Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues

Phytochemistry

Volumn 70, Issue 2, 2009, Pages 228-236

  Piochon, Marianne ^a   Legault, Jean ^a   Gauthier, Charles ^a   Pichette, André ^a  

^a UNIVERSITÉ DU QUÉBEC À CHICOUTIMI   (Canada)

Author keywords

Bisabolol; Blood brain barrier; Cytotoxicity; Glioma; Glycoside; Sesquiterpene

Indexed keywords

BIOLOGICAL PRODUCT; DRUG DERIVATIVE; FUCOSE;

ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECT; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

BIOLOGICAL PRODUCTS; CELL LINE, TUMOR; CELL SURVIVAL; COMPUTER SIMULATION; FUCOSE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

RATTUS;

EID: 60349132204     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.11.013     Document Type: Article

References (35)

1. Agrawal P.K. NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 31 (1992) 3307-3330
2. Boyd M.D. In: Teicher B.A. (Ed). Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval (1997), Human Press, Totowa, NJ, USA 23-42
3. Burger A., and Abraham D.J. Burger's Medicinal Chemistry and Drug Discovery. 6th ed. vol. 2 (2003), Wiley, NJ, USA
4. Cavalieri E., Mariotto S., Fabrizi C., Carcereri de Prati A., Gottado R., Leone S., Berra L.V., Lauro G.M., Ciampa A.R., and Suzuki H. α-Bisabolol, a nontoxic compound, strongly induces apoptosis in glioma cells. Biochem. Biophys. Res. Commun. 315 (2004) 589-594
5. Darra E., Abdel-Azeim S., Manara A., Shoji K., Maréchal J.-D., Mariotto S., Cavalieri E., Perbellini L., Pizza C., Perahia D., Crimi M., and Suzuki H. Insight into the apoptosis-inducing action of α-bisabolol towards malignant tumor cells: involvement of lipid rafts and bid. Arch. Biochem. Biophys. 476 (2008) 113-123
6. Deng S., Yu B., Xie J., and Hui Y. Highly efficient glycosylation of sapogenins. J. Org. Chem. 64 (1999) 7265-7266
7. Egleton R.D., Mitchell S.A., Huber J.D., Palian M.M., Polt R., and Davis T.P. Improved blood-brain barrier penetration and enhanced analgesia of an opioid peptide by glycosylation. J. Pharm. Exp. Ther. 299 (2001) 967-972
8. Flitsch S.L. Synthetic chemistry: glycosylation with twist. Nature 437 (2005) 201-202
9. 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
10. Hitchcock S.A., and Pennington L.D. Structure-brain exposure relationships. J. Med. Chem. 49 (2006) 7559-7583
11. Ikeda T., Kajimoto T., Kondo H., and Wong C.-H. Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin. Bioorg. Med. Chem. Lett. 7 (1997) 2485-2490
12. Issac O. Pharmacological investigations with compounds of chamomile. I. On the pharmacology of (-)-α-bisabolol and bisabolol oxides (review). Planta Med. 35 (1979) 118-124
13. Jakovlev V., Isaac O., Thiemer K., and Kunde R. Pharmacological investigations on the components of chamomile. II. New investigations on the anti-inflammatory effects of (-)-α-bisabolol and bisabolol oxides. Planta Med. 35 (1979) 125-140
14. Jorgensen W.L., and Duffy E.M. Prediction of drug solubility from structure. Adv. Drug Delivery Rev. 54 (2002) 355-366
15. Kadir R., and Barry B.W. α-Bisabolol, a possible safe penetration enhancer for dermal and transdermal therapeutics. Int. J. Pharm. 70 (1991) 87-94
16. Kessler J.H., Mullauer F.B., de Roo G.M., and Medema J.P. Broad in vitro efficacy of plant-derived betulinic acid against cell lines derived from the most prevalent human cancer types. Cancer Lett. 25 (2007) 132-145
