Solubility enhancement of a hydrophobic flavonoid, luteolin by the complexation with cyclosophoraoses isolated from Rhizobium meliloti

Antonie van Leeuwenhoek, International Journal of General and Molecular Microbiology

Volumn 84, Issue 3, 2003, Pages 201-207

  Lee, Sanghoo ^a   Seo, Dong Hyuk ^a   Park, Hey Lin ^a   Choi, Youngjin ^a   Jung, Seunho ^a  

^a Konkuk University   (South Korea)

Author keywords

Cyclosophoraoses; Inclusion complexation; Luteolin; R. meliloti 2011

Indexed keywords

CYCLOSOPHORAOSE; FLAVONOID; LUTEOLIN; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

SOLUBILITY;

ARTICLE; CARBOHYDRATE SYNTHESIS; COMPLEX FORMATION; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; INFRARED SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; SINORHIZOBIUM MELILOTI; SOLUBILITY; VIBRATION;

FLAVONOIDS; LUTEOLIN; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES; SINORHIZOBIUM MELILOTI; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

NEGIBACTERIA; RHIZOBIUM; SINORHIZOBIUM; SINORHIZOBIUM MELILOTI;

EID: 0242694426     PISSN: 00036072     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1026075215921     Document Type: Article

References (31)

1. Abe M., Amemura A. and Higashi S. 1982. Studies on cyclic β-(1,2)-glucans obtained from periplasmic space of Rhizobium trifolii cells. Plant & soil 64: 315-324.
2. Batley M., Redmond J.W., Djordjevic S.P. and Wolfe B.G. 1987. Characterization of glycerophosphorylated cyclic β-(1,2)-glucans from a fast-growing Rhizobium species. Boichim. Biophys. Acta 901: 119-126.
3. Bhagwat A.A., Tully R.E. and Keister D.L. 1992. Isolation and characterization of an ndvB locus from Rhizobium fredii. Mol. Microbiol. 6: 2159-2165.
4. Breedveld M.W., Zevenhuizen L.P.T.M. and Zehnder A.J.B. 1990. Excessive excretion of cyclic β-(1,2)-glucan by Rhizobium trifolii TA-1 Appl. Environ. Microbiol. 56: 2080-2086.
5. Cangelosi G.A., Martientti G. and Nester E.W. 1990. Osmosensitivity phenotypes of Agrobacterium tumefaciens mutants that lack periplasmic β-1,2-glucan. J. Bacterol. 172: 2172-2174.
6. Choi Y., Yang C., Kim H. and Jung S. 2000. Molecular dynamics simulations of cyclohenicosakis-[(1->2 -beta-D-glucohenicosapyranosyl], a cyclic (1->2)- beta-D-glucan (a 'cyclosophoraose') of DP 21. Carbohydr. Res. 326: 227-234.
7. Dylan T., Nagpal P., Helinski D.R. and Ditta G.S. 1990. Symbiotic pseudorevertants of Rhizobium meliloti ndv mutants. J. Bacteriol. 172: 1409-1417.
8. Dylan T., Helinski D.R. and Ditta G.S. 1990. Hypoosmotic adapatation in Rhizobium melilotirequires cyclic β-(1,2)-glucan. J. Bacteriol. 172: 1400-1408.
9. Elangovan V., Sekar N. and Govindasamy S. 1994. Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis. Cancer Lett. 87: 107-113.
10. Gottfert M. 1993. Regulation and function of rhizobial nodulation genes. FEMS Microbiol. Rev. 104: 39-64.
11. Higuchi T. and Connors K. 1965. Phase-solubility techniques. Adv. Anal. Chem. Instr. 4: 117-212.
12. Koizumi K., Okada Y., Horiyama S., Utamura T., Higashiura T. and Ikeda M. 1984. Preparation of cyclosophoraose-A and its complex-forming ability. J. Incl. Phenom. 2: 891-899.
