Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera

Phytochemistry

Volumn 68, Issue 20, 2007, Pages 2531-2536

  Mshvildadze, Vakhtang ^a   Legault, Jean ^a   Lavoie, Serge ^a   Gauthier, Charles ^a   Pichette, André ^a  

^a UNIVERSITÉ DU QUÉBEC À CHICOUTIMI   (Canada)

Author keywords

Anticancer; Bark; Betula papyrifera; Betulaceae; Birch; Chavicol; Cytotoxic; Diarylheptanoid; Glycoside; NMR

Indexed keywords

ANTINEOPLASTIC AGENT; GLYCOSIDE; HEPTANE DERIVATIVE;

ARTICLE; BARK; BIRCH; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FIBROBLAST; HUMAN; IC 50; ISOLATION AND PURIFICATION; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BETULA; CELL LINE, TUMOR; CELL SURVIVAL; DIARYLHEPTANOIDS; FIBROBLASTS; GLYCOSIDES; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PLANT BARK;

BETULA PAPYRIFERA; BETULACEAE;

EID: 34548824325     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.05.018     Document Type: Article

References (26)

1. Baglin I., Mitane-Offer A.C., Nour M., Tan K., Cave C., and Lacaille-Dubois M.A. A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents. Mini Rev. Med. Chem. 3 (2003) 159-165
2. Baglin I., Poumaroux A., Nour M., Tan K., Mitaine-Offer A.C., and Lacaille-Dubois M.A. New ursolic and betulinic derivatives as potential cytotoxic agents. J. Enzyme Inhib. Med. Chem. 18 (2003) 111-117
3. Chen J., Gonzalez-Laredo R.B., and Karchesy J.J. Minor diarylheptanoid glycosides of Alnus rubra bark. Phytochemistry 53 (2000) 971-973
4. Cichewicz R.H., and Kouzi S.A. Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection. Med. Res. Rev. 24 (2004) 90-114
5. Cole B.J.W., Bentley M.D., Hua Y., and Bu L. Triterpenoid constituents in the outer bark of Betula alleghaniensis (Yellow Birch). J. Wood Chem. Technol. 11 (1991) 209-223
6. Ekman R. The suberin monomers and triterpenoids from the outer bark of Betula verrucosaEbrh. Holzforschung 37 (1983) 205-211
7. Frank S., Santamour J.R., and Lundgren L.N. Distribution and inheritance of platyphylloside in Betula. Biochem. Syst. Ecol. 24 (1996) 145-156
8. Frank S., Santamour J.R., and Lundgren L.N. Rhododendrin in Betula: a reappraisal. Biochem. Syst. Ecol. 25 (1997) 335-341
9. Fuchino H., Konishi S., Satoh T., Yagi A., Saitsu K., Tatsumi T., and Tanaka N. Chemical evaluation of Betula species in Japan. II. Constituents of Betula platyphylla var. japonica. Chem. Pharm. Bull. 44 (1996) 1033-1038
10. Fuchino H., Satoh T., and Tanaka N. Chemical evaluation of Betula species in Japan III. Constituents of Betula maximowicziana. Chem. Pharm. Bull. 44 (1996) 1748-1753
11. Fuchino H., Satoh T., Shimizu M., and Tanaka N. Chemical evaluation of Betula species in Japan. IV. Constituents of Betula davurica. Chem. Pharm. Bull. 46 (1998) 166-168
12. Gauthier C., Legault J., Lebrun M., Dufour P., and Pichette A. Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents. Bioorg. Med. Chem. 14 (2006) 6713-6725
13. Habiyaremye I., Stevanvic-Janejic T., Riedl B., Garneau F.-X., and Jean F.-I. Pentacyclic triterpene constituents of yellow birch bark from Quebec. J. Wood Chem. Technol. 22 (2002) 83-91
14. Hase T., and Iwagawa T. The revised structure of furcation, a component of leaves of Viburnum furcatum blume. Bull. Chem. Soc. Jpn 55 (1982) 3663-3664
15. Higuchi R., Aritomi M., and Donnelly D.M.X. Monolignol and dilignol glycosides from Pinus contorta leaves. Phytochemistry 16 (1977) 1007-1011
16. Hua Y., Bentley M.D., Cole B.J.W., Murray K.D., and Alfrod A.R.J. Triterpenes from the outer bark of Betula nigra. J. Wood Chem. Technol. 11 (1991) 503-516
17. Ju E.M., Lee S.E., Hwang H.J., and Kim J.H. Antioxidant and anticancer activity of extract from Betula platyphylla var. japonica. Life Sci. 74 (2004) 1013-1026
18. Marie-Victorin F. Flore Laurentienne. third ed. (2002), Gaëtan Morin Éditeur, Boucherville
19. O'Brien J., Wilson I., Orton T., and Pognan F. Investigation of the alamar blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur. J. Biochem. 267 (2000) 5421-5426
20. O'Connell M.M., Bentley M.D., Campbell C.S., and Cole B.J.W. Betulin and lupeol in bark from four white-barked birches. Phytochemistry 27 (1988) 2175-2176
21. Ohta S., Koyoma M., Aoki T., and Suga T. Absolute configuration of platyphylloside and (-)-centrolobol. Bull. Chem. Soc. Jpn. 58 (1985) 2423-2424
22. Pan H., and Lundgren L.N. Rhododendrol glycosides and phenyl glucoside esters from inner bark of Betula pubescens. Phytochemistry 36 (1994) 79-83
23. Setzer W.N., and Setzer M.C. Plant-derived triterpenoids as potential antineoplastic agents. Mini Rev. Med. Chem. 3 (2003) 540-556
24. Smite E., Lundgren L.N., and Anderson R. Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry 32 (1993) 365-369
25. Smite E., Pan H., and Lundgren L.N. Lignan glycosides from inner bark of Betula pendula. Phytochemistry 40 (1995) 341-343
26. Terazawa M., Koga T., Okuyama H., and Miyake M. Phenolic Compounds in Living Tissue of Woods III Platyphylloside, a new diarylheptanoid glucoside from the green back of shirakamba (Betula platyphylla Sukatchev var. japonica Hara) [Betulaceae]. Mokuzai Gakkaishi 30 (1984) 391-403