura A new ketol from Alnus firma Sieb. et Zucc. (Betulaceae) Tetrahedron Lett. 10 1969 3235 3237
5. Y. Asakawa, F. Genjida, and T. Suga Four new flavonoids isolated from Alnus sieboldiana Bull. Chem. Soc. Jpn. 44 1971 297
6. J. Askling, R.F. van Vollenhofen, F. Granath, P. Raaschou, C.M. Fored, E. Baecklund, C. Dackhammar, N. Feltelius, L. Cöster, P. Geborek, L.T. Jacobsson, S. Lindblad, S. Rantapää-Dahlqvist, T. Saxne, and L. Klareskog Cancer risk in patients with rheumatoid arthritis treated with anti-tumor necrosis factor α therapies Arthritis Rheum. 60 2009 3180 3189
7. J.A.J. Barbara, W.B. Smith, J.R. Gamble, X. Van Ostade, P. Vandenabeele, J. Tavernier, W. Fiers, M.A. Vadas, and A.F. Lopez Dissociation of TNF-α cytotoxic and proinflammatory activities by p55 receptor- and p75 receptor-selective TNF-α mutants EMBO J. 13 1994 843 850
8. R. Barrington, G. Williamson, R.N. Bennett, B.D. Davis, J.S. Brodbelt, and P.A. Kroon Absorption, conjugation and efflux of flavonoids, kaempferol and galangin, using the intestinal CaCo-2/TC7 cell model J. Funct. Foods I 2009 74 87
9. T.J. Batterham, and R.J. Highet Nuclear magnetic resonance spectra of flavonoids Aust. J. Chem. 17 1964 428 439
10. D.R. Benson, and J.O. Dawson Recent advances in the biogeography and genecology of symbiotic Frankia and its host plants Physiol. Plant. 130 2007 318 330 (Pubitemid 46906295)
11. T. Bongartz, A.J. Sutton, M.J. Sweeting, I. Buchan, E.L. Matteson, and V. Montori Anti-TNF antibody therapy in rheumatoid arthritis and the risk of serious infections and malignancies: systematic review and meta-analysis of rare harmful effects in randomized controlled trials JAMA 295 2006 2275 2285 (Pubitemid 43736578)
12. T. Bongartz, F.C. Warren, D. Mines, E.L. Matteson, K.R. Abrams, and A.J. Sutton Etanercepttherapy in rheumatoid arthritis and the risk of malignancies: a systematic review and individual patients data meta-analysis of randomized controlled trials Ann. Rheum. Dis. 68 2009 1177 1183
13. 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
14. E.E. Deschner, J. Ruperto, G. Wong, and H.L. Newmark Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia Carcinogenesis 12 1991 1193 1196
15. E. Dommasch, and J.M. Gelefand Is there truly a risk of lymphoma from biologic therapies? Dermatol. Ther. 22 2009 418 430
16. J. Duke Handbook of Energy Crops 1983 Available at: http://www.hort. purdue.edu/newcrop/duke-energy/dukeindex.html (accessed 09.01.10)
17. V.A. Facundo, and S.M. Morais Constituents of Piper aleyreanum (Piperaceae) Biochem. Syst. Ecol. 31 2003 111 113 (Pubitemid 36093223)
18. H. Fujiki Two stages of cancer prevention with green tea J. Cancer Res. Clin. Oncol. 125 1999 589 597 (Pubitemid 29502339)
19. H. Fujiki, M. Suganuma, S. Matsuyama, and K. Miyazaki Cancer prevention with green tea polyphenols for the general population, and for patients following cancer treatment Curr. Cancer Ther. Rev. 1 2005 109 114
20. P. Godin A new spray reagent for paper chromatography of polyols and cetoses Nature 174 1954 134
21. T. Hashimoto, M. Suganuma, H. Fujiki, M. Yamada, T. Kohno, and Y. Asakawa Isolation and synthesis of TNF-α release inhibitors from Fijian kawa (Piper methysticum) Phytomedicine 10 2003 309 317 (Pubitemid 36597167)
22. T. Hashimoto, M. Tori, and Y. Asakawa Five new diarylheptanoids from the male flowers of Alnus sieboldiana Chem. Pharm. Bull. 34 1986 1846 1849
23. M.Y. Heo, L.H. Jae, S.S. Jung, and W.W. Au Anticlastogenic effects of galangin against mitomycin C-induced micronuclei in reticulocytes of mice Mutat. Res. 360 1996 37 41 (Pubitemid 26153087)
24. M.Y. Heo, S.J. Sohn, and W.W. Au Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate Mutat. Res. 488 2001 135 150 (Pubitemid 32436428)
25. Y.-L. Huang, C.-C. Chen, F.-L. Hsu, and C.-F. Chen Two tannins from Phyllantheus tenellus J. Nat. Prod. 61 1998 523 524
26. M. Ishimatsu, T. Tanaka, G.-I. Nonaka, and I. Nishioka Alnusnins A and B from the leaves of Alnus sieboldiana Phytochemistry 28 1989 3179 3184