13. Kwon C., Choi Y., Kim N., Yoo J., Yang C., Kim H. et al. 2000. Complex forming ability of a family of isolated cyclosophoraoses with ergosterol and its Monte Carlo docking computational analysis. J. Incl. Phenom. 36: 55-65.
14. Lee S., Kwon C., Choi Y., Seo D., Kim H. and Jung S. 2001a. Inclusion complexation of a family of cyclosophoraoses with indomethacin. J. Microbiol. Biotechnol. 11: 463-468.
15. Lee S., Seo D., Kim H. and Jung S. 2001b. Investigation of inclusion complexation of paclitaxel by cyclohenicosakis-(1→2)-(β-D-glucopyranosyl), by cyclic-(1→2)-β-D-glucans (cyclosophoraoses), and by cyclomaltoheptaoses (β-cyclodextrins). Carbohydr. Res. 334: 119-126.
16. Leighand J.L. and Coplin D.L. 1992. Signaling and host range variation in nodulation. Annu. Rev. Microbiol. 46: 307-346.
17. Long S.R. 1989. Rhizobium-legume nodulation: life together in the underground. Cell 56: 203-214.
18. Matsukawa Y., Marui N., Sakai T., Satomi Y., Yoshida M., Matsumoto K. et al. 1993. Genistein arrests cell cycle progression at G2-M. Cancer Res. 53: 1328-1331.
19. McIntire F.C., Peterson W.H. and Riker A.J. 1942. A polysaccharide produced by the crown-gall organism. J. Biol. Chem. 143: 491-496.
20. Miller K.J., Kennedy E.P. and Reinhold V.N. 1686. Osmotic adaptation by gram-negative bacteria: possible role for periplasmic oligosaccharides. Science 231: 48-51.
21. Miller K.J., Gore R.S. and Benesi A.J. 1988. Phosphoglycerol substituents present on the cyclic β-1,2-glucans of Rhizobium meliloti 1021 are derived from phosphatidylglycerol. J. Bacteriol. 170: 4569-4575.
22. Morris V.J. 1990. Biotechnically produced carbohydrates with functional properties for use in food systems. Food Biotechnol. 4: 45-57.
23. Morris V.J., Brownsey G.J., Chilvers G.R., Harris J.E., Gunning A.P. and Stevens B.H.J. 1991. Possible biological roles for Rhizobium leguminosarum extracellular polysaccharide and cyclic glucans in bacteria-plant interactions for nitrogen-fixing bacteria. Food Hydrocoll. 5: 185-188.
24. Peters N.K., Frost J.W. and Long S.R. 1986. A plant flavone, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science 233: 977-980.
25. Qiuyin C., Ronald O.R. and Ruiwen Z. 1997. Dietary flavonoids, quercetin, luteolin and genistein, reduce oxidative DNA damage and lipid peroxidation and quench free radicals. Cancer Lett. 119: 99-107.
26. Shimoi K., Masuda S., Shen B., Furugori M. and Kinae N. 1996. Radioprotective effects antioxidative plant flavonoids in mice. Mutat. Res. 350: 153-161.
27. Szejtli J. 1988. Cyclodextrin technology. Kluwer Academic Publishers, The Netherlands, p. 1-78.
28. Zand R.S., Jenkins D.J.A. and Diamandis E.P. 2000. Steroid hormone activity of flavonoids and related compounds. Breast Cancer Res. Treat. 62: 35-49.
29. Zevenhuizen L.P.T.M. and Scholten-Koerselman H.J. 1979. Surface carbohydrates of Rhizobium. I. β-1,2-glucans. Antonie van Leeuwenhoek 45: 165-175.
30. Zevenhuizen L.P.T.M. 1981. Cellular glycogen, β-1,2-glucan, poly-β-hydroxybutyric acid and extracellar polysaccharides in fast-growing species of Rhizobium. Antonie van Leeuwenhoek 47: 481-497.
31. Zevenhuizen L.P.T.M., Van Veldhuizen A. and Fokkens R.H. 1990. Re-examination of cellular cyclic β-1,2-glucans of Rhizobiaceae: Distribution of ring sizes and degrees of glycerol-1-phosphate substitution. Antonie van Leeuwenhoek 57: 173-178.