Biotransformation of the flavonoid tiliroside to 7-methylether tiliroside: Bioactivity of this metabolite and of its acetylated derivative

Cellular and Molecular Life Sciences

Volumn 53, Issue 7, 1997, Pages 587-592

  Demetzos, C ^a   Magiatis, P ^a   Typas, M A ^b   Dimas, K ^c   Sotiriadou, R ^c   Perez, S ^c   Kokkinopoulos, D ^c  

^a UNIVERSITY OF ATHENS   (Greece)

^b Division of Genetics   (Greece)

^c Hellenic Anticancer Institute   (Greece)

Author keywords

Aspergillus nidulans; Biotransformation; Cytotoxicity; DNA synthesis; Kaempferol glycosides; Tiliroside

Indexed keywords

DRUG METABOLITE; ETHER DERIVATIVE; FLAVONOID; KAEMPFEROL DERIVATIVE;

ACETYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPERGILLUS NIDULANS; BIOTRANSFORMATION; CELL STRAIN HL 60; CHEMICAL STRUCTURE; CONTROLLED STUDY; DNA SYNTHESIS; DNA SYNTHESIS INHIBITION; DOSE TIME EFFECT RELATION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG EFFICACY; HUMAN; HUMAN CELL; LEUKEMIA CELL; LEUKEMIA CELL LINE; NONHUMAN;

ACETYLATION; ASPERGILLUS NIDULANS; BENZOPYRANS; BIOTRANSFORMATION; CELL DIVISION; DNA; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEIC ACID SYNTHESIS INHIBITORS; TUMOR CELLS, CULTURED;

ASPERGILLUS; EMERICELLA NIDULANS;

EID: 0030884980     PISSN: 1420682X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s000180050076     Document Type: Article

References (36)