27. W.Y. Jin, X.F. Cai, M.K. Na, J.J. Lee, and K.H. Bae Diarylheptanoids from Alnus hirsuta inhibit the NF-kB activation and NO and TNF-α production Biol. Pharm. Bull. 30 2007 810 813 (Pubitemid 46570999)
28. F. Keller, and M.W. Klohs A review of the chemistry and pharmacology of the constituents of Piper methysticum Lloydia 26 1963 1 15
29. S. Kitamura, and G. Murata Colored Illustrations of Woody Plants of Japan vol. 2 1979 Hoikusha, Osaka (in Japanese)
30. A. Komori, J. Yatsunami, M. Sugamuna, S. Okabe, S. Abe, A. Sakai, K. Sasaki, and H. Fujiki Tumor necrosis factor acts as a tumor promoter in BALB/3T3 cell transformation Cancer Res. 53 1993 1982 1985 (Pubitemid 23145713)
31. M. Kuroyanagi, Y. Yamamoto, S. Fukushima, A. Ueno, T. Noro, and T. Miyase Chemical studies on the constituents of Polygonum nodosum Chem. Pharm. Bull. 30 1982 1602 1608
32. M.-W. Lee, N.-Y. Kim, M.-S. Park, K.-H. Ahn, S.-H. Toh, D.-R. Hahn, Y.-C. Kim, and H.-T. Chung Diarylheptanoids with in vitro inducible nitric oxide synthesis inhibitory activity from Alnus hitsuta Planta Med. 66 2000 551 553 (Pubitemid 30626482)
33. J.P. Leombruno, T.R. Einarson, and E.C. Keystone The safety of anti-tumor necrosis factor treatment in rheumatoid arthritis: meta and exposure adjusted pooled analyses of serious adverse events Ann. Rheum. Dis. 68 2009 1136 1145
34. S. Lesser, R. Cermak, and S. Wolffram Bioavailability of quercetin in pigs is influenced by the dietary fat content J. Nutr. 134 2004 1508 1511 (Pubitemid 38720730)
35. M. Lipkin, B. Reddy, H. Newmark, and S.A. Lamprecht Dietary factors in human colorectal cancer Annu. Rev. Nutr. 19 1999 545 586 (Pubitemid 29380616)
36. X. Mariette, F. Tubach, H. Bagheri, M. Bardet, J.M. Berthelot, P. Gaudin, D. Heresbach, A. Martin, T. Schaeverbeke, D. Salmon, M. Lemann, O. Hermine, M. Raphael, and P. Ravaud Lymphoma in patients treated with anti-TNF: results of the 3-year prospective French RATIO registry Ann. Rheum. Dis. 69 2010 400 408
37. P. Marimuthu Projection of cancer incidence in five cities and cancer mortality in India Indian J. Cancer 45 2008 4 7
38. K.R. Markham, B. Ternai, R. Stanley, H. Geiger, and T.J. Mabry Carbon-13 NMR studies of flavonoids - III Tetrahedron 34 1978 1389 1397
39. E.J. Middleton, C. Kandaswami, and T.C. Theoharides The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol. Rev. 52 2000 673 751
40. T.J. Murray, X. Yang, and D.H. Sherr Growth of a human mammary tumor cell line is blocked by galangin, a naturally occurring bioflavonoid, and is accompanied by down-regulation of cyclins D3, E, and A Breast Cancer Res. 8 2006 R17 10.1186/bcr1391 Available at: http://breast-cancer-research.com/content/8/ 2/R17 (accessed 09.01.10)
41. M. Neacsu, P.C. Eklund, R.E. Sjöholm, S.P. Pietarinen, M.O. Ahotupa, B.R. Holmbom, and S.M. Willför Antioxidant flavonoids from knotwood of Jack pine and European aspen Holz. Roh. Werkst. 65 2007 1 6 (Pubitemid 46221145)
42. Y. Otake, and T. Walle Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9 Drug Metab. Dispos. 30 2002 103 105 (Pubitemid 34106526)
43. S. Passamonti, M. Terdoslavich, R. Franca, A. Vanzo, F. Tramer, E. Braidot, E. Petrussa, and A. Vianello Bioavailability of flavonoids: a review of their membrane transport and the function of bilitranslocase in animal and plant organisms Curr. Drug Metab. 10 2009 369 394
44. F. Sakamura, S. Ohta, T. Aoki, and T. Suga Triterpenoids from the female and male flowers of Alnus sieboldiana Phytochemistry 24 1985 2744 2745
45. A.M. Sánchez, S. Malagarie-Cazenave, N. Olea, D. Vara, A. Chiloeches, and I. Díaz-Laviada Apoptosis induced by capsaicin in prostate PC-3 cells involves ceramide accumulation, neutral sphingomyelinase, and JNK activation Apoptosis 12 2007 2013 2024 (Pubitemid 47498227)
46. Schoenmakers, I., Gros-Van Hest, M., Löwik, C.W.G.M., 2005. Galangin components for the maintenance of bone health and/or treatment, alleviation and/or prevention of bone disorder. EU Patent EU 1 530 968 A1.