17. Kitagawa I., Baek N.I., Ohashi K., Sakagami M., Yoshikawa M., and Shibuya H. Mammosides B and H1, new ionophoric resin-glycosides from the tuber of Merremia mammosa, an Indonesian folk medicine. Chem. Pharm. Bull. 37 (1989) 1131-1133
18. Křen V., and Martínková L. Glycosides in medicine: "the role of glycosidic residue in biological activity". Curr. Med. Chem. 8 (2001) 1303-1328
19. Madhavan B.N. Final report on the safety assessment of bisabolol. Int. J. Toxicol. 18 Suppl. 3 (1999) 33-40
20. Mastelić J., Jerković I., Vinković M., Džolić Z., and Vikić-Topić D. Synthesis of selected naturally occurring glucosides of volatile compounds. Their chromatographic and spectroscopic properties. Croat. Chem. Acta 3 (2004) 491-500
21. Mbaïraroua O., Ton-That T., and Tapiéro C. Synthèses de 6-O-β-d-apiofuranosyl-β-d-glucopyranosides de monoterpényle. Carbohydr. Res. 253 (1994) 79-99
22. Mikhova B., Duddeck H., Taskova R., Mitova M., and Alipieva K. Oxigenated bisabolane fucosides from Carthamus lanatus L. Z. Naturforsch. 59c (2004) 244-248
23. Patov S.V., Puneov V.V., Kuchin A.V., and Froloa L.L. Synthesis of certain monoterpenoid glucosides. Chem. Nat. Compd. 42 (2006) 431-433
24. Poduslo J., and Curran G.L. Glycation increases the permeability of proteins across the blood-nerve and the blood-brain barriers. Mol. Brain Res. 23 (1994) 157-162
25. Rago R., Mitchen J., and Wilding G. DNA fluorometric assay in 96-well tissue culture plates using Hoechst 33 258 after cell lysis by freezing in distilled water. Anal. Biochem. 191 (1990) 31-34
26. Rio S., Beau J.-M., and Jacquinet J.-C. Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans. Carbohydr. Res. 219 (1991) 71-90
27. Ross A.J., Ivanova I.A., Ferguson M.A.J., and Nikolaev A.V. Parasite glycoconjugates. Part 11. Preparation of phosphodisaccharide synthetic probes, substrate analogues for the elongating α-d-mannopyranosylphosphate transferase in the Leishmania. J. Chem. Soc. Perkin Trans. 1 (2001) 72-81
28. San Feliciano A., Barrero A.F., Del Corral J.M.M., Gacimartin M.V., and Medarde M. α-Bisabolol β-d-fucopyranoside from Carthamus lanatus. Phytochemistry 21 (1982) 2115-2117
29. Schmidt R.R., and Toepfer A. Glycosidation with highly reactive glycosyl donors. Efficiency of the inverse procedure. Tetrahedron Lett. 32 (1991) 3353-3356
30. Schmidt R.R., and Kinzy W. Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21-123
31. Schmidt R.R., and Junq K.-H. Trichloroacetimidates. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology, Part I: Chemistry of Saccharides vol. 1 (2000), Wiley-VCH, Weinheim 5-59
32. Stahl-Biskup E., Intert F., Holthuijzen M., Stengele M., and Schulz G. Glycosidically bound volatiles - a review 1986-1991. Flavour Frag. J. 8 (1993) 61-80
33. Thiele K., Jakovlev V., Isaac O., and Schuler W.A. Äther und ester von (-)-α-bisabolol und analogen mono- und sesquiterpenoiden mit antiphlogistischer wirkung. Arzneim. Forsch. 19 (1969) 1878-1882
34. Urban F., Moore B.S., and Breitenbach R. Synthesis of tigogenyl β-O-cellobioside heptaacetate and glycoside tetraacetate via Schmidt's trichloroacetimidate method: some new observations. Tetrahedron Lett. 31 (1990) 4421-4424
35. Vijayakumar G.R., and Divakar S. Amyloglucosidase-catalyzed synthesis of eugenyl and curcuminyl glycosides. Biotechnol. Lett. 29 (2007) 575-584