1. Mitrokotsa D., Mitaku S., Demetzos C., Harvala C., Mentis A., Perez S., et al. (1993) Bioactive compounds from the buds of Platanus orientalis and isolation of a new kaempferol glycoside. Planta Med. 59: 517-520
2. Vermes B., Chari V. M. and Wagner H. (1981) Structure elucidation and synthesis of flavonol acylglycosides. The synthesis of tiliroside. Helv. Chim. Acta 64: 1964-1967
3. Kaouadji M. (1990) Acylated and non-acylated kaempferol monoglycosides from Platanus acerifolia buds. Phytochemistry 29: 2295-2297
4. Pathak D., Pathak K. and Singla A. K. (1991) Flavonoids as medicinal agents Recent advances. Fitoterapia 5: 371-389
5. Ibrahim A. S. and Abul-Haji Y. J. (1990) Microbiological transformation of flavone and isoflavone. Xenobiotica 20: 363-373
6. Ibrahim A. S. and Abul-Haji Y. J. (1990) Microbiological transformation of (- +)-flavanone and (- +) isoflavone. J. Nat. Prod. 53: 644-656
7. Westlake D. W. S., Talbot G., Blakley E. R. and Simpson F. J. (1959) Microbial decomposition of rutin. Can. J. Microbiol. 5: 621-6309
8. Nshimo C. M., Pezzuto J. M., Kinghorn A. D. and Farnsworth W. R. (1993) Cytotoxic constituents of Muntingia calabura leaves and stems collected in Thailand. Int. J. Pharmacognosy 31: 77-815
9. Bjeldanes L. F. and Chang G. W. (1977) Mutagenic activity of quercetin and related compounds. Science 197: 577-578
10. Bainbridge B. W., Dalton H. and Walpole J. H. (1966) Aspergillus Newsletter 7: 18-20
11. McCarthy R. E, Junius V., Farber S., Lazarus H. and Foley G. E. (1965) Cytogenetic analysis of human lymphoblasts in continuous culture. Exp. Cell Res. 40: 197-203
12. Uzman B. G., Foley G. E., Farber S. and Lazarus H. (1966) Morphologic variations in human leukemic lymphoblasts (ccrf-cem cells) after long term culture and exposure to chemotherapeutic agents. Cancer 19: 1725-1742
13. Minowada M., Ohnuma T. and Moore G. E. (1972) Rosette-forming human lymphoid cells. Establishment and evidence for origin of thymus-derived lymphocytes. J. Natl Cancer Inst. 49: 891-895
14. Weiss A. and Stobo J. D. (1984) Requirement for the coexpression of T3 and T cell antigen receptor on a malignant human T-cell line. J. Expl Med. 160: 1284-1290
15. Gootenberg J. E., Ruscetti F. W., Mier J. W., Gardar A. and Gallo R. C. (1981) Human cutaneous T cell lymphoma and leukemia cell lines produce and respond to T cell growth factor. J. Exp. Med. 154: 1403-1418
16. Popovic M., Read-Connole E, and Gallo R. C. (1984) T4 positive human neoplastic cell lines susceptible to and permissive for HTLV-III. Lancet 29: 1472-1473
17. Schneider U., Shwenk H. U. and Bernkamm G. (1977) Characterization of EBV-genome negative "null" and "T" cell lines derived from children with acute lymphoblastic leukemia and leukemic transformed non-Hodgkin lymphoma. Int. J. Cancer 19: 521-526
18. Klein G., Dombos L. and Gothoskar B. (1972) Sensitivity of EBV producer and non producer human lymphoblastoid cell lines to superinfection with EB virus. Int. J. Cancer 10: 44-57
19. Klein E., Klein G., Nadkarni J. S., Nadkarni J. J., Wigzell H. and Clifford P. (1967) Surface IgM specificity on cells derived from a Burkitt's Lymphoma. Lancet 2: 1068-1070
20. Nisson K., Giovanella B. C., Stehlin J. S. and Klein G. (1977) Tumorigenicity of human hematopoietic cell lines an athymic nude mice. Int. J. Cancer 19: 337-344
21. Kottaridis S., Perez S., Kokkinopoulos D., Delinassios J. G., Pangalis G. A., Kosmidis H. et al. (1985) Establishment and characterization of a B-cell line from a patient with acute lymphoblastic leukemia. Leuk. Res. 9: 113-122
22. Pulvertaft R. J. (1964) Cytology of Burkitt's tumour (African Lymphoma). Lancet 1: 238-240
23. Adams R. (1967) Formal discussion: the role of transplantation in the experimental investigation of human leukemia and lymphoma. Cancer Res. 27: 2479-2482
24. Rovera C., O'Brian T. G., Schneider C., Newmann R., Kemslead J., Greaves M. et al. (1979) Induction of differentiation in human promyclocytic leukemia cells by tumor promoters. Science 204: 868-870
25. Alder S., Ciampi A. and McCullosh E. A. (1984) A kinetic and clonal analysis of heterogeneity in k562 cells. J. Cell. Physiol. 118: 186-192
26. Koren H. S., Anderson S. J. and Larriek J. W. (1979) In vitro activation of human macrophage-like cell line. Nature 279: 328-331
27. Boyum A. (1968) Separaton of leukocytes from blood and bone marrow. Scand. J. Clin. Lab. Invest. 21(suppl. 97): 1-7
28. Mossman T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Meth. 65: 55-63
29. Denizot F. and Lang R. (1986) Rapid colorimetric assay for cell growth and survival: modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Meth. 89: 271-277
30. Romussi G., Bignardi G., Pizza C. and Tommasi D. N. (1991) New and revised structures of acylated flavonoids from Quercus ruber L. Arch. Pharm. (Weinheim) 324: 519-524
31. Nikaido T., Ohmoto T. and Sunkawa U. (1987) Inhibitors of adenosine 3′,5′-cyclic monophospate phosphodiesterase in Daphne genkwa Sieb. et Zucc. Chem. Pharm. Bull. 2: 675-681
32. Cushman M. and Nagarathnam D. (1991) Cytotoxicities of some flavonoid analogues. J. Nat. Prod. 54: 1656-1660
33. Kaneda N., Perruto J. M., Soejarto D. D., Kinghorn A. D., Farnsworth N. R., Tuchinda P. et al. (1990) New cytotoxic flavonoids from Muntingia calabura roots. Planta Med. 56: 672-673
34. Yoshida M., Sakai T., Hosokawa N., Marui N., Matsumoto K., Fujioka A. et al. (1990) The effect of quercetin on cell cycle progresion and growth of human gastric cancer cells. FEBS Lett. 260: 10-13
35. Yoshida M., Yamamoto M. and Nikaido T. (1992) Quercetin arrests human leukemic T-cells in late G1 phase of the cell cycle. Cancer Res. 52: 6676-6681
36. Traganos F., Aldert B., Halko N., Bruno S. and Darzynkiewicz Z. (1992) Effects of genistein on the growth and cell cycle progression of normal human lymphocytes and human leukemic MOLT-4 and HL-60 cells. Cancer Res. 52: 6200-6208