47. J. Schwencke, and M. Caru Advances in actinorhizal symbiosis: host plant-Frankia interactions, biology, and applications in arid land reclamation. A review Arid Land Res. Manag. 15 2001 285 327
48. B.L. Scott, A. Ramakrishnan, M. Fosdal, B. Storer, P. Becker, S. Petersdorf, and H.J. Deeg Anti-thymocyte globulin plus etanercept as therapy for myelodysplastic syndromes (MDS): a phase II study Br. J. Haematol. 149 2010 706 710
49. V.I. Slesarev, R. Ellithorpe, and T. Dimitroff Inhibition of systemic TNF-alpha cytotoxicity in cancer patients by d-peptidoglycan Med. Oncol. 15 1998 37 43 (Pubitemid 28248298)
50. J.H. Stone, J.T. Holbrook, M.A. Marriott, A.K. Tibbs, L.P. Sejismundo, Y.-I. Min, U. Specks, P.A. Merkel, R. Spiera, J.C. Davis, E.W. St. Clair, W.J. McCune, S.R. Ytterberg, N.B. Allen, and G.S. Hoffman Solid malignancies among patients in the Wegener's Granulimatosis Entarcept Trial Arthritis Rheum. 54 2006 1608 1616
51. T. Suga, T. Aoki, T. Hirata, K. Aoki, and Y. Asakawa Structure of alnustic acid, a new secodammarane-type triterpenic acid from Alnus sieboldiana Bull. Chem. Soc. Jpn. 52 1979 1698 1700
52. M. Suganuma, M. Kurusu, K. Suzuki, E. Tasaki, and H. Fujiki Green tea polyphenol stimulates cancer preventive effects of celecoxib in human lung cancer cells by upregulation of GADD153 gene Int. J. Cancer 119 2006 33 40
53. M. Suganuma, S. Okabe, M.W. Marino, A. Sakai, E. Sueoka, and H. Fujiki Essential role of tumor necrosis factor α (TNF-α) in tumor promotion as revealed by TNF-α-deficient mice Cancer Res. 59 1999 4516 4518 (Pubitemid 29428949)
54. M. Suganuma, S. Okabe, E. Sueoka, N. Iida, A. Komori, S.-J. Kim, and H. Fujiki A new process of cancer prevention mediated through inhibition of tumor necrosis factor α expression Cancer Res. 56 1996 3711 3715 (Pubitemid 26272017)
55. M. Suganuma, E. Sueoka, N. Sueoka, S. Okabe, and H. Fujiki Mechanisms of cancer prevention by tea polyphenols based on inhibition of TNF-α expression BioFactors 13 2000 67 72 (Pubitemid 32107347)
56. E. Szliszka, Z.P. Czuba, J. Bronikowska, A. Mertas, A. Paradysz, and W. Krol Ethanolic extract of propolis (EEP) augments TRAIL-induced apoptotic death in prostate cancer cells Evid. Based Complement. Alternat. Med. 2009 10.1093/ecam/nep180
57. M. Tolomeo, S. Grimaudo, A. Di Cristina, R.M. Pipitone, L. Dusonchet, M. Meli, L. Crosta, N. Gebbia, F.P. Invidiata, L. Titone, and D. Simoni Galangin increases the cytotoxic activity of imatinib mesylate in imatinib-sensitive and imatinib-resistant Bcr-Abl expressing leukemia cells Cancer Lett. 265 2008 289 297
58. R. van Horssen, T.L.M. ten Hagen, and A.M.M. Eggermont TNF-α in cancer treatment: molecular insights, antitumor effects, and clinical utility Oncologist 11 2006 397 408
59. A. Waterston, and M. Bower TNF and cancer: good or bad? Cancer Ther. 2 2004 131 147
60. WHO International Agency for Research on Cancer. World Cancer Report 2003 http://www.who.int/mediacentre/news/releases/2003/pr27/en/ (accessed 08.01.10)
61. E. Wollenweber, J.F. Stevens, M. Dörr, and A.C. Rozefelds Taxonomic significance of flavonoid variation in temperate species of Nothofagus Phytochemistry 62 2003 1125 1131 (Pubitemid 36323485)
62. T. Yamanaka, A. Asama, C.-Y. Li, and H. Okabe Growth, nitrogen fixation and mineral acquisition of Alnus sieboldiana after inoculation of Frankia together with Gigasphora margarita and Pseudomonas putida J. For. Res. 10 2005 21 26 (Pubitemid 40181269)
63. K. Yang, S.A. Lamprecht, Y. Liu, H. Shinozaki, K. Fan, D. Leung, H. Newmark, V.E. Steele, G.J. Kelloff, and M. Lipkin Chemoprevention studies of the flavonoids quercetin and rutin in normal and azoxymethane-treated mouse colon Carcinogenesis 21 2000 1655 1660
64. Y.-B. Yu, H. Miyashiro, N. Nakamura, M. Hattori, and J.C. Park Effects of triterpenoids and flavonoids isolated from Alnus firma on HIV-1 viral enzymes Arch. Pharm. Res. 30 2007 820 826